Yachting Itinerary in New England

Yachting in New England and throughout the Hamptons is unlike anywhere else in the world: golden sand beaches and lighthouses; upscale boutiques in picture perfect towns; and stunning mansions on imposing cliffs. Sailing through this region, you will soon see that this coastline has more to offer than purely natural beauty – it possesses a wealth of history and culture dating back to the American colonial past and set against some of the most expensive and desirable real estate in the United States.

Below is a sample 7-day yachting itinerary in New England. Enjoy.

Day 1

Sag Harbor → Shelter Island → Sag Harbor1-Hour Cruise

Take a short cruise from historic Sag Harbor to Shelter Island (30-Min Cruise) where a tender can rendezvous with your yacht to bring you onshore for lunch at Sunset Beach. After a relaxing post-lunch swim, take a sunset cruise back to Sag Harbor (30-Min Cruise) where you can dine aboard or head into town and have farm-to-table fare at Wolffer Kitchen.

Day 2

Sag Harbor → Montauk 2-Hour Cruise

After breakfast onboard, head to the vineyards of the North Fork of Long Island. After lunch onshore, head to the hip surf town of Montauk. Cruise to the famous Montauk lighthouse followed by a sunset cruise around Gardiner's Bay and drop anchor for drinks at Navy Beach before heading back to Montauk Yacht Club for dinner.

Day 3

Montauk → Block Island 2-Hour Cruise

Known for its protected beaches, Block Island was named by the Nature Conservancy as one of the sites in the list of “last great places” in the Western Hemisphere. Visit the Mohegan Bluffs, and take the staircase to the bottom of the clay cliffs, and make sure to try a bowl of New England clam chowder at the National Hotel.

Day 4

Block Island → Nantucket 3-Hour Cruise

From Block Island, take a morning cruise to Nantucket. Known for its pristine beaches and cobblestone streets and famous for its 4th of July fireworks, spend the day exploring this unique New England town. Originally a whaling port, Nantucket has been named a National Historic District and little has changed since the 17th century, with old fashioned lamps still lining the streets.

Day 5

Nantucket → Martha's Vineyard 2-Hour Cruise

Spend the day at the ultra-exclusive enclave of Martha's Vineyard. Martha's Vineyard boasts the oldest working carousel in the country, and if traveling with kids, you might consider taking a tour of the Farm Institute, where you'll see livestock and can explore lush vegetable and flower gardens. And no trip to the Vineyard is complete without some Murdick's fudge.

Day 6

Martha's Vineyard → Newport 2-Hour Cruise

Head to Newport, the quintessential New England town known for its museums, art and jazz festivals, and historic mansions. Head onshore for the famous Cliff Walk and pay a visit to The Breakers, the former summer cottage of the Vanderbilt family. End your journey with dinner at the historic Castle Hill Inn, built in 1875.

Day 7

Newport → Sag Harbor 2-Hour Cruise

After a breakfast in Newport town, take a restful cruise back to The Hamptons with lunch onboard. You'll be back in time for an afternoon in town and for dinner at Beacon restaurant located right on Sag Harbor overlooking the marina.

/static/media/itinerary_hours_icon.ee325043.svg1h 00min

Sag HarborSag Harbor
Shelter IslandShelter Island
Map Data
Map data ©2020 Google
Map DataMap data ©2020 Google
Map data ©2020 Google

For any charter inquiries, please call us at+1 (305) 676 2097or