Best results for Water Activities in Oak Bluffs MA

Reserve your kayak online and enjoy a full day on the water with included gear and basic instruction

Cruise to Daufuskie Island, explore by golf cart, and enjoy a waterfront Lowcountry meal

Rent a kayak or paddleboard and explore State Beach from the water

Paddle from State Beach with a quick lesson and gear included

Rent a kayak or paddle board and explore Oak Bluffs from the water

Schedule island-wide kayak delivery and pick up

Rent a paddleboard for 24 hours at State Beach in Oak Bluffs

Rent a kayak or paddle board for 1–3 months with free delivery

Cruise the Intracoastal on a private 3-hour boat tour for up to 6

Learn boat handling with a private, hands-on lesson from Captain Chris

Cruise longer with a private 5-hour island-hopping charter for up to 6

Cruise the Gulf and island-hop on a flexible 6-hour private boat charter

Paddle Penn Cove with a local guide, learn its history, and spot eagles and herons on a relaxed two-hour outing.

Set your own pace exploring Penn Cove by tandem kayak with a local guide

Enjoy a relaxed 5-mile paddle with gentle Class I rapids and scenic mountain views

Kayak from Washington Island to Rock Island with a guide and picnic lunch

Tailor your paddle with American Canoe Association instructors for skills that match your goals

Beginner-friendly guided paddle to a shipwreck, pictographs, and Door Bluff cliffs

Paddle past a shipwreck and ancient pictographs beneath Door County's tallest bluff on a guided 2-hour tour.

Private 2-hour charter for 7 to 10 passengers; enjoy a personalized cruise

Learn to ski, wakeboard, kneeboard, or tube with certified instructors on a private boat for up to six.

Cruise to a remote island for wildlife watching and a guided kayak tour

Pedal a Hobie Pro Angler to reach bass waters with guide, bait, and tackle included

Pedal Hobie Pro Angler kayaks to bass-rich waters with guide, gear, and no license needed

Explore coastal gems on an intimate six-guest charter with a dedicated captain and flexible shore time

Enjoy a private fishing trip with licensed captain and all gear included

Dive two historic sites with macro life, ideal for certified divers seeking something different

Cruise to Black Point by narrated boat and tour the mansion and grounds

Ride a Yamaha WaveRunner for an exhilarating hour on Martha's Vineyard waters.

Paddle In A Clear Kayak Under the Stars!

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

Soar 600 feet above the water with a dry deck takeoff and landing

Paddle at sunrise with breakfast and coffee included

Start your day with a beginner-friendly paddle board fitness class

Learn SUP basics with instruction and gear as you explore calm waters with a guide

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

Enjoy a carefree day on the beach while we handle all setup, gear, and cleanup

Explore Sengekontacket Pond from State Beach with stable kayaks and a quick on-water intro

Build paddling skills at any level with a private lesson

Build kayak skills with guided games and exploration for kids

Kayak and hike to sea caves and bluffs with a naturalist, plus a light picnic lunch

Paddle calm Green Bay waters beneath Peninsula State Park bluffs on a beginner-friendly 2-hour tour

Start your day with a narrated blackwater cruise featuring wildlife and river views

Paddle to the Schooner Fleetwing shipwreck, hike Door County's highest bluff, and enjoy a charcuterie picnic

Learn SUP skills with expert instructors on Lowcountry waters

Relax on a gentle 2-hour Spokane River float guided by experts—ideal for families and first-timers

Design a personalized 4-hour sea kayak adventure in Door County with gear and light lunch included