Best results for
Sailing in Plymouth, MA
Showing 1-13 of 13 results
Shared Buzzards Bay Sailing Trip from New Bedford
Catch the bay breeze past New Bedford's working waterfront
4.8 • 24 reviews
Private Sailing Charter in New Bedford Harbor & Buzzards Bay
Sail New Bedford Harbor and Buzzards Bay on a private charter
4.8 • 24 reviews
Mattapoisett Harbor Private Sailing Charter
Sail close to the water on an interactive harbor charter
4.8 • 24 reviews
Sailing Refresher Lesson in Mattapoisett
Tailor a hands-on sail to the skills you want to sharpen
4.8 • 24 reviews
Sail Repair and Sail Making Course
Learn to design, build, and repair sails in a hands-on two-day class
4.9 • 82 reviews
2-Hour Sunset Sail in Provincetown
Sail Provincetown at sunset on the historic Schooner Hindu
Sail Boston Harbor on the Cutter Bloodhound
Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival
Bloodhound Daysail In Provincetown
Sail Cape Cod Bay on a family-friendly cruise where you can help raise sails and bring a picnic aboard
Sunset Sail in Provincetown
Watch Provincetown’s shoreline glow from a classic Victorian yacht
Private Sailing Charter in Provincetown
Charter a private sail in Provincetown for up to 34 guests
Sail Boston Harbor on the Historic Schooner Hindu
Sail Boston during Sail Boston 2026 on the restored Schooner Hindu
90-Minute Private Schooner Charter in Provincetown
Private classic schooner sail with lighthouse and cove views