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    Island Spirit Kayak

    Island Spirit Kayak

    Oak Bluffs, MA

    Island Spirit Kayak has been sharing the quiet coves and playful currents of Martha’s Vineyard since 2000. Founder and island native Chick Stapleton started with just three boats and a boundless love for the water; today her hand-...

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    Book Island Spirit Kayak

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    1- to 3-Month Kayak & Paddle Board Rental in Oak Bluffs

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

    From$420kayak
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    Paddle Board Fitness Class in Oak Bluffs

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

    $53
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    Kids Kayak Adventure Tour in Oak Bluffs

    Build kayak skills with guided games and exploration for kids

    $100.70person
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    Sunrise Kayak & SUP Tour in Oak Bluffs

    Paddle at sunrise with breakfast and coffee included

    From$84kayak
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    4-Hour Sea Kayaking Tour In Martha's Vineyard

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

    From$185kayak
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    24-Hour Paddleboard Rental in Oak Bluffs

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

    $84.19SUP
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    Oak Bluffs 1.5-Hour Private Kayak Lesson

    Build paddling skills at any level with a private lesson

    $159kayak
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    Kids Kayak & Paddleboard Tour Series in Oak Bluffs

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

    From$291person
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    Get Kayak Delivery & Pick Up in Oak Bluffs

    Schedule island-wide kayak delivery and pick up

    From$26delivery
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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$89kayak
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    3-Hour Kayak & Paddleboard Rental in Oak Bluffs

    Paddle from State Beach with a quick lesson and gear included

    From$72kayak
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    2-Hour Kayak & Paddleboard Rental in Oak Bluffs

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

    From$56kayak
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    24-Hour Kayak Rental

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

    From$89kayak
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    Beginner Stand-Up Paddleboard Tour in Oak Bluffs

    Learn stand-up paddleboarding with a guided, beginner-friendly tour

    $79.50
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    Kayak Rentals at State Beach, Oak Bluffs

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

    From$56kayak
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    Oak Bluffs Family Beach Party with Setup

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

    $400
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    Glow Paddle Night Kayak Tour in Oak Bluffs

    Paddle a clear-bottom kayak at night with glow lights on State Beach

    From$127kayak

    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