City Guide: Caroline Homlish on Martha's Vineyard

July 15, 2016

Our own Caroline Homlish is an expert when it comes to Martha's Vineyard. Not only did she grow up spending summers on the island but she also just had the most beautiful wedding there in June. Ahead of our private sale in Edgartown, we asked her to share some of her favorite spots!


Martha's Vineyard

Describe the city in three words:

Classic, Natural and Nautical




Menemsha at sunset.


For a Morning Coffee: Head to Rosewater in Edgartown for coffee, homemade granola and a spot on the patio.

For Cocktails: The Port Hunter for live music in Edgartown and The Atlantic for a drink and dinner right on the harbor.

For Ice Cream: Mad Martha’s Ice Cream. Do not be fooled by any of the other ice cream shops. This is the one. Favorite since we both were kids!


Three Restaurants You Love: The Red Cat in Oak Bluffs for local, seasonal and delicious food. Alchemy in Edgartown is one another one of our favorites, great bar and bistro. The Black Dog in Vineyard Haven is an island institution– get the chowder!


Favorite Activity for Kids: Flying Horses Carousel is the oldest working carousel in the US. Catch the brass ring and win a free ride!


Best Beach in MV: Up-Island beaches are the prettiest! Lucy Vincent, Aquinnah, and Squibnocket.


Best Place to Shop: Independent bookstores: Edgartown Books (they’ve got a great café out back) and Bunch of Grapes in Vineyard Haven.


Tourist Spot You Love: Aquinnah Lighthouse with a view of the cliffs.


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