10 Under-the-Radar U.S. Islands

This “little sister” to popular Sanibel Island—which visitors must pass through for access, after crossing the causeway from Fort Myers—is lush with foliage and once attracted the late painter Robert Rauschenberg. From the wildly colorful and quirky Bubble Room (serving slices of three-layer cakes and roasted duck in rooms stuffed with little curiosities) to—at the northern-most end—South Seas Island Resort, tucked into a 330-acre nature preserve with vintage-trolley service on property, this island is delightfully steeped in the timeless past.

Settled by Ojibwe tribes and adjacent to the Apostle Islands National Lakeshore the largest of the Apostle Islands, with 300 or so residents, is accessed from the cute and charming town of Bayfield. Trips are either by personal kayak, canoe or sailboat or—more commonly—the Madeline Island Ferry Line. Once on island, hike along Big Bay State Park’s seven miles of trails or—two blocks from the ferry landing—relax at Joni’s Beach. Book one of six rooms at FARMHOUSE: HAYLOFT, with its farm-to-table breakfast and chic décor.

You’ve already done Oahu and Kauai—what’s next? How about Molokai, a 38-mile-long island with a population of only 7,400 people and lots of unspoiled landscape for you to either sink your toes (hello, sand) or hiking boots into. After scoring jelly-filled “hot bread” doughnuts at Kanemitsu’s Bakery, a James Beard Award nominee that’s been in business for 80 years, visit white-sand shorelines at Papohaku Beach or soaring sea cliffs (tallest in the world) at Kalaupapa National Historical Park. You won’t find a Marriott or Hilton here, just cottages and condos for a more intimate stay.

Instead of taking a quick 60-minute ferry to Santa Catalina Island like every Californian does at least once, hop on an Island Packers four-hour ferry ride from Ventura…to another island within Channel Islands National Park. Although not populated by humans, the 9,500-acre San Miguel Island boasts 27 miles of coastline and unique wildlife (like the deer mouse and island fox) that’s only found in the Channel Islands. The Chumash subsisted on the island’s resources for around 12,000 years. Be prepared to either pitch a tent or take a ferry back before sundown; there are no hotels on the island.

Proof Daufuskie Island (home to 400 locals) is special: the entire island was named to National Register of Historic Places. It’s also home to a high concentration of Gullah, a population of African-Americans who reside in coastal areas of the Lowcountry region and speak a Creole dialect. Reach the island (just off the coast of Savannah, Georgia and Hilton Head, South Carolina) by boat or the Daufuskie Island Ferry (rent a bicycle or golf cart upon arrival). With two distilleries, art galleries, Marsh Tacky horses that nearly outnumber locals, and locally caught crab with sides of okra, butter beans, peas and yams, a day trip might feel like you’ve traveled worlds away.

The Forbes may own four of the Elizabeth Islands, but Cuttyhunk Island (famed for its striped-bass fishing and a popular summer-home destination, with a few B&Bs) is open to the public. Catch the ferry from New Bedford to Cuttyhunk. Initially settled by the Brits in 1641, they named this chain of small islands is off the southern coast of Cape Cod after Elizabeth I, who was the ruling British monarch at the time.

No, that’s not a typo. There’s an island in this heartland state. Once on Sabula (home to only 575 residents and within the Mississippi River, 45 miles south of Dubuque and a three-hour drive from Chicago), wander around the nearby 4,000-acre Green Island Wildlife Management Area, bunk overnight in a century-old B&B (such as La Belle Porte Bed and Breakfast) or camp at South Sabula Lake Campground. There’s even a bar called Homeport with river views and occasional live music.

Home to wild Chincoteague ponies and the Chincoteague National Wildlife Refuge, Chincoteague Island is off Virginia’s eastern shore, in the Atlantic Ocean. The only way to arrive is by a causeway (State Route 175, also called Chincoteague Road) and once on island you can use the trolley to tool around.

This 26,000-acre island 10 miles west of Portland may be nearly double the size of Manhattan’s 14,600 acres, but only 1,078 people live here. You’ll find it 30 minutes north of Portland, where the Willamette and Columbia Rivers meet. The island is a paradise for kayakers and bicyclists, and when in season (early June through mid-August), locals flock here to pick berries, particularly at Sauvie Island Farms.

Reachable via a 45-minute ferry (see options here) traveling 10 miles from the mainland (Crisfield, Maryland), this Chesapeake Bay island is celebrated for its crab cakes and leisurely hikes at Glenn Martin National Wildlife Refuge, and also the nine-layer Smith Island Cake. This delicacy features very thin layers of yellow cake frosted with fudge. Stick a fork into this special cake after dinner out—and order one online the next time you miss it, via Smith Island Cakes.