Romantic Boston: December Suggestions

Discover Boston's Most Romantic Places, Events, And Things to Do during the Holiday Season

Find out about best Boston events during September, such as patio dining while the weather is still warm
Lighted Christmas tree on Boston Common, with Massachusetts State House in the background

Question about romantic things to do in BostonHello!  My name is Shelly. I moved to Massachusetts about a year ago but I don't know much about the state. My boyfriend of three years lives in Florida and he is coming to visit me for Christmas. I digress. Do you have any suggestions on any romantic places we can go and things we can do for the holiday season?  Please?

Kind regards,


Boston Discovery Guide's answer to where to find romantic places and things to do in Boston in DecemberDear Shelly,

Boston feels especially romantic during December because all the festive holiday lights, Christmas decorations, and fun activities. 

Visiting romantic places with your boyfriend will give you two long-lasting benefits: 1) wonderful romantic memories, and 2) a great excuse to get to know Boston better.

Part of what makes Boston so romantic is that it's old - so in almost every neighborhood, you can see lots of beautiful historic buildings, cobblestone streets, narrow lanes and alleys, and small but wonderful restaurants. 

Take advantage of Boston's compact size by walking around and exploring the city together.  December weather can feel crisp, so wear a warm jacket, scarf, and gloves. 

If your boyfriend will be here for New Year's Eve, don't miss the fireworks over Boston Common at midnight - perfect way to celebrate the beginning of a new year of romance!

Read our complete guide to Christmas events in Boston to get the big picture of what's going on. 

Here are my suggestions about romantic places and things to do during the holiday season, plus plenty of other fun activities and events that will feel romantic when you're with someone special  . . .


Romantic Boston Places during December

Share the Best View of Boston and Toast Your Future

Temple Street Park in Boston's Beacon HillWhat's more magical than a skyscraper-top view of city lights, sparkling like diamonds in all directions? 

Imagine a jazz trio playing softly in the background, and your favorite drink - perhaps something bubbly - raised in your hand as you toast your perfect holiday together.

To put yourself in this scene, head to Prudential Tower (800 Boylston, Back Bay neighborhood) and take the elevator up to Top of the Hub Lounge on the 52nd floor.  Settle yourself at one of the little tables ($24/person minimum after 8pm - roughly the cost of one drink and a burger or salad) or at the bar (no minimum) and enjoy the romantic views, music, and just being together.  There's even a dance floor.  More about Top of the Hub

Photo of musicians at Top of the Hub Lounge courtesy of May Wong


Stroll around Boston's Most Romantic Neighborhood

Temple Street Park in Boston's Beacon HillGas lights along narrow cobblestone lanes filled with gorgeous Federal-period homes, Christmas wreaths on almost every door, and holiday lights sparkling everywhere you look - that's Beacon Hill at Christmas. 

Beacon Hill is one of Boston's oldest and most historic neighborhoods, located right across from Boston Common and the Public Garden.  Don't miss picturesque Acorn Street, and the boutiques and cozy bakery/cafes along Charles Street.

An especially romantic Beacon Hill spot is tiny Temple Street Park (shown at Christmas in the photo), tucked away behind the Massachusetts State House across from a Suffolk University Building on Temple St.  Resident doves nesting in the stone wall will coo romantically at you.


Go See the Best Christmas Lights in Boston

Temple Street Park in Boston's Beacon HillA Christmas visit provides the perfect excuse to go see holiday lights, and this year, the biggest light show in town is Blink! at Faneuil Hall Marketplace. 

350,000 golden LED bulbs transform the huge trees throughout the market area into a forest of lights. 

But that's not all.  Between 4:30pm and 10pm, a free light/sound show featuring music from the Boston Pops Holiday Pops concert and synchronized blinking lights entertains shoppers.  Romantic?  Not really...but it is magical, and if you're with someone you love, you'll see it through a romantic lens.


Combine a Boston Harbor Tour with a Romantic Dinner Cruise

Romantic dinner cruise on the Odyssey in Boston HarborFor a special romantic dinner accompanied by spectacular views, go on one of the dinner cruises offered by the Odyssey, modeled after a luxury ocean liner. 

You'll be served a gourmet dinner prepared on board by the talented chef.  Sip Champagne, enjoy the live music, try out the dance floor, or just relax and watch the magical nighttime views of the city skyline and Harbor Islands.

Make your reservations for a special Boston Odyssey Dinner Cruise

Read more about dinner cruises on the Odyssey


Skate around Frog Pond

Ice Skating at Boston's Frog PondNow for some "only in Boston" kind of fun.  

Head over to Boston Common's Frog Pond, rent skates, and go ice skating right in the heart of the city, with Beacon Hill's brownstone mansions in the background.

Afterwards, treat yourself to steaming cups of hot chocolate at the on-site snack bar.

More about ice skating at Frog Pond


Dine in a Romantic Boston Restaurant

Petit Robert Restaurant - Romantic dining in BostonWhat makes a restaurant romantic? 

Candlelight, wonderful wine, sumptuous food, and a cozy ambiance help...but of course dining with the person you love is what really counts. 

Here are a few of my favorite romantic Boston restaurants:

  • Petit Robert Bistro - Classic French favorites in a romantic setting that almost feels like Paris.  468 Commonwealth Ave, Fenway neighborhood, 617-375-0699.  More...
  • Trattoria Di Monica - Small (maybe 24 seats) bistro with brick walls, crisp white linens, and candlelight - plus mouth-watering authentic Italian classics.  67 Prince St, North End neighborhood, 617-720-5472;
  • Mistral - Lushly beautiful dining room, serving elegant French Mediterranean fare.  Pricey.  223 Columbus Ave, Boston's South End, 617-867-9300;
  • Newbury Street Cafes - Stroll up and down Newbury Street in Back Bay, and check out the menus posted near the doors of the numerous cafes and restaurants, and choose the one you like best.
  • Want more ideas?  Read our complete guide to Boston restaurants


Visit a Romantic Boston Ballpark

Fenway Park toursOK, maybe Fenway Park isn't exactly romantic - but if your boyfriend is a baseball fan, he'll love you for taking him on a Fenway Park tour. 

The entertaining tour guides tell you all about Fenway's history, legends, and legendary players, and give you a great behind-the-scenes tour. 

After the tour, go across the street to the Red Sox Souvenir Shop and buy him a t-shirt so that he'll think of you every time he wears it.

Bonus if you're not a baseball fan:  You won't actually have to sit through a game trying to look not bored. 

More about Fenway Park tours


Romantic New Year's Eve Events in Boston

Fireworks at Boston's First Night New Year's Eve CelebrationWelcome the New Year by watching fireworks over Boston Harbor at midnight. 

You can also get the affordably-priced buttons to gain entrance to the gala First Night celebration, Boston's biggest New Year's Eve event featuring hundreds of shows all over the city put on by the local arts community and international performers.

As an alternative, many of the city's bars and restaurants host New Year's Eve parties, with tickets typically ranging from $50-$175. 


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