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East Hampton Roundtrip Charter Itinerary

Enjoy a seven-night New England Yacht charter on this East Hampton Roundtrip Itinerary. It will take you to places that interest you and at your pace. Although the following sample itinerary spans seven days, you may choose to linger in one port longer than another, and it’s all up to you.

East Hampton Roundtrip Itinerary
Mystic waterfront. Photo by Rusty Watson on Unsplash.

Day 1 | East Hampton 

Begin your charter in East Hampton, Long Island. Miles of sandy beaches hug the coast on the oceanside and the bayside. The ocean beaches are great for all kinds of activities but especially for surfing. The water around the bay beaches is much calmer than the ocean, which is excellent for swimming and sailing.

Besides the beaches, there are many places to see in East Hampton, such as the Longhouse Reserve. This magnificent sixteen-acre garden has over 79 outdoor sculptures. Or, visit The Mulford Farm, listed on the National Register of Historic Places. Have a bite to eat at an outdoor cafe before shopping at East Hampton Village.

Day 2 | Mystic, Connecticut

Mystic, Connecticut, is the next stop on your East Hampton Roundtrip Itinerary. This town has lots to see, such as the Mystic Seaport, the Mystic Aquarium, and the Denison Pequotsepos Nature Center. You can shop and dine in Downtown Mystic before returning to the yacht for the night.

Days 3 and 4 | Nantucket (two nights)

Your yacht arrives at Nantucket, a tiny island off Cape Cod, Massachusetts. Charming unpainted cedar-shingled buildings dot the island. Explore the wharves and cobblestoned streets in the Town of Nantucket.

Snap pictures of lovely steepled churches, browse high-end boutiques, and try the local cafes. Visit the Whaling Museum and learn about the island’s role as a 19th-century whaling hub.

East Hampton Roundtrip Itinerary

Day 5 | Vineyard Haven

Travel to Vineyard Haven on Martha’s Vineyard. This vibrant working harbor village has a fun cultural district where you can shop at unique stores and taste delicious ocean-to-table food.

Many activities, such as biking, hiking, and fishing, keep you moving. Of course, more relaxed pursuits like spa treatment (or two). After a day of exploring, enjoy a perfect sunset at the West Chop overlook.

Day 6 | Newport 

Next on your sailing itinerary is Newport, Rhode Island. Its yacht-filled harbor hosted America’s Cup Regatta for many years. This city by the sea is home to mansions, beaches, and dockside restaurants.

Visit the Breakers Mansion, have local lobster at the Newport Lobster Shack, or take a guided tour of the massive Fort Adams. Enjoy oceanfront views on the 3.5-mile-long Cliff Walk.

Day 7 | Montauk 

Montauk, a village at the east end of Long Island, is known for its beaches. Some are Kirk Park Beach, Navy Road Beach, and Montauk Point State Park Beach. If you visit Montauk Point State Park, see the 1796 Montauk Point Lighthouse and Museum.

Other activities to pursue include fishing, horseback riding, and water sports. After an active day, unwind with a cool drink at a local restaurant such as The Shack.

Day 8 | East Hampton 

End your East Hampton Roundtrip Itinerary where you began.

Suggested Yachts

In New England, there is a wide range of yachts to explore the beautiful coastline. Here are a few: