Guided Tours

Conway Tours Hamptons

Immortalized in The Great Gatsby, the Hamptons have long been the summer getaway for the rich and famous.  Discover charming waterfront villages, world-class wineries, beautiful beaches and more during the fall — when the area is far less crowded than during the summer.

Day 1
Cross Sound Ferry

This morning we take the Cross Sound ferry from New London, CT to Orient Point, the gateway to Long Island's famed North Fork area.

Greenport Carousel

We stop first in the cozy waterfront village of Greenport, which features pretty shops and a waterfront park with an antique carousel. 

Raphael's Estate and Winery

Later, enjoy a visit to the impressive Raphael's Estate and Winery, which resembles a Mediterranean chateau. You're free to wander the vineyards and tour the production facility, including the tank room and their barrel cellar. You'll also enjoy a memorable tasting of some of the area's most exclusive wines. 

Hyatt East End

Our accommodation for the evening is Hyatt Place East End in Riverhead. This unique waterfront hotel is ideally located in the center of this charming town often referred to as the gateway to the Hamptons. 


This evening enjoy a fabulous dinner at one of the area's popular restaurants located steps away from your hotel.

Day 2
South and East Hampton

This morning a local guide will lead a most interesting tour of the Hamptons. Explore the famed villages of South and East Hampton, home to such celebrities as Jerry Seinfield, David Lettermen, Steven Spielberg and Martha Stewart. 

Sag Harbor

Visit charming Sag Harbor to view its historic waterfront area amid Greek Revival mansions and Victorian cottages. Later we backtrack toward the lovely seaport town of Port Jefferson before taking the scenic ferry to Bridgeport, CT and continue our journey home.

Sunday, September 13, 2015
Sunday, September 20, 2015
Sunday, September 27, 2015


  • Overnight Accommodations at the new Hyatt Place East End in Riverhead, NY
  • 2 Meals: 1 Continental Breakfast and 1 Dinner
  • Scenic ferry crossings to Orient Point and from Port Jefferson
  • Wine tasting at the impressive Raphael Estate and Winery*
  • Guided “Rich and Famous Tour” of the Hamptons
  • Services of a Professional Conway Tour Manager


Departing from: 
Orient Point
Double occupancy $299 pp Triple occupancy $289 pp Single occupancy $369 pp Child rate $249 pp