
Martha’s Vineyard holds a place in my mind as being a storybook destination with gorgeous homes, the ocean, sailing and hydrangeas everywhere. When I planned our recent adventure to Cape Cod, I set aside an entire day for Martha’s Vineyard…I had to see this beauty for myself. The big day was a foggy one, apparently fog is a constant challenge due to the location of this island. We went Memorial Day weekend and was definitely hoping for a gorgeous sunny day, however, this was not in the stars for us. We didn’t let a little fog and sputtery rain deter us, though! We are travel warriors…and the plus side?? The crowds were not there BECAUSE it was foggy and rainy. We had a wonderfully relaxing day touring the island on our bikes and ate at one of the most popular lobster shacks without having to wait in line. And our reward for braving the elements that morning? The sun came out in the afternoon ☀️ Then, like magic, the crowds appeared.

To get to Martha’s Vineyard, you have to take a Ferry…I chose the Island Queen Ferry in Oak Bluff. You can take your car to the island, but I had plans to ride our rental bikes. I read that parking can be a nightmare when you get to the little towns on the island. Bike parking is a breeze 🙂 The tickets were cheap…$48 for two people, round trip. It was a scenic 30 minute boat ride.

Our List of Experiences…
In my opinion, there is the Martha’s Vineyard experience one must do if it is your first time there. Here is our list of quintessential things for the East Coast traveler looking to take in this storybook island in the future! It is lovely there…

1. Bike Riding
I do think that renting a bike is the best way to see the island. We took Seaview Avenue and made our way to Edgartown, about 6 miles of beautiful seaside views! The ferry docks in Oak Bluff and you’ll find that there is no shortage of places to rent bikes, scooters, jeeps, etc. I chose All Star Bicycle Rentals. The bikes were in excellent condition and fairly new. You get everything you need as well as a helpful island map.


2. Island Fashion
A particular fashion brand I follow is Vineyard Vines. It was actually founded in Martha’s Vineyard back in 1998. They are known for colorful pastels, polo shirts, unique ‘island’ fabric prints, and of course the whale icon. Interestingly enough, Martha’s Vineyard was part of the whaling industry way back in the 1700’s. The Civil War actually brought an end to it. I read that the cliffs on Martha’s Vineyard have fossils of ancient whale bones. Cooooooool……
We had to do a walk thru. I personally love the swimwear and polo shirts for guys. It’s not a trip to Martha’s Vineyard if you don’t leave with a pink polo shirt, right??
The Black Dog is also a famous brand here and the store is a must-walk-thru. The Black Dog is actually a restaurant and their souvenir black dog T-shirts took on a life of its own. The story behind The Black Dog is an interesting one!


3. Lobster Rolls
Ah yes, the lobster roll. Nate might be the lobster’s biggest fan. We had to find THE place to eat in Edgartown. The owner of the bike shop recommended the Seafood Shanty. He warned me though that there was always an hour (or longer) wait. It’s right on the water and has some of the best east coast seafood around. We decided to get there just before it opened to stand in line. They don’t take reservations, first come first serve. As it so happened, because it had been drizzling all morning, there WAS NO LINE! We were sat right away. I ordered the best fried seafood platter I’ve ever had in my life, Nate ordered the lobster roll. This roll was unlike all the others we’ve had..no mayo, just drawn butter…it was smothered in delicious, golden, melted euphoria. There was SO much lobster in this roll, it had to be 2 lobsters and worth the price!! Fair warning, lobster pricing has gone up quite a bit. You’re looking at a $30-50 dollars a roll these days. Yikes…. 🦞


4. The Architecture
The homes here are replicated over and over again…they have an east coast charm that I love. The cedar shingles, the grey wood tones, the ornate porches, balconies, and railings…just storybook. And those hydrangeas?? Sign me up, I want to live here. This style of home is all over the island, you can’t miss them. Edgartown was especially cute. Some of the homes were ship captain homes and have the captain name on a plaque outside the house…so cool. People seem very proud of the history there. Edgartown is considered one of the East Coast’s most elegant communities. Edgartown is also one of the most well-known yachting centers, so if sailing/boating is your thing, this is the place for you.



5. Enjoy Dinner Back at Falmouth
Martha’s Vineyard is a full day. You can certainly eat dinner there and then head back, but the ferry schedule doesn’t go all night. We decided to catch the 2nd to last ferry and head back to Falmouth where a fabulous italian restaurant was recommended by our Inn keeper on Cape Cod. He said that they make their pasta in-house and everything is incredibly savory and delicious. We made reservations right away. Osteria La Civetta, or Tavern of the Owl, is a quaint Italian restaurant not too far from the Falmouth Ferry pier. It was hard to choose what to order, I went with our favorite: Bolognese. It was exceptional…




I’ll be honest, I was a little intimidated to visit Martha’s Vineyard… I had no idea what to expect, I only had my own likely false conclusions about how it was too posh and fancy and that I might feel out of place. So silly, Martha’s Vineyard was just another beautiful place, everyone was so friendly, the food was superb, the scenery mesmerizing. The flowers on the island are bright pink…and they are everywhere. The sand is white, the ocean serene. I only wish we could have squeezed in some sailing and seen more of the island. If you are able to find an affordable night somewhere (it’s crazy CRAZY expensive to stay on the island), book it…there’s so much more to do and see!


We hope you can find time in your busy schedule to squeeze in a trip to Martha’s Vineyard! And listen, if it happens to be raining or super foggy that day, go anyways…the food is still amazing, there won’t be any crowds to contend with, and it’ll still be worth it. For us, after a few hours of drizzly weather the clouds parted and the sun came out… and in that precise moment in time, I was so incredibly happy we were there. The thing about Me and Nate? We make the absolute best of everything. We once toured Nuremberg, Germany in the pouring rain…. all day, non-stop…and it was maybe the best day that week together. We saw so much, we had the best German lunch (so much so we still talk about it…”remember that place? That place we stopped at in the rain?” We are a travel team who believes that sometimes the best adventures together are in the rain ❤️
#GoAdventure
Heather and Nate



