Join the crew for a treasure hunt with sea chanteys, stories, and cannon action
Private 3-hour morning bay cruise for up to 6
Sail Wellfleet Harbor on a private 3-hour charter, with tide-based stops for swimming or beach time
Cruise Cape Cod’s outer beaches with a spotter pilot to look for great white sharks
Enjoy a two-hour self-guided sail aboard a stable Rhodes 19 from Jetties Sailing Center
Learn to sail with a private instructor at Jetties Beach
Glide across Nantucket Harbor on your choice of kayak or paddleboard
Build sailing skills with a private youth lesson for up to 3 sailors
Introduce your toddler to sailing with a 1-hour instructor-led lesson
Learn to ride a LIFT eFoil with a 2-hour lesson for up to 3 or 6 riders
Sail Provincetown Harbor and Cape Cod Bay on a private 6-hour charter
Private 3-hour beach cruise for up to six, with snacks and soft drinks included
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 a restored 1925 schooner at sunset with drinks and charcuterie
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
Choose your beach and use the boat as your home base for swimming and relaxing