Best Boston date ideas
The Prudential Center’s 52nd floor restaurant and lounge whisks lovers up, up and away above the street hustle. With window walls on three sides, this classy American restaurant and lounge offers romantic views over Boston. Inside, stylish decor and giant orange chandelier shades create a warm glow. It’s not just superb drinks and dinner on offer: excellent jazz musicians play in the lounge every night. Ask for table 18 in the dining room; it’s a cozy corner table. Whether the sky is bright blue, grey with clouds, or pitch black and twinkling with city night-lights, there’s never a bad view.
Perhaps it’s a Boston thing, but there are few more romantic places than Fenway Park. So, tickets in hand, nix the usual pre-game beer and sports bar scene and instead head to the almost-hidden Club Room at Tapestry, a classy Mid-Century Modern-inspired, lounge-y feeling restaurant on Kilmarnock Street. Softly lit, with a pressed tin ceiling, and a four-sided central fireplace aglow, enjoy shared plates and cocktails that are out of this world. Then, it’s happily off to Fenway Park, a five-minute walk away. You don’t have to be a baseball fan, or even a sports fan, to appreciate the atmosphere at America’s oldest Major League ballpark.
Riding the Minuteman Bikeway doesn’t have to be a race, but it can be. For a fun, active date idea, bike the 11-mile route, from Bedford to Fresh Pond, in one go. Or make it a round-trip; on the outbound stretch, stop off for selfies while exploring North Cambridge’s Alewife Brook Reservation, Arlington’s Great Meadows, and Lexington’s Battle Green. Consider adding a wager on the home stretch, turning the return journey into a race. The last one back to Fresh Pond covers dinner at Freepoint Kitchen. Located in the hip Freepoint Hotel, this hidden gem features a beautiful patio. The bar menu includes lots of different bespoke Manhattans, and there’s an outdoor fire pit for some star gazing.
OK, so you have tickets to a must-see movie at the AMC Loews Boston Common. Take movie night to the next level by adding dinner for two at Artisan Bistro, the Ritz-Carlton’s chic-casual restaurant. Try drinks in the elegant, horseshoe-shaped bar in the hotel’s lobby; you could grab a bite on one of the incredibly comfy surrounding couches near the high level fireplace. Artisan isn’t trendy, it’s more about doing things well. The AMC is actually connected to the Ritz-Carlton; ask the staff to point out the secret door leading into the movie palace.
Pammy’s—which sits on Mass. Ave. between Central and Harvard Squares—is a great place to start an evening of Cantabrigian bohemia. This hip trattoria has a 1920s feel, especially with the amber glow of globe lights. Nosh on handmade pastas and Italian inspired dishes, and enjoy tasty cocktails. Sit side-by-side at the vintage central communal table, or huddle by the Scandinavian white tile, double-sided fireplace. Dishes are designed to share, or not, and the super sexy desserts are not to be missed. After dinner, stroll the ten minutes to Central Square and check out at a band—or a comedy night or belly dancing—at the Middle East.
This is a bit pricey, but for a special occasion when even the best date ideas won’t cut it, book the The Spa at Mandarin Oriental’s couples suite. It’s the size of most inner-city apartments, with an opulent, marble-clad bathroom that includes double vanities, a massive soaking tub, and a large sauna. The separate, Asian-inspired treatment room is equally spacious and has natural light. The experience includes a personalized time ritual or signature spa treatment. After the spa, head to the hotel’s Bar Boulud for a splendid dinner; cozy up in a cherry red banquette, or grab seats in the bar overlooking bustling Boylston Street.
There’s nothing more romantic than death, just ask Romeo and Juliet. Seriously though, Mount Auburn Cemetery is a worthy date spot. Set on 72 verdant acres, this National Historic Landmark—the final resting place for numerous famous names—is also an arboretum and wildlife sanctuary. (Watch out for the wild turkeys in spring; they get a little tetchy while guarding their young.) The secluded dell is a quiet spot with a lovely pond, and nearby Washington Tower has inspiring views over the city and beyond. All that walking builds a healthy appetite for a superb dinner at Harvest. Tucked in an alley between Brattle and Mount Auburn Streets, this Harvard Square veteran is one of the top restaurants in the area, and boasts a talented culinary team. Dine at the chic bar, in the main room, or outside on the secluded patio, which has a fireplace.
Never been to the ballet? Don’t like ballet? That’s like saying you don’t like vegetables; both come in all flavors. The Boston Ballet’s performances at the Opera House, which is a sight to see in itself, are diverse: from traditional performances (e.g. Swan Lake) set against fanciful stage sets, to modern, visually monochromatic production’s like Wayne McGregor’s Obsidian Tear. As far as vegetables—and other edibles—go, begin the evening at PABU on the second floor of the Millennium Tower. This stylish take on the Japanese izakaya includes a lavish sushi bar. The bar includes high-level banquettes that are possibly the best seats, especially for watching the astute bartenders craft amazing drinks.
The Isabella Stewart Gardner Museum is not the biggest of Boston’s museums, and therefore not the most overwhelming, but it is certainly the most romantic museum in the city. That’s largely because the house itself is so charming. The courtyard is decorated in seasonal blooms, offering a central space where nature is the art. There’s space to concentrate on your date whilst also finding inspiration in the high arts. The best night for a date is Thursday, when the museum and its restaurant, Café G—which has a menu focused on dishes created from seasonal, local, and organic ingredients—are both open later. Third Thursdays have different themed events with resident and visiting artists in all disciplines, too.
Start the evening with dinner at Parsnip, a decidedly sleek, chic restaurant overlooking Winthrop Park, which predates Cambridge itself. Peppered with modern artworks, the understated interior features an ivory and beige color palette. The menu is as modern and progressive as the design, and changes hyper-seasonally, every few weeks or so. Follow with a theatrical experience at Oberon on Bow Street, where The Donkey Show, a disco era retelling of A Midsummer Night’s Dream, is a Saturday night staple. Part play, part stage show, this immersive production invites all to join the actors under the mirrorball. After, return to Parsnip’s third-floor lounge for drinks and revelry.
The Odyssey departs from lovely Rowes Wharf, which is a cut above the average berth, for dinner cruises around Boston Harbor. The cruises feature a three-course dinner and music, usually a singer and guitarist playing a low key set of rock and pop standards. After dinner, a DJ takes over so you can embarrass yourself on the dance floor. Harbor viewing on the outdoor deck is a must-do both before and after dinner. On weekday evenings, the Starlight Dinner Cruise is a shorter trip than the weekend three-hour cruise. Either way, you can expect stunning views of Boston’s skyline and landmarks.
When it comes time to refresh and renew, retail-wise, Newbury Street continues to offer the best and most beautiful parade of stores in Boston. Stop in at Tea Forte, the Concord-based tea merchant, which turns your daily tea fix into a romantic ritual, especially with Art Deco gold pyramid tea infusers. For apparel, try some his and hers preppy glam at Ted Baker. Start at Arlington and shop all the way down to Hereford, and then head to Sonsie for drinks or dinner. This Back Bay mainstay has a beautiful low-lit dining room that exudes a bistro feel. Table 12 is known as the engagement table; here couples often take things to the next level by popping the question.
Head to A4cade for a night off from being an adult and eating healthy. Totally escape into game land at this vintage game arcade, where you can rest your digits while enjoying cocktails creative comfort food. The Area Four pizza team’s speakeasy arcade is filled with classic arcade games (Galaga, Ms. Pacman) and favorites like skeeball and foosball. It’s amazing how a few cocktails makes games more addictive and competitive.
Boston is "America's Walking City," after all, so head to the Seaport to stroll the scenic Harbor Walk. (Just remember to enjoy the harbor views before the Seaport fills up with skyscrapers.) Work your way over to Fort Point Channel and do the return stroll along the Rose Kennedy Greenway, which pairs manicured nature with notable art installations. Follow those urban explorations with a journey through the intriguing world of wine. Housed on the second floor of the Boston Harbor Hotel, Meritage is a wine-focused restaurant with equally adventurous dishes. Try the nine-course tasting menu with wine pairings, and enjoy the beautiful views over Rowes Wharf to the harbor.
For a mid-week date to remember, the Coit Observatory at Boston University offers free public viewings most Wednesday nights throughout the year—cloud cover permitting. The hour-long viewing parties with professional astronomers last about an hour. Then, you are ready for a night of drinks and dinner down the street in Kenmore Square. Start with a perfectly made cocktail at The Hawthorne, then move next door to Eastern Standard. This longstanding American brasserie offers a varied menu sure to please even the pickiest of eaters.