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Isabella Stewart Gardner Museum
Photograph: Courtesy Isabella Stewart Gardner Museum/Nic Lehoux Isabella Stewart Gardner Museum

The 13 best Boston date ideas

Treat someone special to a memorable date night with these fun activities and shared experiences

By Linda Laban, Time Out Boston Staff and Eric Grossman
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Looking for date ideas in Boston? With so many cool things to do around the Hub in normal times, the only limit is your imagination. Here are an assortment of options that pair shared treats—awesome food or a spa indulgence—with a fun activity, all while keeping logistics in mind. If none of these strike your fancy, make a night of it by pairing one of the best things to do in Boston with a meal at one of the most romantic restaurants in Boston. Just remember: if nothing else, get out of your comfort zone, dress up a little, and—for one entire evening—get off your cellphone.

RECOMMENDED: Full guide to the best things to do in Boston

29,000 sq ft of the city's finest cuisine, cocktails and culture

Time Out Market Boston
Photograph: Eva Sakellarides

Time Out Market Boston

Restaurants Fenway/Kenmore

Show off your culinary cred by hosting a date at Boston's coolest gourmet destination. The contemporary culinary hub boasts a tantalizing assortment of curated food offerings, two slick bars and lots more. There are enhanced safety protocols and plenty of seating—both indoors and on a lovely, spacious patio.

Best Boston date ideas

Isabella Stewart Gardner Museum
Photograph: Courtesy Isabella Stewart Gardner Museum/Nic Lehoux

1. Visit Isabella’s house

Museums Art and design Mission Hill

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 seasonally-driven restaurant, Café G are both open later. Third Thursdays have themed events, with resident and visiting artists in all disciplines.

Odyssey Cruises Boston
Photograph: Courtesy CC/Flickr/Larry Lamsa

2. Cruise the Harbor

Things to do Walks and tours Waterfront

The Odyssey departs from lovely Rowes Wharf 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.

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Pammy's
Photograph: Courtesy Yelp/Laila K.

3. Go boho in Central Square

Restaurants Italian Harvard Sq

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 alongside 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 to Central Square and check out a band—or a comedy night or belly dancing—at the Middle East.

Harvest
Photograph: Courtesy Harvest/Dan Salafia

4. Take a peaceful stroll in Cambridge

Restaurants Contemporary American Harvard Sq

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.

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Trillium Brewing Company
Photograph: Courtesy Trillium Brewing Company

5. Pair a scenic walk with a world-class beer tasting at Trillium

Restaurants Contemporary American Waterfront

Boston is "America's Walking City," after all, so head to the Seaport to stroll the scenic Harbor Walk. 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 world of Trillum's innovative, intriguing beers.

Mandarin Oriental Boston
Photograph: Courtesy Mandarin Oriental Boston

6. Relax in luxury at the Mandarin Oriental

Hotels Back Bay

For a special occasion when even the best date ideas won’t cut it, splurge on 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.

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Eastern Standard, Restaurants and cafes, Boston
Photograph: Elan Fleisher

7. Reach for the stars in Kenmore Square

Restaurants Contemporary American Fenway/Kenmore

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.

Freepoint Kitchen
Photograph: Courtesy Yelp/Freepoint Kitchen

8. Break a sweat, then relax in Fresh Pond

Restaurants American creative Fresh Pond

Riding the Minuteman Bikeway doesn’t have to be a race, but it can be. For an 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. If you're riding one-way to Fresh Pond, finish with dinner at Freepoint Kitchen. Located in the hip Freepoint Hotel, this hidden gem features a beautiful patio with a fire pit and prime star gazing, plus a bar menu bosting bespoke Manhattans and other creative cocktails.

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A4cade
Photograph: Zac Wolf

9. Get your game on at A4cade

Bars Central Sq

Head to A4cade for a night off from being an adult and eating healthy. Escape into game land at this vintage game arcade, then rest your digits while enjoying cocktails and creative comfort food. The team behind Area Four pizza operates this 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.

Sonsie
Photograph: Courtesy Yelp/Huijie F.

10. Get chic in the Back Bay

Restaurants Italian Back Bay

When it comes time to refresh and renew the wardrobe, 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. 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.

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AMC Loews Boston Common 19, Movie theaters, Boston
Photograph: BWChicago

11. Get Ritz-y with dinner and a movie

Movies Boston Common

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. Have drinks in the elegant, horseshoe-shaped bar in the hotel’s lobby or grab a bite on one of the comfy couches near the fireplace. The AMC is connected to the Ritz-Carlton, so ask the staff to point out the secret door leading into the movie palace.

Boston Opera House
Photograph: Courtesy Yelp/Lin L.

12. Discover the ballet at the Boston Opera House

Theater Performing arts space Downtown

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 productions 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 banquettes that are possibly the best seats, especially for watching the astute bartenders craft amazing drinks.

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Fenway Park, Sights and attractions, Boston
Photograph: Elan Fleisher

13. Score some romance at Fenway Park

Things to do Sport events Fenway/Kenmore

Perhaps its a Boston thing, but many a local will tell you there are few places more romantic than Fenway Park. So, tickets in hand, nix the usual pre-game beer and sports bar scene and instead head to the city’s most exciting eating space, Time Out Market Boston. 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. 

More cool things to do around The Hub

The 50 best things to do in Boston

Things to do

We’re all about making the most out of what's left of 2020. (Good riddance!) Temps are dropping, but there are still plenty of cool things to do, albeit carefully, while safely getting some fresh air. Among the best things to do year-round in Boston are plenty that take place away from the elements, but given the current conditions, options like awesome hiking, sunny beaches, fun cruises, and outdoor dining should move to the top of your list.

Given the ever-changing nature of government rules and restrictions, not everything listed here might be open to the public — remember to always confirm plans with the venue in advance.

No matter where your interests lie, you can always find something to get excited about in the Hub. The best things to do in Boston run the gamut—from seriously fun to awesomely educational. Looking for culture? Spend a day exploring Boston museums. Hungry? You've come to the right place. There are tons of amazing restaurants in Boston that highlight the city's rich and diverse culinary landscape. We've searched all across the city to assemble this list of the best things to do in Boston. Follow it and never get bored here again.

Done something on this list and loved it? Share it with the hashtag #TimeOutDoList and tag @TimeOutEverywhere.

You can also find out more about how Time Out selects the very best things to do all over the world, or take a look at our list of the best things to do in the world right now.

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