Best results for Provincetown MA

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

Search for whales on Stellwagen Bank aboard a boat reserved exclusively for your group.

Discover feeding and nursing whales at Stellwagen Bank on an intimate boat tour

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

Search for humpback and finback whales then savor a colorful Cape Cod sunset aboard the Beth Ann.

Experience close encounters with humpbacks and finbacks on an exclusive 3.5-hour charter

Cruise Provincetown Bay at sunset with snacks and soft drinks

Cruise for seals, fish, and lobster traps with the kids

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

Cruise to Provincetown's pristine beaches for sun, scenery, and seaside fun.

Cruise past three historic lighthouses and visit a local seal colony

Charter a private sail in Provincetown for up to 34 guests

Spend half a day sailing Cape Cod Bay with a private crew and optional swim stop.

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

Relax aboard the Beth Ann as you glide past Provincetown’s iconic lighthouses at sunset

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