The Destination: Sumba, Indonesia

The Itinerary: Skip Bali in favor of something even more remote: Sumba, an as-of-now still relatively under-the-radar gem of an Indonesian island, where unspoiled landscapes, a vibrant local culture, and natural pools and waterfalls join for a memorable trip that still feels removed from the grips of overtourism. Right now, it’s peak dry season—take advantage of beautiful weather and see the natural beauty up close.

The Accommodation to Book: It’s no longer the only hotel on the island, but for a luxury resort, Nihi Sumba is still top choice. Comprised of 31 villas set along the beach, it’s private and indulgent, with a packed activities list that ranges from sunset horseback riding to spearfishing. Its wellness program, dubbed “Wild Wellness,” is also noteworthy—there’s a spa, yes, but you’ll also find more unique menu offerings including water meditation and equine therapy.

For the Person Still Not Over Love Story

Sandy Neck lighthouse and cottages at the tip of Sandy Neck Peninsula in West Barnstable Massachusetts on an early November morning.KenWiedemann

The Destination: Cape Cod, Massachusetts

The Itinerary: Live out your East Coast prep dreams in the ultimate haven of New England charm. Connected to both Martha’s Vineyard and Nantucket via ferry, this crescent-shaped stretch of land is not all ice cream stands and sandy dunes—though they’re easy to find if you seek them out. Situate yourself closer to the coastline, so you can spend days biking to the beach and creating a ranked list of the best lobster rolls, and spend evenings watching the sun melt into the horizon. All in your finest J.Crew, of course.

The Accommodation to Book: Wellfleet Cottage by the Sea is just that: A cozy, quaint, butter yellow-painted cottage with direct access to the beach. It can accommodate up to four people, but it’s also a sweet option for a couple—you can hear the waves crashing each night, a real-life white noise machine.