Best results for Water Activities in Chatham, MA

Cruise Cape Cod’s outer beaches with a spotter pilot to look for great white sharks

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

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

Sail Cape Cod Bay on the historic Schooner Hindu

Charter a private sail in Provincetown for up to 34 guests

Charter a sailboat in Key West for up to 42 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

Private 3-hour beach cruise for up to six, with snacks and soft drinks included

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

Choose your beach and use the boat as your home base for swimming and relaxing

Learn to ride a LIFT eFoil with a 2-hour lesson for up to 3 or 6 riders