Nantucket's maritime heritage runs deep, and sailing remains one of the best ways to experience the island. From classic catboats in the harbor to sunset sails around Brant Point, there's a sailing experience for everyone - from complete beginners to seasoned sailors.
Sailing Options
Charter Sailboats
The most popular option for visitors. A captain takes you out while you relax and enjoy the experience. Most charters offer:
- Harbor sails - 1.5-2 hours around the inner harbor
- Sunset sails - Evening cruises with stunning light
- Private charters - Full boat for your group
- Day sails - Extended trips to Tuckernuck or beyond
Catboat Rides
Nantucket is famous for its traditional catboats - wide, gaff-rigged sailboats perfect for the harbor's conditions. Several operators offer catboat cruises from Straight Wharf.
Learn to Sail
Nantucket Community Sailing at Jetties Beach offers:
- Adult sailing lessons
- Youth sailing programs
- Small sailboat rentals (for qualified sailors)
- Kayak and SUP as well
Popular Charters
- Endeavor Sailing - Classic friendship sloop, sunset sails
- Shearwater Excursions - Catboat harbor cruises
- Nantucket Boat Charter - Various sailing options
Expect to pay: $50-75/person for group sails, $400-800+ for private charters.
Best Sailing Experiences
Sunset Sail
The most popular option. Watch the sun drop toward Madaket while cruising past Brant Point Lighthouse. Book ahead - these fill up.
Morning Harbor Cruise
Quieter, cooler, and often the best wind. See the waterfront wake up and watch fishermen head out.
Figawi Weekend
The famous Memorial Day sailboat race from Hyannis to Nantucket brings hundreds of boats to the harbor. Even if you're not racing, it's spectacular to watch.
Sailing Tips
- Book sunset sails in advance - they sell out
- Bring a light jacket - it's always cooler on the water
- Sunglasses and sunscreen are essential
- If you get seasick, take medication before boarding
- BYOB is often allowed - ask when booking
- Morning sails often have the best wind