Does the new year get you in the mood to start planning a vacation? Almost every year, I get together with a group of friends for a girls’ getaway.
Last May, we spent a long weekend in Martha’s Vineyard, Massachusetts.
I already wrote a post about the Kentucky Derby Party we attended there and shared photos of the beautiful homes but I never put together a full trip report from our getaway until now. Better late than never…let’s get started…
Getting to Martha’s Vineyard:
We arrived on the island by the ferry from Woods Hole, Massachusetts on a Friday morning after spending the previous day up in Providence, RI. We had debated in the weeks before whether we would pay extra to bring the car over instead of using public transportation when we got there. I am so glad we decided to bring the car! Rain was in the forecast for the entire weekend and we wanted to explore! Plus, it was the off- season so the public transportation was not running on the regular schedule.
Our first stop was our hotel…
Where we stayed:
We stayed at the iconic Harbor View Hotel in Edgartown which was just beautiful!
This hotel came highly recommended from a few people and I can see why! Situated right on the water facing a lighthouse and steps away from dozens of stores and restaurants in the heart of Edgartown…what more could we ask for? When you walk into the lobby, you feel like you are arriving at your own private beach house!
Our room wasn’t ready when we arrived so we were off to explore!
Exploring the island:
We hopped in the car and headed north to Oak Bluffs…
Known for its charming gingerbread cottages, Oak Bluffs was a must-see on our list of Martha’s Vineyard attractions!
These adorable cottages are situated on the campground of what began as a religious summer retreat for New England Methodists in the 1800’s.
I guess I never did my research because I had pictured them to just line one street…
But there was a whole village of these brightly painted cottages…over 300! Too bad it was pouring rain because we took most of the photos from inside the car.
Aren’t they adorable? Apparently, some of them are available for summer rentals too!
After stalking the cute houses, we grabbed our umbrellas and shopped our way up the main street stores.
Shopping, Eating and Drinking:
The Maine Sea Bags Store was stocking their shelves for their grand opening.
And because it was Cinco de Mayo, we had to stop in the Mexican restaurant, Sharky’s Cantina for lunch! In case you didn’t know, the movie, Jaws was filmed in Martha’s Vineyard so the whole “shark theme” made sense!
By the time we arrived back at the hotel, we were soaked to the bone. That fireplace in the lobby couldn’t have been more inviting!
We headed back to our cute coastal themed rooms to change into some dry clothes and decided that we were done with the rain for the evening.
Instead of going out to dinner, we all decided to eat in the hotel restaurant. But first, we had to stop in the bar to indulge in a little Cinco de Mayo celebrating…
After dinner, we ended the night back at the fireplace in that cozy lobby!
The next morning, we grabbed breakfast at an adorable little diner in Edgartown.
And shopped our way through the town…
Exploring the island of Martha’s Vineyard:
The rain was letting up so we drove around the island and explored more…
This is the famous Gay Head lighthouse in the town of Aquinnah.
There were so many pretty places along the water. Thankfully, the sun was finally coming out when we stopped at Menemsha.
I can just imagine coming to this beach during the summer months. Ahhh, New England…
As we made our way up the coast, we stepped back in time with a stop at Alley’s General Store in West Tisbury. The store was built in 1858 and is the oldest operating retail business in Martha’s Vineyard.
We also enjoyed the sculpture gardens across the street.
Luckily with no traffic in the off season, we were able to make it back to the hotel with time to freshen up for the Kentucky Derby Party at the hotel.
After the derby festivities, we headed out for dinner. The Harborview is conveniently located just a few blocks from some fabulous restaurants in Edgartown. We had reservations at Chesca’s and it was wonderful!
And afterwards, we spent another late night chatting by the fireplace in the lounge…practically an essential for a girl’s weekend!
Enjoying the views:
The next morning was bright and sunny so we enjoyed some views from the fabulous porch…
And before heading back to the ferry, we drove through the streets of Edgartown!
I shared more of these stunning exteriors in my post, Beautiful Home of Edgartown.
So many great memories with some of my favorite people! If you are looking for ideas for a weekend getaway, I highly recommend Martha’s Vineyard and the Harbor View Hotel! In fact, I was slightly heartbroken that I was outvoted when deciding on this year’s trip. I was ready to make this an annual tradition!
Some tips to plan your own trip to Martha’s Vineyard:
- You must book your ferry ahead of time if you plan to take your car onto the island.
- If you travel in the off-season (like we did) there is limited ferry service. Check the schedules on the website: Steamship Authority.
- I highly recommend the off-season if you don’t want to deal with crowds. Most stores and restaurants were open and we were able to drive easily from one side of the island to the other.
Recap of where we dined:
- Edgartown Diner
- Sharky’s Cantina ( in Oak Bluffs)
- Henry’s (at the Harbor View Hotel)
- Chesca’s(in Edgartown)
I hope you were inspired by my Weekend Guide to Martha’s Vineyard!
Let me know if you end up visiting any of the places I recommended. I would love to hear your thoughts!
Have you ever traveled to Martha’s Vineyard?
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