Best Date Ideas in Boston: 65 Romantic Things to Do, Restaurants, & Places to Stay

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Looking for fun, unique, and romantic date ideas in Boston? We have you covered! Romantic views, cozy spaces, swoon-worthy suggestions, it’s all here in our helpful guide. 

And, don’t worry, these won’t all break the bank. There’s a whole section dedicated to cheap or free Boston date ideas if you’re looking for those options.

We also have plenty of splash-out romantic ideas if you’re ready for a special celebration.

Boston offers incredible history, beautiful architecture, and endless charm.

Whether you’re looking for a fun first date or a big romantic gesture, there are plenty of wonderful things to do and spaces to explore in Boston.

You might also want to check out our guide on things to do in Boston at night for a wider variety of options for families’ or friends’ nights out, too.

Looking specifically for NYE ideas? This guide will help!

Romantic Things to Do in Boston

There are countless date options for Boston, but some are just a little more on the romantic side. 

These probably aren’t your go-to first date options, so if that’s what you’re looking for then skip to the next section for more fun and interactive date ideas.

But if you’re looking to impress with a special evening out, then this section is for you!

Boston skyline and harbor

Sunset Cruise

Is there anything more romantic than setting sail when the sun goes down with a drink in hand?

This 90-minute sunset cruise lets you see the city skyline illuminated with glowing orange hues.

Departure is from 60 Rowes Wharf.

Welcome to Rowes Wharf sign on the water in Boston Massachusetts

See The Nutcracker

If you’re looking for Boston date ideas in December, you should snag tickets to the iconic Boston Ballet’s performance of The Nutcracker.

This annual event is one of the best things to do in Boston around the holidays and will surely impress any date — whether it’s your third date or your 50th wedding anniversary.

Before the show, stop at one of the city’s Christmas markets to peruse together and enjoy the festive atmosphere.

Go to the Theater

With so many historic and impressive theaters in the Theater District, seeing a show would be a perfect date option.

See what’s on at the fabulous Wang Theater, Shubert Theater, or Emerson Colonial Theater — all beautiful buildings and true vestiges of the past.

Looking for something more off-beat than off-Broadway?

Head to Harvard’s American Repertory Theater (the A.R.T.) for modern and experimental acts.

It’s sure to be a conversation starter!

I still remember going to the Charles Playhouse to see Blue Man Group…and it’s still there decades later (wait, how is that possible?!).

It’s yet another great date idea in Boston for its wild and interactive performance that’s sure to spark plenty of conversation afterward.

Book a Couples Spa in Boston

Definitely not a first date idea…don’t be creepy.

But this one is sure to win brownie points for you long-term couples looking for something special.

Book a couples spa in Boston for a truly luxurious experience that you can share.

It’s one thing to buy a massage for your significant other — it’s something else altogether if you opt to spend time together away from all the usual distractions and stresses of life.

Some excellent options for a couple’s spa day in Boston include:

  • Bella Sante
  • Sway Spa
  • G2O Spa and Salon
  • The Spa at Four Seasons Hotel Boston
  • The Spa at Mandarin Oriental, Boston
  • Exhale Spa
  • Rowes Wharf Health Club & Spa
  • Viyada Thai Spa
  • ​La Moon Thai Spa

Take a Boston Harbor Cruise

Perhaps a little cliche, but nonetheless a romantic date idea in Boston!

Take a Boston Harbor sunset cruise with a glass of bubbly to tick all the mushy rom-com boxes.

It truly is magical seeing the city from the water, so enjoy the views of the shimmering skyline and relax into a beautiful evening together.

Longfellow Bridge with Boston skyline

Get cozy with drinks on a rooftop

Skyline views are always a perfect Boston date idea.

For views with a little extra special vibe, head to The Legal Harborside, where a retractable glass ceiling and a copper fireplace exude romance.

Try to time it for sunset if you’re really looking to impress.

In the Seaport, head to The Lookout Rooftop at The Envoy for heated igloos in the winter with lovely harbor views.

View of The Barking Crab in front of The Envoy from Seaport Blvd in Boston Massachusetts

Or go to Deck 12 at YOTEL (also in the Seaport) for cocktails year-round.

For a more casual rooftop experience, head to the Sam Adams Taproom rooftop in Downtown. Limited views, but plenty of brews!

Fun Date Ideas in Boston

Date night ideas in Boston don’t have to be over-the-top or wildly expensive.

In fact, I’d say these fun ideas could be perfect from first dates to married couples.

Enjoy an activity together while learning, trying something new, or just getting out and about in the city to change things up.

If you’re visiting Boston, these are also perfect for tourists!

We have lots more fun suggestions that would be perfect for dates in our guide on things to do in Boston in winter.

Sam Adams Brewery Tour

Our iconic previously-local label (Sam isn’t actually brewed in Boston anymore…) offers tours of the brewing experience.

Perfect for beer lovers who want to learn more about the process and history of Sam Adams beer-making, a tour of Sam Adams Brewery (30 Germania Street) is a great date idea.

Even better: book a VIP beer tour to really impress your date!

After your tour, walk around the corner to Ula Cafe where you’ll find an utterly delightful space for a coffee and a chat.

Don’t forget to leave a gift on their Pay-it-Forward wall before you leave!

Catch a Sox Game

Here’s the thing: we’re just super serious about our sports in New England.

If you’re looking for summer date ideas in Boston, going to a Red Sox game has to be up there near the top of the list. 

Baseball is classic Americana summertime fun and Fenway Park is the iconic baseball stadium in the United States.

If they’re in town and you’re willing to splash out, date night at Fenway is pure perfection.

Red Sox playing baseball atFenway Park

Take a Fenway Park Tour

Alternatively, it doesn’t matter if it’s baseball season or not; touring Fenway Park is something so few locals do that it’s an awesome date idea!

With a 1-hour guided tour, you’re not stuck talking strictly baseball for too long, but it’s an interactive experience that will surely keep the conversation going.

And you won’t be there for an unknown number of hours like being at an actual game, which is perfect if you’re in the early dating days and don’t want to commit too soon.

Fenway Park sign against blue sky

Rent a Double Kayak

Paddling along the Charles River together in a double kayak sounds like summertime bliss.

Rental a kayak from Paddle Boston — perfect for a sunset date idea in Boston.

Harvard University building over John W. Weeks Bridge Bosto
Fenway Park gate D sign. Boston. Massachusetts.

Taza Chocolate Factory Tour

Flowers and chocolates are the cliche gift options, so why not step it up a notch and go for a tour of the Taza Chocolate Factory instead?

Make Your Own Chocolates!

Head to LA Burdick Chocolates to make your own chocolates together.

This famous spot in Boston is always delicious, but it’s a little extra special when you can create your own homemade samples.

LA Burdick Chocolate Boston Massachusetts

Play Games at The Lawn on D

In the summer, you can swing to your heart’s content together at The Lawn on D.

This fun public space features tons of swings, loads of lawn games, and plenty of food and drinks to keep you happy and having fun.

It’s located right next to the Convention Center in the Seaport District.

Take a Haunted Boston Tour

Need a great excuse to get close?

Try a haunted tour to add a little fright into your night — which is always a good reason to stay close together!

Check out this walking tour or this trolley tour, depending on how you prefer to get around.

Martha’s Vineyard Day Trip

This date idea is a little pricier, so keep it up your sleeve for when you want to impress!

Book a seat on this award-winning, original Martha’s Vineyard day tour which includes all transport options, including the ferry.

The tour drops you off at Oak Bluffs Town Beach, where you have six hours to relax on the beach, go shopping, and dine at the upscale restaurants.

Narrated Island Tour upgrade available with stops in Edgartown and Gay Head Cliffs.

Goldenrod flowers along the path to lighthouse beach in Edgartown, Martha's Vineyard, Massachusetts

Cheap or Free Date Night Ideas in Boston

Date night doesn’t have to break the bank! 

In fact, there are tons of free or cheap date ideas in Boston…and you can always get a little creative.

Cheap Boston Symphony Orchestra Tickets

Want to impress your date with tickets to the symphony, without paying for expensive seats?

Go for the afternoon rehearsal instead.

The Boston Symphony Orchestra rehearses mid-day before a performance and you can score really cheap tickets to watch.

The best part is that they break frequently for the conductor to offer feedback, which is prime time for a quick conversation and sharing your thoughts about the performance thus far.

The Boston Symphony Orchestra rehearses on stage

Free Boston Bruins Experience

You don’t have to splash out on expensive Garden tickets for a B’s game.

Instead, head to Warrior Ice Arena at Boston Landing to watch the Bruins practice for free.

This is a fun date idea because you can stay for as long as you want, chat throughout the practice, and still have entertainment if there are any lulls in the conversation.

Romantic Spots in Boston for a Picnic

Okay, so you’ll still need to buy the food and drinks, but picnics are such romantic date ideas that you won’t regret the minimal costs!

Be sure to bring a big enough blanket, pack picnic-friendly snacks, and don’t forget the bottle opener for beer or wine.

Arnold Arboretum is a perfect picnic spot for a romantic date in Boston.

Other great spots include, of course, Boston Public Garden or the Common.

For more parks to explore in Boston, read this guide.

Boston Common

Did you know Boston Common was founded in 1634 and is officially the oldest public park in the United States?

Drop that into your casual first-date conversation!

Or head to Castle Island to be right on the water with planes overhead; it’s a great conversation starter to see where your date would want to travel.

View of Fort Independence on Castle Island in Boston from across the water

Ice Skating on Frog Pond

Not picnic season?

If you’re looking for the most romantic things to do in Boston in winter, you have to head to Boston Common’s Frog Pond for ice skating.

There’s a romantic air about skating together. 

Whether you’re both terrible and need to hang onto each other for help or one of you can teach and guide the other, this is a special sort of bonding activity that’s also sure to elicit some laughs!

The Common is also one of the best places for Christmas lights in Massachusetts.

Christmas Tree with lights in the evening at Boston Common, MA

Explore Museums Together

The Museum of Fine Arts (MFA) and the Institute of Contemporary Art (ICA) are always good options — but they can both get pricey.

Take advantage of the cheap Wednesday afternoons at the MFA and the free Thursday nights at the ICA.

The Isabella Stewart Gardner Museum is always a top choice, so enjoy the beautiful courtyard and cafe together on the first Thursday of every month, which is free.

John F Kennedy Library uses high-definition, large-screen projections, interactive displays, re-mastered films and original artifacts to show President Kennedy’s 1000 days in office.

Modern John F Kennedy Library building in Boston

Star Gazing at the Observatory

The Boston University Coit Observatory (725 Commonwealth Avenue) holds Public Open Nights most Wednesdays all year-long.

And it’s free to join!

You do need tickets, however, so be sure to book in advance.

Also, note that the Observatory is not fully accessible as you must climb stairs to reach it.

Since this date idea is weather-permitting, you’ll definitely want a backup plan in place.

Book your places and then check in with the BU Observatory on the day to see if the skies will be clear enough or not.

Window Shop and Chat

Head to Bow Market in Union Square in Somerville for an eclectic blend of pop-up shops and permanent storefronts that are perfect for window shopping and strolling along together.

Or head to Newbury Street to explore a wide variety of stores.

Harry Potter Shop and brownstones on Newbury Street in Boston Massachusetts

Strolling around Fanueil Hall and Quincy Market is always fun.

Taste your way through the market together, talking about food likes and dislikes along the way.

In bad weather, the Pru is ideal for shutting away the outside world for a while as you window shop a wide variety of stores.

Christmas decor in the Prudential Center in Boston Massachusetts

Eataly, Formaggio, and Boston Public Market all make for awesome date ideas in Boston — food brings people together! (Or you’ll find out quickly if your tastes are really just not compatible.)

Historic buildings of Boston Faneuil Hall.

Go For a Stroll

Strolling hand-in-hand is ever so romantic.

Romantic dates aren’t always all about the grand gesture…sometimes it’s these little moments that seem so everyday that truly capture the heart.

The Greenway is a perfect spot to walk, talk, people-watch, possibly grab a bite from a food truck, and just generally experience this fantastic part of the city together.

Or head to the Charles River Esplanade for a fabulous view of the Boston skyline — even better if you time it for sunset.

Walking around Boston Public Garden just oozes romance — definitely a great date idea in Boston.

Boston Public Garden pond bridge Massachusetts

The Boston Harborwalk is perfect for a sunny summer day stroll together.

It’s 43 miles long, so don’t plan to cover the whole stretch or this date will be epic!

Add a little learning and extra insight into your stroll by following any of these heritage trails through Boston to see historic buildings and learn about the people who changed history:

  • The Freedom Trail
  • The Black Heritage Trail
  • The Women’s Heritage Trail

Check out our guide to all the best free things to do in Boston for even more fun ideas!

Red bricked Old State House with gold eagle in Boston
Old South Church building with blue sky in Boston

Day Trip to a Waterfall

Do a day trip to a 40-foot waterfall with a 16-foot plunge!

The Cascade in Melrose is less than a 30-minute drive from Boston and offers lots of green space if you want to go for a hike with your other half.

Find out more in this guide to Massachusetts waterfalls.

Most Romantic Boston Restaurants

There is no short supply of romantic restaurants in Boston, the decision of where to go is the only issue.

You could seek out a cozy romantic spot in the North End or splash out on James Beard Award-winning meals.

The setting is as important as the meal itself when it comes to romantic date night spots in Boston, so choose wisely based on how you want this date to go…

Our suggestions below for different areas of the city include everything from the finest dining to quirky conversation-starter settings, so you’ll need to select the best space for setting your own scene.

Back Bay:

  • Eataly (800 Boylston Street)
  • Deuxave (371 Commonwealth Avenue)
  • Mistral (223 Columbus Avenue)

Beacon Hill:

  • Grotto (37 Bowdoin Street)
  • Mooo…. (15 Beacon Street)
  • No.9 Park (9 Park Street)


  • Giulia (1682 Massachusetts Avenue)
  • Oleana (134 Hampshire Street)
  • The Longfellow Bar (40 Brattle Street)


  • Bogie’s Place (25 Temple Place — enter through jm curley)
  • Haley.Henry (45 Province Street)
  • Mariel (10 Post Office Square)
  • Yvonne’s (2 Winter Place)


  • Nathálie (186 Brookline Avenue)

Jamaica Plain:

  • Ten Tables (597 Centre Street)
  • The Haven (JPNDC Brewery Complex, 284 Amory St)
  • Tres Gatos (470 Centre Street)

North End:

  • Euno (119 Salem Street)
  • Mamma Maria (3 N Square)
  • Neptune Oyster (63 Salem Street #1)


  • Lolita (253 Summer Street)
  • Sportello (348 Congress Street)


  • Casa B (253 Washington Street)
  • Celeste (21 Bow Street)
  • Juliet (21 Union Square)

South Boston (Southie):

  • Fox & the Knife (28 W Broadway)

South End (not to be confused with South Boston):

  • B&G Oysters (550 Tremont Street)
  • Barcelona Wine Bar (525 Tremont Street)
  • The Beehive Restaurant (541 Tremont Street)
  • Darryl’s Corner Bar & Kitchen, aka DCBK (604 Columbus Avenue)
  • MIDA (782 Tremont Street)
  • Myers + Chang (348 Congress Street) — check out their Great Date Night Monday-Wednesday evenings
Tables at The Haven Scottish restaurant in Jamaica Plain Boston Massachusetts

Romantic Hotels in Boston + Perfect Getaway Stays

Making a whole weekend of it?

There are plenty of romantic getaways in Boston that you can book, featuring anything from in-room jacuzzi tubs to beautiful views, top-class service, on-site spas, and more.

We also have recommendations that can make your weekend away convenient for all the other activities and restaurants we recommended above.

For an even more comprehensive list, check out our guide to where to stay in Boston.

Boston Massachusetts skyline at night

The Liberty

The Liberty (215 Charles Street) is a unique Boston hotel — it actually used to be a jail!

While that might not sound romantic, the contemporary decor and luxurious rooms make it an extra special spot in the heart of Boston.

The multiple on-site bars and restaurants mean you don’t have to venture far for champagne, wine, or delectable meals together.

Fairmont Copley Plaza

The Fairmont Copley Plaza (138 Saint James Avenue) is a five-star hotel in the Back Bay neighborhood.

Built in 1912, this classic, elegant hotel sets the scene for a romantic getaway.

Enjoy the opulence and splash out for a special weekend together like you’re in The Great Gatsby.

Entrance to the Fairmont Copley Plaza in Boston Massachusetts

The Godfrey

The Godfrey (505 Washington Street) was built in 1908 and boasts a dramatic Gothic Revival facade.

Located just across from Boston Common, this location is perfect if you want to explore as much of the city as you can during the weekend.

Enjoy unique cuisine in their on-site Ruka Restobar, a Japanese-Peruvian fusion of flavors, or head out for easy access to every romantic restaurant in the city from this Downtown location.

The Lenox

The Lenox (61 Exeter Street) is a boutique hotel in Back Bay with beautiful rooms featuring luxury finishes.

The Lenox partners with G20 Spa + Salon, just steps away from the hotel, which is one of our recommended spas for couples in Boston.

If you like supporting local businesses when you travel but want a touch more luxury and pampering, The Lenox partners with a variety of New England providers to offer a local experience you can feel good about.

Boston Harbor Hotel

The Boston Harbor Hotel (70 Rowes Wharf) is a five-star luxury hotel overlooking historic Boston Harbor.

For a special getaway, book a premier room to enjoy a Harbor view without having to lift your head off that comfy pillow.

Boston Harbor Hotel entrance in Massachusetts at night

The Inn at Boston Yacht Haven

The Inn at Boston Yacht Haven (87 Commercial Wharf) offers a dreamy location right on the marina, so you can plan your future mega-rich life together by picking your favorite yacht.

With only 10 rooms, you’ll want to book early to choose a harbor-view room for extra romance.

Battery Wharf Hotel

Battery Wharf Hotel (3 Battery Wharf) offers an on-site spa, so it’s a lovely spot for a romantic stay.

Located in the North End, you can also enjoy views over iconic Boston Harbor.

Ready to splash out?

Book The Presidential Suite for your own private balcony.

If you’re flying into Boston Logan, opt for the private water taxi to arrive in style.

The Marlowe

The Marlowe (25 Edwin H. Land Boulevard, Cambridge) is a Kimpton Hotel, so you can expect high-end experiences with unique character.

Situated in Cambridge, The Marlowe is still close to everything (a 10-minute walk to Downtown) while offering a unique take on the city.

Explore Harvard, hop into one of those 2-person kayaks we suggested previously, and don’t skip the romantic restaurants in Cambridge we recommended.

Mandarin Oriental Boston

The Mandarin Oriental (776 Boylston Street) is one of the city’s premier hotels, perfect for a romantic Boston getaway!

We already recommended their on-site spa for a couple’s massage, but you should also check out their on-site French restaurant, Bar Boulud, for a romantic dining experience.

The Ritz Carlton at Boston Common

The Ritz-Carlton (10 Avery Street) is located in the Theater District, so it’s perfect in combination with seeing a performance together.

Enjoy classic luxury while being in the heart of Downtown Boston together.

Final Words

Did this help you craft some awesome date ideas in Boston? I hope so! If I missed it, share your favorite Boston date spot in the comments.

Shout-out to my sister who helped me brainstorm this fun topic with some of her favorite local date night spots!

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