2026 New England Islands Cruise September 22 – October 3, 2026
Join fellow CCA members for an unforgettable exploration of Southern New England’s most storied islands and harbors. The 2026 National Cruise blends exceptional sailing with rich history, world-class museums, and the timeless charm of coastal New England.
Newport, Rhode Island — Opening Festivities 9.22/23
We begin in iconic Newport with a welcome party at the Sail Newport, offering spectacular harbor views and easy access to the city’s renowned sights. Ample time is built in for wandering cobblestone streets, visiting the famed mansions, or simply soaking up the maritime atmosphere.
Cuttyhunk — A Classic Raw Bar Cocktails & Island Exploration 9.24/25
From Newport we sail to peaceful Cuttyhunk for a classic Cuttyhunk Shelfish Farms Cocktail Party. An additional lay day invites participants to explore the island’s rugged paths and learn about its early history, including the 1602 landing of Bartholomew Gosnold, whose voyage helped shape the earliest European understanding of New England.
Captains Choice 9.26
Martha’s Vineyard — Beauty, History & Culture 9.27/28
Heading east, the fleet arrives at Martha’s Vineyard—one of Southern New England’s most enchanting islands. Stroll among elegant homes, enjoy delightful walking tours, and visit the Carnegie Museum in Edgartown. The Martha’s Vineyard Museum in Vineyard Haven features a special retrospective on the making of Jaws, along with a wealth of local maritime history. The fleet will enjoy a fabulous New England Lobster Bake hosted by the Edgartown Yacht Club.
Captains Choice 9.29
Nantucket — The Quintessential New England Island 9.30, 10.1
Next, we continue to Nantucket, often described as the quintessential New England island. Once the center of the American whaling industry, the island’s Whaling Museum provides a compelling look at its dramatic rise and fall. A highlight of our stay will be a lecture by renowned author and Nantucket native Nathaniel Philbrick, whose acclaimed works bring Nantucket’s maritime past vividly to life.
Captains Choice 10.2
New Bedford — A Grand Finale at the Whaling Museum 10.3
After a leisurely return sail to Buzzards Bay, the cruise concludes in New Bedford at the highly acclaimed New Bedford Whaling Museum—rated one of North America’s must-see museums. Our final dinner will be held in the beautiful third-floor event space, complete with a balcony overlooking one of the last true working harbors in New England.
To help us get a feel for the number of members planning on joining the cruise,(if you haven’t done so already) please complete the Expression of Interest form at https://cruisingclub.org/form/new-england-interest or by going to the CCA website and select 2026 New England Islands Cruise under Upcoming Cruises. If you have any questions about the cruise, please contact Cruise Chair Ray Cullum at raycullum1@gmail.co
