Sailing the US Virgin Islands

Our Time in the USVI

We arrived in Charlotte Amalie tired, salty, and honestly a little emotional after everything it took to finally get here. For a long time, the Caribbean had felt unknown to us. Not impossible ,just far enough outside our comfort zone that it stayed somewhere in the distance while we slowly gained experience, confidence, and worked our way east one sail at a time.There were weather delays, long passages, boat projects, difficult decisions, and eventually the Thorny Path itself. By the time we finally saw the hills of St. Thomas appear through the rain, it felt less like arriving somewhere new and more like reaching a chapter we had worked toward for a long time.

Charlotte Amalie felt alive immediately.After so much time spent in quiet anchorages and small islands, the energy of St. Thomas almost felt overwhelming at first in the best possible way. Cruise ships filled the harbor, music drifted through the streets, people crowded the waterfront, and colorful buildings climbed the hills above the town. Everything felt vibrant, busy, and full of movement.And then came Carnival.Experiencing Carnival in St. Thomas became one of the most unforgettable highlights of our time in the USVI. From the moment we arrived, the island was alive with music, dancing, colorful costumes, steel drums, great food, and an energy that seemed to pulse through every street. It felt completely different from anything we had experienced during our travels up to that point.After spending months focused on weather windows, passages, anchoring, and the routines of daily boat life, suddenly being immersed in such a vibrant celebration of culture and community felt almost surreal. Everywhere we turned there was movement, laughter, music, and excitement. The atmosphere was contagious, and it was impossible not to get swept up in it all.What made the experience even more meaningful was sharing it with friends who had already become such an important part of our journey. The kids ran around together nonstop, laughing, exploring, dancing, and making memories we know they’ll never forget. Watching them experience the joy and freedom of Carnival alongside us made the entire experience feel even more special.Carnival wasn’t just an event we attended or something we observed from the sidelines.It felt like we had stepped directly into the heartbeat of St. Thomas itself, a celebration full of life, pride, tradition, and connection that we’ll carry with us long after leaving the island behind.

As exciting as St. Thomas was, we slowly found ourselves spending more and more time exploring St. John.And almost immediately, we understood why so many people fall in love with it.Maho quickly became one of those places we never got tired of returning to. The water was unbelievably clear, calm, and full of life. Turtles seemed to be everywhere, gliding through the grass beds so naturally that after a while they almost started feeling like part of everyday life.Sophia could spend hours underwater following them completely in her element, surfacing only long enough to smile before diving back down again. Watching her so connected to the ocean in those moments felt really special. Some days we would look up and realize entire afternoons had disappeared between swimming, snorkeling, floating beside the boat, and simply enjoying being there together.

Cinnamon Bay became another favorite for completely different reasons. Long stretches of soft sand, turquoise water, and the kind of beach that somehow felt unreal. It was also the first place there where Tony caught a huge lobster, which quickly turned into one of those memories we know we’ll still be talking about years from now. Some days were spent swimming until we were exhausted, while other days were spent sitting on the beach, talking with friends as the kids swam for hours.

Honeymoon Beach quickly became one of our favorite places to spend the day. It had this easy, relaxed feeling that made it almost impossible to leave once we got there. Paddleboards in the water, boats quietly anchored offshore, calm turquoise water, and long afternoons spent swimming, snorkeling, and simply enjoying being together.

Some of the moments that stayed with us, happened away from the water.One of the most memorable days started from Maho Bay when we decided to take one of the nearby trails winding through the island. The path itself was beautiful, surrounded by tropical vegetation, old stone ruins, and occasional openings with incredible views overlooking the coastline below.There’s something about places like that that makes history feel less distant. Standing among old sugar mill ruins surrounded by ocean views and island hills makes you stop for a moment and think about how much these islands have seen long before any of us ever arrived there by sailboat.We had that same feeling while exploring Annaberg too.

Walking through the old plantation ruins overlooking the water felt like stepping into another time entirely. Moments like that always remind us why we love traveling this way. The places become more than just beautiful anchorages. They become experiences we actually lived ourselves.

One of the things we loved most about our time in the USVI was getting to spend time again with sailing friends we had already shared so much of this journey with. We first met in the Bahamas, crossed paths again in Samaná, and then somehow ended up reunited once more here in the USVI.That’s one of the really unique things about this lifestyle. Boats separate for weeks or months at a time, everyone heads in different directions, and then somehow your paths cross again somewhere completely different.By the time we were all together again in the USVI, it felt comfortable and familiar ,like picking up right where we left off. And one of the moments that stands out most was Mother’s Day at Windmill Bar. We spent the day there with four sailing families together surrounded by incredible views, kids running around, laughter, and that relaxed island atmosphere that somehow made the whole day feel effortless and special at the same time.We all shared meal together and few drinks ;) and somehow, completely unexpectedly, Sophia and I both won bingo our first time ever playing. It turned into one of those simple, funny memories that probably wouldn’t seem important to anyone else, but somehow became one of those moments we still smile about when we think back.

Now, slowly, we’re getting ready for the next chapter.Soon we’ll leave the USVI behind and make our way toward the BVI while waiting for the right weather window to continue farther east toward St. Maarten. Even after all this time sailing, weather windows still shape so much of life out here. Plans stay flexible, routes stay loose, and patience becomes part of the journey itself.Before we leave, there were still a few real-life tasks to take care of too, including getting Bolt ready for the next countries ahead. We took him to the vet for his health certificate, another reminder that even our salty pup is part of every step of this adventure with us.And now, just like the rest of us, he’s ready for the next passage.

The USVI didn’t announce itself as something special. It just slowly became that, between the turtles at Maho, the drums of Carnival, the trails winding through old ruins, and the afternoons that disappeared without anyone wanting to stop them. Bolt is ready. The boat is ready. And honestly, so are we. But there’s something about the moment just before you leave a place like this, when you know exactly what you’re sailing away from,that makes the horizon feel both exciting and a little heavy at the same time. That feeling, we’ve learned, is just what it means to be doing this right.

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