Top Martha's Vineyard Culture

Visit Martha's Vineyard highlights on this half-day, small-group tour from Oak Bluffs. Make the most of your time on the island as you check out Oak Bluffs, Edgartown, and the Aquinnah Cliffs, learning stories about island history and cultures along the way. This Martha’s Vineyard tour is limited to 14 people for personal service from the local guide, and it includes a 15-minute break to explore the Aquinnah Cliffs.

Go at your own pace, anytime! It's your tour. On our historic walking tour of the Edgartown, you will see the iconic sights and secret gems including the whaling church, the oldest buildings, underground railroad locations, the Carnegie library, filming sights of Jaws, the lighthouse and much more. And I’ll tell you this town’s stories of the settlers, natives, whaling, ghosts, myths and legends, the Kennedy’s, it’s history and much more. Pro narration and production! Best deal in town :)

If you have limited time but still want to see all that Martha’s Vineyard has to offer, then book this private sightseeing tour. You’ll pass through the island towns and scenic landmarks with a local guide, who will tell you all about the area, and allow time for plenty of photo stops. You’ll also be driven from place to place in a comfortable, luxury minivan.

Unearth the charm of Oak Bluffs on this self-guided walking tour, where the rich history and vibrant culture of this New England seaside town come alive. Wander among whimsical gingerbread cottages, enjoy stunning harbor views, and learn how this area evolved from a Methodist camp meeting site to a celebrated resort. This tour highlights the unique blend of architecture, community spirit, and African American heritage that defines Oak Bluffs, making it a delightful exploration of summer memories and local stories. — Discover the distinctive Victorian architecture and intricate cottages — Explore the historical significance of Oak Bluffs as a cultural hub — Enjoy scenic ocean views and shaded park paths during your stroll — Perfect for history buffs and those seeking a unique coastal experience

Explore Martha's Vineyard efficiently on a private tour designed for travelers with limited time. This narrated drive offers a personalized overview of the island's towns and scenic coast without navigating on your own. Learn local history and context from a dedicated guide while traveling comfortably between key areas, making the most of a short visit ashore.

Welcome to Martha's Vineyard, the storied island off Cape Cod that has captivated visitors for generations with its windswept beaches and fiercely independent spirit. This self-guided tour takes you across the island's six unique towns, each with its own character. Begin in bustling Vineyard Haven, where ferries have delivered travelers since the whaling era, then explore Oak Bluffs and its fantastical Victorian gingerbread cottages painted in every color. Drive to elegant Edgartown, where sea captains' houses line streets unchanged since the 1800s. Journey west to witness the dramatic clay cliffs of Aquinnah, sacred to the Wampanoag people who have called this island home for over ten thousand years. Discover quiet fishing villages, pristine wildlife sanctuaries, and the rolling farmland that gives the Vineyard its bucolic countryside charm. From presidents and literary legends to fishermen and farmers, this island attracts those who value beauty, solitude, and community.

Discover how a small religious summer camp transformed into one of Martha’s Vineyard’s most popular island destinations on this walking tour through the town of Oak Bluffs. Starting in Ocean Park, you’ll follow the coast to Inkwell Beach before heading into the heart of the town. Along the way, you’ll hear its history and find out what makes this island paradise so alluring to everyone from the rich and famous, to curious Cape Cod vacationers that come for a day. Around Trinity Park, you’ll see Martha’s Vineyard Camp Meeting Association, its cottage museum, and the Tabernacle in Oak Bluffs which is a place of worship. After heading down Circuit Avenue, where I’ll show you the town’s famous Flying Horses Carousel, our tour will come to an end at the harbor. Whether you’re on the island for only a day, or calling Martha’s Vineyard home for the season, this tour is for anyone who wants to dig into Oak Bluffs’ past and enjoy its present.

See more of Martha’s Vineyard without planning routes or navigating on your own on this all-island bus tour. Multiple scheduled stops let you step off to explore, take photos, and browse key areas, while onboard screens provide historical context for what you’re seeing. With guided narration and built-in free time, the tour balances orientation, learning, and independent exploration in one efficient experience.

Get ready to visit one of the greatest vacation spots in the USA, a favorite among celebrities and even presidents! Martha’s Vineyard is home to stunning beaches and coastline, picturesque little towns, and plenty of fun—but this GPS-guided driving tour with walking portions will also dig beneath the beautiful surface and into the island’s surprising history. Learn about the Wampanoag, the origin of the Vineyard’s famous “gingerbread houses,” and the lost language invented by the island’s residents! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

Explore the beauty of Martha's Vineyard on an electric bike tour designed just for you. It offers unique experiences tailored to your interests: secluded beaches, historic farms, the iconic Gingerbread Houses, and more. Let us take you there. Choose 4-6 hour private tour, where every detail is curated to ensure you see a few of the island's gems: lighthouses, Downtown Edgartown, Oak Bluffs, Chappaquiddick. Or call us and inquire about our 3-day Tour De L'ile for an in-depth adventure across the island's six towns. All tours include e-bike use, helmet, water, snacks, and admission to select attractions. - Explore top attractions like the Campground Cottages in Oak Bluffs and Chappaquiddick Island. - Private tours available for groups up to six riders, ensuring a personalized experience. If you have more riders, give us call a week in advance and we will try to accommodate you.

Walk through Edgartown, a remarkably preserved seaport, on a self-guided audio tour that plays automatically on your GPS app. Starting near the historic harbor, you will follow the route while stories unfold around you. Pass landmarks like the Daniel Fisher House, the Old Whaling Church, the Edgartown Light, and the Chappy Ferry. You will uncover the town's quiet wealth and insider architecture—especially historic whaling captains’ homes lacking public signage—while exploring deep Wampanoag history and local cinematic lore. Explore at your own pace—pause to browse shops, stop for seafood, or take in the harbor views. The audio resumes whenever you’re ready, so you can move freely without keeping up with a group. This is a self-guided experience (no in-person guide). Download the tour in advance and use it anytime—it works offline and follows your location along the route.

Enjoy complete flexibility and explore the parts of Massachusetts that most interest you with this collection of self-guided walking and driving tours. Receive 10 different itineraries and choose the day and time to use any of them. Use offline with GPS and learn about each place as you travel through.