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Art, Salt & Sky in the Hamptons
Colonial Villages, a Whaling Port & the East End's Wild Edge | 3 Days Starting from $2,760 per Guest
The Hamptons have long drawn those chasing something – a slower breath, an open horizon, the quiet particular to a place shaped by sea air and old money. But beneath the hedgerows and celebrity buzz lies something more enduring: colonial village greens, a whaling port frozen in amber, and a lighthouse that has watched the Atlantic since 1796. This three-day East End escape moves between the leisurely and the storied, from gallery walls and boutique streets to the dramatic cliffs of Montauk Point, where the land simply runs out and the ocean takes over.
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 Journey Along the East End's Most Storied Shores
Day One – Arrival on the East End
No agenda, no itinerary, just the road east and the slow unwinding that follows. After checking into a local hotel, the afternoon is yours entirely. Wander East Hampton’s boutiques, browse BookHampton, or catch an exhibit at The Church arts space in Sag Harbor. Lunch among gardens in one of the village restaurants eases the city out of your shoulders, and the evening ends over wood-fired dishes or fresh seafood at one of the Hamptons’ most beloved tables.
Day Two – Villages, Whalers & the Edge of the Island
A guide joins the morning as the day opens with a gentle stroll through Southampton, one of America’s oldest English settlements. From there, the route moves east through Hook Mill and East Hampton Village before arriving in Sag Harbor, a former whaling port whose captain’s houses and harbourfront still carry the weight of those long voyages. The afternoon drives all the way to Montauk Point, where the 1796 lighthouse stands above Atlantic cliffs and the views stretch, unobstructed, to the horizon.
Experience Highlights
- Admission to Sag Harbor Whaling & Historical Museum
- Admission to Montauk Point Lighthouse
Day Three – One Last Morning, Then Home
A leisurely final morning invites a walk along Sagg Main or Coopers Beach, pastries at Carissa’s Bakery, or a quiet hour among the sculptures at LongHouse Reserve. After checkout, private transfer heads west on the same roads that brought you here, now offering a last chance to take in the open farmland, village greens, and quiet shoreline scenery before the city comes back into view.
The Roundtree Amagansett
Price Starts at $$$
Nestled between the farmland of Amagansett and the white shores of the Atlantic, The Roundtree is an award-winning historic hotel that captures everything the Hamptons does best – effortless beauty, unhurried elegance, and a sense that time has gently slowed down. Set in the heart of Amagansett Village just steps from world-class restaurants and the finest beaches in America, the newly renovated property offers 14 meticulously appointed accommodations set across sprawling, sun-drenched grounds where hammocks sway, windchimes drift, and a seemingly endless lawn invites guests to simply be. Complimentary continental breakfast, afternoon tea, evening snacks, nightly s’mores and popcorn, beach gear, bicycles, and concierge services ensure that every need is quietly anticipated, leaving guests free to gather or retreat, explore or linger, entirely on their own terms.
Hotel Amenities
Amenities
- Personal Chef
- Holistic Wellness Program
- Complimentary Continental Breakfast, Afternoon Tea, Snacks & Beverages
- Beach Gear
Hotel Location
The Sagaponack
Price Starts at $$$
A sun-warmed reimagining of the classic Hamptons hideaway, The Sagaponack offers a bright, unhurried retreat where timeless seaside charm meets thoughtfully modern comfort. Choose from welcoming Main Inn rooms, spacious family bungalows, or stylishly efficient studio rooms, each stocked with a make-your-own cocktail setup, a locally inspired pantry, and complimentary beach day access so guests can slip into the sand like a local. Steps from celebrated beaches, vineyards, and farm stands, it’s a genuine home away from home in one of the most beloved seaside destinations in the country.
Hotel Amenities
Amenities
- Beach Passes and Locker
- Pantry Access
- Heated Outdoor Pool
Hotel Location
LDV At The Maidstone Hotel & Restaurant
Price Starts at $$$
Built in 1840 and named for East Hampton’s original founding title, The Maidstone is one of the East End’s oldest and most cherished institutions, a place where generations of guests have marked life’s most meaningful moments. Its 19 newly refreshed rooms, suites, and garden cottages are dressed in a natural palette of sand, amber, and soft peach that mirrors the coastal surroundings, each one bespoke, layered, and deeply at ease. Under LDV Hospitality, the tradition continues with an Italian-inspired culinary program rooted in seasonal produce and fresh local catch, turning every evening at the table into a memory worth keeping.
Hotel Amenities
Amenities
- Restaurant
- Complimentary beach chairs, umbrellas, bags, and coolers
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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“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.”
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