Day 1 : We woke up early last Saturday morning in Boston to a forecast of partly cloudy (in other words slightly sunny, unseasonably chilly), which would unfortunately become the weather prediction for the rest of the cruise, regardless we met up with some friends to begin our voyage. After enjoying a sip of Skinny Girl Piña Colada while we spent the day sailing to Cuttyhunk, we decided to vacate the boat and explore the eerie, yet charming island.
It felt like we were wandering through an undiscovered planet in outer space. The minimal signs of human existence, (5 golf carts to every car) juxtaposed with one and a half restaurants (if you count Bart’s Food Cart), led me to believe that NYT hasn’t quite gotten around to doing a “36 hours on Cuttyhunk Island” review.
As for the one dining option, I thoroughly enjoyed the menu of eclectic pizza choices Soprano’s had to offer, as well as their set up, picture this… pebble driveway, line of tiki torches, sea of outdoor picnic tables adorned with artistically placed driftwood. Each dish seemed delicious, but I strongly recommend the pan seared scallop pizza! We continued the relaxed attitude, the island offered, as we boarded the boat and spent the night laughing and playing a few games.
Day 2 : We didn’t let the dreary forecast get us down, we rose with ambition to sail to Menemsha. Since this was my first time visiting any part of The Vineyard, I was eager to soak up all the beauty that each distinct port had to offer.
After we tied up at Menemsha, we indulged in some fresh seafood at Larsen’s Fish Market. It was neat to see locals poke in for a quick cup of fresh lobster bisque, while we waited in the obvious tourist’s line. We’ll have to visit again when the sun is out so we can peruse the town a bit longer!
The day ended with a beautiful sunset + some tasty black cherry ice cream back at Cuttyhunk, wish each Sunday evening view was this breathtaking.
Day 3 : It was quite refreshing to start the week off with the sun beating through our little cabin’s windows. It felt like we had truly earned the clear blue skies! Without wasting a second, we set sail for the harbor of Vineyard Haven. This was the first day I had gotten behind the wheel and took pride in assisting in navigating us through the high seas. The whole day was flawless; we spent time laughing at stories, singing to the radio, and lounging while snacking on fresh summer fruit.
Later on we finished the day by having some refreshing Rosé + a pleasant dinner at a recommended French Bistro, La Cave, with some friends who were joining us on the cruise for the next few days.