Martha's Vineyard, Massachusetts
Contrary to (somewhat) popular belief, Martha’s Vineyard does not belong to lifestyle entrepreneur Martha Stewart. This small island off Cape Cod has timeless appeal, a distinct lack of chain restaurants, illuminating summertime celebrations, and a string of blissed-out public beaches. A New England stunner, it comprises six storybook villages in two regions: "up-island" and "down-island." Look no further than Oak Bluffs and Edgartown in "down-island" for shopping, buzzing bars, and top-notch dining. Running between these two towns is the 2-mile-long Joseph Sylvia State Beach, where the iconic shark pandemonium scene in “Jaws“ was filmed. "Up-island" is more rural and it’s home to Aquinnah Cliffs, which are orangey-red and not to be missed.
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St. John, US Virgin Islands
Come to the U.S. Virgin Islands for Caribbean magic, splashings of rum, and lashings of sun. This archipelagic paradise is comprised of St. Croix, St. John, and St. Thomas, as well as dozens of smaller dreamy islets and cays. All three major islands boast tasty eateries, year-round warm weather, and beaches of indescribable beauty, but St. John takes the cake for nature evangelists. The 5,500-acre Virgin Island National Park takes up two-thirds of the island and it charms with its historic ruins, hiking trails in the dozens, and a 225-yard underwater trail for snorkeling at Trunk Bay.