From Boston With Love: Five Winter Date Ideas

Date Night at The Dagny

Picture this: a cozy, candlelit nook in the heart of Boston — and you don’t even need to venture outside. A winter getaway invites the perfect opportunity for a romantic night in your sanctuary above the city. Settle into the comfort of your Art Deco-adorned room and indulge in refined room service. From seafood specialties to shareable appetizers, we’ll deliver your date night feast directly to your door.

For an intimate dinner, make a reservation downstairs at Fin Point Oyster Bar & Grille. This elegant dining room serves New England classics, ocean-to-table plates, and a locally sourced selection of flatbreads, steaks, and salads. But the star? The spectacular raw bar boasts a dizzying array of delicacies. 

Ice Skating and a Speakeasy

Lace up your skates for a date straight out of a rom-com. Glide side-by-side under the twinkling lights of The Boston Common Frog Pond, an impeccably maintained outdoor skating rink in the center of the city. Warm up afterward with hot cocoa from the Frog Pond Café or indulge in their locally-loved Belgian waffles. In the Fenway neighborhood, you’ll find the Rink at 401 Park, a 6,000-square-foot winter playground where theme nights, live music, and delicious food and drink create a well-rounded experience. Next door, you’ll find neighborhood favorites like Trillium Brewing and TimeOut Market.

Now, let’s talk speakeasies. Once you warm up, venture out for a clandestine cocktail experience. Step into a time capsule of cool at 1928 Beacon Hill, a cozy space brimming with antiques and boasting a delightful bourbon menu. Hecate, a cavern-like bar accessed through a secret alleyway door, is mystical and mysterious — a true destination for the adventurous. Or, opt for Offsuit, a discreet and oh-so-stylish spot serving out-of-this-world cocktails.

Museum and a Show

Boston is the perfect place to connect over cultural immersion, from exhibitions to live entertainment. Start your adventure through the arts by exploring the exquisite exhibits at the Museum of Fine Arts, the Isabella Stewart Gardner Museum, or the Institute of Contemporary Art. Whether you bond over embalmed mummies or imagination-stirring contemporary works, these curated collections and elaborate exhibits will spark interesting conversation.

Continue date night with a little drama. Make your way to the Theatre District, an area dotted with historic theaters and contemporary performance spaces. You’ll find countless Broadway shows, concerts, and dance performances at venues like Citizens Bank Opera House, Boch Center, and Emerson Colonial Theatre. If laughter is your love language, look no further than Nick’s Comedy Stop, a casual comedy club featuring Boston’s best local stars.

Golf and a Game

For the couple that thrives when a touch of friendly competition is involved, tee off on an action-packed date at one of Boston’s indoor golf hotspots, Five Iron Golf, CityGolf Boston, or the upscale, tech-infused Puttshack. No need to worry about the whims of the weather; just focus on perfecting that swing. Whether or not you hit the fairway, it’s guaranteed to impress on the fun-loving front. 

For the second half of your date, channel your inner fan and catch a Boston Bruins or Boston Celtics game at TD Garden, just a 20-minute walk from The Dagny. From puck drop to the final buzzer, Bruins games buzz with electric excitement. Between the roar of the crowd and classic chants, the conversation might be minimal, but there are plenty of nearby watering hotels, from sports bars to Irish pubs, where you’re welcome to debrief over a nightcap.

For couples who prefer a little courtside magic, you’ll feel part of the living legacy of the NBA’s most successful and storied team at a Celtics game. Share the camaraderie of fellow fans, split nachos between quarters, and immerse yourselves into the heartbeat of Boston sports culture. If you’re not already a basketball fanatic, this experience could be a game-changer.

Window Shopping & Afternoon Tea

If your dream date involves strolling hand in hand, window shopping, and feeling a little fancy, this is for you. Spend a slow afternoon sipping tea over good conversation (or a pair of good books) at The Boston Public Library’s Courtyard Tea Room. This historical haven in the heart of the city offers an elevated afternoon tea experience overlooking an ornate Italianate courtyard. Savor a selection of fine teas, craft cocktails and mocktails, classic finger sandwiches and soups, petit fours, and scones in a stunning setting.

Follow this up with a bout of window shopping on Newbury and Boylston Streets just outside, where you’ll find a mix of high-end boutiques, favorite national retailers, and charming local shops. Whether you’re dreaming of a designer splurge or searching for a unique treasure, these bustling streets offer plenty of options for rounding out your winter date.

Boston Beckons

Pair your dream Boston date with the perfect offer. Take your romantic escape to new heights with our extravagant Optimistic Air Package, including a 45-minute private helicopter tour for two over Boston Harbor Islands, a bottle of Champagne, and chocolates.