Best results for Harwich Port MA

Glide across Nantucket Harbor on your choice of kayak or paddleboard

Learn essential sailing skills in a personalized 1.5-hour session for kids aged 5–12

Introduce your toddler to sailing with a 1-hour instructor-led lesson

Learn to ride an electric hydrofoil with expert instruction in Nantucket

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

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

Sail Cape Cod Bay on the historic Schooner Hindu

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

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

Treat yourself to a memorable afternoon sail

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

Book a spacious, stable 30' custom boat for an inshore fishing trip for up to 6 anglers