Southern Massachusetts, elizabeth islands, Martha’s Vineyard, Nantucket, and more...

Nantucket! Take out your map and look at it. See what a real corner of the world it occupies; how it stands there, away off shore, more lonely than the Eddystone lighthouse. Look at it—a mere hillock, and elbow of sand; all beach, without a background. 

Herman Melville as written in Moby Dick, Chapter 14

Sample Itinerary 

Southern New England has so much to offer - we can modify your itinerary locations and length of stay to customize your perfect trip. Maybe spend 3 days in Nantucket, or fit in an afternoon of fishing, surfing or wine tasting...just let us know and we’ll work with your broker to ensure the perfect trip!

Day 1 - Pick Up at noon at South Dartmouth Yacht Club followed by a short sail from Apponaganset Bay to the historic whaling town of New Bedford in the afternoon.

Day 2 - New Bedford to Mattapoisett Harbor. 
Mattapoisett Harbor is a picturesque and historic village. During the heyday of the whaling industry, some of the finest whaling ships in the world were built here. Also a great bay for water sports; tubing, paddle boarding, & waterskiing!  
 
Day 3 - Mattapoisett Harbor to Hadley Harbor. 
Hadley Harbor is one of the best protected and attractive anchorages in the cruising ground south of Cape Cod. Close by is Bull Island, a small island perfect for a relaxing walk, picnic or even birdwatching. Great views of Woods Hole and Nonamesset Island. 

​Day 4 - Hadley Harbor to Taurpalin Cove.  
Tarpaulin Cove is situated on the south side of Nashon Island in the middle of the Elizabeth Island chain. It is a well protected bay, great for water sports, fishing, and going ashore to the beach. Great views of Tarpaulin Cove Lighthouse and of Martha’s Vineyard across the sound. 
 
​Day 5- Taurpalin Cove to Nantucket.
Nantucket is known as the whaling capitol of the world and a centerpiece of Herman Melville's Moby Dick and Nathaniel Philbrick's In the Heart of the Sea. Nantucket’s restaurants are numerous and varied. The island has a great number of museums, one of which is the Whaling museum. Bicycle rentals that we can arrange for you and your group. Beach day or perfect time for hikes or water sports. (We recommend 2 days in Nantucket to make the most of this great destination!)

Day 6 - Nantucket to Edgartown, Martha’s Vineyard
We’ll arrange bicycle rentals for you before we arrive to make sure there available! Go explore the towns numerous upscale galleries, and classy restaurants. Visit the Old Whaling Church, Lighthouse Beach or Waterfront of Katama.

​Day 7- Martha’s Vineyard to Cuttyhunk Island.
Cuttyhunk is the southernmost of the Elizabeth Islands. Explore the small town that feels like a time machine back 200 years, hike to the top of the island for stunning views of the Buzzards Bay, Vinyard Sound, and islands extending to the North East. For dinner we’ll call up the floating Raw Bar and have dinner delivered to us at anchor. New England Clam Chowder, Oysters, Clams, Stuffed quahogs, and shrimp cocktail in the serene harbor. 
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Day 8 - A morning sail from Cuttyhunk Island back to South Dartmouth for drop off at noon to end your trip.

Tell us about your preferences and we can customize a memorable charter for you and your family!