30 great dates in Boston and beyond
From seaside oyster feasting to stargazing to joy riding, here are some creative ways to have fun with your new crush or your longtime sweetheart.
By Kara Baskin, Karen Campbell, Alison Goldman, Jon Gorey, Sandra A. Miller, and Rachel Raczka
1. STEAMY REPOSE
Reserve one of the two private hot tubs at Inman Oasis, a down-to-earth Cambridge spa where you can soak away your stress a deux. Robes and towels provided. Afterward, take your serene selves a few steps away to Moona for craft cocktails and mezza plates. Reserve well in advance for both experiences.
> Inman Oasis, 243 Hampshire Street, Cambridge, 617-491-0176, inmanoasis.com; Moona, 243 Hampshire Street, Cambridge, 617-945-7448, moonarestaurant.com
2. MALL GAZING
Perhaps no traditional courtship ritual is so simple yet enjoyable as a slow, conversational stroll. Meander the length of the Commonwealth Avenue Mall, designed in the style of a romantic 19th-century Parisian boulevard. Soak up the Victorian architecture, sculptures, and tree blossoms, and continue on through the Public Garden and Boston Common. Bookend your stroll with dinner at Deuxave and a drink at Yvonne’s (or vice versa), or simply peel off for provisions anywhere along the way.
> Deuxave, 371 Commonwealth Avenue, Boston, 617-517-5915, deuxave.com; Yvonne’s, 2 Winter Place, Boston, 617-267-0047, yvonnesboston.com
3. ENGINES RUNNING
Tired of taking things slow? The arrive-and-drive option at F1 Boston lets you experience European-style Formula 1 racing on indoor tracks. After a suit-up and a safety briefing, couples climb into their karts and start their engines for a 15-lap race that lasts about 10 minutes. Reservations recommended on weekends. The winner buys beers at Widowmaker Brewing just minutes down the road.
> F1 Boston, 290 Wood Road, Braintree, 781-848-2300, f1boston.com; Widowmaker Brewing, 220 Wood Road, Braintree, 781-849-0205, widowmakerbrewing.com
4. SOUTHERN SOUL
Start with some down-home dishes — like the gumbo or brisket — at Tupelo in Inman Square. Then walk down Prospect Street to the Cantab Lounge, where the frills are few but the music is mighty, for Geoff Bartley’s vaunted Tuesday night Bluegrass Pickin’ Party. The open session draws some of Boston’s best Americana players and features a headliner act at 10 p.m. On Thursdays at the Cantab, the Chicken Slacks get the music-loving audience on their feet with soul, funk, and Motown classics.
5. CAMBRIDGE FUNK
Head to Zuzu’s in Central Square for Soulelujah, a Saturday night funk-soul 45s dance party. It’s a neighborhood standby, so you shouldn’t be surprised to find your fellow attendees in full ’70s attire. After you’ve adequately shaken your groove thing, head across the street to Beantown Taqueria, where Tex-Mex and Mexican soul food is served until 4 a.m.
6. AFTER-HOURS CINEMA
For a fail-safe weekend date, grab a late dinner at Burro Bar, the Brookline sibling of Davis Square’s beloved Painted Burro, where you can down margaritas and short rib “double stack” tacos. Or try the Hopewell Bar & Kitchen, which serves elevated iterations of comfort food, like duck fat-roasted fingerling potato poutine and ponzu-marinated tuna “nachos.” Then catch a late-night flick with Coolidge Corner Theatre’s After Midnite series. Cult classics and rare releases get an 11:59 p.m. start time on Fridays and Saturdays.
>Burro Bar, 1665 Beacon Street, Brookline, 617-277-0427, burrobarbrookline.com; Hopewell Bar & Kitchen, 1277 Commonwealth Avenue, Allston, 617-208-8925, hopewellboston.com; Coolidge Corner Theatre, 290 Harvard Street, Brookline, 617-734-2501, coolidge.org
7. NEON NAMASTE
Newbies and yogi masters alike can stretch with abandon during black light yoga at Back Bay’s YogaWorks. They crank the music, turn off the lights, and encourage guests to show off their brightest neon gear and mats. Afterward, wander over to Citrus & Salt — Chef Jason Santos’s new Baja coast-inspired concept — to cool down and nosh on ceviche, crab tostadas, and the cult-favorite Dole Whip dessert.
8. CARIBBEAN CRAWL
Lose yourself in live reggae on the tiny but mighty stage at Union Square’s Bull McCabe’s. Live music is on tap Tuesday through Sunday — island sounds dominate on Tuesdays — and the intimate pub’s eclectic menu includes Caribbean roasted vegetables, fish tacos, and hot wings. Consider it a crawl and head to Sally O’Brien’s about a block away to hit the dance floor.
9. NAKED OYSTERS
Come summer, local mollusk magnate Island Creek Oysters offers tours of its farm, including the hatchery, that culminate in an intimate, all-you-can-eat raw oyster feast on a skiff boat in Duxbury Bay. You can bring a cooler with drinks, snacks, and condiments you’d like to pair with your shellfish, though you’re encouraged to try at least one oyster “naked” — without any garnishes. While tickets (about $80 each) aren’t cheap, they still tend to sell out quickly when they go on sale in April, and there’s something strangely wonderful about eating oysters hauled out of the ocean and tossing the spent shells overboard.
> Island Creek Oysters, 457 Washington Street, Duxbury, 781-934-2028, islandcreekoysters.com
10. SPIKED LITERATI
Get literary at one of Brookline Booksmith’s events, which include upcoming appearances by author Dr. Daniela Lamas, a critical care specialist at Brigham and Women’s Hospital (March 29); and The English Patient author Michael Ondaatje, in conversation with author Teju Cole at the Coolidge Corner Theatre (May 10). Then discuss over drinks at the tropical and hip Blossom Bar (make a reservation!), where renowned bartender Ran Duan recently updated his parents’ Sichuan restaurant and serves cocktails like the Girl from Ipanema, a concoction that includes creme de menthe and passion fruit.
> Brookline Booksmith, 279 Harvard Street, Brookline (but event locations vary), 617-566-6660, brooklinebooksmith.com/events; Blossom Bar, 295 Washington Street, Brookline, 617-734-1870, blossombarbrookline.com
11. ENDORPHIN RUSH
Couples who don’t mind sweating together should head to Recycle, an indoor cycling studio in the South End that’s both a dance party on a stationary bike and an intense cardio workout in a faux candlelit room, with rhythmic music swelling in the background. Afterward, refuel with a superfood shake at nearby Pressed.
12. MUSEUM MISCHIEF
On the third Thursday of each month, the Isabella Stewart Gardner Museum opens its doors after hours for a night of merriment. Explore Gardner’s enchanting home with a drink in hand (there’s a cash bar), and try whimsical, hands-on activities inspired by current exhibits (a recent night included a calligraphy station). Whether there’s music in the lush courtyard or discussions with artists and writers upstairs, the mood is magical; this is probably as close as you’ll get to attending a cocktail party hosted by an early-20th-century luminary. Tickets are $5-$15; as a bonus, the thoughtfully sourced fare at the museum’s Cafe G is surprisingly good.
> Isabella Stewart Gardner Museum, 25 Evans Way, Boston, 617-566-1401, gardnermuseum.org
13. PICTURESQUE PEDALING
Ride off into the Cape Ann sunset on one of three different bike loops that originate in Gloucester and promise close-up views of romantic coastal scenery. A 14-mile mid-length loop follows Route 127 and winds through charming Rockport. Fuel up with lobster rolls at Roy Moore Lobster Company before heading to Halibut Point State Park and back down to Gloucester.
> Roy Moore Lobster Company, 39 Bearskin Neck, Rockport, 978-546-6696, rockportusa.com/restaurants/roy-moore-lobster-company/
14. SEAPORT SPLURGE
Celebrating an anniversary, or getting out of the house for a rare adult outing sans children? Begin your evening with an icy martini, shrimp cocktail, and live music at Mastro’s Ocean Club, then stroll around the corner for dinner at LoLa 42 (ask for a window table, and order the fries drenched in foie gras gravy). If you’ve still got energy afterward, go dancing in style at the The Grand nightclub. You’ll only park once — it’s all on the same block.
> Mastro’s Ocean Club, 25 Fan Pier Boulevard, Boston, 617-530-1925, mastrosrestaurants.com; LoLa 42, 22 Liberty Drive, Boston, 617-951-4002, lola42.com; The Grand, 58 Seaport Boulevard, Boston, 617-322-0200; thegrandboston.com
15. TAPAS TOUR
Grab your pals and reserve a chauffeured group-date tour of super-chefs Jamie Bissonnette and Ken Oringer’s restaurants: Coppa and Toro in the South End, and Little Donkey in Cambridge. On a JK Food Crawl, groups of four to eight will sample about six small plates (plus drinks) at each spot, skipping — or Ubering — from Italy to Spain to Asia.
> Coppa, 253 Shawmut Avenue, Boston, 617-391-0902, coppaboston.com; Toro, 1704 Washington Street, Boston, 617-536-4300, toro-restaurant.com; Little Donkey, 505 Massachusetts Avenue, Cambridge, 617-945-1008, littledonkeybos.com. To reserve online, go to jkfoodgroup.com.
16. GOURMET DELIVERY
From the comfort zone of your own couch, order from the new delivery-only Puritan Trading Company (an offshoot of Cambridge’s Puritan & Company, run by chef Will Gilson). Marinated salmon crudo, spicy white clam garlic toast, and scallop and linguica dumplings will see you through your Black Mirror spiral. Who needs pizza?
17. WATERFRONT TRYST
Longing to escape the city but can’t get to the beach? Here’s Plan B: Belly up to the raw bar at Charlestown’s Pier 6, right on the waterfront. Hop a water taxi to sister restaurant ReelHouse in East Boston and watch the sun set over mussels and calamari al fresco. Then amble across the street to a bench at LoPresti Park for glittery skyline views.
18. TRAD TUNES
Sip through a session at the Brendan Behan, as cozy a pub as you’ll find in Boston. It hosts a lively, long-running traditional Irish music session from 5 to 8 p.m. on Saturdays and offers a top-notch beer list. Bring in tasty Cuban sandwiches from The Old Havana across the street to pair with the pints, fiddling, and conversation on offer at Behan’s.
19. CINEMATIC VARIATIONS
Put a more creative, indie spin on this tried-and-true combo: Start with dinner at Venezuelan restaurant Orinoco in Harvard Square, then catch a classic or cult flick at the Brattle Theatre; share a pizza at Posto and a popcorn at the Somerville Theatre; get dinner at Area Four or Lord Hobo followed by an indie or foreign film at the Kendall Square Cinema; or splurge on tapas at the beautiful Brookline’s Barcelona Wine Bar (make a reservation) before catching an Oscar contender at the Coolidge Corner Theatre. All four theaters now serve craft beer and wine.
> Orinoco, 56 JFK Street, Cambridge, 617-354-6900, orinocokitchen.com; Brattle Theatre, 40 Brattle Street, Cambridge, 617-876-6837, brattlefilm.org; Posto, 187 Elm Street, Somerville, 617-625-0600, postoboston.com; Somerville Theatre, 55 Davis Square, Somerville, 617-625-5700, somervilletheatre.com; Area Four, 500 Technology Square, Cambridge, 617-758-4444, areafour.com; Lord Hobo, 92 Hampshire Street, Cambridge, 617-250-8454, lordhobo.com; Kendall Square Cinema, 355 Binney Street, Cambridge, 617-621-1202, landmarktheatres.com; Barcelona Wine Bar, 1700 Beacon Street, Brookline, 617-264-8900, barcelonawinebar.com; Coolidge Corner Theatre, 290 Harvard Street, Brookline, 617-734-2501, coolidge.org
20. BARREL BOOZING
Raise a glass at the Bully Boy Distillers tasting room in Roxbury. The digs are cozily romantic, from the barrel room’s chandeliers to the speakeasy-esque tasting room’s floral wallpaper and tufted banquette. Order a draft cocktail or a cocktail flight from the bar that doubles as a test kitchen, then purchase bottles of the spirits and continue your cocktail date at home.
> Bully Boy Distillers, 44 Cedric Street, Boston, 617-442-6000, bullyboydistillers.com
21. STARRY NIGHTS
Have a cosmic experience at the Judson B. Coit Observatory, the Boston University rooftop observatory, which hosts illuminating, hour-long public viewing nights most Wednesdays (tickets go fast for the free events). While you’re waiting for your turn at the telescope, take in the stunning views of the Charles. When you’re ready to come back to earth, head to Insomnia Cookies for a sweet nighttime snack.
22. SALEM SKEE-BALL
Rediscover your skee-ball skills at kitschy Salem Willows Arcade, a scenic waterfront park in Salem, and win your date a plastic prize. Later, head to Bambolina for wood-fired pizza in a casually elegant atmosphere, then mosey across the street to Notch Brewing and sample session-style craft beers while you relax in the outdoor beer garden overlooking the South River.
> Salem Willows Arcade, 167 Fort Avenue, Salem, 978-745-0251, willowsarcade.com; Bambolina, 288 Derby Street, Salem, 978-594-8709, bambolinarestaurant.com; Notch Brewing, 283 Derby Street, Salem, 978-238-9060, notchbrewing.com
23. RETRO FLICKS
Catch a film or jazz show at the Luna Theater, an independent theater housed in a converted mill building that has plush seats, craft beer, retro arcade games, and free cult movies on “Weirdo Wednesday.” No cover for the live jazz shows on Thursday nights. If you arrive hungry, Coffee and Cotton down the hall makes great sandwiches and espresso drinks.
24. FEEL-GOOD LAUGHS
Share a seductress wrap and an Aphrodite hummus bowl for a nourishing organic meal at Life Alive in Cambridge. Stroll around the corner to catch a show at the acclaimed ImprovBoston, where you could become part of this spontaneous comedy experience. Shows run Wednesday through Saturday, and reservations are required.
25. TWILIGHT CRUISING
Rent a sailboat for a golden late-afternoon hour at the Jamaica Pond Boathouse. Cruise among the ducks, geese, and cormorants, then walk the pond path before skipping over to Centre Street for imaginative cocktails and an intimate dinner at Ten Tables (reservations recommended).
> Jamaica Pond Boathouse, 507 Jamaicaway, Jamaica Plain, 617-522-5061 (in season); Ten Tables, 597 Centre Street, Jamaica Plain, 617-524-8810, tentables.net
26. PLANESIDE PICNIC
Order take-out dumplings and ramen from Wagamama, then head over to the Institute of Contemporary Art for a harborside picnic on the museum’s back deck. Watch the nighttime lights in motion as boats sail by and planes soar off the runway at Logan Airport just across the channel. Walk off dinner with a long and lazy stroll along the waterfront.
27. DUMPLING ROMANCE
You never really know a person until you’ve shared dumplings with ’em. The best are at Winsor Dim Sum House & Bar in Quincy (there’s a smaller sister version in Chinatown, with longer waits). Order fresher-than-fresh pork buns and noodles from a cart or menu, and sample everything from tripe to clams in black bean sauce. Best of all, you’ll pay under $25 for the whole adventure (cash only).
> Winsor Dim Sum House & Bar, 706 Hancock Street, Quincy, 617-481-5383; winsordimsum.com
28. GAMING AROUND
Invite another couple or two and check out the mind-bending fun at Puzzle Break Newton, where you’re “locked” into a fanciful room — The Grimm Escape is a twisty fairy tale theme — and collectively tasked with discovering clues that will help you unlock the door to the outside world. Celebrate your escape with dinner and margaritas just around the corner at Cafe Sol Azteca.
29. LEISURELY PICNICKING
Gather a picnic lunch (Savenor’s or DeLuca’s for sandwiches, Cafe Jaffa for mezze staples and wraps) and head over to the Back Bay stretch of the Esplanade, where trees provide ample shade for prime blanket real estate. After a lounge and lunch, walk the trail to Community Boating near the Charles/MGH T stop, where you can watch amateurs (and pros) set up their sails and dangle your feet once the river warms up.
> Savenor’s Market, 160 Charles Street, Boston, 617-723-6328, savenorsmarket.com; DeLuca’s Market, 239 Newbury Street, Boston, 617-262-5990, delucasmarket.com; Cafe Jaffa, 48 Gloucester Street, Boston, 617-536-0230, cafejaffa.net; Community Boating, 21 David G. Mugar Way, Boston, 617-523-1038, community-boating.org
30. PHANTOM COCKTAILS
The Haunted Boston Ghost Tour starts at the Central Burying Ground cemetery and takes you through some of Boston’s creepiest attractions. Afterward, grab a nerve-soothing nightcap at the Omni Parker House, where the barkeeps are usually willing to put up with some questioning about the hotel’s supernatural residents. Indulge in a slice of the Boston cream pie, made in the kitchen where it was invented.