Martha’s Vineyard is now one of my favorite places to visit for a summer get-away. I typically go in late July or early August, but May-Sept is the recommend peak season. Who knows, you may just run into a famous celebrity on the island while they are vacationing for the summer. I did every day just taking a stroll downtown or eating in one of the many restaurants.
And did I mention the best Lobster, Lobster (did I say Lobster) …
According to The Power of Place: An Overview of Black History on Martha’s Vineyard (writerstheatre.org) The Vineyard has long been a famous getaway and resort for the elite, having been frequented by past presidents such as John F. Kennedy, Bill Clinton and Barack Obama.
My advice is to always keep your camera ready…
Where is Martha’s Vineyard?
Martha’s Vineyard Island is located approximately seven miles off the southern coast of Cape Cod in Massachusetts. It is on the East Coast of the United States. The largest island off the Massachusetts coast is only accessible by boat or air.
How to Get to Martha’s Vineyard?
To get to Martha’s Vineyard, you catch a ferry from Woods Hole (near Falmouth) on Cape Cod to either Oaks Bluff or Vineyard Haven.
According to Travel to Vineyard Haven & Oak Bluffs aboard Traditional Ferries | The Steamship Authority The Woods Hole ferry to Martha’s Vineyard takes approximately 45 minutes.
I recommend taking your car over on the Martha’s Vineyard ferry it is best to reserve your ticket in advance so you don’t miss out.
Woods Hole is about a two hour drive south of Boston and from NYC to Martha’s Vineyard takes approximately 5.5 hrs.
Plan to reserve your car (which I recommend to get around the island) and ferry tickets by the summer reservation open date in Jan for travel in the summer. Yes, it requires planning that far ahead to guarantee tickets for the busy summer months.
It seems like it is a journey to get to this beautiful island (it really is) but once you are there the fun begins…
My 10 favorite things to do and see on the Island:
1. Stay in or visit Oak Bluffs, Martha’s Vineyard
Oak Bluffs is a colorful and historic town on the Massachusetts island of Martha’s Vineyard. From sandy beaches and seafood restaurants to eclectic downtown shops (Circuit Ave) and historic cottages, you’ll find more than enough to do and see in Oak Bluffs while visiting the island.
Obama’s visit also spoke to the island’s historical significance to African-Americans. At least five generations of African-American creative and professional classes have spent their summers on Martha’s Vineyard. The town of Oak Bluffs has become a landmark that black families have read about and aspired to visit.
2. Take a Morning Swim at Inkwell Beach
The” Inkwell” or Town Beach in Oak Bluffs is the name of the popular beach frequented by African Americans beginning in the late nineteenth century.
Every morning around 6 am the polar bear swim club (primarily women) take a dip in the ocean at Inkwell Beach as they sing songs in fellowship. After the morning dip, participants congregate to get the latest news and activities to plan the rest of their day.
You may also see others taking a morning jog or stroll along the beach or doing Tai Chi, Yoga or Meditation. It feels like a family reunion. It’s worth getting up early in the morning to revive and renew.
3. Grab lunch at the Lookout Tavern
If you want the best Lobster taco or lobster roll (cold or warm) you have ever tasted along with a great view, head to the Lookout Tavern. Home – Waterfront Dining | Lookout Tavern | Martha’s Vineyard (lookoutmv.com) has a beautiful waterfront view across from the beach and ocean. They are open for lunch or dinner and the atmosphere and food is one of the best in downtown Oak Bluffs.
4. Shop for gifts at the famous C’est la Vie on Circuit Ave
It is one of my favorite stores in Oak Bluffs, MV. If you want to find an eclectic mix of home accents, jewelry, vineyard souvenirs and apparel, C’est la Vie is a must stop for your shopping fix while on the island. It is in the heart of Oak Bluffs on the busy shopping district on Circuit Ave.
I recommend you have a list and budget, as I always find I say I am buying a few items and leave with shopping bags multiple times while on the island. (smile). My guilty pleasure…
5. Get a cold frozen drink at the famous Martha’s Vineyard Donovan’s Reef
One place and person that is a “Must” while visiting Martha’s Vineyard is Donovan at Donovan’s Reef bar stand below the famous Nancy’s restaurant at the Oak Bluffs Harbor.
You can’t miss it with the reggae beats and beautiful mixologist Donovan with the captivating smile and personality to match. (Ok I need to focus). Donovan is from Negril, Jamaica, and when he’s not at MV, that’s where you’ll find him. In Jamaica, he had a reputation for making amazing drinks,
Once learning about his amazing drinks, Nancy’s ) offered him his own space at their restaurant during the summer months. As you watch him twirl bottles, blend fruit, all while singing and dancing, with his captivating smile (I’m distracted again) you know it’s going to be a great cocktail.
The most popular drinks at Donovan’s are his famous Dirty Bananas, Bahama Mamas, Margaritas and Pina Coladas. You won’t miss him he is there 7 days a week, open to close. (smile)
6. Watch the Sunset and enjoy a hand-picked lobster at Menemsha Beach and Larsen’s Fish Market
Menemsha is one of those breathtaking places on Martha’s Vineyard. It’s a quaint fishing village in the northwest end of Chilmark. There is a picturesque harbor, and a beautiful sandy, public beach.
Menemsha is best known for its spectacular sunsets. The village faces west, and the sun sets straight across the Vineyard waters, sinking into the horizons with a beautiful array of color.
You can drive there by car and park or take public transportation. We drove and parked in a nearby parking lot and jumped on the free shuttle with a cute driver who allowed us to do shuttle karaoke with his old school music catalog on the short drive to the beach. (fun times)
Once there, we stood in line to pick our own live lobster to have steamed at Larsen’s fish market. Once steamed, take your food and sit on the beach to watch the sunset (make sure you take your folding chairs and adult beverages for a nice picnic). It was a breathtaking experience…
7. Spend a half day taking the African-American Heritage Trail Bus Tour
Oak Bluffs was the only town of the now six on Martha’s Vineyard where African-Americans were permitted to find lodging. The first African-Americans known to have settled on Martha’s Vineyard were servants, runaway slaves, and whalers after slavery was abolished in the 19th century.
The African-American Heritage Trail tour highlights the background and historic history of the African-American presence on the island. It gave you not only a history tour but allowed you ask questions. You also got to see up close the current homes of the current residents and celebrity vacation homes.
Carve out half a day for the tour. The tour is comprised of 26 sites dedicated to the formerly unrecognized contributions made by people of African descent to the history of the Island. At each of these sites a descriptive plaque has been placed.
There are 3 types of tours offered, a 1.5 hr. Oak Bluffs Tour, 2.5 hr. Oak Bluffs and Edgartown Tour, or the 4-hour All-Island Tour. I highly recommend!!!
Tours, Books, and More – MV African-American Heritage Trail
8. Explore the great island of Nantucket in Martha’s Vineyard
If you want to fit more than one Cape Cod Island experience into one vacation, a day trip to Nantucket island next door is just a ferry ride away.
The Vineyard is considerably larger, with multiple distinct towns and things to do, whereas Nantucket’s action is more concentrated in one downtown area.
The Hy-Line Cruises runs ferry service back and forth — hop the first one from Oak Bluffs in the morning and heading back in the evening just before dinner time. I also included a shuttle bus tour with the ferry ticket to learn and see the historical sites on the island that I would not be able to cover on foot.
You get an opportunity to see the Kennedy’s home and other famous wealthy residents with a guided tour. (I love learning about the local areas I visit).
Afterwards you can shop in the downtown are with its many stores, visit the beaches and dine at the many restaurants on the island.
Don’t enjoy the island too much where you forget to return to the ferry to get back to Oak Bluffs on your scheduled time. No worries. Pack an overnight bag just in case. You can always stay overnight if you have time at many of the hotels. If there are vacancies?? (Hopefully)
9. Witness the Aquinnah Cliffs and Gay Head Lighthouse
The Aquinnah Cliffs – formerly known as Gay Head – is one of Martha’s Vineyard’s most-visited tourist spots. The epic clay cliffs, which were carved by glaciers millions of years ago, are worth the drive to the location.
You can explore the lower beach paths to see the cliffs up close and stretch along the sands at Moshup Beach. Take the upper trails to the top of the cliffs. Catch a glimpse of Gay Head Lighthouse and nearby Elizabeth Islands.
The Aquinnah Cliffs are part of the island’s Wampanoag reservation and under special environmental protections.
The view is breathtaking and one of the island treasures.
10.Head to Martha’s Vineyard famous Fat Ronnie’s Burger Bar on Circuit Ave
If you are hungry after a night of dancing head over to grab one of the custom-made burger or turkey burgers (my favorite). Select your choice of toppings or a delicious lobster roll at Fat Ronnie’s Burger Bar. It is one of the few restaurants open late night until 1 am.
Fat Ronnies’s Burger Bar – Martha’s Vineyard and Miami Beach (fatronniesburgerbar.com) Fat Ronnie’s Burger Bar was opened in 2013 on Circuit Ave in Oak Bluff’s, MV. His family burger business started in Harlem in 1972 with his grandmother’s burger joint called Maxine’s. He has taken his famous recipes to MV.
It will be easy to find with the crowd standing outside to place an order day or night.
Enjoy your trip and tell them Trina from Wholistic Balance sent you…
This is so awesome, I can’t wait until I go and visit.
Great! You will love it!