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    1. Local experiences/
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    5. 4-Hour Kayak & Paddleboard Rental in Oak Bluffs
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    4-Hour Kayak & Paddleboard Rental in Oak Bluffs

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

    From$89/ kayakincl. taxes and fees

    Duration

    2 hours

    Includes

    Life jacket, paddle, lesson

    Highlights

    Meet the team at Little Bridge, State Beach in Oak Bluffs, get set up with gear, and head out on your kayak or paddle board. You’ll get a quick paddle lesson and a verbal tour of the pond conditions before you launch.

    • Park at the beach meeting point and get geared up
    • Learn basic paddle technique in a quick pre-launch lesson
    • Follow a verbal tour of the pond and day’s conditions
    • Explore from the water and look for birds, fish, and crabs
    • Swim if you choose, then return to the beach at the end

    What's Included

    • Life jacket (personal flotation device)
    • Paddle
    • Safety talk
    • Paddle introduction
    • Marine and wildlife identification

    Things to know

    There are no on-site restrooms or changing facilities, so arrive ready to paddle. You can rent a daily dry bag for $1.

    Cancellation Policy

    48 hour notice required on all cancellations or rescheduling. 72-hour notice is required for groups of eight and larger. Full refund for any weather related changes and cancellations if you are unable to reschedule.

    FAQs

    Bring sunglasses, a camera, a hat, a towel, water shoes, and a bathing suit. Do not bring a cell phone, wallet, keys, or other valuables.

    No. There are no facilities on location for changing or restrooms, so arrive ready to paddle.

    You can leave items on shore, or rent a daily dry bag for $1.

    Meeting details

    Little Bridge, State Beach, Oak Bluffs

    Experience provided by Island Spirit Kayak
    Experience provided by Island Spirit Kayak

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Report an issue

    Reference #PYNXTQ

    SUPs

    $89.80

    0

    Single Kayaks

    $89.80

    Sit on top kayak. includes a PFD, paddle, and basic instruction. Jump seat for toddler(5 or under) or a dog.

    0

    Tandem Kayaks

    $112.25

    For two paddlers. This sit on top kayak includes PFDs, paddles, and basic instruction.

    0

    Triple Kayak

    $123.48

    For three paddlers. This sit-on-top kayak includes PFD's, paddles, and basic instruction..

    0

    Single Clear Kayak

    $112.25

    0

    Double Clear Kayak

    $168.38

    0

    Clear Paddle Board

    $112.25

    These boards are see through and are awesome for seeing wildlife!

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    Chick and her team have clearly built something special here, with guides like Sky, Aiden, and Simon earning consistent praise for their friendliness and deep knowledge of local birds, shellfish, and Martha's Vineyard ecology. What stands out is how adaptable they are—when weather doesn't cooperate, Chick personally steps in to find great alternatives. The staff handles groups ranging from solo paddlers to families of 14 with equal enthusiasm, making everyone from first-timers to experienced kayakers feel comfortable and safe on the water. The operation runs smoothly whether you're renting equipment or booking a guided tour. Kayaks are ready and waiting when you arrive, online booking is straightforward, and the two-hour tours hit a sweet spot between educational and fun. They offer kayaking, paddleboarding, and even SUP yoga classes with instructor Maggie Maxwell. The pond tours around Felix Neck Wildlife Sanctuary seem particularly popular, though they also run ocean paddles to places like Oak Bluffs and Edgartown Harbor. People consistently mention feeling the pricing is reasonable and plan return visits, which speaks volumes.

    What people are saying

    Review 1 of 5
    5/5

    These guys were great. When we arrived at the drop-in location in the morning, our kayaks were already on shore, waiting for us. After a brief safety demo, we launched.Chic the owner was super friendly and attentive.

    Photo of Robert H.

    Robert H.

    September 23, 2025

    Review 1 of 1
    5/5

    These guys were great. When we arrived at the drop-in location in the morning, our kayaks were already on shore, waiting for us. After a brief safety demo, we launched.Chic the owner was super friendly and attentive.

    Photo of Robert H.

    Robert H.

    September 23, 2025

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