First Trip to Martha’s Vineyard?

A lot of people ask me questions about Martha’s Vineyard. The questions vary from, “What’s the best way to get to the island?” to “Where should I stay?” and “Are there things that I definitely shouldn’t miss?” For years now, I have had an email more-or-less ready that I can just shoot off to people all around the world. I say ‘more-or-less’ because it always needs an upgrade. Restaurants come and go, hotels change hands—that sort of thing. I also had a separate list for people who were strictly JAWS fans, but now that I have broken down the movie, scene by scene, in a JAWS Locations post, I think I have covered that. So, if this is indeed your first trip to Martha’s Vineyard, there are a few basics that I can probably cover to help you along your way.

Getting Here

There are a couple of different ways to get to the island. The most popular is the Steamship Authority. It’s the only way I have ever traveled to the Vineyard, so I cannot really do any comparison shopping; however, I will say that there is something about taking the ferry that is very Vineyard. Especially, if it’s your first trip to Martha’s Vineyard. It’s a big part of my vacation. When I climb the gangplank in Woods Hole, I know I’m home. That’s where it all begins for me.

Martha's Vineyard Ferry

The ferry is a big part of my vacation.

You would think that it began when I disembarked in Vineyard Haven or Oak Bluffs, but this is not the case. I find a spot on the deck, park my bags, grab two Bad Martha’s and I am home. If you are bringing your car, remember to book far in advance. You need to have a spot reserved, like a plane ticket, and the boats fill up quickly. You can try and get on stand-by but in the summer months—best of British luck to you—as my mother would say. If it’s just you, you can walk on.

Steamship Authority in Vineyard Haven Harbor

I get to Wood’s Hole via Peter Pan Bus Lines. There was one crazy trip with them that was really out of the ordinary and did not leave much to recommend it, but every other trip—there have been lots of them—was fantastic. When I had my less than satisfactory trip with them, it was crazy busy, they had to add on an extra bus with a driver who didn’t usually do that route, and the passengers were insane. People really need to relax. I felt like yelling at all of them, “You’re going to Martha’s Vineyard! How can you all be so angry?”, but instead, I just turned up my headphones. James Taylor, Cat Stevens, and Carly Simon will solve anything if they’re played loud enough.

I get on the bus at Logan Airport. Instead of the bus, you can opt to fly Cape Air directly to the island, but not taking the ferry is mind-boggling to me. It is just not an option. There is also the Island Queen Ferry which runs May through October. It is called the “fast ferry” and it runs out of Falmouth to Oak Bluffs. It is strictly a passenger ferry, so if you are planning to bring your car this is a no-go. They do provide plenty of parking right at the ferry docks on the mainland. As the Peter Pan drops me right at the Steamship Authority, I have never taken this route, but I hear a lot of really great things.

Welcome to Martha’s Vineyard

The first thing you’re going to want to do, is check into your hotel. There are a lot of places to choose from, and different places for every taste. Personally, I am an historic inn/bed and breakfast kind of guy. I have always felt that large hotels, no matter how hard they try, end up feeling…the same. Even if they hang photos and paintings of lighthouses on the walls, a queen room in a large hotel is the same from city to city. Even with the door closed and the blinds shut, I want to feel like I’m on Martha’s Vineyard.

Downtown Vineyard Haven

Now, having said that, larger hotels always offer a level of amenities that appeal to some people; however, I am not one of those people. Martha’s Vineyard is a step back in time—at least, it is to me. It is not of this world. The Vineyard, The Cape, and Nantucket have a quality that is singular to each but one that ties them together swell. I think that a true Vineyard experience shines through in a smaller inn.

The Ashley Inn

My Room At The Ashley House Was Perfect

Edgartown has The Ashley Inn. It is a personal favourite. I was introduced to The Ashley Inn when I went to my first Christmas In Edgartown and it was everything that a New England country inn should be. It was also one of the few places open year round at a reasonable rate. It’s on Main Street and within walking distance of everything Edgartown has to offer. The owner, Fred, is a terrific guy and the breakfasts are excellent.

Oak Bluffs

The only times that I have ever stayed in Oak Bluffs, I rented a house. Renting a house with a few friends can be a terrific way to cut costs and get that Martha’s Vineyard vibe. There are several on-line websites that do this. The houses will vary in cost depending where on-island you are. We went fairly far inland. They tend to get cheaper the farther they are from the beach.

We were still in a nice house, in the middle of the woods, with a big deck for barbecuing. I think it cost us $2000 for the week. That might sound pricey but there were six of us. $335 for a week on Martha’s Vineyard is pretty awesome. Having said that, I’m not sure that I would recommend renting a house for your first trip to Martha’s Vineyard. I think a B&B or an inn would help you get the lay of the land.

Should you bring a car?

I think it’s only fair to tell you from the onset that I don’t drive. So, I never bring a car. This doesn’t mean that I haven’t enjoyed the benefits of having friends with cars (Is this what they mean by friends with benefits?) on-island. My friend Dave always brings his car and we have an awesome time booting around in it.

In fact, I would go as far as to say, some of Dave and I’s best times were in the car. Dave has Sirius radio (I think) and we both really dig eighties alternative music. There’s nothing like tearing down North Road, for lunch in Aquinnah on a hot summer day, blasting English Beat’s ‘Mirror In The Bathroom’—just sayin’. Having said that, I love taking the Vineyard Transit. It’s very user-friendly and a great way to see the island.

I love the Vineyard Transit

Getting a car on the ferry can be difficult and it’s definitely expensive. I get on the ferry round trip for sixteen bucks. That’s pretty good. Once you’re on-island, there are several terrific taxi services available to take you to wherever you are staying if you need help with you’re luggage. After that, the buses are great. There are also lots, and I mean lots, of places to rent a bicycle. That’s probably the best way to get around out of all of them, if the weather is good.

Things To See, Places To Do…

I had to put this heading in so that people wouldn’t think that I had overlooked it. There will be people reading this, who are looking for just that: things not to be missed on a trip to Martha’s Vineyard. That’s an impossible question to answer. The truth is that Martha’s Vineyard is a wonderful place. I encourage you to go without an agenda. Your rental property or hotel room will have a comprehensive booklet about the island’s goings-on during your stay. You can check it for any live music that you may want to enjoy. Surf through the other posts on my website. I have written about some of my favourite things to do and I have broken the island down by township. I’d love to get your feedback. Check as well. Their website is a wealth of information.

Catboat Charters of Edgartown

The true magic of Martha’s Vineyard is in being here. So, on your first trip to Martha’s Vineyard—explore. Open yourself up to what the island has to offer. If you are just looking for a place to lie on the beach and get smashed, then I recommend The Bahamas or Cuba or any of the myriad of places with swim-up bars, drinks served in coconuts, and cougars singing ‘Copa Cabana’ on Karaoke nights. Martha’s Vineyard is about discovering lobster rolls and chowder, going sailing, hiking the hills, and yes, swimming on the beach. Are you a JAWS fan? Do you recognize the romance in lighthouses? Then you can probably stay.

Martha's Vineyard Lobster Roll

The Lobster Roll at The Lookout Tavern in Oak Bluffs

The island is about history and friendship and culture. It has its own sound, its own vibe. Martha’s Vineyard is a centuries-old, scrimshaw whistle with a very distinct tone—you either hear it or you don’t. If you don’t, then you will probably come to the island, enjoy it, and not return. If you do hear it, then the island will become part of your soul. That tone will pierce your heart in the same way that first ballad did at your high school dance. You’ll hear it in the clang of the buoys and the slosh of the waves—it’s in the foghorn. It’s your first trip to Martha’s Vineyard. So, just come.


  1. If I had ONE thing to add to your amazing overview of the “first time” experience, it would be to not over look the Island Queen. For those of us with (often uncooperative) kids who aren’t taking cars across, the Queen’s seasonal trips from Falmouth to Oak Bluffs are a godsend if only for the fact that they have parking pretty much adjacent to the boarding area, so no slogging back and forth via buses. They only run May – Oct but, when they’re running (and I’m not driving over – the Queen is passenger only), they’re my go to every time.

    Other than that one minor addition, this is a great starting point. There is nothing better than a first-timer asking for advice for their first trip to the Vineyard. While my advice may vary from yours in certain places, I would definitely point people to this entry when they ask me in the future.

    1. That is a great addition, Corey. Thank you! I have never taken the Island Queen myself, but I hear good things. I will add that right away!

  2. Also SeaStreak passenger fast ferry (summer only) out of New Bedford and Rhode Island into OB. My elderly parents from CT take it regularly to avoid Cape traffic and easy on/off access. It also has a weekend run from Manhattan.

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