Newport with Woods Hole Itinerary

This sample Newport with Woods Hole Itinerary, prepared by Captain Meagher, combines history, seafood, island life, and shopping. Enjoy jet skiing, seals, and fresh seafood while relaxing on your private yacht.

Martha's Vineyard, Newport with Woods hole itinerary
Martha’s Vineyard

Day 1 | Newport / Cuttyhunk

Welcome aboard your yacht on your Newport with Woods Hole itinerary. As soon as you are settled in, depart Newport for Cuttyhunk Island. Leaving Newport Harbor is always exciting. Newport has the distinction of being the sailing capital of the East coast. It was also home to America’s Cup for 126 years, the longest winning streak in sports history. Today the harbor is filled with both modern and classic sailing vessels. Departing Newport, pass some of the famous Newport mansions, including the Vanderbilt estate “The Breakers.”

You are leaving the Providence river, cruise through Block Island Sound into Buzzards Bay. Then your Captain will anchor in the harbor on the only town on the island of Cuttyhunk. Cuttyhunk is the westernmost Island in the Elizabethan Island chain off Cape Cod.

This small island is fun to explore and offers adequate water sports shelter and a spectacular sunset spot.

Day 2 | Cuttyhunk / Woods Hole

Enjoy a slow cruise to Woods Hole for additional sightseeing and water sports. Look for seals at Gull Island.

Day 3 | Woods Hole to Martha’s Vineyard

In the morning, head to Martha’s Vineyard. This will be a scenic cruise up the Northside of the Elizabethan Islands and through the Woods Hole passage. By lunch time arrive at Martha’s Vineyard.

Here, you can visit Vineyard Haven or Edgartown. Both towns offer great shopping and fine dining. Take a private tour would or go exploring on your own. There are many fine art galleries, scenic walks, and fun nightlife. The “Vineyard” is home to many celebrities and political figures.

Day 4 | Martha’s Vineyard to Nantucket

Take the southernmost route to Nantucket. This unmarked channel is the route the whaling ships used to take, and one Nantucket’s modern fishing fleet uses today. This route takes you within one mile of Nantucket’s northern shore, where you will see seals, sharks, and possibly a whale.

Nantucket Island, at one time, was one of the premier whaling ports in the world. The cobblestone streets made from the ballast of ships and the quaint Captain’s homes are an ever-present reminder of Nantucket’s maritime heritage.

Days 5 and 6 | Nantucket Island

Nantucket is too good to leave. Continue to explore and enjoy this fine island—local cruising on the yacht’s tender.

Day 7 | Nantucket to Newport

Suppose you want to go back to Martha’s Vineyard. But if you didn’t get a chance to see Newport, you could depart Nantucket at 4 am for a lunchtime arrival in Newport.

This Newport with Woods Hole Itinerary is a sample itinerary. Based on your preferences and the weather, itineraries will be customized.

Please call us today at 1 (321) 777-1707 or describe Your Vacation Vision to help you plan your fully-crewed private luxury yachting vacation! Inquire as soon as possible about your custom, crewed yacht charter.

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