Fantasy Island: The Most Romantic Locations to Visit on Martha’s Vineyard

By: Kevin Murray |

Hands down the best months on Martha’s Vineyard for a romantic getaway are September and early October. The weather is still great and the kids are all back in school which means less congestion on the island. The Vineyard has become a hot bed for weddings during these months – creating an atmosphere full of romance, with so many people visiting the island in the name of love. While there are a plethora of places to dine and get your drink on, I’ll focus on the locations that are free of charge, with atmospheres that’ll make both of you look around and say “ahhhhhh.”


Cottage City, Oak Bluffs

With pastel colors abundant, this ensemble of little gingerbread houses will surely be one of the more unique sights you’ll see in your life. Many of the houses were originally built in the 1800’s, providing a side of rich history to go along with that Easter egg color eye candy (and the semi creepy vibe that this is where Wonka let the Oompa Loompas live).

Tip: Try to avoid this place during the middle of the day – hordes of tourists will be littered all over the place taking pictures and cluelessly walking on people’s porches. Your best bet is to visit late in the evening. It’s also a grate spot for a quite, late night promenade – Cottage City is softly lit and there’s a no noise ordinance after 10:00PM.

Lamberts Cove Beach

Lambert’s Cove Beach, West Tisbury

The approach to Lambert’s Cove beach in the fall is something straight out of a novel . You’re serenaded by a light sea breeze with a perfect mixture of forest and beach, while the sounds of leaves crunch under your feet – leading up to what feels like a stairway to heaven made out of sand.

Tip: Lambert’s Cove Inn & Restaurant is right down the street if you’re looking for a romantic fine dining experience off the beaten path (they have call ahead seating enabling you to plan out your night in advance).


State Beach Sunrise, Oak Bluffs/Edgartown

If walking up at the crack of dawn is your cup of tea – State Beach sunrise is for you.  The beach is very narrow, but there’s plenty of parking and the walk to the water is never more than 50 yards from the street.

Tip: You could always sleep on the beach together and make this breathtaking view your alarm clock. You’re almost guaranteed to not be bothered on this beach at night shall you choose to take that route (not that I would know or anything).


Clay Cliffs, Aquinnah

The cliffs provide a panoramic shot all postcards are jealous of. While the views from up top are amazing, the sights from below are even better. It’s difficult to access this beach at the bottom of the cliffs during the summer with private zoning and the naked old folks sun tanning (nude beach). The  fall season allows better access and lessens the chance of seeing a 60 year-old guys junk.

Tip: Bring your camera and make sure the battery is charged – you’ll be in awe. Also, stop by Chilmark Chocolates on your way and satisfy your sweet tooth!

Edgartown Lighthouse

Edgartown Lighthouse, Edgartown

Sitting out front of the fabulous Harbor View Hotel is the Edgartown Lighthouse – it’s easily accessible and a pleasant walk off North Water St.

Tip: Extend your walk through town before visiting the lighthouse. The brick walkways and white picket fences of Edgartown make it one of the more aesthetically pleasing towns in New England – creating the perfect evening stroll.


East Beach, Chappaquiddick Island.

Point blank, you can pretty much have sex on this beach during the day in the off-season and no one would catch you – I’m not even joking.  With miles of coastline and very few beach goers, you can get away with anything out here . Taking my mind out of the gutter for a moment – this is also a great spot for fishing from the shoreline. A few parking spots are located adjacent to the Dike Bridge (yes, scene of the Ted Kennedy incident).

Tip: You can find the Chappy ferry at the end of Daggett St. in Edgartown. East Beach is best reached by car or bike as it’s a few miles from the ferry and at the end of a long dirt road. I’d suggest packing a cooler with plenty to eat and drink if you’re going to make a beach day (the one store on Chappy has the bare essentials and resembles a shack).


Memensha Sunset, Chilmark

The sunsets here are legendary. There’s a perfect angle out to the ocean in between Martha’s Vineyard and the Elizabeth Islands that clears the way for the true star of the evening – the setting sun.

Tip: Parking here is very scarce, especially on the weekends, so it’s best to arrive at least an hour before sunset if not more. Call ahead to Larsen’s or Menemsha Fish Market to have a Seafood dinner ready prior to sunset! If you really want to be alone you, can drive around to Lobsterville Beach some 25 minutes away and get more privacy. The view of the sun isn’t direct, but the sunset still spectacular (this photo is actually from Lobsterville Beach).

Oh, how do you get to the island? I got you covered.

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