Best results for Sailing in Provincetown MA

Sail Provincetown Harbor on a private, captained 2-hour charter for up to six guests

Sail Provincetown Harbor and Cape Cod Bay on a private 6-hour charter

Sail a restored 1925 schooner at sunset with drinks and charcuterie

Charter a sailboat in Key West for up to 42 guests

Sail Cape Cod Bay at sunset on a bring your own food and drinks cruise

Sail Cape Cod Bay on the historic Schooner Hindu

Sail Provincetown at sunset on the historic Schooner Hindu

Taste Truro Vineyards pours on a 2-hour schooner sail in Provincetown

Charter a private sail in Provincetown for up to 34 guests

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Sail Boston during Sail Boston 2026 on the restored Schooner Hindu

Treat yourself to a memorable afternoon sail

Enjoy a relaxing two-hour cruise as daylight fades over the water

Sail Cape Cod Bay on a family-friendly cruise where you can help raise sails and bring a picnic aboard