Standing atop the ruins of an old sugar mill on the north side of St. John, our boys, Porter (11) and Magnus (10), gazed out over beautiful Waterlemon Cay, Leinster Bay, and The Narrows, the latter of which separates the U.S. Virgin Islands from the British Virgin Islands. Behind them, I snapped a picture on my phone and then put my arm around my wife, Jill, to soak in the scene. It was our last day in the USVI and, though we looked forward to checking into the BVI at Soper’s Hole the following morning, it was bittersweet. We were eager to move on, but it was sad to say goodbye.
This was our family’s second season swinging through the Virgin Islands, and each year we’d spent about two months in St. Thomas and St. John before leaving for the BVI and beyond. We relished in the great sailing conditions of January and February, meeting up with old friends and making new ones, exploring picturesque anchorages, hiking to stunning vistas, learning about the history of the islands, and, of course, playing on pristine beaches. Indeed, the USVI offered up a type of cruising that we’d dreamed of many years before.
Yet this hadn’t been what Jill or I expected. It’s not that we had heard negative things about cruising in the USVI, it’s just that the islands hadn’t been high on our radar of Caribbean cruising destinations before we got there. The critiques from some are that it’s not off the beaten path enough, it’s too domestic, it’s too heavily trafficked by tourists, it’s just “too easy.”
While I get all that, for us, the cruising life is what you make of it no matter where you are. Now, having spent so much time there over the past two years, I can fully admit that the experience we had was a revelation of sorts. When you take it slow on a sailboat and let the destination come to you, the waters of the USVI open up to reveal a place that is truly special.
THE PREQUEL
My USVI story actually started over 15 years prior. I worked as a captain and sailing instructor in the BVI, and my only experiences in the USVI were flying in, taking a taxi to the ferry, and getting out. I’d spent so much time on the waters of the BVI, and loved it, that I didn’t really think much about cruising in the USVI. I didn’t know what I was missing out on.
In the years after my stint in the BVI, Jill and I purchased our Grand Soleil 39, Yahtzee, in Seattle in 2012, started a family aboard, and began cruising. We sailed north to British Columbia and Alaska for a few years, and then cruised south to California, Mexico, and Central America. Our intrepid crew of four transited the Panama Canal in February 2022 and took our sweet time on the Caribbean coast of Panama before slowly working our way eastward. And when I say slow, I mean slow.
Essentially going the “wrong way” into the trade winds, we were patient with weather windows and made several east-bound stops along the coast of Colombia then onwards to Aruba and Curaçao. We loved every bit of our time in each of these countries, spending hurricane seasons in Cartagena, Colombia, and Philipsburg, Curaçao. From there, we jumped north across the Caribbean Sea on a mostly decent weather window and ended up in Puerto Rico in early January 2024. Our intention was to spend a good amount of time exploring the south coast and then Vieques and Culebra, but when an unseasonable southerly wind showed up in the forecast, we used it to get to the USVI instead. When the wind dictates your life, schedules don’t stand a chance.
A crack-of-dawn departure and the solid southerly wind put us into Charlotte Amalie Harbor on St. Thomas by midafternoon, and when we dropped the hook and looked around, it was a whole new world. Hulking cruise ships sat moored along the wharf, and they made the mega yachts at the adjacent Yacht Haven Grande Marina look small. Undeterred and excited to explore, our boys implored us to get the dinghy off the foredeck and get ready to go to town. That’s one of the things I love about youth. While Jill and I looked at the scene and saw tourist traps and dollar signs, our boys didn’t see it that way. It was somewhere new and different, and they were ready.
The perceived hustle and bustle of town wasn’t as crowded or gaudy as Jill or I expected, and we took a stroll down the waterfront and stopped for a couple cold beverages at a local watering hole to beat the late afternoon heat. In our years of cruising, being around cruise ships and the masses that they bring to every harbor was nothing new to us. From places like Skagway, Juneau and Ketchikan, Alaska; Cabo San Lucas, Puerto Vallarta and Mazatlan, Mexico; Aruba and Curaçao; we knew the routine. As cruisers, you go with the flow of it and live your life around the noise. Plus, we knew that we’d be leaving the harbor soon anyway, so why not enjoy it?
SEASON ONE
After spending nearly two weeks poking around the anchorages and islands near Charlotte Amalie, we filled up on food, water, and diesel and made for the highly recommended Christmas Cove at St. James Island near the far eastern end of St. Thomas. On approach to the anchorage, the water shifted from a brilliant dark blue to an incredible turquoise that was so clear we could see the anchor hit the bottom. A plume of white sand erupted around it, and we backed down and settled into what felt like a truly Eastern Caribbean cruising scene.
Again, excited by their new surroundings, Porter and Magnus pushed the standup paddleboard into the water and spent what seemed like hours swimming, paddling, and pushing each other off the board. It felt good to just sit and watch them play, and when hunger brought them out of the water, there was only one place to go—Pizza Pi. Christmas Cove is locally famous for having the “pizza boat,” which serves up hot pies and cold drinks to-go by dinghy or at their floating platforms that double as makeshift tables. We got a couple pizzas to take back to Yahtzee, and they were delicious, with the surroundings surely helping the ambience.
A half-mile hop from Christmas Cove to the west is Cowpet Bay, which is home to the St. Thomas Yacht Club (STYC) and St. Thomas Sailing Center. My friend Bobby is the director of the Sailing Center, so I sent him a text to let him know we were anchored nearby and to see how he was doing. About an hour later a knock came on our hull and sure enough, it was Bobby. After chatting and exchanging pleasantries the question came, “Hey, we’re running a North U Performance Race Week at the club next week and had a boat sign up last minute, do you want to coach?”
Heck yes I did! Having been a North U instructor for over a decade, this was a no brainer as it is one of my favorite courses to teach. Also, being a U.S. citizen meant that I didn’t need to obtain a work permit or special visa, and the pay would boost the cruising kitty a bit. Let’s go!
STYC graciously allowed us to move Yahtzee to their T-head dock while I worked the course, and our family got use of the facilities and sailboats while we were there. As always, the week-long class ended up being an absolute blast; racing every day on IC-24s (modified J/24s) and sailing throughout the islands was an unexpected treat. When opportunity strikes, you have to take it.
With STYC in our wake, we enjoyed a beautiful day sail to St. John and what would be some of our favorite beaches in the Caribbean. Considered to be the crown jewel of the USVI, St. John is home to Virgin Islands National Park, which covers about 60% of the island as well as more than 5,500 acres of adjacent ocean. What that means for cruisers is that you can’t anchor in most of the coves and bays around the island and that you have to instead use one of the park’s moorings for a fee. While this prohibits many cruisers from spending lots of nights in the area, it’s worth it.
We spent the last 10 days of our 2024 season in the USVI hopping across the north side of the island from Caneel Bay to Maho Bay and Waterlemon Cay, all of which were highlights. From Caneel Bay and Honeymoon Beach, we hiked the trail over to Cruz Bay to have dinner and stock up at the small grocery store. Out of the water and away from the beaches, hiking is one of the main attractions on St. John and the National Park has more than 20 trails that range from boardwalks to hikes through historic ruins, or up over the island’s peaks through tropical forest.
While we didn’t hit every place on our list of USVI destinations that we wanted to visit, season one left us intrigued and wanting more. As we sailed off to the BVI, it wasn’t a goodbye, but a see you later.
SEASON TWO
Just like a TV show when season one is so good, you really hope season two is better—for us, season two in the USVI was. After a gorgeous downwind passage from the island of Nevis, we sailed back into the islands in January of 2025 and landed at the southeastern portion of St. John first. It felt good to be back.
Our familiarity with the USVI meant we could spend some time in places that we’d loved previously while also hitting spots that we’d missed. Because we’d finished season one on the north side of St. John, we knew we wanted to start season two on the south side, and we lingered in the beauty of Salt Pond Bay and Great Lameshur Bay for over a week. Each morning, we woke to a brief rain shower that was accompanied by a stunning rainbow, and when school and work were done, the days’ activities included snorkeling, hiking, and beach combing—in no particular order. Being a more remote part of the National Park, there were very few boats here, and we would have stayed longer if we hadn’t been in serious need of provisions. Such is life.
Downwind we went from Lameshur to the decidedly different look and feel of Charlotte Amalie. The goal was to get in some civilization time and to do a solid provisioning run, which would have been more difficult in St. John or at the eastern side of St. Thomas at Red Hook. When living and traveling on a sailboat, there is something to be said for big, bright grocery stores with lots of variety and (usually) better prices. Accordingly, we loaded Yahtzee up—and lowered the waterline a little in the process.
Of course, it wasn’t all shopping. We made the trek to Charlotte Amalie’s “99 Steps,” which were built by the Danes in the 18th century to navigate the steep hills of the town and were originally called Store Taarne Gade (Greater Tower Street). Despite the name, the staircase actually consists of about 103 steps constructed using bricks brought from Denmark as ship’s ballast. Lined with colorful flowers and historic buildings, the climb leads to Blackbeard’s Castle at the top and offers great views of the harbor.
From Charlotte Amalie, we again sailed east towards Christmas Cove and the STYC. After having such a great time coaching Race Week during season one, I signed on to coach again. This year’s class was somehow even better. The students were bright, competitive, and eager to learn as always, and the Caribbean conditions delivered. Practice starts and races were extremely tight, and going into the final day of racing, it was anyone’s event to take home. That’s exactly how quality sailboat racing should be. Good times.
With work over, it was time to slow back down into cruising mode again. We hit some places that had previously been on our list, including Secret Harbor in Nazareth Bay on the southeast side of the island and Magens Bay on the north central side. The two couldn’t have been more different but were equally worth a visit. Secret Harbor is a pocket beach with beautiful sand and clear water, and Magens Bay Beach is a long sand stretch that is frequented by locals and tourists.
Somehow, we’d been in the USVI for well over a month at this point, and it was time to turn our sites eastward again. Just like season one, we wanted to finish on St. John and headed for our favorites—Caneel Bay, Maho Bay, and Waterlemon Cay. The beaches here were still highlights, but we decided to explore more inland this time. From Maho Bay, we walked to Annaberg Sugar Plantation, which offers a stark learning experience about when sugar was king of the islands and how the people who processed it paid dearly. Placards throughout the plantation tell the story of a complex history from the violent displacement of Indigenous people to European settlement and the enslavement of Africans during the 18th to 19th centuries. It was eye opening for all of us, but especially so for our boys as they imagined what life would have been like when cane was being turned from a raw plant into sugar and how the people lived, worked, and ultimately died here.
Days later, we were atop the ruins at Leinster Bay looking out across the few miles to the BVI. According to placards at nearby Annaberg, when the British Slavery Abolition Act took effect on August 1, 1834, enslaved people seeking freedom would try to swim across The Narrows to Tortola. Most never made it.
It’s times like these that remind our family how fortunate we are to be in places like this on our boat, and to be able to move as freely as time, weather, and tide allows. That night over dinner, bobbing on a mooring next to Waterlemon Cay, we went around the table and everyone shared what some of their favorite parts of being in the USVI had been. Beaches, restaurants and days on the water made the list. Day sailing dinghies, Hobie cats, and IC-24s were up there, too. But in the end, it was inside jokes about a hike that seemingly went to nowhere and when Magnus thought he was stepping into inches of water in the mangroves and instead plunged in nearly head deep that had us rolling with laughter. It’s moments like these that I hope we’ll hold onto forever.
After so many years of living and cruising on Yahtzee, we’ve come to expect the unexpected and unforeseen. We enjoyed our time in the USVI much more than we thought we would, and when the time comes for “USVI Season Three,” we’ll be ready to find out more about what this exceptional destination has to offer.
Andy Cross is a freelance editor and writer, sailing coach and instructor, who loves exploring the world with his family aboard their Grand Soleil 39, Yahtzee.
