How to Plan the Best Day Trip to Martha’s Vineyard

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Martha’s Vineyard, located just south of Cape Cod in Massachusetts, is a must-visit destination for anyone traveling to New England. The coastal atmosphere, charming towns, and intriguing history make this 87-square-mile island ideal for all types of travelers. There is enough to do on the island to keep you busy for weeks, but it also makes a great day trip from Falmouth in Cape Cod with a quick 45-minute ferry ride. 

Planning a trip to this iconic island can be overwhelming as there is so much to see and do. It is not of the cheapest New England Trips, but with some planning, a day trip to Martha’s Vineyard or a weekend getaway is well worth the cost.

In this post, I share everything you need to know to plan the best trip to Martha’s Vineyard, including tips for booking the fast ferry, finding reasonable accommodation, island transportation, dining, and sightseeing. I also include a list of the best things to do on Martha’s Vineyard. For a day trip itinerary leading you from Oak Bluffs through some of the most popular attractions on the island, check out this day itinerary for Martha’s Vineyard. 

​When is the best time to visit Martha’s Vineyard?

Summer and early fall are the best times to visit Martha’s Vineyard. 

Martha’s Vineyard see the most tourists between Memorial Day and Labor day. The 17,000 residents increases tenfold to nearly 200,000 in the height of summer. Summer is a fantastic time to visit for festivals and community events with all of the tourist activities operating in full swing. 

Expect crowds, warm temperatures, rentals selling out quickly, higher prices and virtually no visitor parking during summer months. If you visit during the summer, I recommend coming for a day trip and doing a walking and biking tour through the island’s most happening towns. You won’t be able to see all of the island on a day trip but you will be able to explore the top sights. 

I love going to the island during the shoulder season in late September to October. The weather is cooler and while some attractions are closed for the season, there is still plenty to do. This is the best time to stay overnight as a visitor and bring a car to explore the entire island since parking is free and not monitored as highly as in the summer. 

How to get to Martha’s Vineyard 

By Plane:

Martha’s Vineyard has its own airport, Martha’s Vineyard Airport (MVY), so it is possible to fly to this island. You can also fly into Boston Logan International Airport (BOS) or Cape Cod’s Barnstable Municipal Airport (HYA) and then take a connecting flight to Martha’s Vineyard.

The flight duration from Boston Logan International Airport to Martha’s Vineyard Airport is typically around 30-45 minutes, depending on weather conditions and your chosen airline. 

Round-trip airfare prices can vary widely depending on the time of year, airline, and departure location. On average, expect to pay a few hundred dollars for a round-trip ticket from Boston to Martha’s Vineyard, but prices can be higher during peak summer months.

By Ferry:

The ferry service is the best way to get to Martha’s Vineyard. There are multiple ferries from different ports year-round to the island. 

  • The Island Queen Ferry is a seasonal, passenger-only ferry service between Falmouth on Cape Cod and Oak Bluffs on Martha’s Vineyard.
  • The Steamship Authority ferry operates year-round and includes the only car ferry to the island. Regular routes depart from Woods Hole, on the Cape to Oak Bluffs or Vineyard Haven throughout the year. The car ferry costs about $215 for a roundtrip car + 1 person from Woods Hole to the Vineyard.
  • Hy-line Cruises operates a seasonal (May-October) passenger ferry from Hyannis port on Cape Cod and a year-round passenger ferry from Nantucket Island to Martha’s Vineyard. 

The ferry ride takes about 45 minutes to reach Martha’s Vineyard and costs $60-$100 round trip per adult depending on the ship and day of week you are traveling. Some boats also allow bikes to be brought on board for an additional fee.

The Steamship Authority does not require advanced reservations for foot passengers and tickets can be bought at the port office. But if you want your preferred time, I’d book in advance just in case, as select routes can fill up quickly. The Car ferry sells out months in advance for summer and sometimes weeks in advance for fall dates.

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How to Get Around the Island 

I highly recommend leaving your car at home when visiting during the summer as parking is virtually nonexistent for visitors. Many parking areas turn into permit-only zones, have limited parking hours and cost upwards of $30 no matter how long you park (typically at beach parking lots).

Taxis, Ubers and public buses are available but not alway the most convenient option. Biking is the number one way to get around the island. 

Public Bus

The Martha’s Vineyard Transit Authority (VTA) operates a bus network covering most of the island, connecting Edgartown, Oak Bluffs, Vineyard Haven, Aquinnah, Chilmark, and West Tisbury. These buses run year-round – you can pay as you go or purchase 1-day, 3-day, or 1-week bus passes. Visit the VTA website for schedules, fares, route maps, and more information.

Car

You can bring your car to Martha’s Vineyard on the ferry or rent one on the island. However, parking can be limited and expensive in some areas, especially during the peak tourist season, so I wouldn’t recommend this option unless you are visiting in the shoulder season or the off-season. 

Taxi and Uber Ride Share services are also available on Martha’s Vineyard but keep in mind that availability may vary, especially during the off-season, and rates can be expensive.

Walking

Many of Martha’s Vineyard’s towns and attractions are easily accessible on foot. Edgartown, Oak Bluffs, and Vineyard Haven have picturesque downtown areas with shops, restaurants, and historic sites that are great for exploring on your own two feet. Plus, the ferry runs between Vineyard Haven and Oak Bluffs, so you’ll still be able to get around the island.

Biking

Although the island is too big to cover by bike only (especially on a day trip), Martha’s Vineyard is a bike-friendly destination with several dedicated bike paths and rental shops. You can rent bicycles and explore the island at your own pace. The flat terrain of this island makes it suitable for cyclists of all skill levels. If you plan to rent a bike, take a ferry that gets you to Oak Bluffs or Vineyard Haven before opening time or you risk the bike rentals being sold out.

Best Things to See and Do on a Martha’s Vineyard Day Trip

If you are only visiting the vineyard for a day, you’ll need to choose one or two areas to enjoy as the island is a bit too big to see it all. I recommend at least 3 full days to explore the island in its entirety but if you are looking for a more relaxing vacation, 4 or 5 full days is ideal.

Martha’s Vineyard consists of six towns, all with their own character and charm and stunning coastlines. The “down island” towns of Tisbury (Vineyard Haven), Oak Bluffs and Edgartown are shopping havens with attractions and restaurants to suit every taste. The “up island” towns of West Tisbury, Chilmark and Aquinnah are quaint, quiet places reminiscent of the island’s maritime past with a more remote feel. 

Chilmark, Aquinnah and West Tisbury, are the more rural towns on the island’s west side. They are harder to get to on a day trip to Martha’s Vineyard. The other three “down-island” towns, Tisbury (Vineyard Haven), Oak Bluffs, and Edgartown, are the busier port towns that are more developed and best for exploring on a day trip to Martha’s Vineyard.

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I’ve dabbled into the six major towns on the island, what they are known for, the best attractions in each area and recommended places to eat. If you are arriving by ferry you will either land in Oak Bluffs or Vineyard Haven which are only 3 miles apart and two of the best areas to explore by foot or bike on a day trip to Martha’s Vineyard.

Tisbury (Vineyard Haven)

Tisbury is home to the island’s busiest ferry terminal and is often the first point of entry for visitors arriving by ferry. Vineyard Haven, the main village within Tisbury, has a bustling downtown area with shops, restaurants, and cultural attractions, making it one of the best places to include on a Martha’s Vineyard day trip. 

Things to do in Tisbury:

  • Main Street and Waterfront Take a stroll along Main Street, where you’ll find shops, boutiques, art galleries, and cafes. If you love reading, check out Bunch of Grapes, an independent bookstore.
  • Visit Owen Park Owen Park is a lovely park along the waterfront in Vineyard Haven. It’s a great place for picnics, strolling, and enjoying scenic views of the harbor. You can watch the ferries come and go from the nearby Steamship Authority terminal.
  • West Chop Lighthouse– If you take a 40-minute walk to this lighthouse from downtown, you’ll experience an off-the-beaten-path version of Vineyard Haven. Although the lighthouse isn’t open to visitors, you can still take some pictures from the street.
  • Martha’s Vineyard Museum– This is the perfect place to learn about the island’s history, culture, and maritime heritage. Unlike other museums, this museum details the area’s history since the island formed (going back much further than the island’s colonization).

Best places to eat in Tisbury: 

  • The famous Black Dog Tavern– This historic restaurant is famous for its seafood, chowder, and waterfront dining in a classic and comfortable atmosphere – it’s a must-visit for anyone on a Martha’s Vineyard day trip!
  • Waterside Market– This year-round market serves lobster rolls, salads, and an all-day breakfast.
  • The Net Result A fish market and takeaway counter offering local fresh seafood from lobster rolls, clams, steamers, fish tacos, and more.

Oak Bluffs

Oak Bluffs is the second port town in Martha’s Vineyard welcoming ferry guests from May – October. This area is renowned for its whimsical gingerbread cottages in the Martha’s Vineyard Camp Meeting Association (MVCMA) grounds. There’s no shortage of lively streets, shops, and restaurants in this bustling port town making it a fantastic option to explore on your trip to the Vineyard.

Things to do in Oak Bluffs:

  • Ginger Bread Cottages Stroll through this iconic religious campground from the 1800s, known for its whimsical and colorful gingerbread cottages.  unique architecture 
  • Cottage Museum This charming museum offers a glimpse inside the 1800s Campground cottage
  • Ocean Park A lovely green space overlooking the ocean surrounded with beautiful carpenter Gothic homes, it also makes an excellent place for a picnic lunch.
  • Circuit Avenue Circuit Avenue is the main street in Oak Bluffs, showcasing a range of souvenir shops, boutiques, restaurants, and ice cream parlors. This lively area is perfect for shopping and people-watching.
  • The Flying Horses Carousel Visit the Flying Horse Carousel, the oldest platform carousel in the United States, that has been beautifully restored after moving it to the island in the 1880s. 

Best places to eat in Oak Bluffs: 

  • Nancy’s Restaurant– Located on the Oak Bluffs Harbor, Nancy’s is a popular seafood restaurant known for its lobster rolls, clam chowder, and casual outdoor seating with water views.
  • The Lookout Tavern Enjoy a casual meal and drinks at The Lookout Tavern, offering a diverse menu of seafood, burgers, and a raw bar. The outdoor patio provides fantastic views of the harbor.
  • Offshore Ale Co- Serving house-brewed seasonal & year-round beers, plus wood-fired pizzas, burgers & other casual pub grub
  • Barn Bowl and Bistro- A family fun spot with games, TV and bowling
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Edgartown

Edgartown is known for its historic and elegant architecture, including beautifully preserved whaling captains’ homes. During a Martha’s Vineyard day trip to Edgartown, you can explore the charming village center, scenic harbor, and beautiful beaches and even take the car ferry to Chappaquiddick Island and enjoy Mytoi Garden, a Japanese-style garden with peaceful walking paths, ponds, and lush plant life.

Edgartown is about 6 miles away or 15 minutes from Oak Bluffs and about 8 miles or 20 mins by car from Vineyard Haven.

Things to do in Edgartown:

  • Edgartown Village Historic District- Explore the lovely streets of Edgartown, with historic homes, boutiques, art galleries, and cafes. There are over 500 buildings in this district, making it a paradise for architecture enthusiasts. 
  • The Jaws Bridge- Head to Joseph Sylvia State Beach where you can jump off the iconic Jaws bridge from the hit motion picture.
  • Jump off the bridge from the hit motion picture.
  • Edgartown Harbor Lighthouse- Visit the Edgartown Harbor Light and enjoy panoramic views of the harbor after climbing to the top.
  • Ferry to Chappaquiddick Island- The 1 minute car ferry to Chappaquiddick is a fun way to spend a few hours exploring a lesser visited side of the vineyard.
  • Felix Neck Wildlife Sanctuary- Just outside Edgartown, Felix Neck Wildlife Sanctuary is a beautiful natural area where you can go birdwatching, hiking, and explore diverse ecosystems.
  • Visit the Old Whaling Church- It is a historic building in Edgartown known for its stunning architecture. It often hosts cultural events and concerts.
  • South Beach- Enjoy the long sandy beach backed by dunes at South Beach, one of the best beaches on the island.

Best places to eat in Edgartown:

  • Detente– Seasonal restaurant with a frequently changing menu offering inventive American fare with European influences, local seafood, hand-rolled pasta, and house-made desserts.
  • Rockfish– A casual upscale setting offering wood-fired pizzas and American bites. 
  • Among the Flowers– Cozy outdoor patio offering breakfast and lunch and homemade doughnuts. 
  • Rosewater Market– Year-round gourmet market serving breakfast and lunch and made from scratch-made baked goods

West Tisbury

West Tisbury is an ideal destination for those seeking a quieter and more nature-oriented Martha’s Vineyard experience. It offers the opportunity to connect with the island’s natural beauty and its vibrant arts and agriculture scene while enjoying a slower pace of life.

This area of the Vineyard is about 7 miles or 15 mins from Vineyard Haven

Things to do in West Tisbury:

  • Alley’s General Store– This classic New England general store is a treasure trove of gifts, candy, and toys. Serving the community since the 19th century, this is the oldest store in Martha’s Vineyard, and it’s the perfect place to pick up a souvenir or two!
  • Lambert’s Cove Beach– Enjoy the natural beauty of Lambert’s Cove Beach, with its calm blue waters and soft white sand. There’s no better place for a Martha’s Vineyard day trip to the beach.
  • Hiking and Nature Walks– West Tisbury offers several hiking and nature walk opportunities. The Manuel F. Correllus State Forest, located nearby, has several trails where you can explore the island’s natural beauty. Walk the Dr. Fisher Trail to see vibrant oak and evergreen trees!
  • West Tisbury Farmers’ Market – If you’re on the island during the summer and early fall, the West Tisbury Farmers’ Market offers a variety of locally grown produce, artisanal products, and crafts all together in one place, the MV Agricultural Hall. 
  • Lambert’s Cove Beach– Lambert’s Cove Beach is a scenic and secluded beach in West Tisbury known for its serene atmosphere and picturesque views. It’s a great spot for swimming, sunbathing, and beachcombing

Best places to eat in West Tisbury:

  • 7a Foods– This charming café, a popular spot amongst both visitors and locals, offers delicious breakfast and lunch options, including egg sandwiches, pastries, and coffee.
  • State Road Restaurant– Located in a historic home, this restaurant is known for its farm-to-table cuisine and extensive wine list. Get cozy in the rustic dining room, or sit outside on the lush patio if the weather is pleasant.

Chilmark

Chilmark, a small fishing village, is known for its pristine beaches, stone walls, rolling hills, and picturesque farmland. This is one of the best places to experience the quiet side of a Martha’s Vineyard day trip.

Chilmark is about an hours bike ride or 30 mins drive from Vineyard Haven.

Things to do in Chilmark:

  • Chilmark Beaches: Chilmark is home to some of the island’s most pristine and less crowded beaches. Lucy Vincent Beach is likely the most iconic beach in this area, with dramatic sand and gravel formations overlooking the water, making you feel like you’ve stepped into a postcard. Squibnocket Beach, another great option, has a rocky coast and excellent surfing. 
  • Menemsha Hills: Hike and explore the Menemsha Hills Nature Reserve, boasting scenic trails with beautiful vistas overlooking the ocean and Vineyard Sound. The trails vary in difficulty and provide excellent opportunities for nature lovers. Trek the Harris Trail to the top of the hill for incredible views of the Menemsha harbor, the Gay Head Light, and the Elizabeth Islands.
  • Watch the Sunset: One of the most popular things to do in Chilmark is to experience the breathtaking sunsets at Menemsha Beach. You can bring a picnic, watch local fishermen bring in their catches, and enjoy the serene atmosphere as the sun sets over the water. When the sun goes down, you’ll be rewarded with a tapestry of oranges, pinks, reds, and purples across the sky.

Best places to eat in Chilmark:

  • Home Port Restaurant– Located in Menemsha, the Home Port Restaurant is a classic seafood restaurant with a picturesque harbor view. This BYOB local hangout has a raw bar on the deck and a takeout window in the back. 
  • The Galley– Another Menemsha favorite, The Galley serves lobster rolls, burgers, fish sandwiches, and soft-serve ice cream with a casual deck showcasing a view of the Menemsha Basin.
  • Menemsha Fish Market– Although it may look like a hole in the wall, that’s only because this fish market is all about the food. Enjoy fish and chips, lobster rolls, clam chowder, and lobster bisque. Fresh Seafood

Aquinnah

Aquinnah, formerly known as Gay Head, is the westernmost town on Martha’s Vineyard and is famous for its striking clay cliffs and the Gay Head Lighthouse. If you love the outdoors, this is the perfect spot for a Martha’s Vineyard day trip and relaxing sunset.

The Aquinnah Cliffs Overlook is about 20 miles or a 40 minute drive from Vineyard Haven.

Things to do in Aquinnah:

  • Gay Head Cliffs: These stunning, multicolored clay cliffs of Aquinnah are the town’s most iconic attraction. You can visit the Aquinnah Cliffs Overlook to enjoy panoramic views – particularly lovely at sunset. 
  • Gay Head Lighthouse: Visit the historic Gay Head Lighthouse, which sits atop the colorful cliffs. Dating all the way back to 1799, this lighthouse offers guided tours during the summer months and provides a fascinating glimpse into the island’s maritime history.
  • Moshup Beach: Relax on Moshup Beach, an unspoiled beach with towering cliffs, large rocks, soft sand, and endless ocean views. This is one of the most beautiful spots for sunbathing, swimming, and enjoying the natural beauty of Martha’s Vineyard.

Best place to eat in Aquinnah:

  • Orange Peel Bakery– This charming bakery offers more than sweet treats. With an outdoor wood-fired oven, this bakery also has delicious pizza. Save room for dessert – the chocolate chip cookies are a local favorite.

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All of the towns have something special to offer so no matter where you choose to explore during your trip to Martha’s Vineyard you can’t go wrong! Not sure what to do in a day? Check out this post and discover more things to see and do while in Martha’s Vineyard here.

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