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.

Day 1: Newport / Cuttyhunk

Welcome aboard your Yacht on your Newport itinerary. As soon as you are settled in we will depart Newport for Cuttyhunk Island. Leaving Newport Harbor is always exciting. Newport has the distinction of being the Sailing capitol of the East coast. However, 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, we will pass some of the famous Newport mansions including the Vanderbilt estate “The Breakers”.

Leaving the Providence river, we will be cruising through Block Island Sound into Buzzards Bay. Then anchoring 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. After we have anchored, local seafood is served fresh from the ocean via the raw bar boat. The Raw Bar boat comes alongside and provides fresh Cuttyhunk Oysters and Clams. In additional to crab spread and hot clam chowder. This small island is fun to explore and offers adequate shelter for water sports and a spectacular spot to watch the sunset.

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

Sometime in the morning we will anchor and head to Martha’s Vineyard. This will be a very scenic cruise up the Northside of the Elizabethan Islands and through Woods Hole passage. By Lunch Time we can be in Martha’s Vineyard. Two great places to visit are Vineyard Haven or Edgartown both towns offer great shopping and fine dining. Private tours would be arranged or its fun just to go exploring on your own. Furthermore, there are many fine art galleries, scenic walks and fun nightlife. The “Vineyard” is home to many famous celebrities and political figures.

Day 4: Martha’s Vineyard to Nantucket

The usual route to Nantucket is through the middle of Nantucket sound which is long, boring, and usually foggy. We will be taking the southernmost route, only reserved for the most skilled mariner or anybody that bothers to read the chart. This unmarked channel is the route that the whaling ships used to take and one which Nantucket’s modern fishing fleet uses today. This route takes us within one mile of Nantucket’s northern shore where we will see seals, sharks, and possibly a whale.

We will break for lunch and some fishing at my secret fishing spot. Hopefully, we will catch dinner, if not I know a great fish market on the Island. The Nantucket boat basin is one of the best docks in New England. All the best shops, restaurants, and nightlife are within walking distance. Then, take a Private island tour like on Martha’s Vineyard. 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

If you want to go back to Martha’s Vineyard it’s up to you. But if you didn’t get a chance to see Newport, then we could depart Nantucket at 4 am for a lunchtime arrival in Newport. Also, Newport like all our destinations has something for everybody.

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

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