6 Places To Propose On Martha’s Vineyard (By Personality)

Whether your idea of a perfect place to propose is jumping out of an airplane or just in your living room, one thing is absolutely certain: you want your proposal to be one to remember. Polish the ring, pick out your spiffiest duds, and let your mind wander with romance because we’ve got 6 places to propose on Martha’s Vineyard sure to knock your love’s socks off.


Photo: Unsplash
Photo: Unsplash


Places To Propose On Martha’s Vineyard For Every Personality

For the Travel Buffs

If your love gets a thrill from planes, trains, and automobiles, grab lunch or breakfast alongside an unofficial airshow at the Right Fork Diner, located at the edge of the grassy airstrips of Katama Airfield. Chow down as the planes fly overhead, then catch a biplane for a scenic tour from the air and pop the question while flying through the sky.


rarebrick_20110403_4230For the Kids at Heart

Embrace your inner child with a proposal on the Flying Horses Carousel. This Martha’s Vineyard fixture is the oldest operating platform carousel in the U.S. — which is just a lovely metaphor for your impending marriage, doncha think?


For the Thrill Seekers

Before your hearts beat as one, get them pumping with a thrilling pre-proposal activity. Hop aboard or charter Mad Max Catamaran for a seaworthy excursion across the blue waters of the Nantucket Sound. Looking for a bit more adrenaline? Leap into your future together as you jump from the Memorial Bridge at State Beach. Sure, it’s only a 15 foot jump, but we hear there are sharks in these waters…


For the Foodies

For some people out there, deliciousness is next to romance. Grab your foodie significant other and treat them to a tasty morsel before treating them to forever. Our favorite foodie places to propose? Stay in the heart of Edgartown and pop the question on the front porch of Chesca’s Restaurant. For the future fiance with a sweet tooth, stop by the classic Martha’s Vineyard ice cream shop Mad Martha’s for a truly “sweet” moment.


Aquinnah Cliffs
Photo: Massachusetts Office of Travel & Tourism


For the Traditionalists

If you’re aiming for classic romance, look no further for a place to propose than the beach cliffs at Aquinnah. Pack a romantic picnic and take a stroll. As the sun falls behind the horizon and the water glistens yellow and red, pull the ring out and ask your love for forever.


For the Homebodies

Combine the best of Martha’s Vineyard’s romance with the comfort of home. Pop the question in a Vineyard Square Hotel & Suites luxury suite with friends and family waiting outside the door. Then, walk down the stairs to Chesca’s or our outdoor courtyard for a toast to your beautiful future together.

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