U.S. Virgin Islands
With three main islands and 50 smaller cays, there is a lot to see in the USVI. Why not go island-hopping via ferry or flight and get a taste of them all? Better yet, charter your own boat and sail this paradise in the Antilles. St. Thomas, the most popular entry point, has a little of everything: white sand beaches, rocky hills, luxury resorts, and dining and shopping in the port town of Charlotte Amalie. Next door, St. John is the quieter isle, home to Virgin Islands National Park with its jungle hiking, snorkeling and the acclaimed beach at Trunk Bay. Farther south, St. Croix is bigger and broader and formed from coral — and it's the home of Cruzan Rum, served throughout the islands.
A Caribbean escape is often a winter pursuit, but the U.S. Virgin Islands have a few things going for them right now: Hurricane season won't arrive until June (lasting through November, though the peak period is August through October). They're open to Americans with a negative COVID-19 test, and you won't need a test to return. The U.S. territory has had fewer cases per capita than every state but Hawaii, and they'd like to keep it that way, with a strict mask mandate, even on beaches. The isles have also made great progress in rebuilding after the devastating hurricanes Irma and Maria in 2017, when many hotels were destroyed. And with the usual cruise traffic curtailed, you just might have more of the beach to yourself.
Don't miss: Locally sourced Caribbean chowder and curries; climbing the historic 99 Steps on St. Thomas; hiking at Virgin Islands National Park; snorkeling or diving at Buck Island Reef; horseback riding on St. Croix.
Getting there: Sun Country resumes nonstop service to St. Thomas next winter; connecting flights to St. Thomas and St. Croix are year-round. Fall hurricane season might offer deals for the daring. Travel hackers could also fly nonstop to nearby San Juan, Puerto Rico, and book a side trip to the USVI.
Note: Visitors must submit proof of a negative COVID-19 test, taken within five days of arrival, at usvitravelportal.com.
Martha's Vineyard
The Kennedys and Obamas famously visited Martha's Vineyard, but so did Grant, Coolidge, Franklin Roosevelt, Nixon and Clinton. Sure, that is rarefied presidential air — but it's the salty air that counts. Most visitors to this triangular island just south of Massachusetts' Cape Cod come for the beaches and the laid-back lifestyle, away from the mainland. But they also get protected woods and marshes, villages of gingerbread cottages and clapboard mansions, harbors lined with working fishing boats and towering sailboats and a sandwich that defines summer in New England, the lobster roll. It is a beachy escape enveloped in pure Americana.
Six distinct villages dot the island. Based on old seafaring terms borrowed by islanders, the towns are either up-island or down-island. For the nautically naive, up-island means west and down-island means east, because the whaling ships that once dominated the harbor "headed up" when traveling west. Up-island towns include Chilmark, West Tisbury and Aquinnah, where the Gay Head Lighthouse marks the westernmost spot. Down-island places include Edgartown, the oldest town; Oak Bluffs, an early enclave for freed slaves and now the island's tourist hub, and Vineyard Haven.
Don't miss: For a nighttime sugar fix, head to the back door of Back Door Donuts, in Oak Bluff, where doughnut business by day is conducted in the storefront, but out the back door at night, a quirky, long and delicious tradition. Martha's Vineyard Agricultural Society hosts the annual Livestock Show & Fair, slated for Aug. 19-22 in West Tisbury.