Martha's Vineyard: Day Trips and Tours from Boston, Massachusetts

One of the most affluent corners of Massachusetts, Martha’s Vineyard is a luxury escape for visitors wishing to see a more tranquil side of the state after spending their vacation amid the skyscrapers and honking horns of Boston. This peaceful haven features several enchanting towns, surrounded by pristine beaches and shimmering seas.

Martha’s Vineyard day trips from Boston offer you the opportunity to glimpse at how the other half live as you tour the local hangouts of several celebrities, including Barrack and Michelle Obama.

Here's all you need to know about Martha’s Vineyard, one of the most exciting day trips from Boston.

How to get to Martha’s Vineyard from Boston, Massachusetts?

Martha’s Vineyard is located just over 10 kilometers south of Cape Cod in Duke’s Country, Massachusetts. It is approximately 140 kilometers south of Boston, the capital of Massachusetts.

From Boston to Martha’s Vineyard by car

When making the journey to Martha’s Vineyard, you’ll find that you can travel as far as Falmouth by car. In order to reach the coastal town, you’ll drive south of Boston along Route 3, which you’ll follow as far as the town of Sandwich.

There, you’ll emerge onto Route 28, which leads you to Falmouth’s port — Woods Hole. Upon arrival in the town, you can board a ferry for the final leg of your jaunt to Martha’s Vineyard.

The drive to Falmouth takes just under 1.5 hours and the ferry takes just over half an hour. While you should allow extra time for connections, you can expect to reach Martha’s Vineyard between 2 and 2.5 hours after departing Boston.

From Boston to Martha’s Vineyard by public transport

Those without access to a car can instead travel to Martha’s Vineyard via public transportation. A bus links Boston with Woods Hole Port and leaves regularly from Boston’s South Station. The route takes just under 2 hours and when you reach your destination, you can board one of nine daily ferries to take you across to Martha’s Vineyard.

Guided tour to Martha’s Vineyard from Boston

Alternatively, book a guided excursion to Martha’s Vineyard and allow someone else to take care of the transportation details for you. These organized day trips tend to last between 12 and 13 hours, starting around 6 AM.

While this pickup may seem early, guided tours include a convenient accommodation pickup, meaning you won’t need to worry about navigating public transportation systems.

All transportation is pre-arranged for you, including the ferry ride across to Martha’s Vineyard, and, when your adventure is over, you’ll return to your hotel where you can spend the rest of the day relaxing or continue sightseeing in Boston.

What is the typical itinerary?

Martha’s Vineyard day trips usually feature very similar itineraries, making it easy to select an excursion. After being collected from your hotel, you’ll begin the journey to Falmouth, located approximately 1.5 hours south of Boston, passing through many other destinations in Massachusetts.

Once you arrive at the dock in Falmouth, you’ll board a ferry to Martha’s Vineyard, which takes just over 30 minutes. Where Martha’s Vineyard day tours differ is on arrival at the town of Oak Bluffs, on the other side of the Vineyard Sound. Here, you may join other travelers for a guided tour of the island, which takes place on a bus and journeys to several impressive landmarks, with a knowledgeable guide offering insightful commentary.

Alternatively, you can stay in Oak Bluffs and visit its main attractions, which include the oldest platform carousel in the U.S., and East Chop Lighthouse. Once your group is reunited, you’ll all travel back to Boston via ferry and bus.

What kinds of tours are available to go to Martha’s Vineyard?

Day trips to Martha’s Vineyard from Boston

Day trips to Martha’s Vineyard begin with a scenic drive in a comfortable vehicle to reach the town of Falmouth, best known for its striking shores. From here, you’ll hop onto a ferry and sail across the Vineyard Sound to reach your destination.

Upon arrival at Martha’s Vineyard, you’ll have the option to embark on a guided tour of the island or roam its picturesque towns at your leisure. If you select a tour, you’ll admire the town of Oak Bluffs, famed for its collection of more than 300 19th-century “gingerbread houses,” which were built after a religious camp grew successful in the town and devout Methodists needed a place to stay for the duration. Today, these pastel houses serve as a tourist attraction and are worthy of a photo.

You’ll also travel to the historic whaling port of Edgartown, now a luxury vacation spot, lined with quaint boutiques, grand villas and ample walking trails. Gay Head Light — also known as Aquinnah Light — is another destination visited on a day tour to Martha’s Vineyard. This 18th-century lighthouse was the first on the island and overlooks the rippling Atlantic Ocean from the soaring Gay Head Cliffs.

Throughout your 3-hour tour, you’ll see all six towns located on the charming island and explore each one’s highlights. After gaining a thorough introduction to Martha’s Vineyard, you’ll enjoy some free time to peruse its shops, sip a steaming brew or continue sightseeing before boarding your ferry back to Falmouth and enjoy a seamless transfer back to your hotel.

How much does a day trip to Martha’s Vineyard from Boston, Massachusetts cost?

A basic day trip to Martha’s Vineyard without a guided tour typically costs US$110 to US$120 per adult, while children under 13 pay approximately US$100 each.

If you wish to add the guided tour option to your Martha's Vineyard day trip from Boston, the cost is just over US$170 per adult and US$150 per child.

Whichever option you choose, you’ll be part of a group capped at 24 travelers and benefit from round-trip transportation, and refreshments.

What will you see and do?

Oak Bluffs

Oak Bluffs was created in the second half of the 19th century and was originally named “Cottage City.” It was the only one of the now six towns on the island that was either planned or developed purposefully with tourism in mind. In its early years, Oak Bluffs served as a vacation spot for those attending religious camps, however, as its permanent population grew, the town was renamed to present it as a year-round destination.

While the town’s main attraction is its plethora of “gingerbread houses,” Oak Bluff is also home to one of the best beaches on the island — the Joseph Sylvia State Beach, with a historic carousel built in 1886 that still operates today.

Edgartown

Edgartown is the oldest settlement on Martha’s Vineyard and was established in the 17th century as a whaling port. Over the following 200 years, this town reached its peak, with over 100 whaling captains building homes in this corner of the island. During the whaling frenzy of the 19th century, Edgartown was known as one of the primary whaling ports in the world.

Today, the town, as well as the island as a whole, is known as a luxurious escape for famous faces. Edgartown’s main highlights include its Mytoi Japanese Garden and wildlife sanctuary, both of which you can explore on a day trip to Martha’s Vineyard.

Aquinnah

Less popular though just as beautiful as Oak Bluffs and Edgartown is Aquinnah, located on the western coast of Martha’s Vineyard. This destination is best known for its historic lighthouse, which was constructed in the final year of the 19th century to protect sailors from “Devil’s Bridge” — a section of ocean littered with treacherous rocks.

The town is still often referred to by its original name — Gay Head — and features several idyllic beaches, backed by craggy clay cliffs, that offer peaceful walking opportunities.

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

The best time to visit Martha's Vineyard is from late spring to early fall, namely May to September. These months offer pleasant weather, with warm temperatures ideal for outdoor activities and beach visits. Summer (June to August) is the peak tourist season, which means larger crowds but also vibrant local events and a lively atmosphere.

Travel tips

• Start your day early to maximize your time on the island. Ferries usually take 45 minutes to an hour, so factor in this travel time.
• Pack essentials, such as sunscreen, comfortable walking shoes, a hat, and layers as the weather can change.
• If weather permits, spend some time at one of the island's beautiful beaches, like South Beach or Menemsha Beach.
• The island is known for its fresh fish and lobster. Casual dining spots are great for a quick and delicious meal.