Martha’s Vineyard, Massachusetts – 2018

When summer 2018 rolled around, my sister Lauren and I were counting down the days to our girls trip to Martha’s Vineyard. It would be our second year going and we fancied ourselves ‘pros’ now. This time, it would just be six of us going instead of the original seven. Our trip started at about 3:00 am, giving us just enough time to stop at Dunkin Donuts for breakfast and make the ferry on time.

Once we got to the island, we went to the house to unpack and then immediately headed to the beach. That evening we went out to Edgartown for a fancy dinner, however, we didn’t make a reservation and ended up on a wait list. To kill time we stopped at Wave Bar (now called Pelican Club) behind Kelley House for a drink. Unfortunately, we ended up being harassed by a man there that the bartender had to kick out. It put a damper on our visit so we left shortly after. We got dinner at Atlantic Fish & Chophouse, which was pretty good. By the time we finished eating, the restaurant was turning into a dance club, our cue to go home – definitely not our scene.


Annual visit to Island Alpaca

On the second day, our first stop was going to see our friends at Island Alpaca! I had made us all matching shoes with an alpaca decal – we wore those to the farm so we could show them off. After that, we headed to Vineyard Haven. We loved stopping there the year prior and wanted to spend more time exploring. We got lunch at the Black Dog Tavern, which was great. We did have to wait a while because it’s a popular spot but we sat by the water while we waited so I can’t complain.



After lunch we walked around to check out some shops. Then we drove out to Aquinnah because we heard the cliffs were incredible. It was fun driving to the western part of the island since the year before we didn’t get out that way. The Aquinnah Cliffs were gorgeous, as was the Gay Head Lighthouse. If you’re on the island, definitely check out the cliffs. On the drive back we stopped to see the historic white oak in West Tisbury, the “Sitting Tree”, which was photographed in 1969 by famous Life Magazine photographer Alfred Eisenstaedt.


Aquinnah Cliffs

After how much fun we had our first year, we decided to extend our second trip to the island by a day. We had beautiful weather so we spent the day at the beach and hung out at the house at night. The next afternoon our ferry was leaving out of Vineyard Haven so we got to town little earlier for some last minute shopping.


One of multiple Black Dog stores on the island

Our trip concluded with more picturesque sunsets on the ferry. It was another successful year in the books! What’s your favorite place for a long weekend trip? Let me know in the comments below.

📍I acknowledge the lands mentioned in this post are the ancestral lands of the Wôpanâak (Wampanoag) and Pokanoket people.

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