Taking a day trip to Martha’s Vineyard is great if you’ve been to the island before and just plan to walk around on a beach, get lunch by the water, or stroll through a few shops. However, you’ll want more time to explore if it’s your first visit.
I visited while staying near Boston during my nearly two-year-long solo road trip through the United States, Mexico and Canada. A lot of things about Martha’s Vineyard surprised me, but none more than the size of the island. It’s much bigger than I anticipated, and that posed a few difficulties and required choices I wasn’t ready to make.
Martha’s Vineyard is a big island with several small, unique communities to discover. There are Oak Bluffs, Edgartown, Menemsha, and Vineyard Haven, to name just a few. Each place has different features, like shopping, fishing, or rural beauty, that are different from the last. But seeing them all in one day is possible – I did it – but it’s not the best way. Here’s what you’ll need to know when planning your trip.
Getting to Martha’s Vineyard – Ferry or Plane?
If you’re going to Martha’s Vineyard from the Boston area, as many are, you’re likely taking the ferry. If you’re lucky, maybe you’re taking a private plane or flying via JetBlue or Cape Air for $400+ per person round trip. However, most of us take the ferry, which is more budget-friendly at $20 a ticket. If you plan, you can even take your car for about $200 more, which you might want to consider.
But, if you’re only going for a day trip on Martha’s Vineyard and taking your car to explore the various communities, you’ll spend most of the day driving, and that’s not the best way to spend a day trip on Martha’s Vineyard.
Book the Martha’s Vineyard Ferry in Advance
If you’re taking the ferry, here are a few tips. You can buy tickets online in advance or at the port that day. If you’re going to Nantucket, they might sell out, but you don’t need to worry about them selling out here. You just show up and board the next ferry. Don’t do what I did. I drove to the Woods Hole port, but you can’t park there. There is only short-term parking at the port, so I had to drive 15 minutes back the way I came to catch the shuttle, wait for it, and go back to the dock. When you go, do not drive to the port; drive to the shuttle location, park, and take the shuttle. The shuttle lot will cost you an additional $10 – $14 per vehicle for the day, depending on the season. I lost 45 minutes in the morning driving back and forth. Regardless, I could immediately jump on a ship and head to the island.
You can also hire a tour company to manage all the details for you, but if you have a vehicle, it’s just as easy to do it yourself and save some money. That said, what I love about tours is the additional history and topical information you’ll receive from guides, so choose what you want the most when deciding.
Martha’s Vineyard Ports
You can leave the mainland from Hyannis, Nantucket, Falmouth or several other ferries in the summer months or the Woods Hole port year-round.
There are a few ports on Martha’s Vineyard you can enter, but not knowing the difference, I grabbed the first boat and it happened to be going to Vineyard Haven (also known as Tisbury), the year-round destination port. The boat I chose was not a traditional passenger ferry. It was a steamship filled with cars and pallets of merchandise.
The ferry ride to Martha’s Vineyard takes about 45 minutes. There I stood, at the bow of the boat, the wind in my face as we departed land, the large houses shrinking in the distance, the ocean overtaking all I could see – except for the trucks, pallets, and other vehicles also on deck being transported to the island.
Once I arrived, I obtained a map from a helpful visitor’s center guide. Seeing the size of the island, I opted to take a guided tour. The guide informed me that all the tours leave out of Oak Bluffs, a few miles down the road. Had I waited at Woods Hole for the next ferry, it would have been a passenger ship landing in Oak Bluffs. Oak Bluffs is probably your best bet in the summer if you’re a first-timer. We live and learn. You’d think I’d know better than to try and wing these things; alas, I now had to learn the Martha’s Vineyard Transit Authority schedule to get to Oak Bluffs.
Getting Around Martha’s Vineyard
Each community on Martha’s Vineyard can be walkable, but they’re a few to several miles apart, so you need transportation to get to each one unless you have a lot of time and ambition. The most practical choices are a car, bus or moped.
The Martha’s Vineyard bus system is probably the only bargain on the entire island. At just $4 per ride or $8 for the day, it’s a steal. The buses run roughly every 15 minutes to every community on the island. It will take longer than a private vehicle, but if you arrive on the 7 am ferry and plan to leave on the last 9:30 pm ferry (in summer), it would be an excellent way to see the island.
In Oak Bluffs, at least a dozen vendors rent mopeds, which would be a fun way to get to one or two nearby communities but not the entire island. The roads are long, wooded, two-lane highways unsuitable for inexperienced moped riders. If you were familiar with the streets, perhaps it would be a good choice, but not for tourists. It can take 30 minutes to get from one community to the next on a moped.
There are many bicycles for rent too, but they’d only be good for visiting the two communities nearest to Oak Bluffs – Vineyard Haven and Edgartown – unless you’re a serious biker with excellent road safety.
Fun Fact: You may hear islanders reference “chappy” it’s short for Chappaquiddick, a small island off the island’s eastern side. It’s best known for the sad Chappaquiddick incident when Senator “Ted” Kennedy drove his car off a bridge, resulting in the drowning death of his passenger trapped inside the vehicle.
Oaks Bluffs
Oak Bluffs is the main tourist area with the biggest community and most amenities on Martha’s Vineyard. It’s where you’ll find the most extensive beaches, rentals, shopping and restaurants.
The ferry leaves you right to a long stretch of beach and you can walk to everything in the Oaks Bluffs area. If you only spend the day in this community, it would be time well spent. There are a few hotels and cottages, plenty of restaurants and dozens of small shops, including the famous “Black Dog” tavern and shop – a Martha’s Vineyard staple. Other points of interest in or near Oaks Bluffs include:
Gingerbread Cottages
A “subdivision” in Oak Bluffs just off the downtown area is home to over 300 small, colorful “gingerbread cottages.” These homes – many for rent – are a favorite place to walk around and appreciate charming architecture. They feature bright colors, elaborate woodwork, interesting shapes, and glorious flowerbeds. They look like something you’d expect to find in a children’s storybook.
Fun Fact: The cottages were built by a Methodist group who used to camp on the site but wanted to upgrade to permanent structures.
Flying Horses Carousel
The Flying Horses Carousel is another Martha’s Vineyard icon. They’re a short distance from the ferry dock in the middle of downtown. Let the music be your guide and you’ll find your way.
Built in 1876, the Flying Horses Carousel is the oldest platform carousel in the country. It includes hand-carved wooden horses with genuine horsehair and glass eyes. The horses don’t move up and down but are fixed to the rotating platform.
Fun Fact: There is a metal arm on the outside of the carousel that used to be a game – the mechanical arm dispenses brass rings and – back in the day before safety was a concern – if you could lean out far enough and grab a ring, you’d win a free ride.
Island Tours on Martha’s Vineyard
In Oak Bluffs, I could book a tour with a company to take me and a couple around the island. The driver took us around the island for the day, stopping in many communities to explain its rich history. It’s a lot bigger than I expected. It was 10 miles longer and nine miles wider than Nantucket, which I’d been to the day before.
We drove along mostly long two-lane wooded roads and could only occasionally peek at the ocean through the trees. Within those trees are many homes hidden from prying eyes like mine, which, I suspect, is why the rich and famous like it. Every few miles, beyond a stretch of woods and ocean, we happen upon a small community.
Edgartown
After Oak Bluffs, Edgartown is probably the most popular. There are a lot of historic homes and beautiful gardens. The downtown has plenty of posh businesses and restaurants and it looks like it came right out of a movie; in fact, it did. If it looks familiar, that’s because the downtown was depicted as Amity Island for filming JAWS. Just think about that as you lay on the beach!
JAWS on Martha’s Vineyard
In Edgartown, Joseph Sylvia State Beach is a popular place for beachgoers. Part of the popularity, other than the long stretch of clean, white sand, is the bridge between the open ocean over the water inlet into the Sengekontacket Pond. You’ve seen this before; it’s the bridge that JAWS swam under to get into the pond. Today, despite the signs that say “Do not jump from bridge,” it’s a pastime for everyone to jump from “JAWS bridge.” Even though that movie was filmed in 1975, when I see clips like the one I just linked, it still gives me chills!
You can also find great views of the Edgartown Harbor Lighthouse and go to the top for just $5.
Fun Fact: The lighthouse used to be on an island, but now a stone causeway connects it to the mainland.
Aquinnah
I was surprised to see there are a lot of farmlands on Martha’s Vineyard. We drove past a lot of it alongside alpaca farms and forest preserves. This part of the island has a lot of long dirt roads that lead to massive homes like the one the Obamas have nearby. If you want to see any of these homes, you’ll need a boat or a private invitation.
Aquinnah has a small cultural center with about a dozen pop-up shops and restaurants staffed with locals selling handmade food and goods. This area has a long history for the Wampanoag people. They have lived at least 10,000 years at Aquinnah and throughout Martha’s Vineyard, where their lives revolve around fishing and agriculture.
Fun Fact: The town of Aquinnah had been called Gay Head for many years, but they changed it to Aquinnah – a Wampanoag word meaning land under the hill – about 20 years ago.
Gay Head Lighthouse on the Gay Head Cliffs
The stunning Gay Head Lighthouse sits on the colorful cliffs at Martha’s Vineyard’s western end, looking out to a vast sea. The cliffs are variegated shades of green, yellow, black, brown, red, and white and are a favorite place for photographers and tourists.
The red brick Gay Head Light built in 1856, is a beacon for sailors near Martha’s Vineyard. The lighthouse was moved back once from the rapidly eroding cliffs of Gay Head and will likely have to be moved again. It’s the only lighthouse in the U.S. with a history of Native American lighthouse keepers.
Sad Fact: A few miles out at sea from this point is where John Kennedy Jr.’s airplane crashed in 1999, killing him, his wife Caroline and her sister.
Tisbury/Vineyard Haven
The port in Tisbury/Vineyard Haven is open year-round and it’s where a lot of commercial importing happens. The docks here are more industrial than the passenger docks in Oak Bluffs. There is also a small downtown, several historic buildings, various shops, lodging, theatres, restaurants, and homes. The community has a rich maritime history, and many Greek Revival-style houses date to the 1800s. Unlike those in Oak Bluffs and Edgartown, most shops and restaurants stay open in the winter.
East Chop Lighthouse
East Chop Light is a historic lighthouse on a bluff overlooking Vineyard Haven Harbor.
West Chop Lighthouse
West Chop Light is a lighthouse station at the entrance of Vineyard Haven Harbor on the northern tip of West Chop.
Fun Fact: You may hear islanders use the term “chop,” which means the entranceway into a body of water. This is why two lighthouses flank the entrance to the harbor at Vineyard Haven on the north shore.
Menemsha
As our tour continued, we drove through Makonikey, along mostly long two-lane wooded roads along the Vineyard Sound. You can see the ocean through the trees, but presumably, there are homes in the woods near the water. Most of the island is this way. In between the towns are hidden houses and, between those, a few small businesses.
We arrived at the Menemsha fishing village in Chilmark in time for lunch. We found an active fishing community with fishing boats docked at the pier, lobster and oyster cages for growing and harvesting, several fresh fish restaurants, and half a dozen small businesses. The Swordfish Harpooner sculpture stands atop a tall dune near the water. It’s a popular spot to sit and watch the sunset.
Costs on Martha’s Vineyard
People most often ask me if Martha’s Vineyard is affordable. I think the adage “if you have to ask, you can’t afford it” applies here. Martha’s Vineyard is at the top of the list for the most expensive of all the places I’ve been in over a year of travel. The houses are hidden by miles of trees and “private property” signs keep you out of all but the downtowns and tourist areas. There’s a lot to this island that a poor girl who grew up in the Detroit suburbs like me will never see or afford.
To give you a relatable idea of the cost, I bought a regular ice cream cone with one scoop of ice cream, no extras, for $9. I felt bad for the family of four ahead of me, who spent $50 on ice cream cones. My mother is rolling over in her grave.
If you take a Day Trip to Martha’s Vineyard for One Day
Plan your transportation and research the places you want to see on the island. No matter your plan, I’d recommend it if you can stay at least one night. If you have a friend with a house, even better.
Still, a day trip to the beach will be worth it if thoughts of JAWS don’t turn you off. For something to do, it’s fun to tour the small towns around the island and the bus is a good and affordable way to do it.
Read more stories about Massachusetts here.
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