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Experience the stories that shaped a nation.
The Gold Coast & the Vine
Gilded Estates, Revolutionary Secrets and the Wines of the North Fork | 3 Days Starting from $3,777 per Guest
Long Island holds two faces rarely seen in the same breath: the lavish Gold Coast estates where American ambition built French châteaux above the Sound, and the quiet Revolutionary-era villages where farmers, housewives, and millers secretly helped change the course of a war. This three-day journey moves between those worlds – through grand halls and spy trails, harbor towns and biodynamic vineyards – ending in the peaceful farmland of the North Fork, where the pace slows, the rows of vines stretch to the horizon, and the wine pours easy.
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 Drive from Gatsby's Shore to the Vines of the North Fork
Day One – Estates of the Gold Coast
The city gives way to tree-lined lanes as the North Shore reveals its gilded past. Oheka Castle opens the day with the grandeur of financier Otto Kahn’s French-style manor, followed by the Vanderbilt Museum, where one family’s passion for science and world travel fills every room with curiosity. Old Westbury Gardens offers a peaceful close – wandering paths, bright blooms, and the stately Westbury House. The evening is yours in Northport, a harbor village where sailboats bob quietly and dinner needs no reservation.
Experience Highlights
- Guided Tour of Oheka Castle
- Admission to the Vanderbilt Mansion & Museum
- Admission to Old Westbury Gardens
Day Two – Spies, Stories & the Vine
Setauket looks peaceful today, but in 1778 it was the nerve center of a spy ring that fed intelligence directly to George Washington. The morning traces the Culper network stop by stop – a colonial churchyard, a saltbox farmhouse, a laundry-lined shore where coded signals crossed enemy waters. After lunch in Stony Brook Village, the route opens eastward into farmland and vineyard rows. A tasting at a local vineyard brings the afternoon to a warm close, and the night settles in at a carefully chosen inn in the heart of wine country.
Day Three – Departure
After a relaxed checkout, guests settle into their private transfer home – a leisurely ride back through the landscapes that framed the journey, with familiar sights passing by one last time and the warmth of the past few days still fresh in mind.
The Northport Hotel
Price Starts at $$$
Nestled in the heart of historic downtown Northport on Long Island’s Gold Coast, The Northport Hotel is a refined 26-room boutique retreat where rich village history meets understated luxury. Ideally situated on Main Street just steps from the harbor and the John W. Engeman Theater, guests are immersed in a charming village alive with shopping, galleries, and nightlife — yet the hotel itself feels like a quiet sanctuary. Arrive to a champagne toast and handcrafted sweets delivered to your room, wake to a complimentary Chef’s continental breakfast of house-made baked goods and freshly brewed coffee, and spend your evenings at the hotel’s restaurant and bar, where expertly crafted cocktails, curated wines, and a menu of fine steaks and seafood make for a thoroughly satisfying close to the day.
Hotel Amenities
Amenities
- Restaurant
- Local Gym Arrangements (for a fee)
Hotel Location
Rose Hill Vineyards & Inn
Price Starts at $$$
Tucked into 22 acres of rolling vines on Long Island’s North Fork, Rose Hill Vineyards & Inn is a beautifully restored historic farmhouse that feels worlds away from the city, yet sits just 90 miles outside of New York. With only four intimate guest rooms, this romantic bed and breakfast offers the kind of unhurried, personal experience that larger properties simply cannot replicate. Mornings begin with a full country breakfast, afternoons invite guests to sip coffee on the front porch or settle onto the patio for a complimentary wine tasting with views across the vineyard, and evenings fall quietly over the vines with more than 40 additional wineries within ten miles to explore at leisure. For those looking to slow down, breathe in, and discover the very best of North Fork wine country, Rose Hill is the perfect place to do it.
Hotel Amenities
Amenities
- Complete Country Breakfast
- Complimentary Charcuterie
- Wine Tasting
- 24/7 Access to Coffee, Snacks & Wines
- Access to Vineyard Tours
- Game Drawer
Hotel Location
The Harbor Front Inn
Price Starts at $$$
Nestled along the Peconic Bay in the heart of historic Greenport Village, The Harbor Front Inn is a warmly inspired seaside retreat that pays tribute to the waterfront boarding houses of a bygone era while delivering every modern comfort. Spacious rooms and suites, an outdoor pool with open water views, and a cozy lobby that invites lingering conversation set the tone for a stay that feels effortlessly unhurried. Just steps from the village’s charming streets, acclaimed vineyards, and the gentle lap of the bay, the inn serves as the perfect gateway to everything the North Fork has to offer — and for those who simply want to watch the boats drift by from a sun-dappled lounge chair, it’s equally perfect for that too.
Hotel Amenities
Amenities
- Continental Breakfast
- Waterfront Pool
- Complimentary Bicycles
- Kite Kits
- Cultural Programming
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 and wine tastings not included.
- Hotel accommodations available for an additional charge.
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Quote from Our Travelers
“American Stories Travel turned our NYC shopping trip into something unforgettable. They set up a personal stylist session that was geared to our tastes. We honestly felt like VIP’s – it was personalized luxury at its best.”
2024 - A.M.
“I’ve always been a Wall Street enthusiast, but the private tour of the Financial District that American Stories Travel set up for me was eye-opening. There was so much happening there that I had no idea about – from the past to present day. I didn’t go in expecting to learn anything new – but boy did I!”
2025 - Z.K.
“The Gold Coast itinerary was a revelation. I’ve lived in New York my whole life and had never seen those estates. Our guide brought the whole era to life in a way that felt personal and cinematic at the same time. Absolutely unforgettable.”
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.
“Niagara Falls exceeded every expectation. Standing at the edge on the Maid of the Mist with the falls in full view was something else entirely. Having a private guide made all the difference — we saw and understood so much more than we would have on our own.”
2026 - T.M.
