Chatham

Starting at Chatham and driving up the cape to the Easternmost tip of Provincetown—and stopping at the historic lighthouses along the way—is an iconic New England experience. While some are closed to the public, many will have staff on hand to share historically significant tidbits and even take you for a look inside. Best of all, there’s no need to pack a lunch: Each town you’ll pass will have plenty of can’t-go-wrong seafood shacks to choose from, where you can also always find the requisite soft-serve.

While you really can’t go wrong with any of the beaches along either Cape Cod Bay or the Atlantic Ocean side, this particular one, at the foot of a historic lighthouse, is unique in that you can swim (or wade) out to a beautiful sandbar where locals like to set out picnics and barbeques. While the surf can be too intense for the littles to handle on certain days, the beach is great for long seal-spotting strolls and shell-collecting expeditions. Fair warning: parking can be a pain, so consider biking.

This oceanside resort, complete with tennis courts, spa, and a fleet of charter boats, has been around for over a century and luckily, the main house has retained its understated glamour even after several updates. Whether you’re staying in the original main house or the newer stand-alone cottages or spa suites, the vibes are distinctly Cape Cod, with huge paned windows (a good chunk of the rooms have ocean views), plush beds, and shades of blue. The property is operational year-round and the deserted beach (the hotels sits on a private stretch) and ample roaring fireplaces make it an unforgettable stay off-season.