Boston might not scream romance right away, but it honestly makes such a great spot for a couples trip. It’s got that mix of history, charm, and city vibes without being overwhelming. You’ve got cute neighborhoods to explore, spots to chill and grab good food, and just the kind of atmosphere that makes walking around with your person feel a little more fun.

If you’re thinking of heading out here with your bae, this guide is put together to make the planning part way easier.

Planning a Trip to Boston

Once you’ve got your date ideas sorted out, it helps to know where to stay, especially if it’s your first time in the city. We’ve got a guide that breaks down the best neighborhoods to stay in based on what kind of vibe you’re going for. If you’re after something extra cozy or luxurious, you can also check out some of Boston’s best boutique hotels that are perfect for couples. And if you’re the type who likes to plan things out, there’s a detailed 3-day itinerary that can help you explore the city without any guesswork.

Iconic Landmarks & Historic Walks

Walk the Freedom Trail Together

If you’re already in Boston, you might as well check out the Freedom Trail. It’s one of those things that’s easy to do and it actually helps especially if you and bae are trying to get to know the city better. 

The trail runs a little over two miles and connects a bunch of historic sites that played a role in the American Revolution. You guys can definitely just follow the path yourself, but if you feel like getting the full tourist experience, there’s a guided walking tour that’ll give you the full rundown of what went down where. Either way, it’s a pretty chill way to spend an afternoon together and get a feel for what Boston’s all about.

Stroll Through Boston Common and Public Garden

Boston Common and the Public Garden are basically the city’s backyard, and they’re seriously some of the nicest places to just hang out with your boo. 

The whole area’s really pretty, especially when the flowers there start blooming or the leaves are starting to change. It’s got wide open lawns, shady trees, and little paths that make it easy to just stroll around and take it all in.

You don’t have to do much to enjoy it. You can walk around the lagoon, ride the swan boats if they’re running, or just find a spot to sit and watch people go by. 

The Public Garden feels a little more romantic with its old bridges and weeping willows, while Boston Common has that chill, everyday vibe. It’s one of the city’s spots that feels easy and familiar, but still really beautiful.

Go on a North End Food Tour or DIY Food Crawl

If you’re looking for another fun way to spend an afternoon together, exploring the North End is always a great idea. This area’s really known for having some of the best food in Boston, and it’s the place where you can just follow your cravings. 

You can go the DIY route and wander into whatever smells good, or if you want more of a guided local experience, there are food tours you can join that take you around the must-try spots without you having to plan a thing. We’ve got a quick guide to the best food tours in north end if you wanna check it out.

The vibes here are cozy and a little romantic, with narrow streets, brick buildings, and old-school charm everywhere you look. It’s the perfect spot for strolling, trying cannoli from different bakeries, or splitting a plate of pasta somewhere tucked away.

Waterfront & Cruise Experiences

Cruise Into the Sunset in Boston Harbor

I said it once and I’ll say it again, sunset cruises are always a good idea. And if you’re spending time in Boston, there’s really no better way to end the day than drifting along the harbor while the sun goes down. You’ll get the perfect mix of everything here; the city views, the open water, and the golden skies all in one.

It’s calm, it’s scenic, and honestly, it just feels a little extra special when you’re sharing it with your boo. Whether you’re doing it for a special occasion or just because, you’ll want to book this in advance since these cruises tend to fill up pretty quickly. 

Go Whale Watching 

Whale watching might not be the first thing that comes to mind when you think of Boston, but it’s actually one of the best places on the East Coast for spotting these ocean giants. Hop on a cruise from the harbor and head out to Stellwagen Bank, a prime feeding ground for humpback, fin, and even minke whales.

Maybe this activity is the much awaited adventure date for you and your boo. Bring a light jacket, find a cozy seat together, and just enjoy the ride.

Visit the New England Aquarium

If you’re not really into the whole whale watching cruise thing, the New England Aquarium is always a safe and solid backup. Aquarium dates honestly never get old. It’s chill, kinda nostalgic, and a fun way to spend time together without too much effort.

You’ve got the massive central tank with sea turtles and reef sharks swimming by, and of course, the penguins always steal the show..Since it’s right by the waterfront, you can easily turn it into a longer date with a walk around the harbor after (which I actually think is a huge plus btw if u ask me lol). 

City Views & Scenic Spots

Get Sweeping Views of the City from View Boston

If you and bae are into views, you really can’t miss View Boston. Sitting at the top of the Prudential Center, this spot gives you sweeping 360-degree views of the whole city. Go around golden hour and the whole skyline just starts glowing. It’s the kind of view that makes you pause for a bit and just take it all in.

This one’s a timed entry, so make sure to book ahead if you want a good slot. The vibe is super chill and perfect for couples who just want something easy but memorable. 

Take a Day Trip to Martha’s Vineyard

If you guys are looking for a quick break from the city, Martha’s Vineyard is a great place to escape to for the day. The best way to enjoy it is by joining one of those day trips that covers your round-trip ride from Boston and gets you on the ferry without the stress of figuring it all out yourself. 

Once you’re on the island, you’ve got two ways to go about it. You can either hop on the guided tour that comes with the package or explore at your own pace if you’d rather wander. Either way, the island’s got that breezy, small-town charm with beaches, lighthouses, and colorful little neighborhoods to stroll through and enjoy.

Quirky and Curious Stops 

Museum dates are basically in every couple’s textbook at this point, and Boston’s got plenty of spots that make it easy to see why. If you’re thinking of checking out a museum or two while you’re here, these are a few fun and laid-back options to start with.

If you and bae are both the curious type, the Boston Museum of Science is a fun stop to explore together. You’ll probably end up trying random experiments or chatting about things you didn’t expect to find interesting. Really perfect for a rainy afternoon or whenever you just want to do something different without the usual museum vibe.

MIT’s campus over in Cambridge isn’t really a museum but it’s also worth a wander if you’re both in the mood for something a little slower and more offbeat. There’s even a student-guided walking tour you can follow if you wanna get the full experience. What’s also great about this is, you’re not far from Kendall Square, which is convenient if you guys are feeling like grabbing a bite or coffee after.

The USS Constitution Museum over in the Charlestown Navy Yard is a fun little stop if you’re curious about Boston’s maritime side. It’s a good place to poke around for a bit, especially if you’re already nearby. Even if you’re not big on naval stuff, you’ll easily enjoy the spot, especially with the harbor views and vibes around the area.

If you’re both into art or just wanna wander through something quiet and beautiful, the Museum of Fine Arts is the perfect pick. It’s got everything from ancient pieces to bold modern art stuff, so you’ll definitely find something to talk about. The vibe’s calm and cozy, plus, the museum café isn’t a bad place to take a little break together.

And if you guys are up for a little road trip, go head out to Plimoth Patuxet Museums and make it a solid way to spend the day. It’s not your usual museum, it’s more like stepping into a living time capsule, with full-scale 17th-century villages and costumed actors staying in character the whole time. It’s a bit out of the way, but the peaceful and unique setting makes it worth it.

Fun & Casual Attractions

Catch a Game at Fenway Park

If you and your boo are into baseball, catching a game at Fenway Park is something you don’t wanna miss. The energy’s on a whole other level when the Red Sox are playing. But even if you’re not in town during game day, you can still swing by and do one of the stadium tours instead. It’s a fun way to check the place out without the crowd.

Fenway’s the oldest ballpark in the league, and walking around inside kinda gives you the feeling of flipping through Boston’s past. The Green Monster, the dugouts, the view from the stands; it’s cool even if you’re just there to explore the stadium together,

Visit the Franklin Park Zoo

If you guys are in the mood for another light-hearted kind of date, the Franklin Park Zoo is also a solid pick. Just like what I have to say about the aquarium, a zoo date never really goes out of style. There’s something kinda sweet about strolling past the exhibits, pointing out your favorite animals, and just enjoying each other’s company in a relaxed setting.

If you’ve decided to go, make sure to book your admission in advance so you don’t have to worry about anything last minute. It’s a chill way to spend the day and sneak in a little adventure together.

Exploring Boston Together

Boston really has a way of pulling you in. Whether you’re just here for a few days or planning to explore a bit more, there’s always something worth checking out. If you’re tagging the kids along, we’ve got a guide on family-friendly spots and activities that’ll help you plan around them without missing the fun. You can also sneak in a quick day trip if you’re up for a change of scenery. And if you’re still figuring out what to see first, there’s a list of top things to do in Boston that’s a good place to start.

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There’s just something about New Orleans that feels perfect for couples. Maybe it’s the music in the streets, the slow pace, or the way the city makes everyday moments feel a little more special. Whether it’s your first time here or you’ve been before, it’s the kind of place that’s easy to fall in love with and even easier to enjoy with someone you love.

This guide is here to make planning your trip with your boo a little easier, so you can just focus on having a good time together.

Planning a Trip to New Orleans

If you’re planning a romantic trip to New Orleans, you’re in for something special. Once you’ve got your date ideas lined up, you might also want to figure out the best area to stay, especially if it’s your first time here and you’re still getting a feel for the city. There’s also a list of cool hotels that match all kinds of budgets and travel styles, so you can pick a place that fits your vibe. And if you’re trying to see as much of the city as you can in just a few days, there’s a full 3-day itinerary that’s super helpful for planning it all out.

Classic New Orleans Experiences

Stroll Through the French Quarter 

If you’re going to be in New Orleans, it’s pretty much impossible to miss the French Quarter. This is where the city’s charm really comes alive, and it’s one of the best spots to explore as a couple. Between the wrought-iron balconies, the hidden courtyards, and the cobblestone streets, it has that effortlessly romantic vibe that just makes you want to slow down and take it all in.

One fun way to dive deeper into the area is by joining a local food tour. It’s a great excuse to try different Creole bites and learn some cool stories about the neighborhood while you’re at it. 

If you’re not really in the mood to eat your way through the Quarter, you can also hop on a haunted carriage tour instead. It’s a fun way to learn the spookier side of New Orleans while riding through the streets at night. 

And if you’re more into strolling on your own, start early in the morning to avoid the crowds and catch the soft light hitting those colorful buildings.

Listen to Live Jazz Together

Jazz is just part of the air in New Orleans, and if you’re visiting with your boo, going to a jazz bar at night is an absolute must. The city’s known all over the world for its jazz roots, so it only makes sense to see it live while you’re here. You’ll hear it in the streets, in restaurants, even coming from random corners, but nothing beats sitting down somewhere with good drinks and letting the music do its thing.

Preservation Hall is probably the most famous, but it gets packed fast and isn’t really the coziest spot out there. If you’re looking for something a little less cramped and chaotic, head to one of the smaller clubs on Frenchmen Street. The Spotted Cat or d.b.a. both have that easy, intimate feel where you can actually relax and enjoy the vibes together.

 And if you really want to dive deeper into the city’s music scene, you can even join a jazz-focused tour that takes you through the roots of it all. 

Ride a Steamboat Natchez Cruise 

Honestly, anything that involves cruising is always worth doing when you’re exploring a new city, and in New Orleans, hopping aboard the Steamboat Natchez is the way to do it. 

This thing’s got the classic paddlewheel, and while it might sound a bit touristy at first, the experience itself is anything but bland. This is where you get to soak in river views, feel the breeze on your face, and vibe to live jazz music while drifting down the Mississippi.

You can choose between the lunch or dinner cruise if you want to turn it into a proper date, complete with a meal and a more relaxed setting that’s perfect for couples. Or, if you’re just here for the scenery and music, the cruise-only ticket still gives you everything that makes the ride special. 

The whole thing lasts around two hours, and it does get really breezy on deck, so bringing a light jacket isn’t a bad idea.

Tours & Unique Experiences

Dive Into New Orleans’ Spooky Side

We all know there are tons of things New Orleans is known for, and right at the top of that list is all the spooky, ghost-and-voodoo type stuff. The city’s got this eerie, mysterious vibe that makes it the perfect place to lean into the haunted side of things. 

So while you’re already here, don’t miss out on joining one of the ghost and voodoo tours. They take you through the French Quarter at night, share wild stories about spirits, witches, and old legends, and honestly, it’s a fun way to get a little spooked together.

There’s also the cemetery tours, which are weirdly fascinating and a lot more beautiful than you’d expect. New Orleans does burials differently, with above-ground tombs and crypts that go way back in history. St. Louis Cemetery No. 1 is the most famous one you can visit. 

It might not sound romantic at first, but if you’re both into creepy history and offbeat experiences, this is one of those only-in-New-Orleans things that actually makes for a great date.

Tour the Wetlands

This might not sound like your typical date spot, but if you and bae are both into nature and a little adventure, Jean Lafitte National Historical Park and Preserve would totally work for both of you.. 

The area is named after the infamous pirate and smuggler Jean Lafitte, who was known for sneaking goods through these very swamps back in the day. Now it’s all protected land, filled with marshes, bayous, and tons of wildlife that give you a glimpse into a completely different side of Louisiana.

If you really want to enjoy it, the best way to explore is by joining an airboat ride tour. You’ll cruise through the swamp at full speed, then slow down to spot gators sunbathing, birds flying overhead, and maybe even hear a few wild local stories from your guide. Just be sure book in advance and bring your camera because the views out there are amazing.

Visit a Plantation 

If the two of you want to understand the deeper parts of Louisiana’s history, visiting a plantation can be a meaningful experience. It’s not a lighthearted activity, but it gives you an unfiltered look at a very painful chapter of the past. 

For many, especially our black folks with ancestral ties to this history, it’s a chance to reflect, acknowledge, and engage with stories that are too often overlooked. Sharing that kind of experience together can be incredibly grounding.

Oak Alley is the one that often shows up in everyone’s travel photos. Its canopy of centuries-old oak trees is striking, and the grounds are well-kept. While there is some historical context offered about slavery, the overall presentation tends to focus more on the physical beauty of the site. It’s a popular stop foIf you want to understand the deeper parts of Louisiana’s history, visiting a plantation can be a meaningful experience. It’s not a lighthearted activity, but it gives you an unfiltered look at a very painful chapter of the past. For many, especially those with ancestral ties to this history, it’s a chance to reflect, acknowledge, and engage with stories that are too often overlooked. Sharing that kind of experience together can be incredibly grounding.

Whitney Plantation, on the other hand, is all about truth-telling. It’s one of the few plantations that centers its entire narrative around the lives of the enslaved. From memorials to preserved slave quarters, everything on the grounds is designed to educate and honor the people who endured unimaginable hardships. It’s not an easy visit, but it’s one that carries real emotional weight and historical value.

Between the two, I’d strongly recommend visiting Whitney. It offers a more accurate and respectful understanding of what life was like during that time. If you’re planning to visit either site, make sure to book a guided tour in advance, since spots are limited and usually require reservations through group tours..

Take a Cooking Class Together

You’re already in New Orleans, so why not take the chance to actually learn how to cook the food you’ve been eating all trip long? A local cooking class is one of the most fun (and delicious) ways to dive deeper into the city’s culture, especially if you and bae are looking to do something a little more hands-on. It’s a fun change of pace, and you don’t need to be a pro in the kitchen to enjoy it.

You’ll get to watch and learn how to cook signature dishes like gumbo, jambalaya, and pralines, all while sipping on drinks and listening to stories from chefs who’ve been doing this for years. No need to stress. This isn’t a MasterChef situation, so there’s no pressure to break a sweat. It’s lighthearted, easy to follow, and yes, you get to eat everything at the end. 

Just a heads up though, these classes do fill up, so try to book ahead. You can choose between a morning or afternoon session depending on your schedule.

Neighborhoods & Culture

Browse Royal Street’s Art and Antiques

Royal Street is like the sophisticated older sibling of Bourbon Street. Instead of drunk tourists, you get amazing art galleries, antique shops, and street performers who are actually talented. Way more romantic for couples who appreciate culture.

The antique shops are perfect for couples who love hunting for unique treasures. Even if you’re not buying anything expensive, it’s fun to browse and imagine what your dream home might look like someday.

Go during the day when the galleries are open and you can really appreciate everything. The street gets a different vibe at night;  still nice, but more about the nightlife scene.

Soak Up Frenchmen Street’s Authentic Vibe

Ditch Bourbon Street and opt for Frenchmen Street instead where locals actually go for music and nightlife. The clubs here are smaller, the music’s better, and you can actually hear each other talk in between sets. You can bar-hop easily since everything’s just a few steps away, but honestly, it’s just as nice to settle into one spot and vibe out together.

It’s not just about the music either. During the day, you’ll find little boutiques, galleries, and chill spots to grab food or coffee, so it’s a cool area to wander through anytime. 

At night, the whole street lights up. Musicians are out on the sidewalks, people are dancing, artists are selling their work, and there’s just this good energy all around. Go late though. Things don’t really kick off until after 10, and if you’re in it for the long haul, maybe pace yourselves a little.

Get Charmed by the Garden District

To cap off this list, head over to the Garden District. It’s one of the prettiest spots in the city and has that quiet charm that makes it perfect for couples. The oak-lined streets, historic mansions, and all the overgrown greenery make it feel like you’re walking through a movie set.

Magazine Street cuts through the neighborhood and has a bunch of cute shops, cozy cafés, and galleries you can just casually pop into.  

If you and bae are into the history side of things, there’s a walking guided tour you can join into that tells you all about the homes, the people who lived in them, and even the nearby Lafayette Cemetery. 

The streetcar ride getting there adds to the whole experience too. Sitting side by side on one of those old green trolleys while the city passes by is such a sweet moment. Just a heads up though, a lot of these homes are still lived in, so it’s good to keep things respectful while you wander around.

Charming New Orleans

That’s just a taste of what it’s like to explore New Orleans with your person, but there’s still so much more to experience. If you’ve got time to venture outside the city, there are some incredible tours and day trips that can easily turn into unforgettable date ideas too. For couples traveling with kids, you might want to check out the family-friendly side of New Orleans since there’s plenty to do that keeps everyone happy. And of course, don’t miss out on all the iconic local eats while you’re here. If you’re wondering what dishes to try first, there’s a guide to the most famous New Orleans foods that’s got you covered.

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There’s just something about San Diego that makes it such a good spot for spending time with your favorite person. You don’t really have to try that hard here. The vibe’s easy, the scenery’s pretty, and no matter what kind of couple you are, it’s not hard to find something you’ll both enjoy. Whether you’re into chill beach days, little adventures, or just want an excuse to be out and about together, this city’s got you covered.

Planning a Trip to San Diego

If you’re visiting for the first time or coming back for a relaxing escape, there’s no shortage of amazing things to experience. If you find yourself still figuring out how to map out your days, you might wanna take a look at our complete 3-day San Diego itinerary to help you pace the trip. You’ll also want to check out the best places to stay in San Diego depending on what kind of trip you’re planning, whether you’re traveling as a couple, with kids, or just exploring on your own.

Classic Date Spots in San Diego

Have A Beach Day At La Jolla 

La Jolla is one of the most beautiful parts of San Diego, and it’s a favorite for couples who need a mix of beach time and cute little adventures. The cliffs here are seriously dramatic, the water’s ridiculously clear, and the whole place just gives off that romantic coastal town vibe. It’s a bit on the bougie side, but honestly, it’s worth it.

If you’re feeling up for something more than just laying on the sand, you can try one of the kayak tours that take you out to the sea caves. It’s a fun way to explore the coast together, and you might even paddle past leopard sharks or sea lions along the way. 

Speaking of sea lions, the ones lounging around Children’s Pool are real divas. They’re loud, goofy, and way too photogenic. You can also just walk the coastal trail and see all the insane views. 

The only catch is parking. It’s rough, especially on weekends. Either get there early or be ready to circle a few times before finding a spot. Worth it though.

Fancy Date Night Neighborhoods

When it comes to planning a great date night in San Diego, Little Italy and the Gaslamp Quarter are two of the best neighborhoods that I can think of. Both are packed with great food spots and have totally different vibes, so whether you’re in the mood for something relaxed or a little more dressed up, you’ve got these two solid options.

Little Italy is all about that cozy, chic energy. The tree-lined streets, the waterfront views, and the cute spots around every corner make it perfect for a slower-paced night out. You can take your time walking around here, maybe grab something sweet, and just enjoy the vibes. If you’re just visiting and want to sample a bunch of different spots without committing to a full sit-down dinner, joining a little italy food tour is actually a fun way to do it.

The Gaslamp Quarter, on the other hand, feels more like a night out. It’s got that dressed-up energy with historic buildings, rooftop bars, and glowing lights everywhere you turn. You can do dinner, walk the streets, people-watch, and if you’re feeling adventurous, there’s even a walking food tour that mixes in a little of the area’s wild history with stops for bites and drinks along the way.

Both neighborhoods are known for their food scenes and give you different kinds of date night energy. Whether you go casual in Little Italy or want something more upbeat in the Gaslamp, you’re set for a fun night out with your bae.

Spend The Day At San Diego Zoo

This place definitely lives up to the hype, especially if you’re both animal lovers or just wanna spend a full day doing something  really fun together. The great thing about it is it’s right inside Balboa Park, so if you’re already there checking it out, this is an easy add-on to your day. 

The zoo is huge, and just like the park, you’ll most likely end up spending a good chunk of your day here. They’ve got every animal you can think of. They are all very well taken care of and the habitats are actually really well done. 

One thing you’ll want to do when you’re already here is ride the Skyfari. It’s this aerial gondola that gives you a full view of the zoo and Balboa Park, and it’s a surprisingly cute moment to just sit back and enjoy the view together. There are also animal encounters, feedings, and some cool behind-the-scenes stuff if you’re into that..

If you’re already planning to do the zoo date, you may pre-purchase your tickets online. It would save you time at the entrance and they sometimes sell out on busy days. Just wear comfy shoes because there’s gonna be a ton of walking.

Spend A Chill Day Together At Balboa Park

Easily one of the best (and probably the most obvious) ways to spend a date with your boo in San Diego is by simply heading to Balboa Park. The park will always be a good bet, whether you’ve been here a bunch of times or it’s your first time visiting. 

The park is extremely massive so it’s way more than just a nice lawn to lay out your blanket. You could honestly spend an entire weekend exploring and still not run out of things to do. 

If you’re in the mood for something peaceful, the Japanese Friendship Garden is a great spot for slowing down and taking a breather. And when the roses are in bloom, the Inez Grant Parker Rose Garden is seriously pretty and smells amazing. Then there’s the Botanical Building and Lily Pond, which is probably one of the most iconic and photogenic areas in the whole park. You’ll definitely want to stop and take a few pictures.

Aside from all the greenery, Balboa Park is also home to a bunch of museums if you’re up for something indoors. And even if you skip those, don’t miss the Spanish Village Art Center. It’s a colorful little pocket of the park with working artist studios, painted tiles, and cozy, art vibes that just wanna make you want to hang around.

Romantic Things To Do In San Diego

Set Sail On A Sunset Cruise

Sunsets are always romantic, but watching one from a yacht out on the bay definitely takes it up a notch. If you’re looking for something easy going  but still kinda special, this is one of those date ideas that just hits right.

You won’t be on a loud party boat either. These sunset sailing cruises are usually smaller, more intimate, and way more relaxed. Just picture the two of you stretched out on deck while the boat glides past the San Diego skyline and under the Coronado Bridge. 

If you’re lucky, a few dolphins might even show up. But honestly, even if nothing wild happens, just being out there on the water while the sun dips down is already perfect.

It’s simple, calm, and it doesn’t need to try too hard to be memorable. Just a heads-up though, these sailings needed to be booked ahead so make sure you’ve really got your heart set on it.

Watch The Sunset At Sunset Cliffs

Sunset Cliffs is hands down (in my opinion 😂), the most romantic spot in San Diego for couples. Like, if you’re gonna do one sunset date here, this is it. This is the perfect place. 

The dramatic rock formations of the cliffs drop right into the ocean, and when the sun goes down, it’s just magical. You’ll literally see couples getting engaged (and even married!) here every weekend.

Bring a blanket and maybe some snacks or a bottle of wine, and just enjoy the show. The sunsets here are different every night, so even if you go multiple times, it never gets old. Just be careful near the edges, the cliffs can be unstable.

Best time to go is about 30 minutes before sunset. That way you can find a good spot and watch the whole sky change colors.

Outdoor Adventure Activities

Hike Together at Torrey Pines

If you and bae are in the mood for something outdoorsy and a little more active, hiking at Torrey Pines is a perfect choice. It’s got the perfect mix of nature and views without it being too intense, and it makes for a chill date.

There are a bunch of different trails to choose from, so you can keep it short and sweet or take your time exploring. Most of them are pretty manageable, even if you’re not a hardcore hiker, and they wind through those iconic Torrey pine trees before opening up to insane views of the Pacific Ocean. 

If you want to avoid the crowds and actually find a decent parking spot, it’s better to go early in the morning. That’s also when the weather’s cooler and the light’s perfect for photos. Bring water, wear your comfy shoes, and just take it at your own pace.

Take A Day Trip To Tijuana

If you and bae are into Mexican food and culture, a day trip to Tijuana might actually be one of the most underrated things you can do while in San Diego. It’s just across the border, and whether you’re going for the food, the atmosphere, or just to do something a little different, it’s worth checking out.

The food scene alone is enough reason to make the trip. From street tacos and birria to churros and regional dishes you won’t easily find back in San Diego, there’s a ton to try. 

You can DIY the trip by taking the trolley to the border and walking over, or you can join one of the guided day tours if you’d rather not think too hard about the logistics. There’s even a tour that focuses entirely on Mexican street food, which is a great choice if that’s your thing and you want someone to lead the way to all the best spots.

Just make sure you’ve got your passports sorted before you go, and try not to overdo it if you’re drinking, especially if you’re heading back the same day.

Chill Beach Dates

Laid-Back Day At Mission Beach

If you still want a beach day but aren’t really feeling the whole bougie La Jolla scene, Mission Beach is the perfect spot. It’s super chill and has that classic Southern California feel. Nothing fancy, just a couple of good vibes and plenty to do if you’re up for it.

Start off by renting bikes and cruising along the boardwalk. It stretches all the way to Pacific Beach, and the ride is easy with nonstop ocean views. When you’re ready to slow things down, grab a spot on the sand and just relax. 

And if you’re both feeling like it, Belmont Park is right next to the beach. You can hop on the roller coaster, play a few arcade games, or just walk around and split a snack. 

Walk The Beach At Coronado Island

Sometimes you just want a change of scenery without going too far, and Coronado Island makes that pretty easy. It feels calmer, quieter, and has that easy coastal charm that makes it great for couples who wanted something a little quieter.

Coronado Beach is wide, peaceful, and the sand has this soft, almost shimmery look to it. It’s not overly crowded most days, and the views are pretty stunning. You don’t have to do much to enjoy it. Even if you’re not staying at the famous Hotel del Coronado, it’s still worth wandering around the property for the views and the old-school charm.

If you’re new to the area or just want to learn a little more about what makes this place special, there’s a Coronado History and Highlights walking tour that gives you a fun rundown of the island’s background. And while you’re already in the area, you can top off the whole experience by heading over to the Coronado Cays for a gondola ride through the canals. It’s peaceful, scenic, and one of those things that feels effortlessly romantic. 

Unique & Quirky Date Ideas

Catch A Movie At South Bay Drive-In Theatre

This is probably hands down one of the cutest things you can do with your partner in San Diego. The South Bay Drive-In is such a throwback. It’s one of the last classic drive-in theaters left in California, and this is your perfect chance to get a feel of what it’s like to do a retro date night with your bae.

You just roll up, park your car in front of the big screen, and tune your radio to catch the audio. Most nights, they play double features, so you’re getting two movies back to back. It’s super casual and honestly way more fun than going to a regular theater. 

Before you go, make sure to check their website for the latest movie schedule and showtimes. They change it up regularly, and you’ll want to be sure you’re heading out on a night with something you actually want to watch. Also, try to arrive a little early for a good parking spot, and bring cash if you plan to hit the snack bar.

Team Up for an Escape Game Challenge

If you and your partner are the type who love solving puzzles or just want to do something totally different from the usual dinner and a movie routine, The Escape Game in San Diego is a fun pick. It’s located in the heart of the Gaslamp Quarter, so it’s super easy to pair with a meal or drinks afterward.

They’ve got a bunch of different themed rooms to choose from, like breaking out of prison, recovering a stolen painting, or escaping from a 1980s-style video game. Each one has its own storyline and set of challenges, and you’ll definitely need to work together to beat the clock. It’s high energy but not stressful, and actually pretty hilarious when you both get way too into it.

It’s one of those things that gets you talking, thinking, and laughing the whole time. Plus, if you’re competitive as a couple (in a fun way), this is a great way to put your teamwork to the test.

Spread Out A Blanket At The Best Picnic Spot

If you’re in the mood for something simple but still kinda special, Kate Sessions Park is where it’s at. This big open hillside has some of the best views in San Diego, and it’s definitely the perfect spot to lay out a blanket, bring some snacks, and chill.

The view alone makes it worth the trip. You can see all of Mission Bay, downtown, and even a bit of the ocean on a clear day. It’s never too crowded, which is nice if you’re trying to have a low-key moment without too much going on around you. And if you can hang out until sunset, even better. 

San Diego for Couples

San Diego is full of fun and memorable experiences for couples, but there’s a lot more to explore if you’re looking to branch out. If you’re planning to bring the kids along next time, you’ll want to check out some of the most interesting things to do in San Diego with kids. For those visiting for the first time, there are a few iconic spots around the city you really shouldn’t miss. And if you’re in the mood for a little adventure outside the city, there are plenty of awesome day trips from San Diego that are perfect for a quick escape.

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If you’re new to the Windy City and still figuring out what to do, this list’s gonna help you out big time. Chicago’s packed with cool spots and fun things to try, but it can get a little overwhelming if you don’t know where to start. Whether you’re just here for a few days or trying to see what all the hype’s about, this guide’s got a mix of everything to help you make the most out of your trip.

Planning a Trip to Chicago

If you’re in the middle of planning a couples’ getaway to Chicago, you’re in for something special. Once you’ve got your dates locked in, you might want to check out our full 3-day Chicago itinerary to help you pace your days in the city, especially if it’s your first visit. We’ve also rounded up some of the best classic things to do in Chicago that first-timers usually don’t want to miss. And if you haven’t settled on where to stay yet, our guide to Chicago hotels has picks for every style and budget.

Classic Chicago Experiences

Snap That Perfect Couple Shot At The Bean

If I’m gonna be real here, you haven’t really been to Chicago until you’ve taken that classic selfie at The Bean. This weird, funny sculpture is found in Millennium Park and it’s safe to say that it’s in everyone’s list, and honestly, I’m not even complaining cause it really deserves all the hype. 

The Bean might be the park’s main draw, but once you guys are there, don’t just snap a photo and bounce. The park itself is a whole experience. From the playful Crown Fountain to the wide open lawn that’s perfect for relaxing, there’s plenty of space to slow down and just enjoy each other’s company. 

If the weather’s good, you can grab coffee nearby, find a shady spot, and turn it into an easy date with your bae.

Cruise Along The Chicago River 

You haven’t really done Chicago right if you skip the architecture cruise. It’s one of the city’s super popular experiences, like the Bean, but this one gives you a front-row seat to the city’s amazing skyline while cruising down the river. Super relaxing, scenic, and surprisingly enjoyable, especially if you’re visiting with your boo.

This one is a history and sightseeing cruise so this is more on the informative side. If you wanted something that’s more on romantic skyline cruising, you can switch this up to a sunset cruise on the river and lake michigan. 

Both are extremely popular and fantastic to experience so just make sure to book your timed slots before your trip. 

Take A Romantic Evening Stroll Down The Riverwalk

Speaking of Chicago River, The Chicago Riverwalk is another good spot for couples. The views here are amazing no matter which way you’re heading.

What makes this place even better is how there’s tons of restaurants and cafes tucked along the path. You can easily grab a table by the water and have dinner with the skyline right in front of you, or just stop for drinks and people-watch. 

Once the sun starts to set and the lights come on, the whole place takes on a really cozy, romantic vibe you and your bae would enjoy. Definitely add this one on those spots you’ve gotta be during nighttime.

Try The Best Pizza in Chicago

Trying deep-dish pizza in Chicago is basically a rite of passage. It’s thick, cheesy, and ridiculously filling. Definitely something you’ll want to tackle together. 

But here’s the thing though: while deep dish gets all the fame, locals will tell you that tavern-style pizza is where it’s at. It’s thinner, crispier, cut into squares, and honestly way easier to eat without needing a nap after.

If you’re both big on food adventures, make it a mission to try both styles and see which one wins. Lou Malnati’s and Giordano’s are the classics for deep dish. On the other hand, spots like Vito & Nick’s or Pat’s are where locals go for that crunchy tavern-style bite.

You can even take it up a notch and join a pizza tour that lets you taste your way through some of the city’s best slices. It’s a fun and casual date idea that’ll leave you full and maybe a little competitive about whose favorite was better.

Walk Down The Magnificent Mile

If you and bae love shopping or just wanna wander around the city together, then you 100% have to go to Mag Mile. Michigan Avenue stretches from the river up to Oak Street, and there’s always something to see here. It doesn’t really matter  if you’re not really out to buy anything, it’s still fun to window shop and people-watch while you take in the city’s energy.

Be aware though that there’s gonna be a lot of people here so if you don’t really like dealing with all of that, try to go around early, right when the shops open, so the crowds are way lighter and it’s more peaceful. 

And if you’re already in there, definitely check out the massive Starbucks Reserve Roastery. And maybe also swing by the Harry Potter store nearby if you’re a big fan.

Dress Up For A Broadway Show In The Theater District

Catching a Broadway show in Chicago is another classic date move, and it totally delivers. The Theater District has a few stunning venues, but if you’re going to pick just one, make it the Chicago Theatre. 

If you’re into all those behind-the-scenes stuff, you guys can also check out the Chicago Theatre tour during the day. It gives you a peak at the history and lets you walk around the stage and dressing rooms. It’s another fun way to appreciate the space even more, especially if you’re catching a show later that evening. 

Make a full night of it by grabbing dinner nearby before curtain time. There are a bunch of restaurants in the area, so it’s easy to find a spot that fits your vibe. And if you’re looking to save a bit, keep an eye out for rush or lottery tickets. Sometimes you can score amazing seats without blowing your budget.

Embrace The Tourist Magic At Navy Pier

I’ll confirm it. Navy Pier is 100% a tourist trap. But honestly, if you’re a tourist, why skip the touristy stuff? 

You’re here to experience Chicago, right? So you might as well do it all, Ferris wheel and all. 

The Centennial Wheel is one of those cheesy-but-fun things you and bae can try. The views from the top are actually pretty amazing, especially if you go around sunset. You get the city skyline on one side and the lake on the other. 

Alternatively, you can just grab some snacks, and stroll along the water while listening to live music or random street performers.

But the real reason to stick around is the fireworks. If you’re visiting in the summer, they put on free shows every Wednesday and Saturday night. And this is where I actually think Navy Pier shines, so try to look for a good spot to see it and enjoy.  

Sky-High Views

Step Out Over The City Together At Skydeck Chicago

It’s not every day you get to stand on top of one of the tallest buildings in the country, so go check out Skydeck at Willis Tower already!

The highlight here is The Ledge, those clear glass boxes that stick out from the side of the building. Stepping onto them feels like you’re floating over the city, and it’s a little scary at first, but it’s also gonna be really fun to do together. Most couples end up laughing through it, especially while trying to snap that perfect photo with the streets way down below.

It’s even better if you go right before sunset. Catch the golden hour glow, and then watch the city lights come to life while you’re both up there. 

Important Tip: Definitely grab your tickets ahead online so you don’t waste time in line.

Experience The Thrills Of TILT At 360 Chicago 

If you cannot handle the crowds at Willis Tower then 360 Chicago is definitely the perfect alternative for you.

It’s up on the 94th floor of the former John Hancock building, and honestly, some people even like it more than Willis Tower. You get a sweeping view of Lake Michigan, the skyline, and all the city lights, just without the long wait.

The big thrill here is the TILT, a ride that leans you out over the side of the building. It kinda sounds intense (it actually is 😂), but I’m pretty sure doing it with your bae would make it feel better. You’ll probably both be holding onto the rails and laughing the whole time.

After the adrenaline wears off, you can chill out at CloudBar, which is right at the top. It’s not the cheapest spot for a cocktail, but when you’re 94 floors up with the city glowing below, it’s hard to complain.

Since it’s pretty close to Navy Pier, you can easily pair this with dinner or a lakeside stroll without running all over town.

Outdoor & Nature

Wander Through Sea Life At Shedd Aquarium

You can never really go wrong with an aquarium date, and Shedd Aquarium definitely makes a strong case for it. It’s set right on Museum Campus by the lake, which already gives it bonus points for the views and walkability.

Inside, there’s a ton to explore. The Wild Reef is full of vibrant corals and sleek sharks swimming just inches away, and there’s something pretty mesmerizing about watching jellyfish drift around. The dolphin presentations are fun to catch too, and they give you a quick breather to sit and just enjoy the show. 

But honestly, half the fun is simply strolling through the exhibits together, pointing out weird-looking fish, and getting excited when you spot something cool. The only downside here is it’s too popular so it’s always packed there so be sure to prepurchase your tickets online on their website to skip the long wait and queues outside. 

Experience Urban Charm In Lincoln Park

Lincoln Park is definitely one of those spots you shouldn’t skip. It’s a great go-to if you’re looking for something chill away from the busy downton.You can spend hours here just walking around together, especially if you’re both into those unplanned, go-with-the-flow kinds of dates.

Definitely check out Lincoln Park Zoo. It’s free btw so no need to think much about the expenses, which is actually pretty rare for a zoo this good, and it has a lot of open spaces so it doesn’t feel cramped at all. Right next to it is the Lincoln Park Conservatory, full of tropical plants and flowers that’s honestly like a hidden gem tucked in the park.

After checking those out, follow the path all the way to North Avenue Beach. It’s the perfect place to relax, kick your shoes off, and wind down after  spending a long afternoon of walking. 

Unique Experiences & Activities

Hop On A Chicago Beer Tour

If you and your partner are into craft beer, a chicago brewery tour is a seriously fun way to spend an afternoon together. You’ll ride a barrel bus (very hippy btw, if you ask me lol)  with an expert guide and visit three different local breweries across the city. 

It’s easy, and you don’t have to worry about driving or figuring out directions. The whole thing is already mapped out, so all you need to do is show up ready to drink some really good beer. It’s definitely for the extroverts, since you might end up chatting with other couples or groups throughout the whole experience.

Tours run on selected days only, so it’s a good idea to book your tour slot in advance. Just make sure to eat a good meal beforehand and wear comfy shoes since you’ll be hopping on and off the bus a few times and sampling beers all afternoon.

Create Street Art Together At A Graffiti Workshop

If you’re looking for something a little different to do with your partner, a graffiti and street art workshop might be the perfect match for the two of you. This one’s for couples who wanted a totally unique experience that’s both fun and actually memorable. You’ll be able to team up with a local artist, learn some spray-painting techniques, and create your own custom piece of art together.

Everything’s provided, from the spray paint and gloves to the protective gear. At the end, you’ll actually have a cool canvas to take home as a souvenir from your trip. 

Take A Couple Of Lessons In Magnificent Mile

If you’ve decided to stroll around the Magnificent Mile and want to do something a little different with your partner, there are a couple of niche classes nearby that are worth checking out. These are what I think are super fun date ideas that let you get creative together while trying something totally new.

Candle making classes are a hit among couples in the city. You’ll learn how to make your own candles from scratch, picking out scents and colors to suit your vibe. Most sessions last around two hours, and by the end, you’ll each have a few custom candles to bring home. It’s a cozy activity that’s perfect if the weather outside isn’t great.

If you’re more into fragrances, the perfume making class is another cool option. It’s surprisingly fun figuring out what smells you both gravitate toward. The instructors break it all down in a simple, engaging way so you actually learn something while doing it. And the best part? You both get to leave with custom perfumes that’ll always remind you of your trip together.

Fall in Love with Chicago

If you’re planning to squeeze in more stuff while you’re in the city, there’s a few other guides you might wanna check out. If you’re coming with kids next time, we’ve got a list of fun things to do in Chicago that’s perfect for the whole fam. For food lovers, there’s a bunch of awesome food tours that’ll take you to some underrated local spots. And if you’re the type who likes seeing all the famous sights, we’ve got you covered with a full guide to Chicago’s top landmarks too.

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