Martha’s Vineyard: Massachusetts’ Juanderland

I still couldn’t get over with the beauty of Massachusetts. When I travel to these states in the U.S., it is all about discovering the real and true America, beyond all the flashing lights of Vegas, the hot road trips in Hollywood Boulevard and the mighty skyscrapers of NYC.

December is a season for travelling and gathering with friends and family. Expect me to wander around the globe every December because spending Christmas in different places makes you fully understand its true essence—love, unity and oneness. May this blog inspire you to craft your own trip with your family and if ever you’ll be needing help to craft your own, we’re always a call away.

#JuanderWithUs as we enjoy the beautiful Martha’s Vineyard in Massachusetts.


From Boston, we took a 45-minute Uber ride to Falmouth. This place boasts a historic downtown area that calls for nothing but relaxation through its endless stretches of beaches and nearby day trips. As much as we wanted to stay and explore around, this place is really not our end-goal visit. We took another 45-minute boat ride to explore the Oak Bluffs at Marthas’ Vineyard.


As you all know, World Juanderers should always travel in style. This black Jeep was waiting for our arrival and it just made the trip to Martha’s Vineyard all the more exciting.

With water on both sides of the road, it almost feel like we were in a movie setting and lines are to be delivered in front of a camera. We were blessed with a magical colored-sky that invites the kids to play with kites and asks lovers to walk around in holding hands.



Finally, we arrived in Edgartown and the first thing that popped in my mind was “Instagram.” It was very “instagrammable” from every angle. I don’t think there would every be a bad photo when you take pictures here. It is one of the most elegant and upscale places in the island and if you’re a fan of big vintage houses, you’d definitely swoon with these photos I will show you.


Don’t even get me started with shopping because this place boasts budget-busting boutiques that would definitely require for your wallets. Expect leaving this place with shopping paper bags to bring back home.


In the Southwest corner of Matha’s Vineyard, we came across Gay Head and the town is widely popular for its terracotta cliffs. The glaciers stand for over 100 million years already and its twisted layers of soil are out of this world. Moreover, it is situated where waves crash. So just imagine the wind breeze, the sound of the ocean and the beam of the sunlight in this crazy beautiful scenery. Life is good!


As much as the view and the people fill our souls, we will still be needing food to fill our tummies. Trips are not complete without actually tasting the sumptuous food they offer.

We arrived in Oak Bluffs, and the first thing we visited was the Lookout Tavern. Even the menu outside was almost calling us, inviting us to come visit and try their deals. If you’re an avid reader of my blogs, you should know how much I love seafood. Watching the Atlantic rolling and feel the wind blowing while eating your favorites was definitely one of the highlights of this trip. It was very cozy and warm inside. The food was fresh and the people were all accommodating.


Our hearts are full and so are our tummies and that is why we were so fueled to embark again on this day trip. As we walk around the island, it is highly impossible for us to ignore the alluring Gingerbread houses. Every one of them is really beautiful but each still, has its own distinct characteristics. It’s like they have their own stories to tell and all of the tourists are left curious wanting to know them.

It is almost like a cluster of fairly-like wooden houses and just looking at the photos make you really conclude why they were called as Gingerbread houses. With its vibrant icing-like designs and it’s coordination of colors, the view can even satisfy your sweet tooth.

This is my personal favorite Gingerbread house. It is super tiny on the outside but I feel like there are so many objects that can be packed inside. From its coordination of purple and pink, indeed, it is like Barbie’s Gingerbread house. I mean, take a look at that chimney!


That sums up our trip in the wonderful Martha’s Vineyard. It was definitely a long day full of amusement, non-stop smiles and poses, and a gentle warning that once you visit this place, it is really hard to not come back.

Have your own adventure planned out in the U.S. Inquire with our #WorldJuanderer travel specialists today. #WithYouWhileYoureOutThere

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