Things to do in Oak Bluffs

Explore Martha’s Vineyard for a week with a family-run rental since 1989

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.

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

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

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

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

Taste wine, beer, and spirits while learning how Nantucket’s top producers craft each pour

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.

Paddle In A Clear Kayak Under the Stars!

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

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

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

Track Cape Cod great whites with a captain and spotter pilot on a private 3-hour tour

Join the crew for a treasure hunt with sea chanteys, stories, and cannon action

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

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

Book a spacious, stable 30' custom boat for an inshore fishing trip for up to 6 anglers

Fish Nantucket inshore waters on a spacious, stable 30' custom boat built for up to six anglers

Fish inshore on a 23' center console skiff built for comfortable rod room and a smooth ride

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