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Land's End: Three Days in Montauk
Where the Road Ends, the Ocean Begins | 3 Days Starting from $1,023 per Guest
Montauk doesn’t ease you in. The city gives way to open sky, salt air, and dunes that seem to belong to a different world entirely — one shaped more by tides and weather than by schedules. At the very tip of Long Island, where the land finally surrenders to the sea, this three-day escape trades the urban tempo for something rawer and quieter. A 1796 lighthouse, bluff-top walks above the crashing Atlantic, and the kind of unhurried beach days that are impossible to replicate back home — Montauk earns its reputation as the end of the road, in the very best sense.
This is a suggested itinerary — we can tailor it based on your group’s interests and pace.
What Our Expert Designer Loves About This Experience?
A 3-Day Retreat to the Salt Air & Open Skies of the East End
Day One – The Drive East & Arrival
The journey is part of the experience. A midpoint brunch stop at one of the South Shore’s waterside restaurants breaks up the drive before coastal roads take over with dunes, big sky, and the first glimpse of the Atlantic. After settling into the hotel, the afternoon opens with a visit to Montauk Point Lighthouse, perched above dramatic ocean cliffs with views that stretch to the horizon. The evening winds down over fresh seafood and ocean air at one of Montauk’s most beloved tables.
Experience Highlights
- Admission to Montauk Point Lighthouse
Day Two – All Yours
No guide, no itinerary, just Montauk in full. Spend the morning at Ditch Plains or Navy Road, rent bikes to pedal around on, or sign up for a surfing lesson. The bluff walks at Shadmoor State Park offer sweeping coastal views for those who’d rather wander, while a half-day fishing charter or a sunset boat cruise gives the day a different rhythm entirely. Lunch and dinner draw from a generous roster of waterfront restaurants; the hardest part is choosing.
Day Three – Departure
After checkout, the drive west retraces the route through Montauk’s dunes and open farmland — one last look at the East End before the city slowly reappears. Settle in, let the coastal scenery roll past, and take the time to revisit the moments that made the trip: the lighthouse above the cliffs, the sound of the surf, the easy pace of days with nowhere to be. There’s no rush. The road home is part of the journey.
Marram Montauk
Price Starts at $$$
Nestled within rolling sand dunes overlooking the Atlantic in the heart of Montauk, Marram is a 96-room boutique resort where barefoot luxury and coastal simplicity go hand in hand. Rooms are dressed in essential materials and a pared-down palette designed to quiet the mind and invite genuine rest, while just steps away the beach stretches out with the kind of uninterrupted ocean views that make it easy to forget the world beyond. Walk to Shadmoor State Park, catch a wave at Terrace Beach, explore on complimentary cruiser bikes, or settle in at Mostador Marram, the hotel’s seasonal outdoor café celebrating refined Latin American cuisine. For those who want to trade the city’s pace for salt air and simplicity, Marram delivers exactly that.
Hotel Amenities
Amenities
- Restaurant
- Outdoor Pool
- Complimentary cruiser bicycles
Hotel Location
Gurney’s Montauk Resort
Price Starts at $$$
An icon of the Montauk coastline, Gurney’s Resort commands a dramatic stretch of 2,000 feet of private beach, with 158 rooms, suites, and beachfront cottages all delivering sweeping ocean views. The Dune Lounge and its beloved fire pits set the scene for lively evenings of cocktails and light fare, while the world-class Seawater Spa offers a deeply restorative program of marine-based therapies, contrast bathing, and advanced wellness treatments rooted in the healing power of salt, sand, and sea. For the full Montauk experience with every luxury in place, Gurney’s is simply unmatched.
Hotel Amenities
Amenities
- Restaurant, Beach Club and Lounge
- Indoor Pool
- Spa and Bathhouse
- Private Beach
- Fitness Center
- Car Service
- Complimentary Bicycles
- Concierge Service
- Retail Store
Hotel Location
Hero Beach Club
Price Starts at $$$
Perched at the very tip of Long Island in the storied village of Montauk – fondly known as The End of the World – Hero Beach Club is a chic, relaxed sanctuary that has long drawn free spirits, surfers, artists, and adventurers from across the globe. Elegantly designed rooms and suites offer calming ocean and garden views, private balconies, and outdoor spaces crafted for genuine unwinding, while the beachfront setting provides the perfect backdrop for a stay that feels equal parts invigorating and restorative. For those who want to reconnect with the ocean, recharge completely, and experience Montauk at its most authentic, Hero Beach Club is a natural home base.
Hotel Amenities
Amenities
- Complimentary Wellness Events
- Beach Service
- Fire Pit and Heated Pool
- Lobby Bar and Shop
- Complimentary Bicycles
Hotel Location
More Information
- This experience is offered from April through October, starting on Friday or Saturday ONLY. Holidays may not be available.
- Cost of meals not included.
- Hotel accommodations available for an additional charge.
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2024 - A.M.
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2026 - D.W.
“I had no idea Long Island could feel this different from the city. The drive east, the lighthouse, the quiet of Montauk at sunset — it was exactly what we needed. American Stories Travel thought of everything, and not once did we have to worry about a single detail.”
2025 - P.H.
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