A Long Weekend in Montauk
No overplanning required.
There are plenty of ways to spend a summer weekend. Some involve reservations, itineraries, and a schedule packed from morning to night.
Montauk works best when you leave a little room.
The best weekends out east usually follow the same rhythm. Coffee before the beach. A long stretch outside. Lunch that turns into the afternoon. Dinner that starts at sunset and ends whenever it ends.
You don't need much. A few good layers. A place near the water. And enough flexibility to follow the day wherever it goes.
The best weekends aren't packed with plans. They're built around a few good ones.
Where to stay
For a quieter side of Montauk, book a stay at Duryea's Sunset Cottages. Tucked along Fort Pond Bay, the newly opened cottages offer everything we love about summer weekends: waterfront views, cedar shingles, outdoor living, and easy access to the harbor.
If waking up steps from the ocean is more your speed, Marram remains one of the best beachfront stays in town. Simple, thoughtful, and centered around the beach, it captures the relaxed spirit that keeps people coming back year after year. Plus, they provide complimentary cruiser bikes for guests.
If you're traveling with family or a group, look for one of the waterfront cottages around Montauk Harbor or Fort Pond Bay. Many come with docks, outdoor grills, and front-row seats to sunset.
The morning ritual
Every great beach town has a breakfast spot that everyone knows.
In Montauk, that's John's Pancake House.
Families have been starting their weekends here for decades. Pancakes, eggs, coffee, and the kind of no-frills atmosphere that feels increasingly rare.
For something a little newer, Lighthouse Café near Montauk Point Lighthouse offers one of the best views on the East End. Grab breakfast before exploring the grounds or heading back toward town.
And if you're packing for the beach, stop at Joni's Kitchen. Their sandwiches have fueled countless sun-filled mornings, boat rides, and afternoons at Ditch Plains.
What we wore
Some pieces earn their place in the weekend bag because they solve a problem, like the Bayberry Trunk with its no-chafe liner or a Saltaire Hoodie to keep you toasty at night. Others are there because you keep reaching for them.
The Oceanfront Shirt falls into the second category.
Made from lightweight double-faced cotton gauze, it’s just easy. Throw it over swim trunks for a walk into town. Wear it open over a tee for lunch. Button it up and you’re all set for dinner. It handles all three without asking much of you.
The less you have to think about what you're wearing, the better the weekend tends to go, right?
The long afternoon
Montauk afternoons are best spent near the water.
Rent a paddleboard and explore the calmer waters around Fort Pond Bay. Take a surf lesson at Ditch Plains, one of the most beginner-friendly surf spots on the East Coast, thanks to its unique double break waves. Borrow a bike from your hotel and spend the afternoon cruising between the harbor, the beach, and Montauk Point.
Or do none of those things.
Find a stretch of sand, open a book, and chill.
For days like these, the Anchor Rashguard becomes one of the most useful pieces you can pack. Lightweight, quick-drying, and built with UPF 50 protection for long hours in the sun. It keeps everybody comfortable whether you're paddling out, chasing kids through the surf, or spending the day on a boat.
Lunch becomes dinner
One of the best things about the "End of the World," as it's affectionately known, is how easily plans evolve.
A quick bite turns into another drink. An afternoon by the water becomes sunset.
Navy Beach remains one of our favorite spots for exactly that reason. It’s on a protected cove off Bayside Beach, providing beautifully calm water. There’s good food (at the restaurant or delivered right to your lounge chair), and enough room to settle in for a while.
For something even simpler, stop by one of the local fish markets at Montauk Harbor and bring dinner home. If your rental has a grill and a view, there aren't many better ways to spend an evening.
Sunset, then one more stop
Before heading home, make time for Montauk Point Lighthouse.
The vista hasn't changed much in more than two centuries, which may be part of the appeal. Stand on the bluff, watch the light shift across the water, and let the weekend slow down one last time.
And if you're not quite ready to call it a night, there's always Liar's Saloon. A longtime local favorite known for late-night karaoke and zero pretension, it's exactly the kind of place that belongs in a town like Montauk.
Because the best weekends aren't really about checking things off a list.
They're about a few memorable meals, long afternoons outside, and returning home feeling like you got away—even if it was only for 48 hours. See you out there.