THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Swap skyscrapers for salt air on a long‑day tour east from Manhattan. Visit historic Southampton, sip at a local winery, explore Sag Harbor’s harborfront, and finish with outlet bargains in Riverhead.
Swap skyscrapers for salt air on a long‑day tour east from Manhattan. Visit historic Southampton, sip at a local winery, explore Sag Harbor’s harborfront, and finish with outlet bargains in Riverhead.
By 7 a.m., the city slips from the windows and the road unfurls toward a coastline shaped by ice and sea. Long Island’s terminal moraine drops away into rolling lawns and narrow lanes where clipped hedges and shingled facades frame views of the sound. This full-day circuit threads Southampton’s historic village, a family-run winery, Sag Harbor’s maritime harbor, and the bargain rows of Tanger Outlets in Riverhead.
Verified experiences and guided adventures in the surrounding area.
Operated by Empire Vacations · Sag Harbor, New York
By 7 a.m., the city slips from the windows and the road unfurls toward a coastline shaped by ice and sea. Long Island’s terminal moraine drops away into rolling lawns and narrow lanes where clipped hedges and shingled facades frame views of the sound. This full-day circuit threads Southampton’s historic village, a family-run winery, Sag Harbor’s maritime harbor, and the bargain rows of Tanger Outlets in Riverhead.
The coastline you pass is geologic history: glacial debris left the island’s uplifted spine and created barrier beaches, marshes and tidal creeks that shaped local livelihoods. Southampton began as a 17th‑century colonial settlement and evolved into a summer enclave; Sag Harbor’s identity was defined by 19th‑century whaling and maritime trade—look for low brick warehouses and narrow wharves that hint at that past.
Expect short, walkable stops rather than long hikes: stroll Southampton’s main street, sample small-production wine at a long‑running vineyard, and take a harbor-side walk in Sag Harbor to see working marinas and occasional seals. The day closes with ample time at Riverhead’s Tanger Outlets for outlet shopping.
Practical notes: departures are early (meet at Port Authority, typically 6:30 AM) and the trip runs roughly 11–13 hours round-trip. Transportation is by 15‑passenger van or full-sized bus; bring a valid ID for tasting, comfortable shoes for town walking, layers for changing coastal winds, and a small daypack. The operator supports reforestation through One Tree Planted—small choices on the tour help protect fragile dunes and marshes. Plan for limited free time at each stop if you want to linger.
easy.
11–13 hours.
Light activity: able to stand and walk short distances across uneven sidewalks and docks; should tolerate several hours on a coach.
Most departures meet in front of the Port Authority Bus Terminal on 42nd Street (between 8th & 9th Avenues); check your voucher for exact meeting instructions and arrival time.
Meals are not included; the itinerary often includes a short lunch stop in town and time to purchase food at outlets—pack snacks for the morning drive.
Yes—infants and small children can travel in strollers and there are infant seats available; advise the operator of any special needs at booking.
The tour notes wheelchair-accessible transportation and some accessible stops, but accessibility at historic sites and docks can vary—notify the operator at booking to confirm accommodations.
Southampton was settled in the 1640s and later grew into a prominent summer community; Sag Harbor prospered in the 1800s as a whaling and shipbuilding port, traces of which remain along its waterfront.
Barrier beaches and dunes on Long Island are fragile—stay on marked paths, avoid trampling dune vegetation, and support local reforestation and beach‑stewardship efforts like the operator’s One Tree Planted partnership.
Empire Vacations operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
By 7 a.m., the city slips from the windows and the road unfurls toward a coastline shaped by ice and sea. Long Island’s terminal moraine drops away into rolling lawns and narrow lanes where clipped hedges and shingled facades frame views of the sound. This full-day circuit threads Southampton’s historic village, a family-run winery, Sag Harbor’s maritime harbor, and the bargain rows of Tanger Outlets in Riverhead.
By 7 a.m., the city slips from the windows and the road unfurls toward a coastline shaped by ice and sea. Long Island’s terminal moraine drops away into rolling lawns and narrow lanes where clipped hedges and shingled facades frame views of the sound. This full-day circuit threads Southampton’s historic village, a family-run winery, Sag Harbor’s maritime harbor, and the bargain rows of Tanger Outlets in Riverhead.
The coastline you pass is geologic history: glacial debris left the island’s uplifted spine and created barrier beaches, marshes and tidal creeks that shaped local livelihoods. Southampton began as a 17th‑century colonial settlement and evolved into a summer enclave; Sag Harbor’s identity was defined by 19th‑century whaling and maritime trade—look for low brick warehouses and narrow wharves that hint at that past.
Expect short, walkable stops rather than long hikes: stroll Southampton’s main street, sample small-production wine at a long‑running vineyard, and take a harbor-side walk in Sag Harbor to see working marinas and occasional seals. The day closes with ample time at Riverhead’s Tanger Outlets for outlet shopping.
Practical notes: departures are early (meet at Port Authority, typically 6:30 AM) and the trip runs roughly 11–13 hours round-trip. Transportation is by 15‑passenger van or full-sized bus; bring a valid ID for tasting, comfortable shoes for town walking, layers for changing coastal winds, and a small daypack. The operator supports reforestation through One Tree Planted—small choices on the tour help protect fragile dunes and marshes. Plan for limited free time at each stop if you want to linger.