THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Spend a day trading Manhattan streets for oceanfront villages, two short ferries, and tastings at North Fork wineries. This private tour pairs Sag Harbor history with the region’s farming-to-vineyard story and practical logistics for a full 12-hour outing.
Spend a day trading Manhattan streets for oceanfront villages, two short ferries, and tastings at North Fork wineries. This private tour pairs Sag Harbor history with the region’s farming-to-vineyard story and practical logistics for a full 12-hour outing.
You roll east on Sunrise Highway before the city loosens its grip — morning light hits clapboard facades in Southampton, fishermen load boats in Sag Harbor, and the Atlantic keeps time with a steady, salt-scented rhythm.
Verified experiences and guided adventures in the surrounding area.
Operated by Family in New York, Inc. · Southampton, New York
You roll east on Sunrise Highway before the city loosens its grip — morning light hits clapboard facades in Southampton, fishermen load boats in Sag Harbor, and the Atlantic keeps time with a steady, salt-scented rhythm.
This private full-day tour stitches together seaside villages, two short ferry crossings (to Shelter Island and the North Fork), and a string of boutique vineyards. Sag Harbor’s 18th-century whaling houses and its old yacht club recall a maritime past; the North Fork’s gently rolling farms and sandy loams reflect glacial deposits that make the region surprisingly hospitable to Cabernet Franc and Merlot vines. Local culture pivots between seafood—harvested that morning—and a fast-growing wine scene that turned truck farms into tasting rooms over the last 40 years.
Expect easy walking in village centers and at tasting rooms, brief ferry time sitting with the wind, and short drives across farmland and coastal roads. Practicalities matter: tastings require government ID and some wineries limit group size; the operator provides hotel pickup in NYC, a roomy air-conditioned vehicle, and a licensed guide. Dress smart-casual and layer for coastal breezes; bring a small cooler for purchases and space to stow bottles. Plan to leave early to avoid outbound traffic and build time for ferry schedules—this is a 12-hour day that balances scenic stops with three or four winery visits and a harbor-side lunch.
For travelers who like a mix of shoreline scenes and terroir, this itinerary delivers approachable hiking of culture—short walks, plenty of seats, and a chance to watch sunlight move across vineyards and water alike.
easy.
12 hours.
Suitable for most people who can manage short walks and standing during tastings; no special fitness required
Yes — the tour offers pickup and drop-off from New York City hotels within the operator’s service area; confirm your pickup time when booking.
Children under 21 can join the tour but must use appropriate child seats or boosters by law; tastings are restricted to guests 21 and older.
The tour and transportation are wheelchair accessible, though some vineyard terrain and ferry ramps may require assistance — notify the operator in advance.
Full refunds are available if you cancel at least 24 hours before departure; within 24 hours is non-refundable.
Sag Harbor rose as an 18th-century whaling port; the North Fork transitioned from mixed agriculture to a recognized wine region in the late 20th century.
Dune systems and vineyard soils are sensitive; choose wineries practicing sustainable viticulture, avoid trampling vines, and pack out all trash.
Family in New York, Inc. operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
You roll east on Sunrise Highway before the city loosens its grip — morning light hits clapboard facades in Southampton, fishermen load boats in Sag Harbor, and the Atlantic keeps time with a steady, salt-scented rhythm.
You roll east on Sunrise Highway before the city loosens its grip — morning light hits clapboard facades in Southampton, fishermen load boats in Sag Harbor, and the Atlantic keeps time with a steady, salt-scented rhythm.
This private full-day tour stitches together seaside villages, two short ferry crossings (to Shelter Island and the North Fork), and a string of boutique vineyards. Sag Harbor’s 18th-century whaling houses and its old yacht club recall a maritime past; the North Fork’s gently rolling farms and sandy loams reflect glacial deposits that make the region surprisingly hospitable to Cabernet Franc and Merlot vines. Local culture pivots between seafood—harvested that morning—and a fast-growing wine scene that turned truck farms into tasting rooms over the last 40 years.
Expect easy walking in village centers and at tasting rooms, brief ferry time sitting with the wind, and short drives across farmland and coastal roads. Practicalities matter: tastings require government ID and some wineries limit group size; the operator provides hotel pickup in NYC, a roomy air-conditioned vehicle, and a licensed guide. Dress smart-casual and layer for coastal breezes; bring a small cooler for purchases and space to stow bottles. Plan to leave early to avoid outbound traffic and build time for ferry schedules—this is a 12-hour day that balances scenic stops with three or four winery visits and a harbor-side lunch.
For travelers who like a mix of shoreline scenes and terroir, this itinerary delivers approachable hiking of culture—short walks, plenty of seats, and a chance to watch sunlight move across vineyards and water alike.