With their enchanting ambience and impeccably good taste, Boston’s restaurants are natural charmers with no shortage of smooth moves. Whatever you’re looking for, ambience-wise, the city’s got you covered. In the North End, Carmen has you covered if you’re looking for a humble, traditional romantic evening with roses, red wine and candlelight; in the Leather District, o ya offers more lavish indulgence (because nothing says love like an $800 dinner). Most romantic eateries here are small and intimate—but a notable exception is Top of the Hub, with its panoramic views of the city skyline. Working there through my college years, I played bit parts in more first wedding anniversary dinners, awkward first dates and marriage proposals than I can count. Trust me, the ultimate romantic touch to an evening is a dining room full of well-wishing strangers clapping for a proud declaration of a couple’s love.
This restaurant, like its menu, is quaint with an understated eccentricity—and serves up one of Boston’s most extravagant dining experiences. Try the fried Kumamoto oyster nigiri, drizzled with yuzu kosho aioli and topped with a dollop of squid-ink bubbles. A pair of seats at the chef’s counter grant a front-row view into the alluring world of world-class sushi preparation.
Homey, warm and inviting, this Jamaica Plain restaurant makes dining out feel like a cozy night in. When founder Krista Kranyak first opened it in 2002, she was the only waitress on the floor, and the only one needed. The menu is delightful, unexpected and daring, highlighted with pastas, meats and sausages all handmade on premises.
Dimly lit, quiet and intimate, this tiny trattoria in North Square has just nine candlelit tables, which seem to be a world away from the usual North End hubbub. Share a bottle of Chianti or Barolo with a couple of tasty small plates from the bar while perusing the menu.
Top of the Hub
From fifty-two stories above Back Bay, this dramatic venue lets you watch night fall over the city while sipping champagne with your sweetie. Tables against the window can’t be guaranteed with a reservation, but making one early, right when the dining room opens, can almost assure you a worthy view. You’ll also want to linger into the late evening to enjoy the live jazz band in the lounge.
This spot is the failsafe date night go-to in the inherently romantic Beacon Hill neighborhood. In the midst of winter, sitting concealed in this charming Charles Street cellar means cozying up to the fireplace with your honey; in summer, it means dining out in the elegant, “secret garden”-like, ivy-covered courtyard.