Endeavor Sailing offers daytime sails, sunset cruises, and private charters aboard a classic Friendship Sloop departing from Straight Wharf in downtown Nantucket. Led by Captain James Genthner, the charter welcomes both novice and experienced sailors for relaxed excursions around Nantucket Harbor and Nantucket Sound. Guests can help raise the sails, learn about the island’s maritime history, or simply enjoy the scenery from the deck of one of Nantucket’s longest operating sailing charters.
The Nantucket Preservation Trust Walking Tour offers guided explorations of Nantucket’s historic architecture, neighborhoods, and preservation efforts through downtown walking experiences led by knowledgeable local guides. Organized by the Nantucket Preservation Trust, the tours highlight the island’s historic homes, streetscapes, and cultural history while sharing stories about preservation and Nantucket’s architectural heritage.
Travel to Nantucket with Hy-Line Cruises, offering high-speed passenger ferry service from Hyannis in about one hour. With frequent departures and easy boarding, it’s one of the fastest, most convenient ways to reach the island.
Barrett’s Tours is Nantucket’s oldest tour company, offering historic bus and van tours, wedding transportation, private charters, and ferry and airport transfers. Founded by Chester Barrett as a horse and buggy tour operation, the company continues to provide narrated island tours focused on Nantucket’s history, scenic landmarks, and local stories. Daily tours depart from Federal Street with both scheduled and private transportation options available.
