Eight romantic summer dates in the Boston area

The Yotel Sky Lounge in the Seaport.
Marlo Marketing/Communications
The Yotel Sky Lounge in the Seaport.

The weather is steamy, the sun is shining, and your thoughts have turned to romance — exciting and new, or maybe old and comfortable, and you want to spice things up. Here are eight summertime date ideas in Boston and beyond, whether you hope to woo a potential paramour or rekindle a flame.

The Mystery Matchers: Rooftop R&B

You saw, you swiped, you settled on a date. But you’re nervous! Fear not: Head to the Seaport’s Yotel (65 Seaport Blvd.) on Thursdays at 8 p.m. to listen to crooner Louie Bello, whose sultry R&B tunes will drown out any hint of awkward conversation. The candlelit Sky Lounge has panoramic neighborhood views and potent cocktails — and if things go well after a couple of “hot & dirty” ’tinis, you can continue the evening across the street at Babbo (Italian) or Committee (Greek, with a lovely patio). Not a match? Drown your sorrows in cheese fries at Shake Shack.

The Second Daters: Al fresco films

Things went well the first time, and you’ve moved on from a quick weeknight drink to a Friday evening commitment. Start by strolling the Greenway and marveling at its new “Glow” exhibit, featuring vintage neon signs, illuminated until 10 p.m. If only your night could conclude at the late, lamented Siesta Motel in Saugus! Then squire your companion across the street to one of the films in the Boston Harbor Hotel’s Movies by Moonlight series, which start at dusk each Friday. View screen classics like “When Harry Met Sally” and “Breakfast at Tiffany’s” from a heated patio at the hotel’s Rowes Wharf Sea Grille (70 Rowes Wharf).;

The Whimsical Wooers: Moonlit cruises


Perhaps you lack access to a yacht and a private chef, but you still yearn to romance your beloved on the ocean — with gourmet food, naturally. Consider Chefs at Sea, a three-hour cruise on Gloucester Harbor aboard a Beauport cruise liner, hosted by some of Boston’s top chefs. Board at 6:30 p.m. on Wednesday evenings for live entertainment and dancing, a cooking demonstration, and multi-course meals courtesy of Jason Bond (Bondir), Rory Lee (Moona), Kevin O’Donnell and Michael Lombardi (SRV), and more. There’s a cash bar, too. Taking the train? A Beauport hotel shuttle — maybe a Range Rover — will whisk you from the station to the Rowe Square dock. Tickets are $80 per person, and cruises commence July 11.

The Nightcrawlers: An evening in Central Square

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Begin your night at the Central Square Theater (450 Massachusetts Ave.) with a performance of “Les Liaisons Dangereuses,” a frisky French tale of romance and rivalry featuring, in this interpretation, sword-fighting and full nudity. (The show runs through July 1; tickets are $16 and up.) After that, stroll to A4cade (292 Massachusetts Ave.) for tiki drinks, pinball, skeeball, and retro video games. Finally, duck into Little Donkey (505 Massachusetts Ave.) for a late-night dessert with indulgences such as beaters of fresh cookie dough and creamsicles, served from 11 p.m. until midnight.

The Charitable Romantics: Poolside barbecues

Recline poolside on the roof of the Colonnade Hotel (120 Huntington Ave.) at a backyard barbecue-style feast with food from chefs including Cultivar’s Mary Dumont, Puritan and Company’s Will Gilson, Tapestry’s Meghann Ward, and the Tip Tap Room’s Brian Poe, plus cocktail pairings. Dinners happen on alternating Tuesdays beginning June 12 at 5:30 p.m. Tickets are $30, and sales benefit anti-hunger organization Share Our Strength’s No Kid Hungry. Your date will go swimmingly.;

The Moonstruck Musicians: Outdoor Back Bay concerts

Slip out of work a tiny bit early to lounge in the Prudential Center’s South Garden (800 Boylston St.) while listening to Berklee musicians on Thursdays from 5 to 7 p.m. There’s a variety of genres at these free shows, from drummer Santanio Jackson to jazz by the Vlade Guigni Trio to pianist Rina Yamazaki. Grab a couple of glasses of wine at an al fresco bar provided by Porto restaurant while you groove (bring cash). After that, amble down the block to Bar Boulud’s new oyster bar (776 Boylston St.) for a glass of rosé and a shareable seafood tower.;

The Land Lubbers: A day trip to Worcester

If beach traffic makes you grouchy — or you’re not sure you want to be trapped in a car with your date for two hours — head inland to Worcester while laughing at those sad characters heading eastbound on the Mass Pike. Why? There’s a burgeoning shopping and dining scene. Grab a drink at Wormtown Brewery (72 Shrewsbury St.) — known for its DDark Roasted Brew collaboration with Dunkin’ Donuts — and visit Worcester Wares (50 Foster St.), a boutique that sells crafts from local makers, from city-themed puzzles to silver-plated Worcester tie clips. Dignified! Then visit the Crompton Collective (138 Green St.), a boutique marketplace inside a converted Worcester mill, with vendors selling everything from antiques to cider. Before dinner, stop at Table Talk’s retail shop (153 Green St.) to grab pie for the road (note: they close at 5 p.m. on Saturdays). Then visit Deadhorse Hill (281 Main St.) for a massive, shareable “horse feast.” No set menu; let the chef surprise you with things like chips, walnut butter, and caviar or scallop crudo in tea broth.;;;;

The Sporty Soulmates: Sunday cycles and sips through Cambridge


Grab a Blue Bike at the Alewife MBTA stop. Then take the Alewife Linear Park to Urban Hearth (2263 Massachusetts Ave.), a cozy spot for coffee and shareable, savory snacks like shakshuka skillets and wild mushroom tartine. Then cycle toward Harvard Square and the Charles Hotel’s Italian restaurant, Benedetto (1 Bennett St.), for an aperitivo on the patio. (There’s bike parking at the lower courtyard.) Or visit the new oyster bar at Les Sablons (2 Bennett St.) across the street for lobster rolls and cocktails courtesy mixology maven Jackson Cannon (The Hawthorne). Finally, coast down Memorial Drive — closed to cars on Sundays — toward Kendall Square. Plop onto a wicker swing at Catalyst’s brand-new patio (300 Technology Square), sip a glass of rosé, and carbo-load with pappardelle with mint and braised lamb for the ride back. There’s plenty of on-street bike parking nearby.;;;;

Kara Baskin can be reached at