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Martha's Vineyard, MA
Weekend Vacation Getaway

Destination Overview

In the age old debate of which is better, Nantucket or Martha’s Vineyard, I had always been a Nantucket guy, mostly because that’s where I have vacationed for the last 20 years. In the last few years, however, I have come to appreciate and love the Vineyard as well and found it to be a perfect weekend retreat. It has a similar, yet very different character from Nantucket and it also has one of my favorite places to stay...anywhere.

Click picture to enlargeMenemsha BeachTall ShipsSeafood Shanty Deck

A short seven miles from the Cape Cod coast and bounded by the Vineyard Sound, Nantucket Sound and the Atlantic Ocean sits the beautiful “Vineyard” as it is called by regulars. 20 miles long and 9 miles wide at its widest point, the island is the summer home or vacation spot for a host of celebrities including 60 minute’s Mike Wallace, humorist Art Buckwald (now deseased), singer Carly Simon, author William Styron, newsman Walter Cronkite, Good Morning America’s Diane Sawyer and former President and First Lady Bill and Hillary Clinton.

The island has a year round population of about 14,000 which swells to 85,000-100,000 at the height of the season in July and August. Most activity revolves around the three primary towns each of which has a character of its own. Vineyard Haven, the main port into which most of the ferries arrive, sits on the edge of Vineyard Haven Harbor and is home to a collection of shops and restaurants. It is about 2.5 miles from Oak Bluff and 8 miles from Edgartown; Oak Bluffs is a kind of honky tonk boardwalk town with gingerbread style homes, a carousel, an arcade, ice cream shops and a waterfront promenade. It has some very good restaurants, is the place for renting boats, kayaks and jet skis and is the nightspot capital of the island. Edgartown is an elegant seaport with narrow streets, beautiful old whaling captain’s homes, fashionable boutiques, wonderful restaurants and exceptional accommodations.

What makes the island particularly interesting is that its geography changes depending upon where you are on the island. In the west are the cliffs of clay, the north, rocky boulders, the south, small ponds and in the center, dense forests.

The season here is relatively short. Most restaurants are only open weekends until mid-May and many close after mid-October. The short season also means that everyone has to make their money in a short period of time, so things are expensive, think $25 for the 8 mile trip from the ferry to Edgartown or a 1/2 lb of chicken salad and a Pellegrino for $12. Be prepared!

See my Photo Scrapbook.

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Click picture to enlargeNewes From AmericaBrine PondOak Bluff Promenade

Making Your Travel Plans

To make your travel plans you can go to our Weekend Planner for all the contact information.

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Getting There

The most common way to reach the island is by ferry from Woods Hole, Massachusetts, about a 4 1/2-5 hour drive from New York City or 1 1/2 hours from Boston. If you are taking your car over ($155 R/T), this is where you will depart. The Woods Hole ferry lands in Vineyard Haven, about 20 minutes (or $25.00 cab ride) from Edgartown. There is also ferry service from Falmouth, MA which takes you directly into Edgartown and from New Bedford, MA.

A Fast Ferry service now runs from Quonset Point, Rhode Island. It has two advantages for those traveling from the south (NYC area). First, you can get there faster than to Woods Hole and second, it has dockside parking ($10/day). It's about $73 round-trip, takes about 90 minutes and arrives in Oak Bluffs. 

Steamship Authority or Hy-Line from MA ports takes about 45-60 minutes and costs about $15.00 round-trip.

If you are departing from Woods Hole and not taking your car, I suggest you park at Island Parking, about 100 feet from the terminal. It is more expensive ($25/day in season) but so much more convenient that getting on a bus to one of the lots 5 miles away. Get there a little early and stop in at Pie in the Sky, 10 Water Street, right around the corner from the ferry. Homemade breads, pastries and soups. Gourmet coffee and breakfast items and wonderful sandwiches. Much better choice than what the boat has to offer. Call ahead and they’ll have your order ready to take on the ferry.

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When To Go

The island population explodes in July and August, so unless you don’t mind crowds and waiting for everything May/June and September/October are the best months to go. Having said that, however, a recent trip in August was very enjoyable and if you can remember to make dinner reservations early in the day, you’ll be fine. The island can be very charming in winter, but call ahead to be sure which restaurants are open. Some of the websites say they are open all year but actually aren't.

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Getting Around

Islanders discourage visitors from bringing cars. Cabs are everywhere, but can be expensive. Seems like every ride is $20. Bikes or mopeds are an easy way to get around and many of the good restaurants and activities not in Edgartown are in Oak Bluffs, a short cab ride ($35 round trip) away. Public transportation is very good if you want to explore the island that way.

You may want to rent a car for a day and visit the towns of Vineyard Haven (shops and restaurants) Oak Bluffs (boat rentals and boat trips, restaurants and shops) and end the day by visiting the clay cliffs at Gay Head and then sunset at Menemsha Beach (two very good restaurants are nearby). We suggest Sun 'n Fun in Oak Bluffs. Good Jeep prices and meeting Don Sr. is worth the visit, a real character!

Two of our favorite restaurants are at the opposite end of the island and the cab ride can be as high as $60 each way. Worth the expense because the restaurants are good but the roads there and back are dark and windy and local and state police have a reputation for laying in wait for you.

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Accommodations/Dining

There’s no longer any need to roll the dice on where you stay or to settle and stay at a “safe” national chain. BestWeekends Travel Advance Team takes the worry out of where to stay when you go away.

The BestWeekends Travel Advance Team does all the work for you. We research each destination by scouring the guidebooks, articles, blogs, reviews and rating systems. Then we visit the destination and stay in the properties. Finally, we talk to the locals to be sure we didn’t miss anything. The result: we post on our site only the best of what we experienced. You can book with confidence knowing that “we’ve been there” and that no one pays us for a review. Inside see our Featured Properties.

When you are away on vacation, there’s few things worse than a bad dining experience. We agree, so we follow the same process for identifying restaurants as we do for accommodations, but with an extra step. We believe that the best dining experience has the strongest combination of food, ambiance and service. Good food is a given in our recommendations, but the best food in the world just doesn’t taste as good in a poor setting and the best setting with poor service just doesn’t cut it for us. The BestWeekends Travel Advance Team only presents those restaurants that meet our strict criteria. Mangia….enjoy! See our Favorite Restaurants.

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Things To Do

There’s fabulous seaside golf, tennis, biking, sailing, kayaking and horseback riding for the very active. You can rent a powerboat to explore or fish on your own or you can charter a fishing boat and let someone else do the work. There are nature walks, historical tours, boutique shopping, excellent art galleries and antique shops or you can just relax on the many beautiful beaches. The full list of Things To Do.

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BestWeekend' s Exclusives

After selecting our favorite places to stay and eat, we sat down and made a list of all the other things that would save you time and make your stay more enjoyable. The result is “Special Things” and “Good To Know, Good To Go,” BestWeekends Exclusives.

Special Things identifies unique, fun and romantic things for couples to do together in a particular destination. Good to Know is our list of the “best” of everything from breakfast to burgers, cocktails to after dinner fun and much, much more. Why stumble around trying to find the “best”….we’ve already done it for you!

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Don't Miss

  • Breakfast at Dock Street or Right Fork
  • Golf/tennis at Farm Neck
  • The clay cliffs at Gay Head
  • A bi-plane ride
  • Sunset at Menemsha
  • Fuller Street Beach
  • Drinks at the Seafood Shanty
  • Dinner at L'Etoile

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News and Resources

The local newspapers are the MV Times and the Vineyard Gazette. Martha's Vineyard Magazine runs the "Best of Martha's Vineyard" series.

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