Martha’s Vineyard MA - Jim Flynn's BestWeekends

Martha’s Vineyard MA

Martha’s Vineyard MA 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.

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 singer Carly Simon, 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!

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.

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 ($171 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 $99 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.

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.

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.

Things To Do


Close to town, Fuller Street Beach and Lighthouse Beach are the choices. Fuller Street was rated one of the Top 10 Beaches in the US by Travelocity. A bit of a trek by car is the Long Point Wildlife Refuge ($10 parking, $5pp). It has a great beach and a fresh water pond as well.


Mink Meadows in Vineyard Haven, the public course on the island, is a 9 hole track with two sets of tees that make 18 holes about 6200 yards. It’s a beautiful little course that costs about $100 with a cart in-season. The real island gem though, is Farm Neck, in Oak Bluffs. This is a spectacular golf course, mostly private, with great holes along the water and through the woods. Short, but very challenging. In season tee-times for non-members start as early as 6am. Members play from 7am-1pm. Recently met someone who had been on the membership waiting list for 19 years! Restaurant has a great lunch, open to the public, that many think is the best on the island. $175 in season with cart. Call the Pro Shop directly well in advance or have your local Pro call for you.

Here’s what Zagat said about Farm Neck; “Yet another contender for Pebble Beach of the East. Well kept course with endless character, beautiful views of the Atlantic terrific risk/reward holes that can bring golfers to their knees.”


There are miles of bike paths crisscrossing the island, suitable for walking, jogging or biking. They are all clearly marked everywhere. Try the beautiful  Trade Wind Field Preserve on County Road in Oak Bluffs for a wonderful place to walk and experience the beauty of the island.

We like Wheel Happy for bike rentals.. South Water Street. Good prices and selection. About $20/day. $15 for second day.

Boat Rentals/Water Sports

Martha’s Vineyard Oceansports. Oak Bluffs. Rent a Boston Whaler (13 ft. $350 half day (4 hours) and fish or just cruise around the island and its harbors. Also offers waterskiing, parasailing and jet skiing.

Boat Rides

Mad Max. Dock Street. 60 foot catamaran sails twice a day for 2 hours. Opt for the sunset sail. $50 per person. BYOB and snacks.


Cape Pogue Wildlife Tours on Chappiquiddick, Daily 9am and 2pm, $35.


Menemsha Blues Charter. 1/2 day for 6 people $700. Best party boat is the Skipper, also out of Oak Bluff. $70/person


The Vineyard has an extensive group of wonderful art galleries featuring local and national artists. Some of our favorites include Eisenhauer Galleries, N. Water Street, Old Sculpin on Dock Street, Kennedy Gallery on Dock Street and the Edgartown Art Gallery on N. Water and S. Summer. The Martha’s Vineyard Times can also provide information on current and upcoming shows.

Tours and Sights

MV Sightseeing. Many pick-up spots. Trolley cars. 2 1/2 hours. $33. For a longer and more personalized tour try Stagecoach Taxi. 4 hour tour at $45-$60 includes stops for lunch, celebrity homes and more not offered on traditional tours. There is also a Ghosts, Gossip and Downright Scandals Tour that sounds like fun, but we haven’t done it yet. Martha’s Vineyard Museum is an interesting stop that tells the story of the island’s history and the Polly Hill Arboretum has 50 acres of woodlands and 20 acres of trees and gardens.

Bi-Plane Ride

Bi-plane rides from Classic Aviators at Katama Airport at South Beach are a wonderful way to see the island from the air. There are trips of varying duration, but 15 minutes is all you really need. Two people for $129, takes you around the Edgartown area. For an extra $65, they’ll do so rolls and flips. Even if you don’t pay for it they’ll usually do at least one roll. Lots of fun.

Horseback Riding

Enjoy the beauty of the Island on horseback with Arrowhead Farm.  Trail rides through the State Forest to the Tisbury Great pond. $130.


There are loads of wonderful shops and boutiques on the Island with an equal number in Edgartown, Oak Bluff and Vineyard Haven.

Regular Events

  • Farmer’s Market, West Tisbury. Saturdays 9-12.
  • Chilmark Flea Market. Chilmark. Saturdays, 8:30-2pm.
  • Artisans Summer Festival. West Tisbury. 10-2, Sundays.
  • Antiques Show. West Tisbury. Fridays. 9-3.

Dont 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

The Best Of...

Food & Drink


Dock Street Coffee Shop. End of Main Street on Dock. Local’s place. Opens at 7am. Just a counter with old red vinyl seats. Short order cook is right in front of you. Old time diner. Among the Flowers. Mayhew Lane. Opens at 8am. Sit outside ‘among the flowers’. More upscale than Dock Street. Very good food, diminished only by the use of paper plates and plastic utensils. On our most recent visit we happened upon the Right Fork at the Katama airport as we were waiting to take a bi-plane ride. The place was packed for lunch so we came back the next day and had a wonderful breakfast while watching the planes take off and land.


Best outside spots are the upper deck of the Seafood Shanty on Dock Street; Raw bar, sushi and other good pub food. Great chowder. Atlantic on Main Street has waterside seating and tables on Main Street. Diverse menu. Inside, particularly in cooler weather, enjoy fireside dining at Newes from America on Kelly Street. Locals think the restaurant at Farm Neck Golf Coursehas the best lunch.


My favorite is the juicy burger and fries at Alchemy on Main. Another great choice is Newes From America. Kelly House. Kelly particularly if you are a beer drinker as they feature a great collection of beers, some brewed locally.

Lobster Roll

Can’t confirm this because I haven’t been there on a Friday, but everyone raves about the lobster roll, served only on Fridays from 4:30-7:30 at Grace Church on Woodlawn Ave. Vineyard Haven.

Raw Bar

The Atlantic features fresh oysters from nearby Katama Bay, local little neck clams and local lobster.


Alchemy. Main Street. Lots of choices. Great Dirty Martini. Also uses freshly squeezed juices in all their other drinks. Excellent wines. Real vibe….it’s fun being here. Atlantic, also on Main Street has a wonderful collection of curated cocktails. Has become a local’s favorite.


The Seafood Shanty. Dock Street. Outside rooftop bar overlooking the harbor. Great spot. Alchemy, Main Street when it’s too cold or rainy to be outside. Atlantic, also on Main Street has a wonderful collection of curated cocktails. Has become a local’s favorite.



Menemsha Beach. Extreme western end of island. See ‘Special Things’. Two of our favorite restaurants, the Beach Plum and the Outermost Inn are also on the western end of the Island and  great places to enjoy the sunset over dinner.

After Dinner Fun

Alchemy, Main Street. Often has easy listening entertainment. Stylish crowd. Downstairs bar at Atria on Main Street is probably the best bar in Edgartown after dinner. Sharky’s is a great bar in Oak Bluffs with Mexican food as well. The new Atlantic in Edgartown has live music throughout the season.

While Away a Rainy Day

Wharf Pub. Lower Main Street. Great pub food. Lots of beers. Wonderful appetizers, sandwiches, burgers, dogs. Good long bar. Locals love it. No better place when you can’t do anything else. Also love the Lookout Tavern in Oak Bluffs. Perched on a hill overlooking the water. Lots of beers and good snacking foods. Always stop here when we come into Oak Bluffs on the ferry.

Picnic Fixins/Wine & Cheese

Soigne. Upper Main Street is one of those great little specialty food stores. Great sandwiches a wonderful cheese and pate selection. Fresh breads and pastries and a very good and reasonably priced wine selection.

Sweet Tooth

Murdick’s Fudge. Mad Martha’s Homemade Ice Cream. N. Water Street. Next door to each other. You can get a month’s worth of sugar here. Great ice cream flavors and unbelievable fudge.

Morning Paper

Edgartown Paper Store on Main Street. Opens at 6:30am and has pretty much any Boston or New York paper.

Get Pampered

Boucle, North Water Street. Full spa facilities. Hair, nails, make-up, facials, massage.


Triangle Fitness. Post Office Square.

Tourist Trap

Black Dog. Vineyard Haven or anywhere else on the island. Once it was cool to have a Black Dog T-shirt. Now they’re a marketing machine. Still a good gift for the uninspired.


The Tourist Trap. Kelly Street. Good selection and prices. Nice people.

Island Prints & Photos

Edgartown Art Gallery. Multiple locations. Vineyard Square Hotel on N. Water and S. Summer Street.

Special Things

Start the Day

Pick up a cup of coffee at Espresso Love (open at 6:30am) on Church Street, you’ll probably end up with one of their great muffins too, then a newspaper at Edgartown Paper and head down to the end of Main Street. Cross over to the wharf, pick a bench and enjoy the Harbor coming alive with fishing boats. If the rest of the day is as good as this, it’ll be a good one.

Island Picnic

Stop in at Soigne (See “Good to Know”) and pick up all the fixins for an intimate picnic. Hop on the Chappy ferry at the end of Dagget Street (bike or car) for the 3 minute trip to Chappaquiddick Island. About 2 miles down on the right side is Brine’s Pond Reserve, a wonderful place for a quiet and very private picnic. Let your mind wander.

Day is Done..Watch the Sun

Make your way to the most western part of the island at Menemsha, about a half hour drive from Edgartown. ($60 round-trip cab). A travel magazine said the sunset here is second only to Key West. Bring a bottle of wine (Menemsha is dry) and stop in at Home Port and pick up a lobster (or other) take-out dinner and take it to the beach and enjoy a romantic sunset. Or, enjoy the sunset from the Beach Plum Restaurant.

Where To Stay

Charlotte Inn

OVERVIEW of the Charlotte Inn

If I only had one more day on this fine earth, I just might want to spend it at the Charlotte Inn. This is a magnificent inn with museum quality antiques and oil paintings that still manages to be one of…

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Harbor View Hotel

OVERVIEW of the Harborview Hotel

At the eastern end of the Island, perched on a bluff overlooking the Lighthouse and Edgartown Harbor, the Harbor View Hotel opened in 1891 and remains the island’s premier full service hotel. While boasting all the modern amenities you would expect,…

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Hob Knob Inn


OVERVIEW of the Hob Knob Inn

Affectionately named after her grandparent's sprawling country home in Ohio….The Hob Knob, owner Margaret H. White has created a charming and comfortable eco boutique hotel which may be the only truly "green" property on the island. Everyone has their preference…

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Vineyard Square Hotel

OVERVIEW of the Vineyard Square Hotel

With wonderful views of the harbor, the 28 room Vineyard Square Hotel and Suites is perfectly located in the center of town, surrounded by shops, art galleries and restaurants. Virtually anywhere you would like  to go in Edgartown is only steps away.…

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Where To Eat

Atlantic Fish & Chophouse

On my last visit to the Vineyard I was pleasantly surprised to find a new restaurant in Edgartown, the Atlantic Fish & Chophouse down at the end of Main Street. The ambiance, food, wine and entertainment were so enjoyable that I ended up eating there twice during my short stay.  Created by restaurant veterans, Eli…

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Located a block from town, adjacent to the Vineyard Square Inn, Chesca's is a comfortable restaurant enjoyed by locals and visitors alike. It is mentioned often by people who live here as one of their favorites. Start with a cocktail from the bar and sit on the outside porch in a rocking chair and watch…

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It's not often that food, ambiance and service all come together at the same time. But when it does it can be a magical evening. Such was the case when we visited Detente. Tucked into a corner of Nevin Square just off Water Street, this wonderful husband and wife owned delight has it all working.…

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L'Etoile has consistently been rated one of the top restaurants on the island and for over 20 years served wonderful meals from its space in the Charlotte Inn. In 2006, the restaurant moved from the Charlotte Inn to 22 North Water Street. The chef and most of the staff remain the same. I loved the…

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Outermost Inn

At the western tip of the island, beneath the Gay Head lighthouse and with sweeping views of the ocean is a very special restaurant. The Outermost Inn, owned by Hugh and Jeanne Taylor (brother of James and Livingston)  offers spectacular sunsets and wonderful food. While it is 18 miles from Edgartown, the trip takes about…

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The Terrace

The Terrace is located within the magnificent Charlotte Inn, one of the most beautiful inns we have ever seen. Set in a candlelit conservatory dining room and during the warmer months, garden terrace, the restaurant is elegant and sophisticated. The cuisine is American with French influences and the menu is crafted from the bounty of…

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