Best results for Water Activities in Chatham, MA

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

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

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

Charter a private sail for up to 42 people from MacMillan Pier

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

Share a whale watch trip from Provincetown and split the boat with other travelers

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

Set your own course for a private outing on the water

Enjoy a two-hour self-guided sail aboard a stable Rhodes 19 from Jetties Sailing Center

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

Build sailing confidence with instruction tailored to your experience

Refine your sailing technique and build confidence on the water

Book a private whale watch to Stellwagen Bank in Provincetown

Enjoy a private evening cruise past Provincetown’s historic lighthouses

Private whale watch with a sunset cruise in Provincetown Harbor

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

Explore Stellwagen Bank's whale feeding and nursing grounds by private boat