Whether you’re a seasoned island hopper, hailing from New England, or you’re venturing out to this storied spit of windswept land for the first time, a trip to Martha’s Vineyard is an ideal way to spend a summer weekend (or week, or two weeks...or month). Between the romantic ferry ride to the island, to the charming neighborhoods and the beautiful, white sand dunes, you’ll fall in love with this New England paradise in no time.
However—you won’t be the only one! So it’s best to plan far ahead to make the most of your summer trip to Martha’s Vineyard. Each year as the Atlantic warms up and the ice cream shops open their doors, the population of this 100-square-mile island can reach over 100,000 people, many of whom will bee-line it for the beach, so take that into consideration when planning your seaside day at South Beach or Lucy Vincent (to name a few). If you’re hoping to secure a rental, do so months in advance (keep in mind that many vacationers who come each summer book their rental a full year ahead). If you’d like to skip the rental, though, you’ll be spoiled for choice when it comes to luxury beachside hotels that deliver stunning accomodations and a good dose of R&R.
Our recommendations for how to plan a successful summer trip to Martha’s Vineyard, below.
Martha’s Vineyard Ferry
While the Vineyard does have a local airport (MVY), we recommend going the good ol’ fashioned route: take the ferry. You can opt for a passenger ferry (there are different options departing from New York, Rhode Island, and various locations on Cape Cod), or take the year-round car ferry that departs from Woods Hole, Massachusetts (it’s a good idea to take your car if you plan to stay on island for more than a week, but be sure to secure your reservation well in advance).
True to New England form, weather on Cape Cod and the islands can be a little temperamental—it will certainly be beautiful in the summer months, but there may be occasional rain, wind, or cool nights. While July and August are certainly warmer than June, visitors can expect mild temperatures throughout the summer, lots of sun, and a pretty consistent seabreeze (which can sometimes turn a bit gusty).
There are six main towns on the Vineyard, each full of color and character, varying in history and landscape. Locals tend to divide the island into up-island (the west) and down-island (the east). Up-island, you’ll find the more remote and rural villages of Aquinnah, known for the dramatic Gay Head Cliffs; Chilmark, home to picturesque land preserves and stunning coastline; and West Tisbury. Down-island is home to three larger villages: Edgartown, a stately New England paradise full of whaling-era architecture; Oak Bluffs, where there’s no shortage of buzzing nightlife and popular public beaches; and Vineyard Haven, the main port. Villages in the east tend to be a little more popular with tourists and seasonal visitors.
Top-notch, comfortable accomodations abound on the Vineyard, ranging in style from charming B&Bs to upscale boutique hotels, so there’s no shortage of options when choosing where to stay. Aptly nicknamed “Edgartown’s royal escape,” The Richard is the epitome of cool, coastal charm and sophistication, featuring 16 stately guest rooms in the heart of historic Edgartown. Another lovely inn in Edgartown (named one of America’s most charming inns by Departures) is the 19th-century Hob Knob, which has been a social hotspot on island for decades, and offers delicious, organic meals alongside elegant accommodations. Alternatively, Lambert’s Cove Inn is a quiet, romantic retreat set on an eight-acre farm in West Tisbury, featuring access to a private beach and intimate accomodations perfect for getting out of the hustle and bustle of the larger hubs. If you’re staying in Oak Bluffs, opt for the Summercamp Hotel, a boutique property designed around the concept of summer camp nostalgia and upscale retro vibes, yielding an unforgettably whimsical boutique experience.
Things to do
An obvious must for your list of things to do during a trip to Martha’s Vineyard: some serious beach time. The public beaches on the Vineyard are postcard-perfect, and range from windswept, cliff-backed beaches like Aquinnah Public Beach to wide, family-friendly swaths of sand like Joseph Sylvia State Beach in Oak Bluffs. If you’re hoping to get out on the water, book a whale watching tour during peak season to learn about these beautiful creatures that grace the waters of the north Atlantic each year. If you’re more interested in getting the lay of the land, you can book a bus tour that will take you around the whole island, so that you can get your bearings and learn about the Vineyard’s extensive settlement history. Renting bikes and spending a day or two exploring is another great way to see the island, visit a bunch of towns, stop for a quick 18 holes, and gaze at some of the best ocean views in the northeast.
Consider the fact that you’re very close to a couple other popular (and equally beautiful) summer destinations when you arrive on the Vineyard. In order to get there, you’ll pass through Cape Cod, which is a haven of idyllic New England beach towns in itself. If you’re catching the ferry from Woods Hole, factor in a couple hours to amble in and out of the shops and galleries of this sweet town and grab a sandwich at Pie in the Sky. If you’ll be on the Vineyard for a week or more, it’s well worth your time to plan a day or two to MV’s neighboring island, Nantucket.