Popping the Question: Where to Propose in Boston

Eight perfect locales to ask her or him, "Will you marry me?"

When you’ve made it your mission to ask for her (or his!) hand in Boston, these locales set the perfect mood. 

Top of the Hub

It’s no wonder The Travel Channel dubbed this one of the world’s most romantic dining destinations. At 52 stories above the city, 360-degree views put the world at her feet. The staff is well versed in the language of love—thousands of Boston proposals have happened here. A call ahead ensures an intimate table and a coordinated effort, with everything from a plane banner fly-by to a ring atop her chocolate cake.

800 Boylston St., Boston, MA, 617.536.1775


Boston's Public Garden in spring

Public Garden

Complete with a pond and romantic draping willows, America’s first public botanical garden sets an urban lover’s scene. Ask near one of its sculptures (perhaps the graceful bronze angel) for a private moment, while a lagoon bridge proposal ensures an audience’s applause.

Boylston Street at Arlington Street, Boston, MA


Rowes Wharf

The iconic arch of the Boston Harbor Hotel sits on the ocean’s edge and next to a mega-yacht marina. Get your heart racing with a spin on the celebrated Rotunda ice skating rink that pops up in winter, and then make her heart race with a romantic proposal and beautiful water views as the backdrop.

70 Rowes Wharf, Boston, MA


Isabella Stewart Gardner Museum

Starry-eyed art buffs capture quiet time in the courtyard of this premier art museum that also happens to cultivate the essence of romance in its interior courtyard rife with lush greens, jade trees, and sculptures. Ask him to be yours in the gorgeous cloisters that frame the area

25 Evans Way, Boston, MA, 617.566.1401


The winter-lit trellis at Christopher Columbus Park

Christopher Columbus Waterfront Park

Following a romantic evening of wining and dining in the North End, stroll over to this beautiful neighborhood park to propose. Asking for her hand beneath the softly glowing blue-lighted winter trellis. 

Atlantic Avenue at Richmond Street, Boston, MA


The Frog Pond skating rink on Boston Common

Frog Pond Skating Rink

Straight out of a Currier & Ives painting, the skating scene in the country’s oldest public park is a romantic winter wonderland set with strolling couples, steaming cups of hot cocoa and trees draped in holiday lights. Bundle up, strap on rented skates, and enjoy an evening of hand-in-hand skating. Spin down onto one knee to accomplish your quest—and be prepared foroohs and aahs from your fellow skaters.

Boston Common, Beacon Street near Park Street, Boston, MA, 617.635.2120


Summer on Commonwealth Avenue Mall

Commonwealth Avenue Mall

When city slickers celebrate love, they like to do it in city style. Surround yourself with Boston’s iconic brownstones as you stroll this historical avenue inspired by the grand boulevards of Paris. The shady, tree-filled promenade runs from the Public Garden to Massachusetts Avenue, so you’ll have several blocks to rev up your nerve to propose. Sculptures along the way teach you Boston’s history while you plan your own future.

Commonwealth Avenue at Arlington Street, Boston, MA 


Castle Island

In fair weather, finding a spot on the grassy slopes of Castle Island and Fort Independence is a fit place for a king to ask his queen for her hand. Steal a moment to enjoy the panoramic view of Boston Harbor and its islands.

Day Boulevard, South Boston, MA