Doliver Island, ME
Penobscot Bay is home to more than one furnished island for rent. Doliver isn’t one of them. It’s tennis-court-size and rocky, with one tree and a sign. Stop at the Old Quarry Store, in Stonington, on Deer Isle, to pick up a kayak, a chart, and a fog forecast (207-367-8977). Doliver is a half-day’s paddle south. Spend a day or two visiting some of Doliver’s 60-plus granite neighbors, many managed by the Maine Island Trail Association. Permits aren’t necessary; getting there early is.
Cayo Costa State Park, FL
This 2,400-acre barrier island is the Sunshine State as it used to be. No highways, just mangrove swamps, packed-shell bike trails, and 7.5 miles of dune-studded beach. Bring a spinner, live shrimp, and a 12-pound line. Drive from Fort Myers to Pine Island and catch the hourlong ferry ride ($35 round-trip, reservations required; tropicstarcruises.com). Drop your gear in one of 12 cabins ($30; floridastateparks.org/cayocosta), wade into the surf, and go get dinner: redfish, snook, or speckled sea trout (excellent grilled with lemon).
Eagle Island, GA
If you prefer your solitude with a mint julep, consider Eagle Island. A 15-minute boat ride speeds guests from Darien, Georgia, to this private ten-acre kingdom topped with a ten-bed reclaimed-cypress lodge (from $400; privateislandsofgeorgia.com). Take the resident kayak for a spin, spy on nesting bald eagles, pluck dinner from the blue-crab traps—or just settle for a julep in the hot tub.
Posey Island State Park, WA
You can stay on this one-acre, two-campsite spit, at the elbow of the Salish Sea, only if you arrive by man- or wind-powered means, so your neighbors are kayakers, not powerboaters (campsites, $9; parks.wa.gov). Catch the ferry from Anacortes to Friday Harbor (from $35; wsdot.wa.gov/ferries). Drive ten miles to Roche Harbor and rent a sea kayak (sanjuanislandoutfitters.com) for the easy quarter-mile trip to Posey, and watch out for breaching orcas as you dip your paddle.