Our Complete Getaway Guide
A last, lingering toast to summer — bakery pastries, golden hour picnics, and a lighthouse at the end of the road.
There is something wonderful about planning one final, proper getaway for the last official weekend of summer, and we can’t think of a better place to do it than the Hamptons. This year, we’re sharing every detail of our own long weekend itinerary, from what we packed to where to sleep to where to watch the sun go down, so you can put together a getaway of your own without any of the guesswork.
Where to stay. For lodging, we have two favorites depending on the mood you’re after. If you want something polished and easy, we recommend the Hilton in Sag Harbor, right in the heart of a village that still feels like the classic East Coast. If you’re leaning toward something a little more tucked away and cottage-like, book one of the cottages at The Roundtree in Amagansett — they’re charming, private, and exactly the kind of place that makes a weekend feel like a proper escape.
Mornings. Start every morning at Carissa’s the Bakery. It is, quite simply, a wonderful spot to grab a pastry and coffee, or if the day calls for something cooler, a cold drink and a full brunch. If the weather cooperates, sit outside — there is nothing better than a warm morning, a good pastry, and nowhere in particular to be.
Beach days. Naturally, a Hamptons weekend calls for time at the beach, and we spend plenty of it simply relaxing in the sun. But our favorite tradition is packing provisions for a golden hour picnic once the beach begins to clear out. There’s a particular quality to the light and the pace of that hour — the day seems to slow down just a little, as though it wants to hold onto the last moments of summer sun a bit longer. For provisions, we always stop at Round Swamp, Loaves & Fishes, or Citarella Gourmet Market — any one of the three will set you up with everything you need for a beautiful spread on the sand.
A drive to the lighthouse. No Hamptons weekend feels complete without a drive out to Montauk Point Lighthouse. The views out over Block Island Sound and the Atlantic Ocean are the kind that make you stop scrolling and just look for a while. It’s a lovely afternoon detour, and well worth the drive to the very tip of the island.
Dinner on the way back. On your way back into the Hamptons, stop for a casual dinner at LUNCH, or if you’re after something even more relaxed — think flip-flops and a picnic table — pull over at Clam Bar in Amagansett. Both are exactly the kind of easy, unfussy dinner a beach day deserves.
Window shopping. The Hamptons offer no shortage of wonderful shopping, but for a slightly less crowded, classic East Coast feel, we recommend strolling the streets of Sag Harbor. It has all the charm without quite as much of the crowd, and it makes for a lovely, slow afternoon.
A special dinner. For the one truly special dinner of the weekend, make a reservation at Vine Street Cafe. Yes, it requires taking the ferry across to Shelter Island, but this wonderful little spot — highly regarded by longtime patron Ina Garten herself — is absolutely worth the trip. Consider it the perfect way to close out the weekend.
Put it all together and you have a long weekend that honors summer properly: good food, good light, a little sand between your toes, and a lovely lingering beach day sunset before the season turns. We can’t think of a better way to send summer off.
