Best results for Water Activities in Chatham, MA

Sip, Savor & Cruise: Narrated Harbor Views with Cocktails and Ice Cream Treats Onboard

Watch Cape Cod's vibrant sunset while enjoying onboard cocktails and treats

Cruise shallow channels to observe Gray seals and historic lighthouses with a naturalist guide.

Fish Cape Cod Bay on a private 4-hour charter for up to 6 people

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

Sail Provincetown Harbor and Cape Cod Bay on a private 4-hour charter

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

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

Book a private whale watch to Stellwagen Bank in Provincetown