Water Activities in Brewster, MA

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

Sail Provincetown at sunset on the historic Schooner Hindu

Paddle Cape Cod’s barrier beaches with an ACA-certified guide

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Paddle Cape Cod waters with gear delivered to your launch area

Charter a private boat for Pleasant Bay’s Fourth of July fireworks

Paddle into a Cape Cod sunset with an ACA-certified guide

Explore Cape Cod waters with paddle gear delivered to your launch spot

Sail Wellfleet Harbor on a private 3-hour charter, with tide-based stops for swimming or beach time

Fish Cape Cod waters on a private 8-hour charter for up to 6 people

Enjoy a private evening cruise past Provincetown’s historic lighthouses

Private whale watch with a sunset cruise in Provincetown Harbor

Learn sailing fundamentals with private on-water instruction

Fish Cape Cod Bay on a private 3-hour charter for up to 6

Learn paddleboarding basics with an ACA certified guide

Sail Cape Cod Bay on a family-friendly cruise where you can help raise sails and bring a picnic aboard

End the day with a guided paddle as Cape Cod’s evening sky changes

Explore Shark Alley by private motorboat with expert guidance and aerial spotting

Paddle Popponesset Bay at your own pace with included gear

A relaxed guided paddle with a midway ice cream boat stop

Set your own course for a private outing on the water

Private family kayak lesson with ACA (American Canoe Association) certified guides

Paddle through a clue-filled pirate quest with a water cannon showdown

Cast, jig, and troll for striped bass and bluefish with crew support