Our American Islands List

Recently I was talking with my friend Pia on her podcast, “Everything is the Best,” and she asked me about an island off the coast of Georgia that she’d seen on our Yolo TikTok (yes, we do have a TikTok!). When I told her that Cumberland Island was home to one of my favorite hotels in the world—the Greyfield Inn—she was surprised, remarking that that while she (being married to an Italian) is so familiar with islands like Ponza and Sicily, she knows way less about islands in our own backyard.

Part of this is because it’s incredibly hard to find them. There just isn’t a site that puts together all the small, charming, family-owned properties that we crave—and those places don’t have marketing budgets to attract the travel writers/content creators who would bring them into our world. So with international flights pricing painfully high this summer, we decided to research the fringes of this continent—islands off the U.S. coasts, or adjacent—and places to stay. 

There’s something about the smallness of island life that is so symbolic of the freedom of summer: riding bikes to the beach barefoot, daily trips to seafood shacks and ice cream stands, and navigating your way around via the placement of lighthouses—lots of lighthouses! Some of my favorite travel memories are from summer vacations in the Northeast. For years we went to Maine—one August, we rented a great old house on the water on Chebeague Island and did nothing but ride bikes, go clam-digging, swim, beachcomb, eat soft-serve, play Uno, and watch the sunset. (I found this note (below) that Clara made when she was around 9 that sums it up perfectly!) And while we as a family spend so much time in Europe now (which really started when I went to Traveler in 2013 and then once we bought a house in France in 2015), I find myself longing for those hallmarks of the American summer and the ease and simplicity that exists when you’re on your own turf.

Arguably, renting a house is the way to go in a lot of these places. But if you’re priced/booked out or don’t want to commit to a full week, our list—of inns, B&Bs, and small hotels (and a couple of special rentals) on islands (or peninsulas!)—should give you a good start. It’s hardly comprehensive: there are over 4,600 islands off the coast of Maine alone! But we researched it through a mix of shaking down friends for their favorites, and extensive Google deep dives—meaning that we can’t personally vouch for them all, but they passed muster via their websites/reviews. Many properties on the list are super affordable, and a handful seem like worthwhile splurges (especially if you’re saving on airfare). And anyhow, we can take some amount of doily and lace (or “Life’s a Beach” throw pillows) in exchange for location. Because the point is that you won’t spend much time indoors anyway.

So here you go, proceeding clockwise from the northeast, along the contiguous US (and a little bit of Canada). We’ll deal with Hawaii on its own another time!