top of page


No tags yet.



Martha's Vineyard is a beautiful island off the coast of Massachusetts, sister island and similar in nature to Nantucket and Cape Cod. When I told friends that I booked a trip to Martha's Vineyard, I was inundated with opinions, both positive and negative, about what to expect from my experience. I was told that it’s ritzy and upscale, but pretentious and snobby. I was told that it was overpriced and overrated by some people, and that it was the perfect relaxing getaway by others. None of these were my lasting impressions of Martha's Vineyard. It was so much more than that.

GETTING THERE We booked a trip in August for Labor Day weekend. Needless to say, flight prices were insane. Instead, we took Amtrak from NYC to Kingston, Rhode Island. From there we took a Little Rest Limo shuttle to the Fast Ferry. This saved us a few hundred dollars; however it turned a 2 hour flight into an 8-9 hour travel experience. Albeit beautiful and scenic (the ride from New York to Rhode Island on the train is beautiful and comfortable and the Fast Ferry feels sort of like a boat ride with the right weather and company) I would definitely opt for booking a flight early and going that route.

inkwell beach martha's vineyard soul society 101 martha's vineyard soul society
waterfront yachts oaks bluff nancy's martha's vineyard soul society 101.JPG

DAY 1 Once our ferry ride docked around 5pm on Friday August 29th 2014, we were excited to FINALLY explore Martha's Vineyard. We were greeted with clear blue skies that met the water full of gleaming white yachts and sailboats – very picturesque. We jumped into a short 5 minute cab ride up the waterfront to our bed and breakfast, Pequot Hotel, in the Oak Bluffs area of the island, an area I highly recommend everyone to stay because of its proximity to the beach, restaurants and bars and an abundance of public transportation. Martha's Vineyard doesn't really have many hotels in the traditional sense. It's really full of bed & breakfasts and houses that are rented for vacation. The Pequot hotel (actually a bed and breakfast) is a popular stay for solo guests and couples who didn’t rally up enough people to rent a house. Every morning there's obviously a spread of breakfast, with mimosas on Sundays. Every afternoon they offer fresh baked chocolate chip cookies, lemonade and tea. Its charm is quirky and eclectic and like the other surrounding beautiful homes, their terrace is lined with rocking chairs and swings. You automatically feel a sense of coziness and quaint, almost southern living.

photo 1.JPG

Because we started our day late, we dropped our bags, showered and went on the hunt for food. Our first stop, one of the most popular dining spots on the island, Nancy's Restaurant. Nancy's, like all other restaurants in Oak Bluffs was a 5-10 minute walk from Pequot. At Nancy’s there's an upstairs, classy establishment, a fried foods and quick pick-ups window downstairs where you can sit outside in an umbrella lined seating area that overlooks another waterfront. Pretty fun and sexy, especially because every summer, Donovan's Reef (Jamaican man who sells tropical mixed and frozen drinks) sets up shop alongside Nancy's and not only provides the drinks that set the vibe, but also blasts sweet reggae music that just adds to the already existent Carib-esque island vibe of Oak Bluffs. The food at Nancy's is awesome - the best lobster rolls on the island (more on this later), fried shrimp and calamari, oysters, all amazing! Of course New England is known for fresh, delicious seafood and Nancy's is the poster-child for that.

marthas vineyard 1.JPG

DAY 2 I traded in sirens and loud car speakers of Brooklyn, New York for the beautiful sound of silent nights. After and awesome night's sleep I woke up ready to conquer my island home away from home. We walked up the nearby strip, Circuit Ave, and walked up the beach line and beautifully manicured gardens to arrive at the best breakfast on the island that I've tasted to date - Biscuits. The line for Biscuits was long but so well worth it. Everything from Bacon Cakes (bacon in pancake batter,) to Pigs In A Biscuit and chicken biscuits covered in sausage gravy. At this point I was a bit annoyed that no one informed me just how much I was enjoy the good on the island. I felt like my stomach had fallen in love.

photo 3.JPG

Biscuits left us feeling like we needed to walk off some of those calories so we strolled and strolled, took photos of the beautiful homes and mansions and strolled some more until we ended up at Inkwell Beach. We popped a squat and relaxed for hours. It was definitely one of the nicest beaches I had seen in the Northeast.

Fast forward a few hours of sun-induced nap time and we're up again. Strolling through the picturesque streets until our noses caught wind of an amazing scent. The infamous backdoor donuts, freshly baked donuts and other pastries open 7pm - 1am randomly behind the Post Office in Oak Bluffs (again, just adding to the cute and coziness of Martha's Vineyard.) Over the course of 3 days we tried about 7 different things on the menu, our favorite being the Honey Dipped donut. Other people love the apple fritters but it was a bit too intense and sweet for my taste buds. Don't be alarmed if there's a super long line, it only increases your chances of having a fresh batch of donuts (which is EVERYTHING) and the line goes way quicker than you think. Walking distance from backyard donuts is Ben & Bill's ice cream shop where we ordered a medium and here's what we got.

photo 4_edited.JPG

Being in the greedy mode that we were in, we made a concoction that changed the game - Ben & Bills grapenut ice cream with buttermilk donut crumbs from backdoor donuts. They need to get together and have a love child because this right here!!!.... Wooh!

photo 5.JPG

DAY 3 We woke up early and took a beautiful morning walk along the beach in the opposite direction to a soul food jazz brunch at Lola's. For $25 you get unlimited southern brunch food served in a huge mansion... Sounds amazing, and it would be if the food were actually good. Everything from bacon, to collard greens, to macaroni and cheese, fried chicken and waffles was under seasoned. I left totally underwhelmed and a bit queasy. It was our first restaurant “miss,” but it led us to yet another unseen part of the beautiful island so we did not complain. Since we had spent most of our time thus far between the Oak Bluffs and Edgartown areas, both very popular and established areas, we decided to take an MV-regular's advice and trek to the other side of the island which is more rural and scenic and perfectly positioned for viewing the sunset. There were two options to hang out at the other side of the island - Menemsha and Aquinah. Aquinah was our first choice since we heard from several sources that it's the most beautiful part if the island, but the one restaurant at Aquinah, Aquinah Shop, was closed for a private event that night so we decided on Menemsha which we heard was also beautiful and had a few restaurant options. What we wish we knew is that getting to the other side of the island was a pain - taking 3 buses for either option. Buses on Martha's Vineyard run on schedules so at least you know exactly where you're connecting, but what we thought was a 45 minute trip turned into a 2-3 hour trip. Although we were able to see more cutesy little areas of the island along the way, like Vineyard Haven, the next time I visit, I would absolutely either invest in a driver for this day trip or rent a car.

photo 2.JPG

Finally arriving to Menemsha and it was simple and beautiful. There's a beach, a few small beachy mom-and-pop style restaurants/fish markets, and the sunset. Because the area is understated, at first you might not know what the huge draw is. Then you eat the amazing seafood and you get it. Although we tried two other lobster rolls and no one topped our favorite, Nancy's' in OakBluffs, Menemsha Fish Market had the best clam chowder and lobster bisque I've ever tasted, and Larsen's Fish Market had a slamming white cheddar lobster Mac and Cheese that could not be denied. We walked down to Menemsha beach which was rocky but peaceful and at 7:19, the sunset was everything you could ever ask for and without words and justified the trek to the less-populated side of the island. It felt like you were at the end of the Earth, as close to the sun as you would ever be, and something about that helps to put your life into perspective.

lobster macaroni and cheese seafood martha's vineyard best places to eat list so
rondel holder what to do houses in martha's vineyard walking around where do bla

WOULD I GO BACK Absolutely! Whenever I needs quiet, chill extended weekend getaway, MV will be a top thought. People come for weeks, for me 3-4 days is perfect. It's almost like a Caribbean island, with southern hospitality with a woodsy/camper appeal, with great American food! Everyone is super friendly and down to earth, and it quickly feels like home.

photo 1.JPG


  • Unknown.jpeg
  • Unknown-2.jpeg
  • Unknown-1.jpeg


bottom of page