Well Done Travel – Martha’s Vineyard


Well Done Travel – Martha’s Vineyard



The Vineyard is hands down my favorite New England summer time destination. I’ve visited the island at least once a year for the last 20 years. Originally these were family vacations but gradually turned into personal explorations. The Vineyard is a complete vacation for any Well Done Man, offering nightlife, food, golf, music and glorious beaches of every shape and size. There is definitely something magical about this island and if you’ve never been or perhaps have been summering on the cape you’re entire life, you owe it to yourself to hop a ferry and check it out.



Getting there

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Hop a ferry and leave it all behind

Ferries to MV leave from Woods Hole or Falmouth. It’s a 45 minute ride and the views are spectacular. You can see the island the entire way and as you inch closer passing lighthouses and harbors you gain a deeper appreciation for the place that you are about to visit. Depending on your departure time you will either land in Vineyard Haven or Oak Bluffs. I have consistently stayed in Oak Bluffs, and suggest you do too as it offers some of the best restaurants, bars and culture on the island. However, no matter where you dock, you can pretty much get anywhere on the island in less than 20 min. Taxis are everywhere and there is usually a line of them waiting to take you to your destination when you get off the ferry.

Day One

To get the full island experience I highly suggest you alternate days between Oak Bluffs and Edgartown. They are very different places but both equally delightful in their own ways. Let’s start with Oak Bluffs.

OB is diverse and rich in culture and history. People from all walks of life come to this island to relax and you never know who you might run into. I have personally eaten next to Larry David and James Taylor in OB.  You’ll want to take a walk around and check out the Ginger Bread Houses, a village right off the center of town filled with almost identical summer cottages featuring bright colors where everyone hangs out on the porch to great people walking by. In the middle of the village is the Tabernacle an outdoor auditorium that doubles as a local place of worship and a center for town meetings and events. I’m not a religious man but if God exists he definitely hangs out here.

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Back Door Donuts by night

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Bustling bakery by day

You can’t lose with breakfast at Slice of Life, which consistently serves some of the best eggs on the island however the first place you’ll want to go is Martha’s Vineyard Gourmet Café & Bakery. This downtown bakery is famous for their Apple Fritter which is hands down the best donut I have ever tasted. Donuts may be a breakfast item but you’ll find yourself craving this thing all day long. If that’s not enough, for your convenience, when the bakery closes at 7pm, they morph into “back door donuts” – a drive thru style walk-up donut stand that operates out of the backside of the building and is open till 1am.  Yes, there is a serious line here when the bars get out.


A Vineyard tradition is to bring your luggage to The Lookout for one more drink on the island – until you see your ferry of course.

My favorite lunch spot in Oak Bluffs is The Lookout Tavern.  Amazing fried seafood, burgers and delicious sushi, this place literally has everything. They have awesome TVs for watching the game and a front porch that has spectacular views of the Ocean and the Ferry dock (hence the name Lookout). This place is packed morning to night and it’s a great way to spend a few hours in the afternoon when you want to get out of the sun. Last year I watched a few World Cup games here and the atmosphere was amazing.


The Sweet Life is open air dinning at it’s best


Oak Bluffs also offers one of the finest restaurants on the island, The Sweet Life. It’s 5 star Cuisine with impeccable service and fresh ingredients and is your go to option when you are looking to add a little elegance to your Vineyard vacation. It’s the perfect place to wow a female companion you may be traveling with or do a little star watching, Obama loves this place.


You’ll feel like you never left the beach at the Sand Bar


Circuit Ave is the center of Oak Bluffs and after dinner that’s where you will be able to find most of the the night life. Live Music can always be found at The Ritz and the local bands that play here are great. The bar is a trip and people know how to party here. If a DJ is your thing, check out the Lamp Post. It’s a younger crowd but the dance floor is always bumping with plenty of beautiful women. A third option is The Sand Bar, an awesome spot for drinks located in Oak Bluffs Harbor. It’s true to its name as a large portion of the floor is actually sand and when the lights go down this place turns into a kick ass party.


Day Two


Edgartown’s beautiful town center is lined with shops and awesome places to eat.

Edgartown will feel very familiar for those who have ventured over to Nantucket. There is amazing shopping, great restaurants, hip night spots and a certain air of exclusivity that many, including myself, crave from time to time. What Edgartown lacks in eclectic-ness it more than makes up in beauty. The buildings are immaculate as each brick sidewalk is completely surrounded by classic and very large white and grey New England style homes. Walking through the side streets of Edgartown is a heavenly experience in itself.

the shanty

The Shanty is beautiful and laid back. Anything on the menu is delicious.

You really can’t lose no matter where you eat in Edgartown but my first stop is always the The Shanty. A huge back deck that hangs over the harbor and it really is the place for ocean side eating and drinking. They have awesome seafood and killer drinks. You’ll want to hang out on their deck forever and I’ve personally spent many hours saddled up to their bar. On the higher end, another lunch spot that definitely shouldn’t be missed, and an Edgartown classic, is The Wharf. Nestled right into the docks of Edgartown Yacht Club this place has amazing food and expert service. Look for their specialty cocktails that are made with fresh ingredients and absolutely some of the best on the island. With tables that are literally on the dock you can sit outside and watch the boats pull in or hangout in their beautiful dining room where the people watching is top notch.


A hidden gem – The League of Gentlemen should be your first stop if you’re looking for some island gear.

Shopping is all part of experience in Edgartown and as expected they mostly cater to the women but there are a couple places that should serve as your island outfitter if you’re looking for some new duds. I almost always end up buying something at League of Gentleman. It’s a very small off the radar (no website, no facebook) shop and the owner procures the finest stuff from all over the U.S. Stop by, you will not be disappointed. If you’re looking for a new bathing suit or something a little more functional I highly recommend checking out The Boneyard Surf Shop or the New England Classic Vineyard Vines.



When the sun goes down you’ll definitely want to check out Port Hunter. This place is absolutely rocking on Friday and Saturday Nights with great live music and a really cool setting. Also they serve up $7 Tito’s and Sodas, which means that when you wake up you’ll wallet will thank you but your head probably won’t. If you want more of a bar scene head back to The Shanty who packs them in at night or the classic standby Alchemy for a slightly more upscale crowd. Like I said you really can’t go wrong with any of them.






One of the most amazing things about the Vineyard is that all four sides of this island present you with dramatically different and beautiful beach options. A perfect day for me is to hit at least 3 of them. There are probably hundreds of individual beaches on MV but here are a few of my favorites.


State Beach

One of the largest beach and most popular beach on the on the Vineyard – It stretches more than two miles on the road between Oak Bluffs and Edgartown and just about all of it is swimmable. The water here is calm and beautiful. You can park along the beachside of the road but make sure you get there before 10am on the weekends because the spots fill up quick. For the kids, there’s two bridges for jumping off into the ocean including the one where they filmed a rather famous scene in movie Jaws.

South Beach

south beachBecause of its Atlantic Tide facing shore it has by far the roughest surf on the whole island and really not recommended for young kids. You’ll find mostly younger folks here (20s and 30s) with coolers filled with beer and other beverages. This is definitely the party beach but make no mistake, like most places down here it is breathtakingly beautiful. You can spend the whole day here and one of my favorite activities is to head into Edgartown for an ice cream at Mad Martha’s after a day at South Beach.


Jetty Beach



A much lesser known beach on East Chop and next to Oak Bluffs Harbor.  I’ve found this place to have the most incredible swimming water on the whole island. Clear, fresh and typically seaweed free. If you’re an ocean purest, as I am, it is definitely worth taking a dip here.  As a bonus while you wade you can watch the ferries come in.


Gay Head

GayHeadA true harbor beach that faces the southern coast of Rhode Island, the water is amazingly calm and the very shallow. Be on alert there is a section of this beach that is most definitely nude, which is totally cool if you’re into that sort of thing. Nakedness aside the true spectacles here are the cliffs that line the entire shore of Gay Head. There is a viewing area at the top and yes it is while worth the climb.






The 14th at Farm Neck

Farm Neck
One of my greatest annual pleasures is playing this public course. It is immaculate in every way and runs along the ocean between Oak Bluffs and Edgartown. It’s not cheap but if you’re a golfer the experience is magical.

Mink Meadows
The only other public course on the island (there are two other private courses) we usually play this as a warm up for Farm Neck. Prices are very reasonable and it’s very well maintained.

Sam Calef

Sam Calef

Sam Calef is Founder and Managing Partner at Well Done Boston. He always has time for interesting people, the whole truth and a trip to the beach.

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