1. It’s summer, which means there’s a good chance you can end up on the Vineyard if you live in the Northeast. Realistically you’ll end up at Martha’s Vineyard for one of two reasons: 1) your family / friend’s family has a house there or 2) your buddy decides to get married there. There’s an off chance that you end up there with on a guy’s getaway, but you’ll have to make the most of your time when you’re there. A big positive is that there are bachelorette parties that travel there. Considered a black hole by some bros, there’s still the opportunity to pillage them if you can.
2. There’s really only two places to stay while you’re there despite the fact that the island is broken up into six different towns. You either want to be in Oak Bluffs or Edgartown. Oak Bluffs is on the north part of the island and is slightly less elite than Edgartown. It’s likely the most affordable option of the two for housing and hotels although you’ll be further away from the beach. Both places provide the best options for bars and restaurants. If you somehow end up somewhere other than those two towns, you’re going to be traveling around the island much more than you wanted to at night. Taxis are generally available and can get you where you need to go, but they get pricey when you’re staying far away from the restaurants and bars.
3. While renting a house is always the optimal situation when traveling to a beach town, the prices in Martha’s Vineyard might be too much for you to handle. Thankfully there are plenty of hotels, motels, and inns. As mentioned before, Edgartown is on the more expensive side. Your best locations for the money would be Edgartown Commons and Edgartown Inn. (Original names, don’t you think?) The Suites at Vineyard Square could also be the answer for people and space.
4. Your best options in Oak Bluffs when thinking value is probably the Surfside Motel. Step up a level and you’re going to be looking at the Wesley Hotel, the more modern Pequot Hotel, and the Dockside Inn. Another idea for Oak Bluffs is to stay at the Island Inn, which is located a mile out of town. They offer townhouses that can fit three guys in beds and one on the pull-out couch while having a living room to hang and a fridge full of beer. It doesn’t hurt to have tennis courts on the property and the golf course next door.
5. Now that your housing is squared away, you’re probably looking for something to do. If you’re looking for real waves, you need to head to the south side of the island. The beaches on the north are too calm and don’t have as much sand to enjoy. There just isn’t as much public beach space as you’d expect because of all the private beach property connected to the houses. The busiest beach around is South Beach located just south of Edgartown. You can get there for free via bus or park for free as well. That’s most likely where you want to spend your days since it offers everything you’d expect out of a beach other than a true beach party. Another cool idea would be a head up to State Beach located between Oak Bluffs and Edgartown. There’s a bridge you can jump off into the water that provides a little thrill. Don’t worry when you see a long line of people looking to jump. Everyone’s jumping for a good reason and not looking to end their days on earth.
6. As you’d expect there are a few golf courses to enjoy on the island. A round at the semi-private Farm Neck, the one located next to the Island Inn, isn’t cheap, but you can say you played on the same golf course as some of the presidents. Twilight rates are the cheaper play here if you’re don’t get smashed at the beach. You can also shoot nine holes Mink Meadows and maybe have a little fun combining drinking and golfing. The other two courses are private, so good luck getting on. If you’d rather just mess around with arcade games, air hockey, and skee ball, there’s a Ryan Family Amusements in Oak Bluffs to get your rocks off.
7. I hope you like seafood because there’s seafood aplenty on the island. There’s basically a lobster roll available at any place. Oak Bluffs has more than a few places to get good eats. Offshore Ale Company is the only brewery on the island and they’ll give you plenty of good beers to enjoy with your meals. They do a better clam chowder than the award winning Martha’s Vineyard Chowder Company in this man’s opinion, but the latter wins the battle of the lobster roll. Giordano’s is known for the best pizza in town and while it’s good enough, don’t expect to enjoy something legendary. Skinny’s Fat Sandwiches is the quickest way to eat by grabbing one of a variety of well-made sandwiches and subs. Sharky’s Cantina is where it’s at for all your cheap Mexican food needs (the nachos are dynamite) and they have really good margaritas. Get your ice cream at Mad Martha’s or Ben and Bill’s Chocolate Emporium. Linda Jean’s makes some good flapjacks and other breakfast items if you wake up early enough to partake.
8. The good thing about Edgartown is that it has a couple of your favorite options from Oak Bluffs. Sharky’s Cantina, Skinny’s Fat Sandwiches, and Mad Martha’s make an appearance in this town as well. The best option for standard bar food is at the Wharf, where they do everything well. (I’m a fan of the Stuffed Quahog and Blackened Chicken Sandwich.) The best burger in town is at Atria Brick Cellar Bar. Your options are rather limitless. Murdick’s Fudge is good for when you’re craving a local dessert delicacy.
9. Nightlife on the island isn’t as prime as other beach towns, but there are still places to do work. If you’re going to spend the night out in Edgartown, you have a few options on where to work your game. The Seafood Shanty goes from restaurant to nightlife spot at around 10 p.m. A DJ shows up to bang out some music on the ones and twos. The place gets packed with the younger age crowd and the inside dance floor heats up. There’s also an outside deck if things get a little too hot for you inside. The Wharf does the same restaurant to nightlife transition. It has the low key pub on one side of the property, but they also clear the tables out of the restaurant side to bring on the dance party. A slightly older crowd parties down the street at the year-old Port Hunter. They’ve got an indoor shuffleboard court that’s always bringing stiff competition and a nice relaxed scene at the bar.
10. The nighttime scene in Oak Bluffs has a similar vibe. Your most likely destination is going to be The Lamppost / Dive Bar. (Don’t get thrown off by the multiple names because it’s the same place.) The ground floor is your standard bar, but things pick up as you move up levels. You’ve got DJs and cover bands for the summer season to fill all your nightlife needs. If you’re into pool tables and live bands, you’re in luck at the The Ritz Café.
[Boat image via ShutterStock]