Water Activities in Oak Bluffs, MA

Build kayaking and paddleboard skills on a 4-day kids series at Sengekontacket Pond

A tailored on-water session for families and groups

Cruise Nantucket waters while uncovering the island's whaling-era landmarks

Build paddling skills at any level with a private lesson

Make Nantucket Harbor your private setting for an evening cruise timed for sunset

Refine your sailing technique and build confidence on the water

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

Get out on the water aboard a 17-foot Boston Whaler

Set out on a self-guided paddle through Popponesset Bay

Take your group out on a 17-foot Boston Whaler

Paddle Scorton Creek and create your own blown-glass piece

Stand-up paddleboard tour up Scorton Creek with an ACA Certified guide

Paddle open-ocean routes to remote spots with guides on Martha’s Vineyard

Paddle at sunrise with breakfast and coffee included

A fishing-ready center console with rod holders and a live well

Build kayak skills with guided games and exploration for kids

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

Beginner stand-up paddleboard tour with ACA-certified guidance

Paddle Sengekontacket Pond with a private guide tailored to your group

Take the helm of a 19-foot center console with fishing-ready features

Try fishing in Cape Cod Bay on a 2-hour kids-friendly private charter

Explore Martha’s Vineyard waters with your group

Paddle Popponesset Bay at sunset and into the full moonlight

Paddle a Cape Cod inlet at your own pace