16 Actually Great Date Ideas in Boston

Cocktails and oysters at the Hotel Commonwealth

Kenmore Square
Surprise your date with a night in Kenmore Square that doesn’t revolve around an overcrowded Sox bar. Kick your night off at The Hawthorne with a classic cocktail or one of the house creations like the Esperanto (crema de mezcal, La Ciggarrera manzanilla, Carpano Antica, and orange bitters). Once you’ve worked up an appetite, head across Hotel Commonwealth’s lobby into Island Creek Oyster Bar for some of the ocean’s best bivalves (oysters average $3/each). Between the perfectly concocted cocktails and aphrodisiac power of the oysters, you two will be primed to plan your second encounter. If you don’t want the night to end, tack on a visit to the Boston University Observatory, where you can see the beautiful Boston skyline with the telescopes on hand.

Sample the South End's best pizza at Picco

South End
Impress your date with a triple threat of pizza, beers, and homemade ice cream at Picco. Split a large pizza with a well-done crust; the Alsatian with sautéed onions, bacon & Gruyère doesn't disappoint. As you digest, go a couple doors down to Beehive at the Boston Center for the Arts (free to get in) for a cocktail and a taste of live jazz, blues, funk, Latin, and soul.

Hit the frog pond

Beacon Hill
You can help keep each other get stable (physically, at least) on the ice at Boston Common Frog Pond. After showing off your moves/skating ability, or lack thereof, you can warm up with hot cocoa at the rink's cafe.

Authentic Italian and improv comedy 

North End
When going out for dinner and drinks at an authentic Italian restaurant in the North End, there're Monica's, Prezza, and dozens of other trattorias worth hitting. Then get ready for a pee-your-pants funny improv show at the Improv Asylum. Protip: put your name on the waitlist at Neptune Oyster (since it typically has a two-hour wait!), then watch the comedy show at the Improv Asylum while waiting for the restaurant to call your cell when a table frees up -- and then head over there when the show is over.

Walk the Esplanade to Harvard Square

Back Bay to Harvard Square
For a date that's easy on your wallet, go for a stroll along the Esplanade and head towards Harvard Square.  There are often different festivals going on in the Esplanade around the holidays, and it also offers one of the best views of fall foliage in Boston. Once you've finished the three-mile walk from Back Bay, reward yourselves with a drink, either downstairs at Russell House Tavern or in the beer garden at Charlie's Kitchen.

Seafood at Yankee Lobster Co. and an outdoor concert

Seaport
Once summer hits, take your date out for chowder, fresh steamers, and one of the city's top lobster rolls from Yankee Lobster Co. If you're lucky enough to snag a spot outside, you can listen to live music from a concert going on at the Blue Hills Bank Pavilion. You can pick up concert tickets next door and experience the phenomenal acoustics under the outdoor pavilion.

A Sox pre-game with BBQ

Fenway
You know there's no shortage of sports bars to hit before first pitch, but buckle down for some of the best BBQ in town at Sweet Cheeks. The roadhouse-style barbecue joint is good for Berkshire pork ribs and biscuits by the bucket with house-made honey butter, giving you a strong base for ballgame beers.

Take a boozy tour of Bully Boy Distillers

Roxbury
Kick off date night with a visit to Boston’s first craft distillery, where you and your date will get a behind-the-scenes look at how your favorite hooch is made. Tours travel past mash tuns and copper stills to see how Bully Boy produces its award-winning lineup of rum, vodka, and whiskey. Visitors will hear about how brothers Will and Dave Willis found a stash of Prohibition-era spirits in their family’s farmhouse vault, inspiring them to start the distillery. Tours last one hour and cost $10 per person, available on Saturdays by appointment.

Unleash your inner rockstar at The Painted Burro

Somerville
For the more daring daters, Tuesday-night karaoke at Davis Square’s lively Mexican spot is a hit, especially when paired with tacos and tequila. Serenade your date while painting a clear picture of your expectations with your best rendition of “This Is How We Do It” -- as you tip back one of the signature margaritas, made with the house tequila, and tear into a pork carnitas taco. The karaoke only costs you your dignity, making this a pretty economical date with a tequila list that has options for every budget.

Get beer-geeky together at PARK

Cambridge
Head to Harvard Square and embrace your inner beer nerd at PARK Restaurant & Bar’s weekly Cask Beer Thursday. The restaurant taps a new cask of local craft beer that’s just the thing to wash down its famous PARK Patty Melt, Bacon 3-Way, or whatever else you fancy from the menu.

A quick jaunt to the tropics (aka Franklin Park Zoo’s indoor exhibit)

Dorchester
Bring your date to the Franklin Park Zoo during the off season for a mini-tropical getaway without leaving the city. Warm up inside the zoo’s waterfall-filled Tropical Forest exhibit, which is kept at a balmy 72 degrees year-round. Check out ring-tailed lemurs, Baird’s tapirs, mandrills, capybara, ocelots, and the western lowland gorillas -- observed up close and personal at five floor-to-ceiling glass viewing stations.

Not-your-typical dinner and a movie

Chestnut Hill
The luxury movie theatre at Showcase SuperLux takes the movie-going experience to a whole new level; it’s like flying in first class. Kick back in the extra-wide, super-plush reclining seats and enjoy a full three-course meal with a menu that includes Lobster Campanelle, Korean Sirloin Steak, and Thai Chicken Bites. After 6pm the theater is 21+ only, so you can order a cocktail, wine, or beer without feeling awkward that a little kid is sitting next to you.

Go van Gogh without losing an ear

Various locations
With an extensive list of rotating Boston area venues (Jerry Remy's, Back Bay Social Club, Clerys), Paint Nite makes for an engaging and accessible date activity. It gives budding artists (and regular folks alike!) a blank canvas, step-by-step instruction, and two hours to create a masterpiece. It costs about $45 per person and includes all painting supplies. Drinks are suggested, especially if you need help bringing out your inner Picasso!

Ferry over to one of the Harbor Islands

North End
You can actually camp out on the Harbor Islands in the summer, which is a great date idea once the relationship has reached "I'm OK with being a little grungy" status. Walk around the island to see the gorgeous views of the city. If you’re feeling adventurous, there are kayaks and other rentals available.  The boat leaves from the North End so when you’re back, you'll have plenty of pasta spots waiting for you.

Culture and cuisine in Fort Point

Fort Point
With stunning views of the Boston waterfront and an ever-changing array of modern art, going to the ICA is a great start to a night on the town. Follow up your visual feast with dinner down the street at Tavern Road with a litany of “for two” options, like a 22oz ribeye steak with seasonal accompaniments.

Everything awesome at Adult Night in LEGOLAND

Somerville
The third Wednesday of every month, starting at 6pm, LEGOLAND becomes adults-only. Be a kid again with no kids around, trade war stories of how your parents gave away your Lego collection when you left for college, and afterward, walk next-door to Earls Kitchen & Bar for craft cocktails.

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