Sailing the Caribbean: A Trip Beyond Expectations

I got back from my Caribbean sailing vacation over the weekend, and to say it was incredible would be an understatement. When I wrote that my instagram was going to be fire, I had no idea just how 🔥 it was going to be — especially since I had zero frame of reference for how a Caribbean sailing trip should go. Based on the itinerary I assumed we would be sailing to various islands and enjoying some water activities, and while that’s technically what happened, the reality far exceeded my expectations. Let me try to put into words what made this trip so unforgettable.

First, the weather and water was amazing. The forecast indicated the temperature would be between 78-81 degrees Fahrenheit everyday, which was a welcome respite from the frigid Bay Area winter. Add to that the amazing Caribbean waters, and it really felt like we were transported to a tropical paradise. There was usually a breeze so it never felt too hot, and when it did get warm you could just take a dip in the water. 

Second, the islands were all unique and beautiful, and it was great to explore them all. Not only that, but with the exception of Tortola (where we set sail from), all of the other islands we visited were smaller and therefore less accessible by large cruise ships, lending to a more local and intimate feel. We couldn’t even dock at most of the islands we visited — we had to attach the catamaran to a mooring ball close to shore, and then take a dingy (an inflatable raft with a motor) to shore. On a couple of the islands (Jost Van Dyke, Cooper Island) we swam to shore, and for The Baths on Virgin Gorda, you had to take a dingy to get closer to shore, and then you had to swim. Once on land, you would walk around barefeet and shirtless, because that’s #islandlife. Of course there was usually food and drinks so you can relax and chill out on dry land, and on a couple occasions we also did some short hikes (we brought flip-flops and shoes in our dry bags when needed).

Third, there was plenty of adventure to be had on the trip. I didn’t anticipate how challenging the swimming portion of this vacation was going to be, but suffice it to say I intend to do more swim training stateside so I can be more equipped for future ocean excurions. At the same time, there’s something magical about swimming and snorkeling in the clear blue Caribbean waters, and we did that almost everyday. We also brought a kayak and paddleboard on the boat, so people could do that at the various islands we visited. Nearly every island stop was a mini-adventure of its own, and I loved every bit of it.

Fourth, it was great getting to know everybody on the boat. This deserves another blog post by itself, but I’ll just say here that I honestly didn’t expect the 12 of us to get along so well. Would it have been more fun if the trip consisted of just my friends? Perhaps, but there’s something special about meeting people you wouldn’t otherwise cross paths with — like the 2 UN employees on board, which is a contrast from the usual tech crowd in Silicon Valley.

Lastly I’d be remiss if I didn’t mention the tireless efforts of my friend Jeremy, who got up early every morning to make us coffee and also prepared all the gourmet meals on the boat. Also props to Ari for the steak dinner on the last night and for being the sous chef (and captain) throughout the trip. I didn’t expect food to be a highlight on this trip, but it absolutely was. 

As I sit here trying to put this experience in words, I realize that no photos, videos, or blog posts can truly capture the magic of it all. The beautiful Caribbean landscapes, the thrill of open-water swims, the late-night conversations under the stars — it feels surreal now that I’m back to the grind. This trip didn’t just make me rethink what a vacation should look like; it reshaped my perspective on adventure, connection, and embracing life to the fullest. I’m incredibly grateful to Jeremy and Ari for not only introducing me to the British Virgin Islands, but also inspiring me to see the world — and experience it — in a whole new way.