The Ultimate New England Experience

The Ultimate New England Experience

Summer is upon us, which for many New Yorkers and Bostonians means preparing for their Hamptons or Nantucket beach vacations. Just mentioning The Hamptons or Nantucket conjures thoughts of Americana, pristine coastline, lighthouses, and celebrities and titans of industry rubbing shoulders at summer time galas. But no matter how many times you have been to these summer retreats, you haven’t truly experienced this area until you have explored it by water on your own private yacht.

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.

The following is a sample 7-day itinerary bringing you and your guests to some of the most well-known sites in New England that you’ll be sure to enjoy. Check out our yachts located in The Hamptons.

Day 1 | Sag Harbor

YachtLife's Suggested 7-day Itinerary - Sag Harbor

Embark on your yacht in Sag Harbor and take a short cruise to Shelter Island where a tender can rendezvous with your yacht to bring you onshore for lunch at Sunset Beach. This East End staple feels more like St Tropez than Long Island with it’s yellow and white parasols and Mediterannean vibe. After a relaxing post-lunch swim or a jet ski ride, take a sunset cruise back to Sag Harbor where you can dine aboard your yacht or head into town and have farm-to-table fare at Wolffer Kitchen.


Day 2 | Montauk

YachtLife's Suggested 7-day Itinerary - Montauk

After breakfast onboard, head to the North Fork of Long Island, home to dozens of vineyards and charming small towns. Make sure to pay a visit to the lavender fields at Lavender by the Bay before heading into town for lunch at the Frisky Oyster in Greenport. After embarking on your yacht, head to the hip surf town of Montauk. Cruise to the famous Montauk Lighthouse and then drop anchor at Navy Beach where you can take in the breathtaking sunset before heading back to Montauk for dinner at the Crow’s Nest where you’ll have some of the freshest local food with a lake front view.


Day 3 | Block Island

YachtLife's Suggested 7-day Itinerary - Block Island

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 | Nantucket

YachtLife's Suggested 7-day Itinerary - Nantucket

From Block Island take a morning cruise to Nantucket, made famous by the Kennedy family for their family compound in Hyannis Port. Originally a whaling port, Nantucket has been named a National Historic District and little has changed since the 17th century with its old fashioned lamps still lining the streets. Nantucket is better known for its pristine dune-backed beaches, cobblestone streets and famous for its 4th of July fireworks. Spend the day exploring this unique New England town.


Day 5 | Martha’s Vineyard

YachtLife's Suggested 7-day Itinerary - Martha’s Vineyard

From Nantucket, take a short cruise to the storied island of Martha’s Vineyard, a summertime favorite of sitting US presidents. Martha’s Vineyard boasts the oldest working carousel in the country, and if traveling with children, 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. Have dinner in town before heading back to your yacht for a well-deserved night’s rest.


Day 6 | Newport

YachtLife's Suggested 7-day Itinerary - Newport

Wake up to breakfast aboard while you take a leisurely cruise to the yachting capital of the US – Newport, Rhode Island. Home to the prestigious New York Yacht Club and some of the nation’s most impressive and historic mansions, this quintessential New England town is also known for its museums and art and jazz festivals. In Newport you will be able to stroll down the famous Cliff Walk and pay a visit to The Breakers, the former summer cottage of the Vanderbilt family. If admiring the mansions were not enough, you will also have the opportunity to dine at the historic Castle Inn, which was built in 1875.


Day 7 | Sag Harbor

YachtLife's Suggested 7-day Itinerary - Sag Harbor

After a breakfast in Newport town, take a restful cruise back to The Hamptons with lunch onboard. This morning cruise will get you back into Sag Harbor just in time for a late lunch in town followed by a lively dinner at Le Bilboquet restaurant overlooking the marina.


This one-week charter brings you to some of the most iconic New England towns on a journey covering just over 270 nautical miles. It’s truly an experience not to be missed and will make for lifelong memories for you and your guests. Enjoy this historic part of the world as it was meant to be seen – by the water.



Topping Rose House (Bridgehampton)

Topping Rose House is a luxury haven in the heart of the Hamptons, where old and new come together harmoniously in the spirit of this legendary area of eastern Long Island.


Gurney’s Montauk Resort (Montauk)

Gurney’s Montauk Resort (Montauk)

Situated on Montauk’s most pristine stretch of oceanfront real estate, Gurney’s is a Hamptons icon and the only year-round resort in Montauk.


American Hotel (Sag Harbor)

The American Hotel was built in 1846 at the height of the Whaling era. The Hotel is an elegant and professionally run establishment with an inimitable edge and character.


National Hotel (Block Island)

The National Hotel is the flagship victorian hotel on Block Island, located in the center of downtown in Old Harbor across from the ferry landing and New England’s best beaches.


Gurney’s Newport Resort (Newport)

Situated on Goat Island and surrounded by Narragansett Bay, Gurney’s Newport Resort & Marina offers the seclusion of a private island yet is just a jaunt from the shops and eateries of downtown Newport.



Sunset Beach (Shelter Island)

With Edi Cungu’s menu that celebrates the healthy and delicious summertime food of the French Riviera and coastal Italy Sunset Beach is one of the summer hotspots enjoy an afternoon on this seaside bar & cafe.


The Crow’s Nest (Montauk)

Removed from the crowds in Montauk this rustic mediterranean restaurant, is well worth a visit. Enjoy its variety from fresh whipped ricotta to blue crab claw tagliatelle. Spend the evening hanging out on the lounge chairs overlooking Montauk Harbour, and at nightfall, don’t miss the fire pit s’mores.


Le Bilboquet (Sag Harbor)

This hot French bistro is one of the places to be and be seen in the summer. Go for the moules-frites, niçoise salad, or the best cajun chicken you have ever tasted (it’s what they’re known for).


Cru (Nantucket)

With an envious waterfront location, in the heart of Nantucket harbor, Cru offers the ideal back drop any time of day. This casually elegant venue offers an experience unlike any other to enjoy a glass of champagne, indulge in caviar and perfectly-shucked oysters or sip on a glass of rosé at sunset.


L’Etoile (Martha’s Vineyard)

A vibrant modern restaurant located in a restored historic whaling captain’s house on the island of Martha’s Vineyard with a menu that is inventive, fresh, and seasonally-driven. If the weather permits, sip the local “startini” in their charming bar-l’étoile-lounge.



4th of July

4th of July

The oldest continuous 4th of July celebration in the country is in Newport, RI. The city puts on a majestic firework shows accompanied by numerous Independence related activities such as 21 gun salute and an annual reading of the Declaration of Independence. It is certainly the place to be for this important holiday.


Newport Jazz Festival (Newport)

Newport Jazz Festival (Newport)

One of the must-attend jazz festivals in the country, The Newport Jazz Festival is held every summer (August) in Newport, Rhode Island.


Hamptons Polo (Bridgehampton)

Hamptons Polo (Bridgehampton)

The most exclusive polo event in the Hamptons will be held on Saturday June 29th and July 6th. With only 500 tickets available, guests enjoy the thrill of the polo match with preferred seating and a VIP cocktail party.


Nantucket Film Festival (Nantucket)

Nantucket Film Festival (Nantucket)

Packed with celebrities and glamour, The Nantucket Film Festival is a film festival founded in 1996 which focuses on screenwriting is going to be held from June 19 to June 24.


Art Market + Design (Bridgehampton)

Art Market + Design (Bridgehampton)

The East End’s premier Art Fair, returns to the center of Bridgehampton this July 7th through 10th for its sixth edition, with top presentations of modern and contemporary art enhanced by a striking design component pulling from dealers and designers from around the world.

We hope the above remarks were helpful. Remember, YachtLife is here to help you find the perfect yacht for any occasion but whenever booking a yacht charter, work with your broker ahead of time to ensure everything is ready for your once you embark. Once aboard your yacht, the captain and crew will be there to make sure you are safe and have an unforgettable experience.

Have fun and enjoy yourself. You are going on an amazing vacation and this is an opportunity for you to relax and unwind. To help you out, we have put together some other sample itineraries here. You deserve it.

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