Martha’s Vineyard- A Traveler’s Paradise

Martha’s Vineyard has always been known as a vacation playground for the traveling elite. This intimate island is definitely a vacation playground with a lot less of the glitz and glam of other hotspots like the Hamptons. I have had the pleasure of visiting almost every summer for the past 28 years and below you will find my greatest tips for exploring MV as a vacation destination. You will find this small island off the coast of Massachusetts is ideal for laid back vacations and should definitely be on your travel list.

About The Island

Martha’s Vineyard, or the Vineyard as it’s fondly called by residents and summer visitors, is located in the southern portion off the coast of Cape Cod and is approximately 87 square miles. There are 7 towns which comprise of  Tisbury (includes Vineyard Haven and West Chop), Edgartown (Chappaquiddick& Katama), Oak Bluffs (East Chop), West Tisbury, Chilmark (Menamsha), and Aquinnah. A large percentage of visitors stay in the main towns of Vineyard Haven, Oak Bluffs, and Edgartown. It is fascinating how each town has its own vibe and soul as well as aesthetic. West Tisbury and Aquinnah are what we call soggy towns. They only sell beer and wine. Chilmark is a dry town so you need to bring any alcohol with you.

You can drive the entire island in less than a day and see all of its treasures but it would take months to enjoy them all. The island is home to approximately 16,000 year-round residents and hosts anywhere from 100,000 to 150,000 visitors a day during summer. There are no stoplights, no fast food places such as McDonald’s or Taco Bell, or franchises except for Stop & Shop, Dairy Queen, Clarion Inn Hotel, and national rental car companies which adds to its charm. I think of it as an artisans’ island, where many art galleries, bookstores, and playhouses are located. Several book signings, musical and dance performances, public talks on politics and societal issues, artists openings, and different festivals or outdoor markets occur multiple times weekly in the summer providing an option to please everyone. If you are a beach lover there are over 19 beautiful and distinctive beaches both public and private to fit anyone’s particular wants and needs.

When To Visit

Of course, just like many places, you can visit the Vineyard all year round but typically most people vacation there from Memorial Day through Labor Day. The island has great shoulder seasons though, with beautiful weather and fewer people. You should definitely consider it as an alternate option if you want a more secluded feel. It’s also important to note that you can and should visit during the holidays such as Christmas, Thanksgiving, and New Year’s for a real small town celebratory experience. I have fond memories of the few holidays I spent there.  Although many shops and some restaurants are closed during that time, you still have a decent amount of excellent options to choose from and get to really know some of the residents.

​July and August are in high season, with August moving past July in regards to the number of visitors. This is when 1 million and one activities take place leaving the island buzzing all around creating lines for the best breakfast spots (you either chat with someone new or window shop), seasonal traffic, and many pedestrians coming in and out of town. During this time the Vineyard host several events weekly, many are my favorites, which add to the number of travelers, such as the African-American Film Festival, the Comedy Festival, many fraternities’ and sororities’ events, charity fundraisers, art walks, and book signings. During the third week of August, Wednesday starts the busiest time with Illumination Night in the Gingerbread Cottages Campground in Oak Bluffs, the AG Fair in West Tisbury, and the Oak Bluffs fireworks. Anyone who lives or comes from the city won’t be bothered by the number of people in August.

Where To Stay

Now that you are sold on visiting where should you stay you say? You want to stay, typically, in one of these three towns: Vineyard Haven, Oak Bluffs, or Edgartown as it’s easy to get around just by walking or biking. If you want real seclusion or a lot of space then you should head out to Chilmark, West Tisbury, or Aquinnah. There aren’t enough hotels or B&Bs for everyone who visits during the summer months, which is why renting a home is extremely popular if your stay is longer than four days.

If it’s a short visit, my favorite choices are the Mansion House or Vineyard Square in Vineyard Haven, the HarborView Hotel, Hobknob Inn or Nobnocket Boutique Inn in Edgartown, the Summercamp, MV Surfside, or the Dockside Inn in Oak Bluffs. Outside of these towns, your best choices are the Winnetu Oceanside Resort, Lamberts Cove Inn, Beach Plum Inn, and the Menemsha Inn. If you are looking for a home rental it’s best to contact a travel consultant who knows the island, an island realtor, or a referral through someone you trust who has stayed at the property. Some properties include ferry tickets to bring your car over and some don’t include any linens so you would either bring your own or rent them on Island.

How to Get There

Well, it’s an island and the only way you can get there is either via plane or ferry, or a combination of plane, train, bus, or automobile. There is no long bridge or tunnel that connects the mainland to Martha’s Vineyard which you could drive through. This exclusivity is part of the hype because not everybody is willing to dedicate the time it takes to get there. Things are much easier now than when I started going 28 years ago. It wasn’t as many options. Now you can fly directly onto the island with air carriers such as Jetblue and Delta from many cities direct like New York, Boston, and Washington DC. You can also fly to Boston and catch the Peter Pan bus to Woods Hole, then the ferry to Vineyard Haven or Oak Bluffs. There are fast ferries from New York, and Providence, Rhode Island. The ferries from Woods Hole allow you to bring your car. Options for driving your car are driving to Woods Hole and parking in one of their many lots before taking the ferry over, or you can pay to bring your car over on the ferry as well. The latter option requires much planning and reservations made months in advance.

​Martha’s Vineyard has an excellent public transportation system so a car on Island isn’t a necessity. The bus system rides through all seven towns often and has room for bicycles. This is an ideal way to get around the Vineyard. There are also several rental car companies so you can choose a car for just a day, a week, or a month. Biking is also a pretty good option and both Oak Bluffs and Edgartown have substantial bike paths independent of the roads. Of course, there are always taxis, van shuttles, Uber and Lyft. The best and most direct option would be to fly into Martha’s Vineyard Airport (MVY) and avoid all of the Cape Cod weekend traffic. The only problem with that is you miss out on the ferry ride over which is my favorite part to kick off my stay.

Must Do Experiences

Here are items that are on my list every summer to accomplish when I visit. So many things to check out and so little time unless you’re able to stay for a few weeks or for the entire summer. Fortunately for me, I take that option often since I am now traveling from Florida. So I’m able to squeeze in some relaxing time as well as engage in every island activity that piques my interest. Here are the things you must do when you are in Martha’s Vineyard, either for a day trip or a vacation and enough left over to bring you back for more. First on the list is to wait on line to purchase a freshly made, hot donut from Back Door Donuts. Be prepared to wait at least 30 minutes if you go after 8 pm (and you should). Jump off the bridge at State Beach is another iconic thing to do in Martha’s Vineyard for kids and adults (there is usually a small wait for others to jump) and make sure someone gets it on video and you bring a teeshirt home. These two items are a right of passage for anyone visiting the Vineyard.

Children of all ages (that includes you) will get a thrill out of riding the Flying Horses in Oak Bluffs in hope of catching the brass ring. It is the oldest operating carousel in the United States. If you are an early riser or just want to meet some people then head over to the Inkwell (2nd section of beach from Ocean Park in Oak Bluffs) to swim with the Polar Bears. Yep, this group of men and women meet early, daily to swim and exercise in the refreshing waters, as well as socialize about what has and is going on in Martha’s Vineyard. I have so many things I love to do while there that I couldn’t possibly list them all here but I couldn’t cut these specific to the Island experiences. One of the last 3 things I highly recommend is visiting the Edgartown Lighthouse. There is a small fee to climb to the top and take in the views (my daughter still loves doing this and she’s 23). The last two are my absolute favorites and I wouldn’t be able to decide on just one. You must experience a Menemsha sunset on Menemsha Beach with a picnic style lobster dinner (my favorite is from Larsens and you need to call ahead to order). Bring a blanket or chairs, some drinks, and sides, then just pick up your lobster with it’s already cracked shell and dunk it in that wonderfully melted butter while watching the sunset is heaven on earth. Last but not least is Outdoor Shakespeare and set in the middle of a tree heavy park next to an stunning cove. A different performance is played each summer. It’s a little hard to find by itself until you see all the cars lined up alongside the road and then you walk about 200 feet into the park. I like to bring a variety of cheese, some wine, and crusty bread and we bring a pizza for the kids.

I hope those of you who visit Martha’s Vineyard love it as much as I do. It really becomes a piece of your heart once you know what her secrets are.

If you want all of my Martha’s vineyard recommendations, including Where to Eat, then subscribe to my Quarterly Newsletter, Jettied Story, to keep an eye out for my upcoming E-Book on Everything You Need To Know About Visiting Martha’s Vineyard.
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