things to do in Oak Bluffs, MA

Paddle a Cape Cod inlet at your own pace

Build kayak skills with guided games and exploration for kids

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

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

Ride Cape Cod’s coastal bike path with ocean views and local history

Paddle Sengekontacket Pond with a private guide tailored to your group

Paddle a Cape Cod inlet at your own pace

Build foundational paddling skills with an ACA-certified guide

Take your group out on a 17-foot Boston Whaler

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

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

Explore Martha’s Vineyard waters with your group

Meet ghostly hosts with Revolutionary War stories to tell

See three layers of Nantucket’s geological past in one exposed bluff

Cruise, fish, and relax aboard a spacious 200hp Whaler

Explore Nantucket waters on a spacious 275-hp boat for up to 9 people

Take to the water in a Boston Whaler Montauk

Customize a private 4-hour Martha’s Vineyard island tour with flexible stops

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

Tour Martha’s Vineyard’s 6 towns in 3 hours, with a stop at Aquinnah cliffs

Tour all 6 Martha’s Vineyard towns in 3 hours, with time for photos and a Menemsha stop

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

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

Join a 6-hour Cape Cod Bay fishing charter with a licensed captain