Things to do in Oak Bluffs
Discover amazing Oak Bluffs activities and premium in-home experiences.
Oak Bluffs is a vibrant seaside town where charming gingerbread cottages meet sandy shores and azure waters. Known for its spirited atmosphere, lively harbor, and historic Flying Horses Carousel—the oldest in the nation—this enchanting destination invites visitors to enjoy leisurely walks along Ocean Park or savor fresh seafood while watching sailboats drift by. Whether you're biking through scenic paths or indulging in sweet treats from local bakeries, Oak Bluffs offers an idyllic slice of coastal life that captivates at every turn.
Popular Activities in Oak Bluffs
Martha's Vineyard Sunset Tour
Watch the sun set over Menemsha Beach aboard a comfy shuttle with dinner options and local commentary
Three Hour Martha's Vineyard Island Tour
Discover all six Martha's Vineyard towns in a small-group guided bus tour.
Martha's Vineyard Jet Ski Rental
Ride a Yamaha WaveRunner for an exhilarating hour on Martha's Vineyard waters.
Ocean Parasailing Flight
Soar 600 feet above the water with a dry deck takeoff and landing
Private 3-Hour Martha’s Vineyard Tour
Discover Martha’s Vineyard’s iconic cliffs and villages on a flexible private tour.
Harborside Seafood Picnic Private 4-Hour Tour
Savor a seafood picnic in Menemsha during a custom island tour
Martha's Vineyard Glow Paddle Night Tour
Paddle a clear kayak under the stars with glow lights and expert guides
Family Beach Party
Enjoy a carefree day on the beach while we handle all setup, gear, and cleanup
4–7 Day Kayak Rentals
Explore Martha's Vineyard waterways for up to a week with fully equipped single or tandem kayaks.
High-Performance Road Bike Rental
Rent top-tier carbon or aluminum road bikes to explore the island.
Marthas Vineyard Private 4-Hour Island Tour
Customize a half-day private drive and discover Martha's Vineyard landmarks with a local guide
Private Sunset Cocktail Cruise
Savor sunset views around Cape Cod and Martha's Vineyard on an exclusive evening cruise for your group
Tandem Kayak Rental for Two
Enjoy flexible 24-hour to one-month kayak rentals and explore at your own pace.
24-Hour to 1-Month Canoe Rental on Cape Cod
Enjoy hassle-free paddling with flexible rental periods and no age restrictions.
Stand-Up Paddleboard Rental
Explore Cape Cod waters with flexible 24-hour to month-long paddleboard rentals.
Autocamp Half-Day Bike Rental
Pedal scenic Cape Cod trails with quality bikes and gear included for four hours.
Cape Cod Canal Full-Day Bike Rental
Pedal scenic canal paths at your own pace with quality bikes and included gear
Sandwich Great Marsh 2–3 Hour Kayak and Paddleboard Rental
Paddle scenic Cape Cod marshes at your own pace with quality gear included.
Lawrence Pond 2–3 Hour Kayak and Paddleboard Rental
Paddle Lawrence Pond at your own pace with included gear and flexible 2–3 hour rental.
2–3 Hour Mashpee Kayak and Paddleboard Rental
Explore Popponesset Bay with quality gear and the freedom to paddle for up to three hours.
Kayak and Stand-Up Paddleboard Rentals
Glide across Nantucket Harbor on your choice of kayak or paddleboard
Rhodes 19 Sailboat Rental
Enjoy a two-hour self-guided sail aboard a stable Rhodes 19 from Jetties Sailing Center
Private Sailing Lesson on Nantucket
Build confidence on the water with a dedicated instructor and custom coaching for up to three sailors
Youth Private Sailing Lesson
Learn essential sailing skills in a personalized 1.5-hour session for kids aged 5–12
Nantucket eFoil Lesson
Learn to ride an electric hydrofoil with expert instruction in Nantucket
21ft Boston Whaler 210 Dauntless Boat Rental
Cruise Nantucket Harbor with up to 8 friends on a stable, powerful 200hp center-console.
Four-Hour Fishing Charter
Cast lines in Cape Cod Bay with experienced crew and soak in scenic coastal views
In-Home Experiences
Electric Townie Beach Cruiser Rental
Cover more ground effortlessly with pedal-assist power on colorful cruisers.
Large E-Bike Hybrid Rental on Cape Cod
Ride scenic Cape Cod trails with helmet and lock included
Cape Cod Sunset Paddleboard Tour
Paddle calm Popponesset Bay at dusk and catch Cape Cod’s vivid sunset colors
Cape Cod Explorer Kayak Tour
Paddle secluded barrier beaches and spot local wildlife on this guided Cape Cod kayak outing
Cape Cod Sunset Kayak Tour
Paddle tranquil bays and witness a brilliant Cape Cod sunset on this guided tour
Kayak the Creek Nature Tour
Paddle serene tidal flats with certified guides and spot coastal wildlife on a relaxed two-hour excursion.
Explore the Charm of Oak Bluffs
Oak Bluffs is a vibrant seaside town known for its colorful gingerbread cottages, lively harbor, and rich history. As you stroll through the streets, you'll be captivated by the Victorian architecture that gives this place its unique charm. A visit to Oak Bluffs wouldn't be complete without experiencing the Flying Horses Carousel—the oldest operating platform carousel in America. It's a delightful ride back in time that's perfect for all ages.
For those who love nature, head over to Ocean Park where expansive lawns meet stunning ocean views. This is an ideal spot for picnicking or simply soaking up some sun while enjoying live music during summer concerts. Don't miss out on exploring nearby East Chop Lighthouse; it's one of Martha's Vineyard’s iconic landmarks offering panoramic vistas that are sure to inspire awe.
Whether you're savoring fresh seafood at local eateries or cycling along scenic trails like State Beach Road, Oak Bluffs offers endless opportunities for discovery and relaxation. The island vibe here is both welcoming and invigorating—a refreshing alternative to busier destinations nearby. With its blend of cultural richness and natural beauty, Oak Bluffs promises memorable experiences around every corner.