Build paddling skills at any level with a private lesson
Paddle open-ocean routes to remote spots with guides on Martha’s Vineyard
Paddle at sunrise with breakfast and coffee included
Build kayak skills with guided games and exploration for kids
Start your day with a beginner-friendly paddle board fitness class
Savor sunset views around Cape Cod and Martha's Vineyard on an exclusive evening cruise for your group
Cruise to Provincetown's pristine beaches for sun, scenery, and seaside fun.
Cruise Provincetown Bay at sunset with snacks and soft drinks
Sail Cape Cod Bay on a family-friendly cruise where you can help raise sails and bring a picnic aboard
Sail Cape Cod Bay at sunset on a bring your own food and drinks cruise
Charter a private sail in Provincetown for up to 34 guests
Sail Provincetown at sunset on the historic Schooner Hindu
Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival
Sail Boston during Sail Boston 2026 on the restored Schooner Hindu
Taste Truro Vineyards pours on a 2-hour schooner sail in Provincetown
Charter a private sail for up to 42 people from MacMillan Pier
Experience close encounters with humpbacks and finbacks on an exclusive 3.5-hour charter
Relax aboard the Beth Ann as you glide past Provincetown’s iconic lighthouses at sunset
Search for humpback and finback whales then savor a colorful Cape Cod sunset aboard the Beth Ann.
Choose your beach and use the boat as your home base for swimming and relaxing
Cruise for seals, fish, and lobster traps with the kids
Cruise past three historic lighthouses and visit a local seal colony
Start your day with a private 3-hour cruise to secluded beaches and tidal islands around Wellfleet Harbor.