Visiting Martha’s Vineyard: How to Get There, What to Do, and the Best Towns to Explore

Growing up, some of my most treasured memories come from sailing to Martha’s Vineyard. After hours of sailing, the moment the island’s shoreline appears on the horizon feels like a quiet celebration. The salty breeze, the gentle rocking of the boat, and the sight of the island’s familiar contours bring a deep sense of peace and excitement all at once. That first glimpse of Martha’s Vineyard always signals the start of an unforgettable escape to one of New England’s most charming coastal destinations.

If you’re planning your first trip or returning for another visit, this Martha’s Vineyard travel guide will walk you through everything you need to know, from how to get there to the best things to do and where to explore. I’ll share personal insights and practical tips to help you experience the island’s unique rhythm and beauty.

What It’s Like Arriving by Boat and Sailing to Martha’s Vineyard

Sailing to Martha’s Vineyard is a special experience that sets the tone for your entire trip. The island’s coastline slowly comes into view after hours on the water, with sandy beaches, classic lighthouses, and rolling greenery. The sound of seagulls and the smell of saltwater fill the air, creating a welcome that feels both timeless and refreshing.

From my own trips, I remember the excitement building as the boat neared Vineyard Haven, one of the island’s main harbors and ferry ports. I always loved watching the colorful gingerbread cottages of Oak Bluffs and the historic shoreline of Edgartown come into view. Arriving by sailboat gives you a perspective of the island that you do not get any other way.

Things to Do in Martha’s Vineyard

Martha’s Vineyard offers a variety of activities that suit every pace and interest. Whether you want to relax on the beach, explore by bike, or spend time on the water, there is something for everyone.

Beaches to Visit

Martha’s Vineyard beaches are some of the most scenic along the East Coast. My favorites include:

• South Beach near Edgartown: Known for its wide sandy shoreline and stronger Atlantic waves, great for long beach days

• State Beach in Oak Bluffs: Calm waters and easy access, perfect for a relaxed afternoon

• Menemsha Beach: A quieter spot with some of the best sunsets on the island and a laid-back fishing village feel

Each beach has its own personality, which makes it easy to find one that fits exactly what kind of day you want.

Biking Around the Island

Biking is one of the best ways to experience Martha’s Vineyard. There are miles of scenic, mostly flat bike paths that make it easy to explore different parts of the island.

Popular routes include:

• The network of bike paths connecting Oak Bluffs, Edgartown, and Vineyard Haven

• The ride from Edgartown toward South Beach or out toward up-island areas like Chilmark for more experienced cyclists

Tips for biking:

• Rent a bike from local shops in Oak Bluffs or Vineyard Haven

• Bring water and sunscreen since some areas have limited shade

• Expect busier paths during the summer months

Sailing and Water Activities

If you enjoy being on the water, sailing around Martha’s Vineyard is a natural way to explore. You can charter a sailboat or join a guided trip to experience the coastline and surrounding waters, including areas near the Elizabeth Islands. Kayaking and paddleboarding are also popular in calmer bays. In some areas, you can also take windsurfing lessons on the island depending on the season.

Exploring the Island

Beyond outdoor activities, Martha’s Vineyard has plenty to explore at a slower pace. Spend time walking through town centers, visiting local farms, browsing art galleries, and taking in the history that gives the island its character.

Best Towns to Visit on Martha’s Vineyard

Each town on Martha’s Vineyard offers something a little different.

Edgartown

Edgartown feels historic and polished, with white clapboard homes and a quiet coastal atmosphere. It is known for:

• Boutique shopping and galleries

• Waterfront dining

• The iconic Edgartown Lighthouse

It is a great place for a slower afternoon or an evening by the harbor.

Oak Bluffs

Oak Bluffs is more colorful and lively, known for its energy and charm. Highlights include:

• The famous gingerbread cottages

• The historic Flying Horses Carousel, the oldest operating platform carousel in the United States

• A walkable downtown with shops and casual dining

It is a fun stop if you want a more social and vibrant atmosphere.

Vineyard Haven

Vineyard Haven has a relaxed, local feel and serves as a primary arrival point for many visitors. It is ideal for:

• Coffee shops and bakeries

• Bookstores and local shops

• Easy access to ferries and transportation

Best Coffee Shops, Bakeries, and Local Food Spots

Some of my favorite places to stop include:

• Artcliff Diner for breakfast and coffee

• Back Door Donuts for fresh donuts, especially at night when they open their back door service

• Among The Flowers Bakery for pastries and coffee

• The Net Result for casual seafood

These spots are simple, local, and part of what makes the island feel so welcoming.

Where to Stay in Martha’s Vineyard

Where you stay can shape your experience on the island.

• Edgartown offers more upscale inns and historic bed and breakfasts

• Oak Bluffs has more budget-friendly options close to the beach and town

• Vineyard Haven is convenient for ferry access and getting around

You can also find private cottages and home rentals if you want something more quiet or unique.

How to Get to Martha’s Vineyard Without a Personal Boat

If you are not arriving by sailboat, there are still easy ways to get to Martha’s Vineyard.

• Ferries run year-round from Woods Hole, with seasonal routes from Falmouth and New Bedford

• Flights into Martha’s Vineyard Airport are available from cities like Boston and New York, often on regional or seasonal routes

It is a good idea to plan ahead during the summer since transportation fills up quickly.

Visiting Martha’s Vineyard

Visiting Martha’s Vineyard feels like stepping into a slower pace where the ocean, small towns, and everyday moments all stand out a little more. Whether you arrive by boat, explore by bike, or spend your time moving between beaches and towns, it is the kind of place that stays with you and keeps you coming back.