Martha's Vineyard Day Trip Itinerary
Authors: Marco & Angelo

Authors: Marco & Angelo

We own the Candleberry Inn, a boutique bed and breakfast in central Cape Cod. We're glad to share our recommendations on all the great things to explore throughout Cape Cod.

15 Tips for Planning a Martha’s Vineyard Day Trip

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    Cape Cod has so many things to do, even on a rainy day. But if you’re looking for even more places to explore, a Martha’s Vineyard day trip is just the ticket!

    This island is a popular year-round destination — quaint towns with charming shops, fresh seafood, local events, and outdoor activities. At about 100 square miles large, it has a beautiful landscape as well — fields, hillsides, woods, and breathtaking beaches.

    In our guide, you’ll get a load of tips to help you plan a day trip to Martha’s Vineyard from Candleberry Inn in Brewster. And for more Cape Cod travel planning, you can request our free Vacation Guide.

    To avoid crowds and see as much as possible, the best time for a Martha’s Vineyard day trip is on a weekday.

    Get our free Cape Cod Vacation Guide, full of the best things to do in Cape Cod. The best activities, restaurants, museums, events, views, and much more!

    Click here to request the guide.

    baked good and fruit at our Cape Cod B&B


    Indulge in a Gourmet Breakfast First

    Before you take off for The Vineyard, enjoy a freshly prepared breakfast at Candleberry Inn. Start with a fresh fruit course with ingredients that are personally picked and prepared by innkeeper Angelo.

    For the main course, we alternate daily between sweet and savory hot dishes, many inspired by our Italian family recipes. Our full drink service includes espresso, coffee, tea, and juice too. We can even prepare a Brewster Sunrise for you — a tasty Cape Cod specialty.

    We’re happy to work around dietary restrictions and requests with advance notice.

    Catch a Ferry to The Vineyard From Hyannis

    Martha’s Vineyard is located about 40 miles from the southeast coast of the Cape, so you can only reach it via boat. Hy-Line Cruises and Steamship Authority in Hyannis are the two largest ferry services to The Vineyard from the Mid Cape, and the docks are about 30 minutes from Brewster. Alternatively, you can take a ferry from Woods Hole, which is approximately one hour from Brewster.

    Once you arrive, you can park at the respective ferry terminal. While it’s the most convenient option, you can save money by using an off-site parking lot. If you choose off-site parking, you’ll need to arrive earlier to find out which lot is available, then catch a free shuttle to the terminal.

    The high-speed ferry service operates from May through October, offering earlier departure times and later arrival times during peak summer months than during offseason months. The trip between Hyannis and Oak Bluffs on Martha’s Vineyard only takes about one hour.

    Plan How You’ll Travel Around Martha’s Vineyard

    When you’re making an itinerary for a Martha’s Vineyard day trip, one thing that you have to consider is how you will travel around the island.

    There are various ways to get around the island, and you can decide which way is best for you. When you step off the ferry there will be several options available including private tours (bus or car), guided tours, public buses, larger group tours, car rentals, bike or e-bike rentals, or using a driving service like Uber. You can also take your car, but this option is only available from the Woods Hole terminal and advance reservations for the vehicle are required.

    Martha's Vineyard Day Trip Itinerary

    Start Your Martha’s Vineyard Day Trip in Oak Bluffs

    Since you’re arriving on The Vineyard via Oak Bluffs, there’s no reason not to spend some time here first. The town was originally called Cottage City, so you know you’re in for a charming experience. It’s also known as the liveliest town on the island.

    The first thing you might want to do when you arrive is walk along Seaview Ave, which runs next to the water. Ocean Park is located on this street and offers picturesque views and features a historic gazebo.

    Your next stop should be the Flying Horses Carousel, the oldest continuously operating carousel in the country. It was built in 1876 and moved from Coney Island New York to Oak Bluffs in 1884.

    After the carousel, you should take a walk down Circuit Ave. This bustling main street has a slew of candy stores, ice cream shops, restaurants, and boutique shops.

    Another must-see in Oak Bluffs are the colorful gingerbread houses. These whimsical houses have unique architecture and were part of the largest religious community of its kind. Built in the 1800s, there are 318 gingerbread cottages remaining. The Cottage Museum tells more about their history.

    Martha's Vineyard Day Trip Itinerary

    Visit Another Town (or Two) on Martha’s Vineyard

    The Vineyard is home to six fantastic towns, each with its own atmosphere and attractions. However, it will be very difficult to visit them all in a single day. That’s why we suggest choosing one or two of the towns below to visit after exploring Oak Bluffs.

    If you want to experience more of the towns below, you can skip exploring Oak Bluffs. In the end, you should choose the towns that look the most attractive to you.

    Tisbury & Vineyard Haven

    Just a 10-minute drive from Oak Bluffs, Vineyard Haven has some lovely views of the water. The Vineyard Haven Harbor Cultural District is a great place to go shopping for gifts. There are many creative businesses here — from boutique shops to galleries to wonderful restaurants.

    Just south of downtown, the Martha’s Vineyard Museum has a range of exhibits, including some about the history of the island, its lighthouses, and its maritime culture. The museum hosts events regularly as well.

    North of town, West Chop Lighthouse is a delightful spot to visit. The historical lighthouse is surrounded by splendid vistas and a variety of trails. The sunsets here are amazing.

    Edgartown & Chappaquiddick Island

    A favorite Martha’s Vineyard day trip destination, Edgartown has a very walkable downtown with a lot of lovely shops and restaurants.

    Many of the businesses, including inns, have been converted from the homes of the whaling captains who settled the area. Even if you don’t shop or eat here, you’ll appreciate the outstanding architecture as you absorb the scenery.

    Not far from downtown, Edgartown Lighthouse stands at the entrance to Edgartown Harbor. It’s open to visitors throughout the year.

    If you don’t mind a short ferry trip (and have the time), you can hop on The Chappy Ferry to Chappaquiddick Island. Here, you can visit Mytoi, an intimate Japanese garden of exotic plants and native flora.

    Martha's Vineyard Day Trip Itinerary

    Chilmark & Menemsha

    In Chilmark on the west side of The Vineyard, you’ll find tree-lined country roads and rolling hills that overlook the ocean. The small town center is worth visiting, but what you might be more interested in is the authentic fishing village of Menemsha.

    Menemsha transports you back in time, and it has some of the freshest seafood you’ll ever try. You can get samples of lobster bisque, clam chowder, and others at the Menemsha Fish Market and have a fresh lobster roll lunch on the dock with the fishermen sitting nearby!

    The village has some antique shops and quiet beaches nearby too. Aside from that and the beautiful views, the fascinating draw to Menemsha is that it was a filming location for the movie “Jaws.”


    On the westernmost end of the island, Aquinnah has some of the most gorgeous vistas of the Atlantic Ocean from atop cliffs. Considered one of the island’s gems, the sunsets are to die for here!

    Overlooking the red clay cliffs and beach, Aquinnah Lighthouse (Gay Head Lighthouse) also overlooks the Elizabeth Islands to the north. You can climb to the top of the tower for the best view.

    At the overlook, a Heritage Exhibit kiosk tells about the Aquinnah Wampanoag peoples. To learn more about them, head to the Aquinnah Cultural Center. Additionally, shops in the area sell native handmade clothes, home decor, jewelry, pottery, and more.

    West Tisbury

    The agricultural heartland of Martha’s Vineyard, West Tisbury is known for its small farm stands. It’s home to several nature trails and beaches too. Lambert’s Cove has one of the best beach spots on the island and is a wonderful place for walking miles of beach.

    If you’re interested in enchanting sculptures, check out the Field Gallery, which features the works of emerging and established artists. Beyond sculptures, the exhibits include jewelry, paintings, photography, and more.

    In addition, West Tisbury has some great shopping experiences, including the historic Alley’s General Store where you can get housewares, penny candy, and other goods. Plus, the West Tisbury Farmer’s Market is renowned for its extensive selection of goods.

    Martha's Vineyard Day Trip Itinerary

    Eat at Delicious Martha’s Vineyard Restaurants

    You’ll come across a plethora of restaurants during your Martha’s Vineyard day trip. We’ve decided to highlight some of our favorites for you below.

    Depending on when your ferry departs for the return trip to Hyannis, you may have time to enjoy dinner on The Vineyard. Keep that in mind when planning your trip.

    Back Door Donuts | Oak Bluffs

    If you want a small snack before lunch or dinner, Back Door Donuts has been satisfying sweet tooths since 1948. The bakery has a variety of doughnuts to try, but you don’t want to leave without getting one of its incredible, giant apple fritters!

    Offshore Ale Company | Oak Bluffs

    For lunch or dinner, Offshore Ale Company is a year-round brewpub that has been making award-winning beer for more than 20 years. From lobster rolls and clam chowder to pizza and quesadillas, everyone will find something to enjoy on the menu.

    Mad Martha’s | Oak Bluffs, Vineyard Haven, & Edgartown

    Another option for the sweet tooth, Mad Martha’s is THE place to go for ice cream on The Vineyard. It has 24 flavors, some of which are unique — such as apple fritter, Chilmark coffee, and MV sea salt caramel. Dairy-free flavors are available as well.

    Among the Flowers | Edgartown

    Stop for lunch at Among the Flowers if you want a quick bite to eat. This cafe serves healthy salads and sandwiches, as well as all-day breakfast items — we’re looking at you Belgium waffle. You can get delicious smoothies to go too.

    The Seafood Shanty | Edgartown

    With indoor and outdoor seating, The Seafood Shanty has been serving residents and visitors for more than 50 years. It has a fresh raw bar with oysters from Katama Bay and a variety of sandwiches, entrees, and sushi for lunch and dinner. You can also order beer, wine, specialty cocktails, and frozen drinks.

    Sitting on the upper deck gives you a nice view of Chappaquiddick Island and the harbor.

    Martha's Vineyard Day Trip Itinerary

    Rest at Candleberry Inn After Your Day Trip

    After you return to Cape Cod from your Martha’s Vineyard day trip, you can head back to Brewster and Candleberry Inn. Our nine cozy rooms and suites will help you recharge for more adventures the next day.

    When you’re ready to plan your Cape Cod getaway, find a room at our historic inn. We recommend the Garden Suite because the soaking tub is ideal for relaxing after a long day.

    Get our free Cape Cod Vacation Guide, full of the best things to do in Cape Cod. The best activities, restaurants, museums, events, views, and much more!

    Click here to request the guide.

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