5 Romantic Things to Do for a Valentine’s Getaway Weekend in Boston

This Valentine’s Day, surprise your significant other by planning an unexpected adventure filled with mystery and enchantment! And for this, there’s no need to cross an ocean—set your sights on Boston, Massachusetts, just a five-hour drive from Montreal! This metropolis in the heart of New England will delight you with its cobblestone streets, refined cuisine, and intimate spots.

Picture the look of surprise on your partner’s face when you ask them to clear their Valentine’s weekend for a romantic getaway and to pack their passport… without revealing anything more.

In February, Bostonians brave the cold in style: iced coffee in hand, heated terraces, and outdoor happy hours. Let yourself be charmed by the city’s warm and relaxed winter atmosphere while taking advantage of the low-season rates!

Here are five ideas for a romantic weekend getaway in Boston:

1. Sip a Cocktail in a Heated Igloo With a Spectacular View of Boston Harbor

The rooftop at The Envoy Hotel is already known as one of the best spots in Boston, and its terrace becomes even more magical in the winter! You’ll stay nice and warm during this romantic rendezvous in a private igloo, where you can take in the panoramic views of the Atlantic Ocean and downtown skyscrapers.

Each igloo is heated, illuminated, and even comes with its own blanket for extra coziness. Try their famous winter cocktails to fully embrace this luxurious experience. Reservations are required and give you access to a private igloo for two hours, with a minimum spend on food and drinks. You’ll leave with unforgettable VIP photos that are sure to make everyone envious!

2. Take a Foodie Tour

If your love language is food, Boston is a foodie capital that will not disappoint. There’s nothing better than joining a guided food tour led by an expert to uncover the city’s best bites!

Together, you’ll explore the culinary traditions of the historic North End neighbourhood, known for its Italian flavours and regional New England specialties. Your guide will take you off the beaten path to hidden gems for an authentic dining experience. You’ll leave with full stomachs and happy hearts!

3. Feel the Enchantment in a Speakeasy

Add a touch of intrigue to your Valentine’s weekend in Boston by visiting one of the city’s charming speakeasies. These bars, inspired by the Prohibition era of the 1920s, offer a cozy ambiance with dim lighting and refined decor.

Most of these exclusive little bars have a secret entrance, a password (provided when you book), and an elegant dress code.

The most talked-about speakeasy in Boston is undoubtedly Hecate—a truly mysterious spot! Alternatively, try The Gallery, which you can access by walking through a hidden library shelf at the chic restaurant Yvonne’s.

For seafood lovers, don’t miss Next Door, which looks like a locksmith’s shop from the outside but is actually a raw bar. Figuring out how to get in is part of the fun, and you’ll be rewarded with extravagant cocktails and seafood dishes. Keep in mind that reservations at these popular spots are essential.

4. Set Sail and Enjoy a Decadent Meal on a Romantic Dinner Cruise

Celebrate your love at sea and feel like you’re truly on vacation! Several companies offer romantic dinner cruises in Boston Harbor. Departures take place from the picturesque Seaport District, so be sure to note your pier number.

After the crew’s welcome speech, you’ll settle into the warm interior of the boat. Once on the water, you’ll spot distant islands and the iconic Boston Light on Little Brewster Island. Romantic packages often include champagne and a three-course meal.

At sunset, you’ll have the chance to watch the city lights twinkle as the sun dips behind the skyscrapers. Later in the evening, you can even dance the night away to a live jazz band aboard!

5. Enjoy English-Style Afternoon Tea at the Oldest Public Library in the United States

What could be more romantic than glamming it up and visiting one of Boston’s most coveted wedding venues: the Boston Public Library? This architectural gem, frozen in time, allows a select few to take a step back in history at the Courtyard Tea Room!

You and your partner can enjoy a traditional afternoon tea experience that will make you feel like you are in England. This highly sought-after activity requires advance booking! In the heart of February, you’ll be glad to warm up with a cup of tea in this elegant setting while savouring pastries, scones, and finger sandwiches served on tiered trays. There are even boozy cocktails for festive couples.

With the popularity of the Bridgerton series on Netflix, this experience of high-society London has gained even more traction.

‍Good to know: Don’t miss the chance to explore the rest of the Boston Public Library if you’ve never been—it’s well worth it.

Bonus: Take Advantage of Romantic Packages

Visiting Boston in February, during the low tourist season, means you’ll benefit from significant savings on your hotel room and can treat yourself with the money saved.

Some hotels, like The Newbury Boston, Boston Harbor Hotel, and Fairmont Copley Plaza, even offer romantic packages that include champagne and chocolates in your room. You can even enjoy a romantic dinner and a luxurious suite with a fireplace.

An Exceptional Valentine’s Day in Boston!

‍There’s nothing better than offering a surprise experience to rekindle your love! To ensure your unforgettable Valentine’s weekend getaway in Boston goes smoothly, make sure to book your accommodations and activities in advance.

Even though it’s just a short trip, don’t forget to get travel insurance with a quick quote from soNomad before leaving for the U.S.