7 Day New England Bareboat Sailing Itinerary

Rose Island

A 7-day sailing itinerary for Newport, Cape Cod, Martha's Vineyard and Nantucket!

A yacht charter starting from Newport offers a large number of charter yachts, moorings, excellent provisioning options, historic towns, and sailing culture. Newport is also renowned for the mansions built by many of America's leading families! The below itinerary will guide you through America's vibrant history, allowing you to explore some of the wealthiest areas in the US! Follow our itinerary and sail to Martha's Vineyard, known for the Jaws filming location, the beautiful city of Boston, or dine in some of the best restaurants on the Hamptons. The Hamptons is home to gourmet restaurants, bars, designer stores, and many hiking and picnicking destinations. Be sure to go whale watching in Wetherill State Park during your yacht charter!  

New England Charter Yachts

Day 1 - Newport 

newport rhode island
Start your charter in Newport, one of the largest ports on the East Coast of America. Spend the evening walking around the harbors and eating at one of the many fish food restaurants - you have to have the New England Clam Chowder - it's a must! Before your charter starts, you may want to hire a few bikes and do the scenic 10-mile ride tour along Ocean Drive. A great place for lunch is the Castle Hill Hotel and Restaurant! Most of the mansions are located on Bellevue Avenue on the way to the Ocean Drive they truly are something to experience! You can also walk the famous Cliff Walk; a steady 3-mile path along a rocky coast that provides a rear view of the mansions on Bellevue. You can take a guided tour of many of the numerous mansions there. The Museum of Yachting is located in Fort Adams State Park and exhibits much of Newport's storied yachting history.


Day 2 - Edgartown, Marthas Vineyard. 

Marthas Vineyard yacht charter with boatbookings
Edgartown, situated on the South-Eastern corner of Marthas Vineyard was the island's first settlement in the 1600's, today it is a quaint seaside town which attracts guests from all over the world. Marthas Vineyard has stunning sandy dune beaches, perfect for lunches! There are many activities you can take part in on land, such as hiking, fishing, and swimming in the shallow warm water. New England prides itself on culinary delights, and Edgartown is no different! Feast on seafood until your heart's content, wash it away with some crisp white wine - what more could you want?!

New England Yacht Charter Overview

Day 3 - Nantucket

nantucket yacht charter
Get ready to embark on a sail over to one of America's most famed islands - Nantucket! Nantucket is a hot spot for wealthy celebrities, with some of the most expensive real estate in the world. Cruise into the main port, missing the ferry that brings tourists over for the day. There is an option to use mooring buoys or the marina - if there's space! This is prime fishing territory so most of the bats you will see will be sport fishing boats! The island is small, quaint with very trendy shops and some of the best restaurants in the Cape. We highly suggest eating at Straight Wharf Restaurant - the food and service are impeccable!

New England Yacht Charter Guide

Day 4 - Chatham

chatham cape cod ma yacht charter

Chatham is a beautiful seaside town which is located on the southern corner of Cape Cod. Famed for its sandbanks and oyster crab ponds this is an area of outstanding natural beauty! The town is located along one road, which has fantastic shops and a lively pub! We would highly recommend Bluefins Sushi and Sake restaurant for some amazing, fresh tuna and wild Goose tavern for the biggest oysters you have ever seen! You can hire Kayaks if you don't have them already on board and paddle out to the sand bars. The Oyster Pond is well worth visiting which is accessible from the channel - marvel at the huge houses that overlook the water. 


Day 5 - Hyannis

hyannis yacht charter

Hyannis, located on the southern coast of the Cape, west of Chatham. Hyannis is a dynamic town, with strong New England vibes! With great restaurants that you would expect from a seaside town in New England, this is the ultimate place to moor and rest up for the evening. Hyannis is a large town with a ferry port that gives the Cape direct access to the southern Islands, Marthas Vineyard and Nantucket. It is definitely worth checking out Barnstable, a town located close to Hyannis. It's famed for its natural beauty and gorgeous beaches. 

Newport Rhode Island Yacht Charter

Day 6 - Back to Newport

Chapoquoit Beach buzzards bay yacht charter
Wake up fresh and early and embark on your sail back to Newport to you are able to get off the yacht the next day. Cruise through the Nantucket sound and look back at the stunning Cape. Continue west sailing through Buzzards bay (pictured above). Tie off in Newport and treat yourself to one last meal on the stunning coast of New England. 

Marthas Vineyard Yacht Charter Information

Our Charter Yachts

Boatbookings can find you the ideal charter yacht no matter where you want to explore in New England. Click here to see our New England Charter Yachts or simply contact us and we'll recommend the best boat for you.

See our New England Charter Yachts Enquire

This website uses cookies --- I understand and accept