Things to do in Oak Bluffs

Explore Oak Bluffs with flexible 1–6 day bike rentals and many models to choose from

Customize your island tour with a Menemsha seafood picnic and complimentary wine

Enjoy bike delivery with 1 day rentals for all ages

Explore the island on quality e-bikes and pedal bikes for 1 Day.

Watch the sun set over Menemsha Beach aboard a comfy shuttle with dinner options and local commentary

Discover all six Martha's Vineyard towns in a small-group guided bus tour.

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

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

Discover Martha’s Vineyard’s iconic cliffs and villages on a flexible private tour.

Explore Martha's Vineyard waterways for up to a week with fully equipped single or tandem kayaks.

Paddle In A Clear Kayak Under the Stars!

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

Rent top-tier carbon or aluminum road bikes to explore the island.

Customize a 4-hour private drive to historic towns, lighthouses, beaches, and scenic cliffs with a local guide

Savor sunset views around Cape Cod and Martha's Vineyard on an exclusive evening cruise for your group

Enjoy flexible 24-hour to one-month kayak rentals and explore at your own pace.

Enjoy hassle-free paddling with flexible rental periods and no age restrictions.

Explore Cape Cod waters with flexible 24-hour to month-long paddleboard rentals.

Explore Popponesset Bay with quality gear and the freedom to paddle for up to three hours.

Paddle Lawrence Pond at your own pace with included gear and flexible 2–3 hour rental.

Paddle scenic Cape Cod marshes at your own pace with quality gear included.

Pedal scenic canal paths at your own pace with quality bikes and included gear

Pedal scenic Cape Cod trails with quality bikes and gear included for four hours.

Paddle Popponesset Bay to Ockway Bay with an ACA-certified guide and enjoy brilliant evening colors

Explore secluded beaches and wildlife with ACA-certified guides

Watch a Cape Cod sunset from the water with an ACA-certified guide

Watch wildlife on a relaxed Scorton Creek paddle with ACA certified guides

Enjoy a two-hour self-guided sail aboard a stable Rhodes 19 from Jetties Sailing Center

Build confidence on the water with a dedicated instructor and custom coaching for up to three sailors

Glide across Nantucket Harbor on your choice of kayak or paddleboard

Learn essential sailing skills in a personalized 1.5-hour session for kids aged 5–12

Explore historic Nantucket on a 90-minute narrated tour of landmarks and lighthouses

Learn to ride an electric hydrofoil with expert instruction in Nantucket

Cruise Nantucket Harbor with up to 8 friends on a stable, powerful 200hp center-console.

Cast lines in Cape Cod Bay with experienced crew and soak in scenic coastal views