Chincoteague Island

Sailor Sailor Seaport Shift (c/o) // Vera Bradley Chainstrap Crossbody (Similar) // Multistrand Beaded Necklace (Similar) // Aviators

Chincoteague is only a 3 hour drive outside of DC but it feels like a world away, it was perfect for a long weekend trip. Show of hands: Did you read Misty of Chincoteague in middle school? If you didn’t, maybe you read The Babysitters Club and the name rings a bell because Mallory was obsessed with the Misty book series? In case you haven’t, here’s a quick back story on this beautiful island and its famous wild ponies.

According to legend, the wild ponies arrived on Assateague Island after surviving a shipwreck off the Virginia coast and have lived on the island ever since. The Chincoteague ponies, who actually live on Assateague, became famous after Misty of Chincoteague was published in the 1940s (Scroll down to see Misty’s hoof prints immortalized outside the town’s movie theater). My mom and I arrived about a week after Pony Penning Day, a tradition dating back to the 1920s. On Pony Penning Day, they round up the ponies and swim them back to the mainland to be auctioned off. All the funds go to the fire department, who are the official caretakers of the wild ponies.

Luckily, it was easy to get a view of the ponies. We first spotted them when we were heading to the beach on Assateague. You can see them in the distance (Note to self: Bring binoculars next time) just grazing and hanging out! My mom and I went on a boat tour of the island and we were able to get pretty close to several herds! Our boat captain had enough binoculars to go around and even a book to identify the various ponies by their markings. It was an incredible sight!

When we did manage to tear ourselves away from the ponies, we loved walking around Chincoteague’s historic district. There is an abundance of adorable boutique shops and a particularly amazing ice cream parlor that gave very generous scoops and makes their waffle cones right in front of you. Seriously, go to the Island Creamery. Skip lunch and have an ice cream cone, you’re welcome in advance.

Chincoteague’s beach town vibe just calls for an easy, breezy shift that can go from day to night. Enter Sailor Sailor! Sailor Sailor is an American made brand with dresses, tops and skirts made with performance wicking material. Translation: When it’s a billion degrees out, you’ll stay cool. Thank god!

I love the Sailor Sailor Seaport Shift‘s fun nautical fish net print (It was a tough decision though since they have so many whimsical patterns) and their upturned collar, which is very different from typical shifts. This shift was incredibly comfortable to walk around in all day and then go straight to a fresh seafood dinner! Because when you’re by the water, you need to get oysters. It’s pretty much mandatory, right?

My favorite part of the Sailor Sailor Seaport Shift though is that this dress packs incredibly! What do I mean by that? Well, I packed up my clothes into a duffel using the rolling method. When we arrived to our hotel, I unrolled the shift and hung it up in the closet. The Seaport Shift had minimal wrinkles from traveling but as soon as I hung it up, the wrinkles worked themselves out and we were ready to go! When you’re traveling, you don’t always have an iron or steamer so having a dress that won’t wrinkle is clutch. I was downright giddy when I discovered this feature! Hellooo, Sailor Sailor!

P.S. This shift paired with a navy cardigan is a cute outfit to wear to work on a casual Friday.

* * *

Let’s Chat!

Twitter | Pinterest | Instagram | Bloglovin’