Cape Cod

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.

Just-caught seafood is Cape Cod’s claim to fame and if you’re only here for a few days, having a turkey sandwich for lunch just doesn’t feel right. Moby Dick’s, which has been family-operated since the 80’s, has the quaintness of a clam shack and the menu of a full-on restaurant, meaning that you can order an oyster platter, steamed lobster, and grilled fish in addition to the basics like chowder and fried clams. It’s also one of the few spots around with a respectable gluten-free offering.

In the land of never-ending seafood, this fine-dining spot in Falmouth is where you go for a really great steak, a veggie-rich salad, or house-made ravioli (though there is a good chance that it will be stuffed with lobster).

During the summer season, the Wellfleet Drive-In Theater grounds become a sort of meeting spot for the entire community. At night, it functions as an old school drive-in theater and during the day plays host to an adorable kids playground and miniature golf course. On the weekends, the space morphs into a sprawling flea market with dozens of stalls devoted to everything from kitschy Cape Cod memorabilia to one-of-a-kind antiques.

Entirely worth a day trip from anywhere else on the Cape, John Derian’s telltale mix-and-match style is on full display at his teeny Provincetown outpost, which happens to sit just steps from his summer home. Once you’re done picking through the intricate serving platters, paperweights, and cake stands in all their découpage glory head over to Nor’East Beer Garden for a dozen of the freshest Wellfleet oysters and a cold one or two. Staying overnight? With its insane ocean views and excellent restaurant, the centuries-old Red Inn is your best bet.

Nestled into a particularly picturesque nook of Pleasant Bay, this unapologetically grand resort is top-notch through and through—everything from the manicured lawns to private cabanas to the four stellar on-site restaurants has been meticulously thought out. There’s a world-class golf course, tennis, and an adults-only pool, but the real action is, as to be expected, at the beach, where you and the kiddos can take sailing lessons among other watersports and activities. Accommodations-wise, choose between sprawling rooms in the main house, rustic cottage-style suites, or a sprawling private villa.

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.