Girls’ Weekend Guide to Beautiful Martha’s Vineyard

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:

Lobby of Harbor View Hotel in Martha's Vineyard

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!

Lounge at the Harbor View Hotel

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…

Ocean views from Oak Bluffs, Martha's Vineyard

Known for its charming gingerbread cottages, Oak Bluffs was a must-see on our list of Martha’s Vineyard attractions!

Oak Bluffs Gingerbread Cottages

These adorable cottages are situated on the campground of what began as a religious summer retreat for New England Methodists in the 1800’s.

Row of Gingerbread Houses in Oak Bluffs

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.

Pink Gingerbread Cottage in Oak Bluffs

Aren’t they adorable?  Apparently, some of them are available for summer rentals too!

Oak Bluffs Cottages

After stalking the cute houses, we grabbed our umbrellas and shopped our way up the main street stores.

Display at Sea Bags store

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!

Sharky's Cantina sign in Oak Bluffs

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!

Fireplace at the Harborview Hotel in Edgartown

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.

Blue and White Nautical Room at the Harborview Hotel

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…

Cocktails at Henry's at the Harborview

After dinner, we ended the night back at the fireplace in that cozy lobby!

Cozy fireplace in the lounge at the Harborview

The next morning, we grabbed breakfast at an adorable little diner in Edgartown.

Edgartown Diner

And shopped our way through the town…

Vineyard Vines store in Edgartown

Hydrangeas in a windowbox

Vineyard Vines store in Edgartown, Martha's Vineyard

Antique store in Edgartown

Exploring the island of Martha’s Vineyard:

The rain was letting up so we drove around the island and explored more…

Gay Head Lighthouse in Aquinnah

This is the famous Gay Head lighthouse in the town of Aquinnah.

Dock in Menemsha

There were so many pretty places along the water.  Thankfully, the sun was finally coming out when we stopped at Menemsha.

Beach Sculpture in Menemsha

Menemsha Beach

I can just imagine coming to this beach during the summer months.  Ahhh, New England…

Alley's General Store in West Tisbury

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.

Sculpture Garden in West Tisbury

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.

Kentucky Derby Party at the Harborview 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!

Chesca's Restaurant in Edgartown

And afterwards, we spent another late night chatting by the fireplace in the lounge…practically an essential for a girl’s weekend!

Fireplace at the Harborview

Enjoying the views:

The next morning was bright and sunny so we enjoyed some views from the fabulous porch…

Rocking Chairs on the Porch of the Harbor View Hotel

And before heading back to the ferry, we drove through the streets of Edgartown!

Houses of Edgartown

I shared more of these stunning exteriors in my post,  Beautiful Home of Edgartown.

Exterior of the Harbor View Hotel in Edgartown, Martha's Vineyard

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:

Have you ever traveled to Martha’s Vineyard?

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20 Comments

  1. Simply LKJ
    January 19, 2018 / 3:53 pm

    Have always wanted to take a trip there. The cottages are adorable. What a gorgeous hotel as well.

    • Calypso In The Country
      January 20, 2018 / 7:50 pm

      It really is a wonderful place, Lauren!

    • Calypso In The Country
      January 20, 2018 / 7:51 pm

      I am glad to hear that you have been there! I hope to get back someday!

  2. Deb Morehead
    January 20, 2018 / 11:40 am

    Thank you so much for sharing your experience.I have always wanted to go to Martha's Vineyard . I feel like i have been there now with your pictures and story.I am so glad you get to have such a wonderful time with your friends.It is so important to be able to share these special times with them. I can't wait to hear about this years weekend with the girls.

    • Calypso In The Country
      January 20, 2018 / 7:54 pm

      Thank you, Deb! I am so happy to hear you liked my post. We are still in the planning stage for this year but I always look forward to spending time with those girls…no matter where we go!

  3. Pam Richardson
    January 20, 2018 / 1:58 pm

    Shelley, I enjoyed your post so much with my morning coffee! We had a 3 day stay on Martha’s Vineyard in October 2016. We loved it. Oaks Bluff was so charming. We enjoyed the light houses and a few hours on Chappaquidick and of course, eating and shopping! Where are you girls planning to go this year?

    • Calypso In The Country
      January 20, 2018 / 7:56 pm

      Thanks, Pam! I am glad you enjoyed it! Yes, I do remember reading your post about Martha's Vineyard. In fact, I am going to pop over to reread it again! We didn't make it to Chappaquidick this time. I think we probably could have used at least another day there. Still planning for this year but I will keep you posted!

  4. Preppy Empty Nester
    January 21, 2018 / 1:42 pm

    Great post, Shelley. I love MV and can't wait to get back there this Spring. Enjoy your Sunday!

    • Calypso In The Country
      January 24, 2018 / 4:55 pm

      Thanks! I am dying to go back!

  5. Mother of 3
    January 21, 2018 / 10:30 pm

    Sounds like a wonderful weekend trip to Martha's Vineyard. My husband and I went once but it was a madhouse on the island as the president was there that weekend and many roads were closed. I did enjoy it but would never want to go back during the regular season. I bet I'd love it in the off season!

    • Calypso In The Country
      January 24, 2018 / 4:56 pm

      Yes, I have heard that the population goes from something like 15,000 in the off season to over 100,000 in the summer! With the president there, it must have been crazy!!

  6. Miss Kitty
    January 23, 2018 / 1:48 am

    Oh My! I loved seeing the photos of your trip to Martha's Vineyard! I went there over twenty years ago but did not see many of the lovely places that you posted. One of my most memorable stops was at the gate/entrance to Jackie Kennedy's place on the island. It's hard to remember that she was only First Lady for three years or so…she made such a lasting impression on me. I saw your post over at "Dwellings" blog party.

    • Calypso In The Country
      January 24, 2018 / 4:58 pm

      Wow – I didn't even think about Jackie Kennedy's place when I was there! I always loved her – such style and grace! Thanks for stopping by!

  7. Leanna - Of Faeries and Fauna
    January 23, 2018 / 4:28 am

    This looks like an incredible place to visit. Everything is so quaint and pretty. I wonder if the rain kept the tourists away which is why it all looks so quiet and stunning.

    • Calypso In The Country
      January 24, 2018 / 4:58 pm

      It really was incredible…I am sure the rain helped but like I commented above, the population goes from 15,000 to 100,000 in the summer!

  8. Ellen Ross | Ask Away Blog
    January 24, 2018 / 1:02 pm

    Looks like you had SO MUCH FUN!!! I love that pink house too. OMG I woulda just stood outside and gawked the whole day until I was told to leave haha

    • Calypso In The Country
      January 24, 2018 / 4:59 pm

      Thanks, Ellen! It really was a wonderful weekend. Aren't those cottages adorable? If it wasn't raining so much, we probably would have walked around more – and maybe tried to peek in a few!

  9. Nikki G
    January 26, 2018 / 10:34 pm

    What a lovely trip! Thank you for linking up at OVER THE MOON Link Party. I am happy to tell you that you are one of my features on this week’s Party which will go live Sunday night at 5 central.Please link up again!:) gwingal

  10. Shirley@Housepitality Designs
    February 8, 2018 / 5:25 pm

    Oh Martha's Vineyard is so amazing…stayed at the Charlotte Inn and loved every minute….Would want to go back in the Spring the next time….thanks for taking us along on your adventure!

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