~ Martha’s Vineyard is one of my favorite places in the world. There’s something so special about that island that no island can match…the secret beaches, the caribbean-looking blue waters that you might be surprised to find on parts of the island…secret ponds…farms….it’s really just magic! It was really special to introduce Matt to the island and see his reaction to everything for the first time!
Having grown up going to FOCUS camp there (and then having worked for FOCUS after), I was spoiled! I was let into all of these little gems that are lesser known to island tourists. Today, I want to share a bit of what we did on our trip and hopefully, this can help shape your trip next summer!
Matt’s first experience there happened during Covid…and while it wasn’t exactly what I had planned, I am SO grateful to the friends who helped us make this trip happen! I know travel during Covid can be a polarizing subject. We feel very lucky that we were able to comply with the MA travel law since we have testing close to our house and get our results within 24-48 hours (*I know this isn’t the case for a LOT of states with testing results). We both travelled with our test results printed out (just in case)!
Here’s how this trip came to be: I was lying in bed MISSING the Vineyard terribly in May. I thought I would pull open my Hopper app to see how much flights were. Usually flights during high season are around $800-$1,000 and many of them require you to switch to a tiny little puddle jumper Cape Air plane (the best part!). In all the summers that I have gone, I have only flown once (*ah! Missing the days when a ferry ride there was just a drive away!)! But when I checked that morning in May, ROUND TRIP flights were UNDER $200. UNHEARD of!
So, with hopes that Covid might pass by August, we pulled the trigger! OH how naive we were! While Covid has definitely taken a LOT from so many this summer….I was DETERMINED to make this trip happen and make it special. I’m so glad we did it. It was our favorite trip that we’ve taken together!
We were lucky enough to stay at my dear friend and former FOCUS co-worker’s rental property. We honestly felt so at home and she made us feel so cozy and welcome. She owns several rentals around the Vineyard and I’ve linked to them below!
Brenda’s studio that we stayed in was right outside of Oak Bluffs (referred to by many as simply “OB”). While I wouldn’t recommend staying right in town (personal preference), staying outside of either Oak Bluffs or Edgartown makes everything so central to get to! Both of those towns are pretty close together.
There are 3 towns on the Vineyard: Oak Bluffs (colorful gingerbread-looking houses and a great harbor), Edgartown (QUINTESSENTIAL New England…my favorite town!), Vineyard Haven (more quiet but still very New England). Each town is different with something to unique to offer, and I love that about the island!
Car Rental note: when we went, rental cars were a bit of a nightmare. I guess they didn’t bring on as many cars this summer due to Covid. Cars were over $200 A DAY. It was insane. I called my friend, Margot, to see if she knew of anyone on the island that could rent us a more affordable car and….get this…SHE LOANED US her CAR! How over-the-top nice and wonderful is she?! Margot…we love you! Thank you for making this trip happen!
*I do think it is essential to have a car on the island to FULLY experience it’s magic and get out to Menemsha and Aquinnah (about 40 mins away from Edgartown and Oak Bluffs).
Brenda’s Awesome Rental Properties
~ This is the studio we stayed in and loved!
~ This one bedroom is right next door and is adorable. We loved the deck on this property! Both of these rentals are in the BEST location close to the 2 main towns – Oak Bluffs and Edgartown!
~ WE LOVE FOOD! While I have been to some amazing restaurants on the Vineyard and have had the insane pleasure of attending Taste of the Vineyard…I still wanted to do my homework before we went. Things change on the island year to year in the restaurant industry! I think each night was perfect and would highly recommend all of the below!
Alchemy, Edgartown – I’ve been to Alchemy a few times before and have never been disappointed. This summer, they set up a big white tent across the street for social distancing and it almost felt like we were at a wedding…but I loved it! We both really enjoyed our meals. The scallops were phenomenal! I was able to make a reservation online, which I did a week in advance. *Thing to note: the Atlantic down the street is very popular and has awesome food but really not nice people working there. Every review on yelp will tell you so and we had a bad experience just asking for availability. Go to Alchemy instead!
Scottish Bakehouse, outside of Vineyard Haven- This place is a local favorite and it’s definitely a favorite of mine! It’s a tiny little cottage with a huge farm in the back! They have the absolute best baked goods and OMG I WAIT for their breakfast sandwiches all year round. They are incredibly gluten-free friendly and make their own GF bread! This is definitely a “grab and go” place, however there are some picnic tables out front. Matt loved it just as I thought he would!
The Aquinnah Shop, Aquinnah – BEST seafood meal I’ve had in my LIFE (like…over the summers I lived in the BVI’s and over Bahamas and over the Italian islands, too!)!!! This was a recommendation from locals and I wasn’t sure what to expect in the beginning. I thought, “the Aquinnah Shop? The one that sells shells and souvenirs?” Well…yes…that one, but there is a separate restaurant off to the side that sits on the cliff with the absolute BEST view of the sunset. Apparently they switched ownership 2 years ago and got an amazing chef. We experienced the NICEST servers and customer service…you can actually text them to make a reservation. I went back and forth with the sweetest hostess via text for 2 days and she reached out each time there was a cancellation. I couldn’t believe how lucky we got….we had a prime table overlooking the cliffs and the water. The hype about the spicy shrimp appetizer is REAL! Best shrimp I’ve ever had. GO. If you go to one place on the Vineyard…GO HERE! All of the lighthouse photos below were taken right next door!
The Black Dog Tavern, Vineyard Haven Harbor – You might recognize this black dog from a t-shirt you’ve seen before! The Black Dog originated on Martha’s Vineyard and while they own a handful of Black Dog Bakeries around the island to get goodies and breakfast sandwiches from, I recommend grabbing breakfast at their one and only restaurant. It’s in an old beach house that has ALL it’s original charm and could not be more authentic. It overlooks Vineyard Haven harbor and it’s fun to watch the ships and ferry come in as you sip on your coffee. I love their breakfast menu, too!
Menemsha Fish Market, Menemsha – One of my FAVORITE island traditions is packing a picnic dinner (and some wine and maybe a charcuterie tray) and heading out to Menemsha a couple hours before sunset. Menemsha is where the fishing boats come in and there are 2 little shacks that you can pick up INCREDIBLY fresh seafood at to add to your picnic dinner. “Lobster Rolls and Menemsha Sunset” are really 2 things that go hand-in-hand and are a part of this special tradition. Make sure that you get there very early to wait in line for your lobster rolls and get a parking spot. We got there 2 hours before sunset and still had to circle twice (but then got the best spot in the house!). This is one of the most beautiful sunsets on the island and everyone claps and all the boats honk their horns when the sun goes down. It’s a really magical Vineyard tradition!
Nancy’s, Oak Bluffs – THIS is the place of the famous NANCY’S DIRTY BANANA. Best. Drink. Ever! They also have a great sunset view over the harbor and we really enjoyed our appetizers there as well! Couldn’t let Matt leave the Vineyard without a Dirty Banana! Definitely a Vineyard staple.
Mad Martha’s (3 locations on the Vineyard) ~ While there are quite a few different places on island to get ice cream, Mad Martha’s is really the BEST, in my opinion. Every summer it seems to be exactly as wonderful as I remembered it and never disappoints!
Hike Menemsha Hills ~ I LOVE that the Vineyard has so many great walking and hiking trails. The views on this hike are my favorites on the island. I’ve always been on some kind of time crunch when doing this hike and have always hike down one way and back up the the same way, but this time, we went down the far left trail and then walked along the rocky beach to get to the far right trail to hike back up. I so highly recommend doing it this way and don’t miss a single lookout point!
*click here to get to the MV Trustees page and click on “directions.” When you are close, go very slow! The sign is teensy and only has a little “t” on it for “trustees.”
SAIL! ~ it was important for me to get Matt out on the water while we were there. He had never sailed before! It’s such a big part of my life and is probably the #1 thing I love the most. I’m so glad that we found Diane and had the chance to sail on Wing! She is hands down the nicest and for sure the most affordable charter we found. She also made a special effort to sail by Lambert’s Cove, my favorite beach on the island! It was such a special day!
Experience the TashMiracle that is TASHMOO! ~ Lake Tashmoo (which now is open to the ocean) is such a special spot. If you have a vehicle that won’t bottom out on the craziest, windiest, longest, dirt road ever, then you should absolutely make your way there for sunset and bring supplies for a beach bonfire! In the lake at night in the summer, there are bioluminescence! It’s seriously so magical.
Lighthouse Beach ~ Lighthouse Beach is such a special spot. You can do a beach day there or a little farther down on on Fuller Street Beach. I think Lighthouse Beach is more of an “activity” because it’s such a stunning spot to really explore – you really need to walk around and I think it’s best to visit early in the morning (like we did) to avoid any crowds!
South Beach ~ This is a fun public beach that is pretty easy to park at and get onto during the busy season. If you are familiar with Nantucket, this is the MV equivalent to Nobadeer. If you are looking for waves, this beach is the place to go!
Aquinnah Beach ~ This has been a favorite of mine since camp days and it’s another great public option. I believe there is a fee for daily parking during the busy season, but worth it to be right next to those stunning clay cliffs that define the Vineyard!
Lambert’s Cove ~ NUMBER ONE FAVORITE! If you go to the Vineyard in September, this beach is open to the public. It has blue caribbean waters and every time I’m there…I’m SHOCKED I’m in New England. It’s tiny, quaint, charming, and jaw-droppingly stunning.
Lucy Vincent Beach ~ If you HAPPEN to be on the Vineyard at any other time besides summer…GO! Oh my gosh – GO! I had never been there before the September that I lived and worked on the Vineyard for a month when I returned from Italy. I was SHOCKED. The giant rock formations reminded me a bit of Bermuda. It’s so special! It’s private, unfortunately, in the summer months.
Lambert’s Cove! 
The walk out to Lambert’s! 
It’s my favorite beach in the WORLD, I think!
~ There are SO many reasons I would choose this place over anywhere else in the region. I have been to Nantucket for weeks at a time, and have loved my time with friends there! However, I don’t love the crowds, the traffic, or how there aren’t a lot of spots that are completely hidden, secret, or private. The Vineyard is FULL of kind islanders who will welcome you with open arms. I was lucky enough to experience that firsthand when I lived there that September. There are also THREE towns to explore – each with their own unique aspects that make them special. Lastly, there are places to HIKE and secret beaches and ponds to be discovered. The fact that you can be completely solo on a body of water during any holiday weekend makes this place a golden gem!
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