Kayak Tours


No Experience Required!

Many of our guests are first time paddlers.  Our tours accommodate all levels of skill and ability.  We ask only that you bring your spirit of adventure and a healthy sense of humor.  Before each kayak tour there is an instructional session to familiarize you with your equipment and paddling techniques. You will then have the opportunity to practice your new skills on the tour with a game of Kayak Ultimate Frisbee!


2 Hour Kayak Adventure

Explore the Island’s wildlife and beaches while learning skills in an exciting environment.  Equipment, Guides and fun provided!
  • Departs Daily: 10am & 1pm
  • Length: 2.25 hours
  • Cost: $65 Adult $45 Children 5-12


Sunset & Moonlight Paddles

These romantic and fabulous tours depart an hour before sunset.  We paddle out in the calm, colorful waters of dusk, enjoying the wildlife and beauty of the watery coast.  We land for a beach picnic as the sun sets and the moon rises!  We use the light of the moon or our glowsticks to explore the pond on our return trip, listening and watching for nocturnal animals and maybe singing!  Equipment, guides & beach picnic provided!
  • Length: 2.5 hours
  • Cost: Adult: $75, Children 5-12: $55


Sunrise on the Ocean

Watch the sun’s reflection on the water’s glassy surface and the gentle ripples from your wake as the sun slowly rises over the water. Breakfast and coffee provided.  This is Chick’s favorite time on the water, owner recommended trip!
  • Departs Daily: 1 hour prior to sunrise
  • Length: 2.5 hours
  • Cost: Adult: $75, Children 5-12: $55


Full Day Kayak Adventure

Drift paddles, open ocean adventures and remote locations. Lunch picnic, and snacks provided, a true sea kayaking experience.  Departure locations based on wind & tides.  Full Day locations: Aquinnah loop around the cliffs, Edgartown to the Chappaquiddick ‘Gut’, one-way Tashmoo to Menemsha drift or East & West Chop day in the rip!
  • Departs Daily: 9am
  • Length: 5-6 hours
  • Cost: $120 p/p


Pub & Paddle

Nothing is better than a cold beer after an awesome paddle, unless it’s a whole beer tasting at Offshore Ale!
Your guide will lead you on a one way adventure along the North shore of Oak Bluffs. Your paddle will take you through the beautiful harbor of Harthaven, where there’s an active Osprey nest, tons of shellfish beds and a great location for some Kayak Ultimate Frisbee. Your will conclude in Oak Bluffs Harbor where you will get a brief walking tour, through the Ginger Bread Cottages, to Offshore Ale!
At Offshore, their official Brew Master will give you a behind the scenes look of the making of Offshore Ale beer while sampling their deliciousness. All tastings, a beer & souvenir mug included.
  • Departs: 10am
  • Minimum: 3 paddlers
  • Cost: $120 p/p

Call for more information: (508) 693-9727








Pedal & Paddle Adventure



This a great option for youth groups, families and adventurers looking to enjoy the island by land and sea in one day!
Cottage City Bicycle in Oak Bluffs and Island Spirit Kayak pair up to create a seamless awesome experience for you and your party.
The bike tour takes begins & ends in the center of Oak Bluffs town, making it easy to find and have a wonderful breakfast before, or lunch after! The tour pedals around the famous Gingerbread Cottages, past East Chop lighthouse and along the ocean sea wall on a Barrier beach bike path with an ocean on one side and beautiful ponds on the other. Surrounded by water and the sea air we park our bikes for a snack break on State Beach and fuel up for next adventure- a kayak tour!
Sengekontacket Pond is a protected wildlife preserve loaded with shellfish and wildlife, which your guides will introduce to you. After a game of kayak Ultimate Frisbee, we will return to Oak Bluffs town.
All equipment, guides and snack break included! Minimum party of 3.
This tour does not depart from the Island Spirit Kayak location.
Departure location: Cottage City Bicycle, 5 Oak Bluffs Avenue, Oak Bluffs, MA 02557


Call for more information: (508) 693-9727

Cuttyhunk & Multi-Day Adventures



2017 Departure Dates:  June 18, July 18, August 17, September 16, 17 & 18Spend your evening at the Cuttyhunk Fishing Club and days on a guided exploration of the Elizabeth islands, an unforgettable and truly unique experience. Accommodation, transportation, equipment and meals provided.  The island is so special and the paddle there from Menemsha is just amazing!!!“The trip to Cuttyhunk was a blast! We loved everything about it- great food, great B&B, great people and great kayaking…” – Linda & Elkan, PAThis tour requires a 4-paddler minimum.

  • Day 1
    Depart Menemsha Beach at 6am. The water that time of day is absolute glass and the sun is just coming up. We have the option to trawl for fish on our way and pause for a floating breakfast about half way.  Arrive on Cuttyhunk Island!  Bonnie from the Fishing Club usually greets us with a golf cart to bring us up to the Club.  We will then go for a walking tour of the island, it’s not very big, but is loaded with charm. Check out some souvenirs and buy lobster for the evenings dinner! Delicious picnic lunch. Afternoon paddle around Penikese Island.  Relaxing at the Club, sunset on the porch over looking Aquinnah Lighthouse. Dinner is fresh Cuttyhunk lobsters and more!

    • Optional moonlight paddle. Depending on the time of year. The phosphorescence in the harbor can be even better than Vieques(which is one of the best in the world).
  • Day 2
    We will hike in the morning through some old fishing trails, past historic old houses with the opportunity to throw in a line! Lunch on the beach. Afternoon paddle and/or lessons, good opportunity to practice Eskimo Rolls or surf kayaking in the currents.
    Relax on a charter boat back to Martha’s Vineyard complete with champagne toast!

Multi-Day Adventures

Squibnocket Loop.
A moderately challenging paddle which meanders down the Wampanoag herring creek, through an underground tunnel to Menemsha Pond, over a barrier beach and into the Nantucket Sound. Squibnocket is a private fresh water pond surrounded by massive beach dunes and is teaming with oysters, swans, and ospreys. Departs 9am, lunch included.
Pub & Paddle.
A one way paddle along East & West Chop off the Vineyard Sound. Challenge the island’s infamous chops of confusing tides and rips while being rewarded with spectacular views and passing two lighthouses. The paddle concludes at the base of Oak Bluffs Harbor. Your guide will bring you on a walking tour of the town to Offshore Ale Co. Here you will be treated to a tasting tour of the island’s only brewery. A welcome reception of chicken wings and beer followed by pizza and more beer in a private function room overlooking the pub below and the ocean afar, are a perfect end to this rewarding paddle. Departs 10am, lunch included.
An open ocean crossing paddle from Edgartown to Chappaquiddick island, home of the famous Dyke bridge. A beach lunch with views of breathtaking cliffs and Striped Bass fishing at one of the most premier spots are highlights of this day. Departs 10am, lunch included.
Aquinnah Sunrise.
Watch the sun’s reflection affect the brilliant clay colors of the Aquinnah Cliffs. This paddle includes a possible surf launch and landing. Breakfast and coffee provided.
Optional day: Golf, biking, beach tour, snorkeling, hiking and fishing are all available, or just take the day to relax or sunbathe!
Sunset Champagne and Hors’douerves Sunset Paddle.
This paddle departs one hour prior to sunset returns under the stars with glowsticks lighting our kayaks and a trail of Phosphorescence, bioluminescent organisms, lighting our wake.
Menemsha Drift Paddle.
Our paddle is with a 4 to 7 knot current along the northern shore of the island ending at the best place to watch the sunset over the Vineyard Sound. Lobster clambake provided.
Due to tides and weather, trip times and locations may be altered.

Call for more information: (508) 693-9727

Stand Up Paddleboard(SUP) Tours

Beginner Paddle Board Tour
First timers are welcome to this all inclusive instructional tour. SUP over quahog beds, schools of fish, around an oyster farm and mini islands! Equipment, guide and excitement provided!
  • Departs Daily: 9am & 11am
  • Cost: $55 per person
  • Ages: 11 & Up

LED SUP Adventure
Ridiculously fun and unlike anything you’ve ever paddled! High intensity LED lights illuminate the water under your board, making you look like a floating UFO, while giving you a front row view of the sea life as well! This tour is very easy & includes a full instructional session on shore prior to launch. Perfect for beginner & families.
  • Departs Nightly: 20 minutes prior to sunset.
  • Cost: $75 per person
  • Ages: 12 & Up

SUP Yoga
Clear your mind and breath in the ocean air. What is more relaxing than yoga on a SUP? We don’t know. NO EXPERIENCE NECESSARY For SUP or YOGA!
Siobhan Beasley, SUP YOGA Instructor
Siobhan has been practicing yoga for over 10 years, and completed her 200 hour yoga teacher training with Sherry Sidoti at FLY Yoga School on Martha’s Vineyard. In addition to SUP Yoga classes, Siobhan teaches yoga at Yoga Haven, Yoga on the Vine, several of the island schools, as well as the local jail. She feels most at home (and happiest!) in, on, or near the ocean, which makes it her favorite place to practice yoga!
  • Departs: Thursday, Friday & Saturday 8am – 9:30am
  • Cost: $40 per person

What to Bring/Wear

Please Bring:

  • Sunglasses
  • Hat
  • Water bottle
  • Smile


  • Camera
  • Towel
  • Water Booties
  • Bathing Suit


Do Not Bring:

  • Cell Phone
  • Wallet
  • Keys


We Provide:

  • Dry Bags
  • Safety talk
  • Paddle Introduction
  • Light Beach Snack
  • First Aid Kit
  • Marine and Wildlife Identification
  • Upbeat & Professional Guides

We do have a place for you to leave personal belongings you do not wish to bring out on the water with you.