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  • Writer's pictureALEXANDRA


We’ve been making it a yearly tradition to take my mom on a trip for her birthday and this year we decided to head to the Cape! None of us had ever been to Cape Cod, Martha’s Vineyard, OR Nantucket so we were super excited to spend a long weekend exploring, eating, and relaxing. In this guide you’ll find all of my favorite things we did in Martha’s Vineyard! Let me know if I missed anything that we should check out on our next visit!

Since we only had an afternoon in Martha’s Vineyard, we woke up early and headed out on the ferry from Hyannis Port. We spent the late morning strolling the streets, shopping in Oak Bluffs and taking in the crisp, ocean air, before heading to our first tourist attraction - The Flying Horses Carousel - the nation’s oldest platform carousel. Constructed by Charles Dare of New York Carousel Manufacturing in 1876, it is one of only two Dare carousels that still exist. Originally operated as an attraction on Coney Island, it was moved to Oak Bluffs in 1884 and includes stationary carved wooden horses with manes and tails of real horse hair and inset glass eyes.

Next, we hopped on the local bus to Edgartown for more shopping and a bite to eat at The Seafood Shanty. Not only was the food DELICIOUS, but the views were stunning. Plus, they have the "Best Damn Bloody Evah!" The restaurant is located right on the water and you can watch the Chappy Ferry go by. FUN FACTS: For thirty-seven years, the Chappaquiddick ferry was owned and skippered by a blind man. It has been struck by a seaplane, splintered by a hurricane, and burned by a mid-channel fire. The ferry served as the setting for a pivotal scene in “Jaws” (as well as a principal camera boat) and played a role in a tragic car accident that changed not only the undiscovered island of Chappaquiddick forever, but possibly American history too.

After lunch we stopped in to Murdick’s Fudge for some dessert! Murdick’s has THE BEST fudge around and the family recipe has been passed down for generations since they originally opened in 1887 as Murdick’s Candy Kitchen. We couldn’t resist getting three flavors — Chocolate, Vanilla, and Vermont Maple Walnut (for a tiny taste of home!).

With our bellies full we headed back to Oak Bluffs on the local bus. It was time to check out the Gingerbread Houses! These vibrant Victorian cottages are clustered together, each with a quaint and colorful design reminiscent of the house made of gingerbread and candy in “Hansel and Gretel.” In the 1800s, this corner of the island was frequented by a group of Methodists that held annual religious retreats and meetings on Martha’s Vineyard. As the camp meetings became more frequent the group built permanent cottages to accommodate them year-round, and these cottages are now used as summer homes on the island.

Before heading back to the mainland, we had to stop by Donovan’s Reef at Nancy’s Restaurant for their famous “Dirty Banana!” Jamaican bartender, Donovan, mixes half of a banana with vodka, coffee liqueur, Baileys Irish Cream, banana liqueur and his own personal secret ingredient in the blender. Trust me - you have to try it!

Let me know if you make the trip to Martha's Vineyard and what your favorite parts of the island are!

xoxo. Alexandra



Hey guys! My name is

Alexandra Dempsey, I am 31 years old and live in Stowe, Vermont.

I recently decided to start this blog to give you all a look into the life of a tour wife - the highs, the lows, and EVERYTHING in between!

My rock star husband, Ryan Dempsey

of Twiddle, stands by me every step

of the way as we journey on this whirlwind we like to call the "tour life."

Follow along on my travels, hear

stories from fellow tour wives, and

earn about some of my favorite things. Hope you enjoy and

thanks so much for reading!!

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