Valentine's Day for 2024 falls on Wednesday, February 14 - and Boston has lots of special romantic events and things to do going on throughout the weekend leading up to the big day.

Whether you want to declare your love, wow your secret crush, or just have some memorable fun on Valentine's Day, you'll find plenty of Cupid-worthy Boston events and things to do taking place from Friday through Sunday (and of course on Monday too).

Here are Boston Discovery Guide's recommendations for ways to celebrate ranging from romantic to silly, elaborate to simple - and everything in between!

Best of all, some are not just for Valentine's Day - they're perfect any time you're looking for romantic things to do in Boston.

Find sweet deals on Boston hotels offering special Valentine's Day packages

Boston Harbor Special Valentine's Day Cruises

Boston Harbor Sightseeing and Special Event Cruises

Romantic Boston Harbor Cruises for Valentine's Day:

  • Romantic Valentine's Day Jazz & Champagne Tasting Cruise - Toast your valentine on this romantic evening cruise as you sample 3 champagnes and nibble on chocolate-covered strawberries while a live jazz band plays in the background.  Capacity is limited, and these special cruises always sell out early.  February 9, 10, 14

Take your Valentine to a Concert or Show, Dinner, & Weekend in Boston

Valentine's Day Concerts & Shows in Boston

More concerts during the rest of February

Valentine's Day Theater Performances & Shows in Boston

Theater shows and performances on Valentine's Day in Boston, MA

Enter DISCOVERY10 to save 10% on TicketLiquidator & TicketNetwork tickets.  Good for purchases made through 12/31/24.

Find all Boston theater shows in February

Spend the weekend in a Boston Theatre District hotel

Make dinner reservations at a Boston Theatre District restaurant

Stay in Boston with these Special Valentine's Day Hotel Packages

Valentine specials at hotels in Boston MA

To make your Valentine's Day celebration extra-special by staying over in the city, check out the super savings packages offered by many of Boston's top hotels.  

Opt for the "Lovers Rock" Valentine's Day package at Verb Hotel, "Be Mine in Beantown" at The Boxer, the "Romance Package" special at the Revere Boston, or the "Boston is for Lovers" package at the Midtown Boston Hotel - plus many more!

Find your dream Valentine Boston hotel package

Indulge in Dim Sum & Ice Skate on Frog Pond

Chinese New Year Parade on Valentine's Day in Boston

Celebrate Valentine's Day with a non-traditional experience by heading to your favorite Chinatown restaurant for dim sum.

Check out our dim sum suggestions

After you've satisfied your cravings for soup dumplings and fried chicken on waffles, head over to Frog Pond and take a spin around the ice.  Mid-February weather is usually perfect for skating.  

More about ice skating on Frog Pond and other places in Boston

Go to a Special Concert

What is more romantic for Valentine's Day than a musical serenade?  A special concert played on some of the world's finest and oldest string instruments will be an evening to remember.

On February 15, Boston orchestra A Far Cry performs its signature work, Tchaikovsky's beautiful Serenade for Strings, on 18 of the world's finest violins, violas, cellos, and double basses by crafted over 300 years ago by Stradivari, Guarneri, Amati, and other masters at Jordan Hall.  Find details and ticket information on A Far Cry's website.

A Far Cry is the Chamber Orchestra in Residence at the Isabella Stewart Gardner Museum - another romantic place to visit on Valentine's Day.

Take a Romantic Dinner Cruise

Boston Harbor Romantic Dinner Cruise on Valentine's Day in Boston, MA

For a special romantic Valentine's Day dinner in a unique setting, go on one of the Boston Harbor dinner cruises offered by the Odyssey

You'll love the gourmet dinner served in the elegant dining room.  Sip Champagne, enjoy the live music, try out the dance floor, or just enjoy romantic moments as you gaze at spectacular nighttime views of the city skyline...and each other

Make your reservations for a special Boston Odyssey Dinner Cruise

Go on a Fun Boston Food Tour!

Make Your Valentine a (Glass) Heart

Learn how to make glass hearts of all types - blown glass, shaped glass, fused glass - and give it to your love.  Diablo Glass Studio (123 Terrace Street, Boston) offers special small-group classes on February 9 and 14 - check them out.

Go to the Movies

Boston has a fantantic selection of movie theaters offering everything from first-run blockbusters to classics, indie films to IMAX science specials.

More about best Boston movie theaters of all types

Explore Fort Point Art Galleries

Fort Point art gallery
Head over to the artist-filled Fort Point neighborhood and explore the art galleries such as Society of Arts and Crafts (100 Pier 4 Boulevard at the corner of Seaport Ave), FPAC Gallery (300 Summer Street), Gallery at Atlantic Wharf (290 Congress Street), and Gallery at 249A (300 Summer Street).

Need a unique card or gift for Valentine's Day?  Stop by the Made in Fort Point store (315 A Street) where you'll find an assortment of art and other items such as jewelry, ceramics, books, and even furniture made by the neighborhood's artists and artisans. 

End your Fort Point visit with dinner at one of the nearby top chef-owned restaurants.


Where to propose marriage in Boston

Ready to pop the big question? 

Here are 2 romantic venues to consider:

  • Parker's - Classically sumptuous restaurant at the Omni Parker House Hotel where Boston Cream Pie was invented and JFK proposed to Jackie.  Stay at the hotel
  • Bistro du Midi - Plush seating, romantic lighting, and an excellent selection of French wines and classic Mediterranean bistro cuisine will make you feel like you are in Paris, the City of Love.  More about Bistro du Midi and other French restaurants in Boston 

Photo courtesy of Johnathan Nightingale

When Love Fails, You Need Break-Up! The Musical

Laugh away your sorrows at Break Up! The Musical at Laugh Boston on February 14 at the Westin Waterfront Hotel.  Comedians Misch Whitaker and Pat Parhiala will choose an audience member's tragic breakup story - it could be you! - and turn your heartbreak into laughter in an improvised-on-the-spot musical. 

Champagne Dinner Dance & Valentine's Brunch

Champagne dinner dance and Valentine's brunch in Boston

The Boston Wine Festival, underway from January through early April at the Boston Harbor Hotel, offers a special Valentine's Dinner Dance on February 15 featuring live music, dancing, and incredible food matches with memorable Champagnes from Moet & Chandon.

Alternately, opt for the lavish Champagne Brunch on Sunday, February 16.

Find out more about the Wine Festival & the best wine bars in Boston

Looking for Love?  Where to Meet Someone Special in Boston

Where to meet someone special in Boston MA

Here at Boston Discovery Guide, we regularly get emails from newcomers to the city who ask, "Where can you meet someone in Boston, outside of school/work/bars/dating apps?"

As travel website publishers, this isn't exactly our area of expertise . . . but Valentine's Day provides the perfect excuse for offering a few suggestions.  Of course, you should act on them well before February 14th if you're trying to line up a date for Valentine's Day.  But no pressure.

We can't guarantee you'll find love - but pick activities you enjoy and you're sure to have fun, become more familiar with Boston, and make some new friends.

BDG's Suggestions for Where to Meet People in Boston

  • MFA First Fridays - Art, wine, tapas, music - February 7 and first Friday of every month, 6:00-9:30pm, ticket is free with museum admission ($25), 21+; cash bar and food for purchase - but best to get ticket in advance as they do sell out   More info:
  • Trivia Night - Lots of Boston bars have these low-pressure game nights, usually on a Monday or Tuesday.  Check out a few in your neighborhood, and find your favorite. 
  • Meetups - Have an interest in something ... anything? lists groups for just about every interest you can imagine - for example:  20s Brunch Club, Davis Square Runners, Divorced and Dating, Boston Single Wine Tasters, Classic/Indie Movie Group, Beantown Gamers, Hey Siri: 'How Do I Make New Friends after College?' - and many, many more! is also a good way to find professional groups (especially if you work in tech) and volunteer organizations.  More info:
  • ICA Boston First Fridays - Art, DJs, live performances, gallery talks, complimentary drinks - February 7 and first Friday of most months, 5-10pm, $15 ticket includes museum admission, 21+; ICA's Water Cafe offers small plates and full bar.  More info:
  • Glass Fridays - Spend the last Friday evening (6:30-9:30pm) of each month in Diablo Glass School's flameworking studio learning how to make glass paperweights, beads, or even shot glasses, followed a glassblowing demo, wine, and socializing.   More info: 
  • Wine Tasting Events - Several wine stores in Boston host these periodically, and they're usually free.  If you're into wine, you can check out whose preferences match yours.  You'll find some events listed here.
  • Social Boston Sports - Bowling, dodgeball, basketball, skiing - there's something for everyone, plus fun special events.  Costs varies by sport/event but are reasonable.   More info:
  • Boston Ski & Sports Club - With 45,000+ participants each year, this is the largest sports club in the Boston area, organizing teams for everything from lacrosse to tennis to frisbee to indoor baseball, planning ski trips and other outings, and hosting social events.   More info:
  • Boston Center for Adult Education - Classes in cooking, dance, computers, languages, art, and much, much more give you the chance to learn something new.  Many are just one session in length - perfect for fitting into tight schedules.   More info from BCAE
  • Gyms - Some Boston gyms are known as being more "social" than others - so if you want to get exercise, get in shape, take a class - and perhaps meet someone - visit several gyms to find the vibe that works for you. 

More Valentine's Day Weekend Events in Boston 

  • Casablanca and The Princess Bride - Find out if you and your love share the same passion for romantic classics - catch both of these films at the Brattle Theatre in Cambridge on February 13, 14, and 15 - More
  • Valentine's Day Concerts at Berklee - Choose from 5 different concerts and performances featuring soul, jazz, blues, guitar, singers, and more.  Admission ranges from free to $15.  See the Berklee website for details: click on Events, and search for February 14.
  • Swing Dancing at Faneuil Marketplace - Want to do something different and fun?  Learn the basics of swing dancing from instructors at Boston Swing Central and enjoy live swing music by The Easy Winners Sextet from 1pm-3pm on February 15 at Faneuil Marketplace - no partner or previous experience necessary!  Or join the event's "Longest Kiss" competition at 1pm.  Find out more about Swing & Lindy dancing
  • Valentines Day Party Singles Meetup - Want to maybe meet your valentine?  Or at least have lots of fun?  Sign up for a Boston-area Valentine's Day Party - or one of the other many meetups going on in and around Boston every day - great way to meet others and have fun!  More:

More To See & Do in Boston on Valentine's Day

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