Martha’s Vineyard Travel Guide

Having grown up in Newport, RI, I didn’t get the chance to spend much time in Martha’s Vineyard because I already lived in a New England beach town. We spent most of our summers in Rhode Island with occasional trips out to Block Island.

When we arrived on Martha’s Vineyard, I immediately understood why it’s one of the most popular travel destinations in New England. From incredibly stunning beaches, miles of rugged coastline and fields of wildflowers to farms, clay cliffs, and an amazing food scene, it’s a magical place.

Before heading to Martha’s Vineyard I did a ton of research and planning, but it wasn’t until I got there and experienced the island that I really got a better understanding. This Martha’s Vineyard Travel Guide has everything you need to plan a trip, from how to get there, what to do, where to stay, when to go and so much more!

Martha’s Vineyard Travel Guide

At almost 100 square miles, Martha’s Vineyard is bigger than Nantucket and Aquidneck Island where I grew up. There are several different towns in Martha’s Vineyard including Oak Bluffs, Edgartown, Vineyard Haven, West Tisbury, Chilmark, and Aquinnah. It takes about 45 minutes to drive from one end of the island to the other.

In this guide, you’ll find: helpful information on each town and what they have to offer, how to get to Martha’s Vineyard, where to stay on the island, the best time to go to Martha’s Vineyard, and what to do while you’re there. If you’re planning a trip to Martha’s Vineyard, this guide has everything you need (especially for first timers).

Where Is Martha’s Vineyard

Martha’s Vineyard is an island in Massachusetts located just south of Cape Cod in the Atlantic Ocean. It’s part of Duke’s County which also includes Chappaquiddick Island (right next to Martha’s Vineyard accessible by ferry).

When Is The Best Time To Go To Martha’s Vineyard

Summer is peak season in Martha’s Vineyard, and also when the island is bustling with tourists and summer residents. It is the busiest season and also when the weather is the warmest throughout the year. Summer is a great time to go to Martha’s Vineyard, but also when it’s at the most crowded.

Early fall is arguably the best time to go to Martha’s Vineyard. The island is still very much open, the weather is incredible, still warm but not too hot, and much of the island is more accessible. There are many beaches that are not accessible to visitors until mid-late September.

By the end of October through May much of the island closes including many of the inns and resorts. If you’re looking for solitude, it would be a good time to go, but you would not get the full experience, and the weather is much colder from late fall through early spring.

Martha’s Vineyard is great for a weekend getaway or a longer stay. There is plenty to do there, and you could easily fill a week or longer with activities and events around the island. That said, if you only had a weekend, you could fit plenty in during a 2-3 day stay. Check some of our other favorite weekend getaways in New England here.  

How To Get To Martha’s Vineyard

Martha’s Vineyard is only accessible by boat or plane. The only airline offering year round flights to Martha’s Vineyard Airport (MVY) is Cape Air, which offers daily flights from Boston, and seasonal routes from New Bedford, Hyannis and Nantucket in Massachusetts, New York’s ZYP and Westchester, New York. One of the best ways to get flight deals is through flight aggregator WayAway.

Other seasonal flights (during the summer months) can be found at Tradewinds, JetBlue, Delta, and American Airlines.

To get to Martha’s Vineyard by boat, there are several ferry options. The only year-round ferry options are SeaStreak and Steamship Authority. The Steamship Authority which operates out of Woods Hole on Cape Cod has daily service and is the only ferry that can transport cars and motorcycles. You have to make a reservation in advance to bring a car. The fast ferry from New Bedford on SeaStreak is about a 50 minute ride. Pets and bikes are allowed on board.

There are additional passenger ferries available seasonally during the summer months from Massachusetts, Rhode Island, New York, and New Jersey.

Where To Stay In Martha’s Vineyard

There are a ton of hotels, inns, and Airbnbs on Martha’s Vineyard, but rather than include a long list, I am going to share one property that really stands out.

Winnetu Oceanside Resort

The Winnetu is located in Edgartown, one of my favorite towns on the island. It was about a 20 minute drive from Oak Bluffs where we arrived on the ferry (the resort shuttle picked us up and dropped us off at the ferry). It’s the only resort located on South Beach (which is walkable on a short path from the resort). The resort is also an easy bike ride to downtown Edgartown, or accessible via their complimentary resort shuttles.

There are too many incredible complimentary amenities to list but a few that really stand out. From June-September the Winnetu has a complimentary daily children’s program along with additional activities for kids throughout the season. The resort also has a spectacular heated pool and hot tub, tennis lessons, yoga, various lawn games, daily fire truck rides and more. It was one of the most family-friendly resorts we’ve been to.

The Winnetu also has a variety of accommodations including suites, cottages, home rentals and dog friendly accommodations. It was quieter during our stay in September, but there were various groups at the resort from girls trips to large multi-generational families and couples. We loved going to the pool everyday and enjoying lunch at their pool restaurant/bar. We walked down to the beach every afternoon and it was great that our room had beach chairs, and the resort had bins of sand toys for kids to use during their stay. They also have a little turtle pond which was a huge hit with our 4-year-old.

One of the best parts of our stay was the in-room kitchenette with a Nespresso coffeemaker, toaster, stovetop, full size fridge and dishwasher. When traveling with kids that is an absolute game changer. The other standout aspect of our stay at The Winnetu was the staff. Everyone was incredibly warm, friendly and accommodating, whether it was providing recommendations, arranging a shuttle, or anything else we needed during our stay. You can use code JESS for 10% off your stay at The Winnetu.

What To Do In Martha’s Vineyard

Martha’s Vineyard consists of six towns: Oak Bluffs, Edgartown, Vineyard Haven, West Tisbury, Chilmark, and Aquinnah. Each town has its own vibe, attractions, and scenery. I broke this section up by town because I think it’s easier to navigate the island and understand where things are this way. It should also (hopefully) make planning your trip easier.

Oak Bluffs

Oak Bluffs is one of two towns where the ferry docks. It can get pretty busy and crowded downtown with tourists, but there are definitely some gems to check out. The downtown part of Oak Bluffs is very walkable, and can be a spot you check out before you head out on the ferry or when you arrive.

Take a Guided Tour around the island

There are several tours from Oak Bluffs which is a great option if you don’t have a car and want to see the island in a few hours. This 3-hour tour takes you to popular spots in Edgartown, Oak Bluffs, and Aquinnah, including a stop at Aquinnah Cliffs and Menemsha. If you’re looking to do a private group tour, this tour can accommodate up to 5 people, where you’ll visit key landmarks on the island.

go for a ride at Flying Horses Carousel

If you have kids with you, Flying Horses Carousel is a must visit while in the Vineyard. It’s the oldest working carousel in the US, having been in operation for over 100 years.

visit East Chop Lighthouse

The East Chop Lighthouse is about a 20-30 minute walk or short drive from downtown Oak Bluffs. Parking is limited so it’s best to walk or you can drive by.

see where Jaws Was Filmed at Joseph Sylvia State Beach

This 2 mile stretch of sandy beach is one of the main locations where the movie Jaws was filmed. It’s a nice calm beach, great for kids. Parking is fairly easy along the road but fills up early during the summer.

see the gingerbread houses

Tucked away in a quaint neighborhood you’ll find charming historic homes known in Martha’s Vineyard as the Gingerbread Houses. The colorful homes are over 150 years old, and their history dates back to a group of local Methodists who held religious camp meetings at the site.

Pet an Alpaca

A great place to go if you have kids, Island Alpaca is an alpaca farm with over 50 alpacas, and a cute gift shop. They also have alpaca yoga and walking tours. There were baby alpacas when we visited and they were so cute!

Edgartown

Edgartown was one of my favorites on the island. It has beautiful beaches and a cute downtown area with lots of great shops, restaurants, boutiques and views of the harbor.

Take a Ferry to Chappaquiddick

Take the very short Chappy ferry ride to Chappaquiddick (we recommend bringing a bike instead of car). The small island is incredibly scenic with hundreds of acres of untouched conservation land that is accessible to the public. Make sure to bring a picnic, water, and plenty of snacks for your adventure.

visit katama beach (south beach)

A popular beach on Martha’s Vineyard, South Beach is a free public beach facing the Atlantic. We could walk to the beach from the Winnetu and spent several hours there each day. The surf and shore break can be on the bigger side, so use caution when swimming with little kids and novice swimmers.

Shop at the Black Dog Store

Chances are you’ve probably seen the iconic Black Dog merch at some point in your lifetime. The brand originated on Martha’s Vineyard and their shop in Edgartown has a great selection of tees, sweatshirts, and hats.

Get Oysters at 19 Raw Oyster Bar

This authentic and fresh restaurant in Edgartown is one of the most popular spots for lunch and dinner. 19 Raw Oyster Bar has an amazing assortment of fresh seafood (oysters obviously), clam chowder, burgers, steaks, salads and more. 19 Raw is open seasonally from April 1 to October 30 and they do not take reservations.

explore edgartown books

This adorable bookstore is in the heart of downtown Edgartown. This quaint and cozy independent bookstore has a friendly and helpful staff, and plenty of reading options for every genre and reading level. If you’re hungry, check out Behind the Bookstore, a small cafe with great coffee, serving breakfast and lunch, tucked behind Edgartown Books.

Chilmark

do a tour and tasting at Grey Barn and farms

The Grey Barn is a must visit. This incredibly scenic working farm has cows, chickens, and friendly cats roaming the property. The market features fresh cuts of meat, cheese and bakery items (the chocolate cookies are amazing), along with a nice selection of goods. We were there on a Saturday and there was also a coffee truck serving up delicious coffee drinks. You can also schedule private tastings which includes a guided tour of the property followed by cheese tastings (and it’s BYOB).

The Chilmark General Store

A great place to stop and grab lunch for the beach, the Chilmark General Store has pizza by the slice (or whole pies), sandwiches, and ready made salads. The market also has lots of fresh local produce, specialty foods, and household necessities.

Lucy Vincent Beach

Lucy Vincent Beach is an incredible private beach in Chilmark known for its dramatic sand formations along the shoreline. It is only accessible with a beach pass (for residents or if you’re renting a home in Chilmark), however it is open to the public after September 15 (until June 1).

watch the sunset at Menemsha Public Beach

Menemsha is one of the most famous and iconic places to watch the sunset on the East Coast. The beach is free and open to the public with parking nearby. It’s located in the heart of Menemsha’s fishing village where you can watch lobster boats and fisherman coming in to the docks.

get fresh seafood at Larsen’s or menemsha Fish Market

These two fresh seafood spots are located right next to each other and both had lines out the door. Larsen’s was recently renovated so it has a more modern look, but some locals told me Menemsha is the local favorite spot. Both serve up fresh chowder, lobster, crab cakes, steamers and more. A great spot to get lunch or dinner to go and watch the sunset at the beach.

West Tisbury

Field Gallery

Not far from Grey Barn but technically in West Tisbury, this outdoor and indoor contemporary art gallery features a variety of works including sculptures, paintings, photography and more.

Granary Gallery

The Granary Gallery located in the iconic red barn is the oldest and largest gallery on the island featuring antiques and fine art. A very fun place to explore if you’re an art lover.

Aquinnah

Aquinnah is the western most part of the island with a more rural landscape. Driving or biking around is absolutely beautiful with rolling hills and fields, the Aquinnah Cliffs and the Gay Head Light. Aquinnah has a rich Native American history with the ancestors of Wampanoag people having lived for at least 10,000 years there. The Wampanoag Tribe in Aquinnah are the legal caretakers of over 500 acres of land which remains mostly undeveloped.

Visit Gay Head Light and Aquinnah Cliffs

The Gay Head Light and Aquinnah Cliffs are a must see when you’re in Martha’s Vineyard. It can get crowded on the weekend and there is minimal parking so I recommend going early during peak season. You can also pay for parking at the public beach parking lot and walk up. Gay Head Lighthouse is open to the public seasonally, and you can also get a fantastic view of it from the lookout point where you can see Aquinnah Cliffs on the other side. It’s an incredible view.

Head to Moshup Public Beach

You can also see the Aquinnah Cliffs from Moshup Beach which is public. There is a parking lot with a daily parking fee and a meandering path down to the beach. The cliffs are a federally protected landmark so there is absolutely no climbing on or disturbing the clay in anyway.

Vineyard Haven

Vineyard Haven is the other ferry port on Martha’s Vineyard. It was the one town where we did not get to spend much time during our trip. That said there are some great spots to check out including West Chop Lighthouse, The Black Dog Tavern, and Martha’s Vineyard Museum.

Is Martha’s Vineyard Worth Visiting

The short answer is yes, Martha’s Vineyard is absolutely worth visiting. The question is, what’s you budget, when do you want to travel, and what do you want to do? If you plan to go to Martha’s Vineyard in the summer, the prices for lodging are going to be the highest. It’s also going to be more crowded, but the weather is great. If you want less crowds and a lower rates, look into going in the late spring or early fall. If you’re seeking solitude, winter is definitely an option, just know there will be far less options for dining out and lodging.

Martha’s Vineyard is a beautiful and special place in New England. If you love the ocean, wildlife, fresh seafood, art, and charming small towns, chances are you’ll love Martha’s Vineyard.