If By Land

I recently read that the average American walks 5,117 steps a day, or approximately 2.5 miles. I also read that to be a “healthy” walker you need to get in 10,000 steps per day, and if you take 5,000 steps per day or less, you are officially classified as “sedentary.”

I recently read that the average American walks 5,117 steps a day, or approximately 2.5 miles. I also read that to be a “healthy” walker you need to get in 10,000 steps per day, and if you take 5,000 steps per day or less, you are officially classified as “sedentary.”

Yes, ours is a culture of car drives and cab rides, and we’re all a little guilty of needing to get off our rears.

Then I read about Virgin Islands National Park on the island of St. John with its 20 distinct hiking trails weaving through 15,000 acres of protected land. A hiking-centric destination accessible by charter sailboat? I told my crew to pack their hiking boots.

Our fight against sedentarianism (n: the act of being a lazy American) began shortly after we landed in St. Thomas, when we walked from the CYOA Yacht Charters base in Frenchtown to the Pueblo grocery store in Charlotte Amalie to provision our Fountaine Pajot Salina 48º, Island, for the week. Not only was the walk a fun way to catch a glimpse of the urban island that is St. Thomas, it was much cheaper than taking a cab. Besides which, it was February and we were in the islands, mon, enjoying 50 more degrees of heat than we’d left behind in our northern homes. We didn’t mind sweating a little.

The next morning, as we were sailing toward St. John and looking over our charts, hiking books and cruising guides, we unanimously agreed there was no way we could do this all in one week. There were trails ranging from 0.2 mile to 12 miles, trails that climbed over luscious hills that are home to over 800 plant species, passed by antiquated ruins and dipped into drop-dead gorgeous beaches. There were also sugar plantations near Cinnamon Bay, Taino petroglyphs on the Reef Bay trail and even an underwater snorkeling trail in Trunk Bay. Clearly, we needed to get ashore and start exploring.

Our first stop was in Hawksnest Bay, where we experienced mooring, National Park style. Rather than being accosted by a boat boy in a sketchy dinghy who zooms at you from his beach shack and demands $30 (as is customary in many of the islands), the moorings off St. John operate on the honor system. Visitors insert $15 into a pay station floating in the mooring field while a friendly Park Ranger casually patrols from his RIB. Even the dinghies have a well-kept-up traffic system, with red and green buoys framing the preferred dinghy channel to the beach. Dinghy anchoring is also strictly prohibited to protect the marine sanctuary below the water. 

We followed one such dinghy channel ashore for a quick swim, and then sailed along the northern edge of the island, past Cinnamon and Maho bays to Francis Bay, where we knew we’d be the most protected from the northeasterly breeze for the night. Quickly, we piled into the dinghy and zipped ashore, pulling the little boat clear out the water and onto the sand in Francis Bay before enjoying a beautiful sunset stroll along all of the beaches we’d just sailed past. 

Cinnamon Bay was especially appealing with its picnic tables, public showers and a fleet of kayaks, windsurfers and small boats for rent, all next to a great big campground and, of course, a number of trailheads. As the waves lapped the gorgeous white-sand beach in front of us, it suddenly dawned on us that we had the entire place to ourselves. Here we were, on some of the most perfect beachfront property in the Caribbean, and the only permanent residents were some Hobie Cats and charcoal grills. St. John, I like your style.

Our next destination was lovely Waterlemon Bay, on the northeastern corner of the island, where we met the Johnny Horn Trailhead for a hike across the island, clear to Coral Bay. The trail began with a short walk to the Annaberg Sugar Mill ruins, which date back to the late 18th century, when St. John was covered in sugarcane that was harvested for rum and molasses.

In fact, most of modern day St. John’s vegetation consists of second-generation growth: plants that grew following this period when the island was clear-cut for what was then an important cash crop. These days, wild tamarind and sea grapes create an arch over the trail as it winds to and from the ruins, where a living history character serves up samples of “dum bread,” a traditional island treat that tastes like moist, sweet coconut.

From the mill, the trail continues another 2 miles up and over the desert-like ridges that define the eastern half of the island, passing three different ruin sites along the way. To the west, we could see Bordeaux Mountain, the highest point on the island, and to the north, our boat on its mooring. We also passed by deer and tarantulas, century plants and soursops, until the trail turned sharply down, met a dirt road, passed the Emmaus Moravian Church and ended in Coral Bay, home of the famous Skinny Legs bar. Of course, we deserved a burger and a cocktail after that hike, so we sat at a picnic table in the open-air restaurant, surrounded by kitschy T-shirt shops, and took a load off, before doubling back to the boat.

By then, it was clear that one of the best parts of sailing around St. John is getting off the boat. The next morning we casually continued around the island clockwise, past Coral Bay (too packed with liveaboards to stay there overnight) clear to the southeastern side where we dipped into the beautiful Lameshur Bay. It was a gorgeous day, and the beach was crowded with resort tourists, but there were still a number of available moorings, and after securing the boat we promptly dinghied ashore for a hike to the nearby petroglyphs.

The trail was a bit sketchy at first, but after a mile or so it cleared out and met up with the Reef Bay Trail, which we followed to a wall of ancient rock paintings above a still pool—petroglyphs that were thousands of years old and attributed to the Pre-Colombian Taino people. 

From our high vantage point, we looked down on Lameshur Bay and were treated to a strange site: our nice-looking, crowded anchorage, directly beside a just-as-nice-looking, empty one. Both beaches had been buzzing during the day, but as the sun set, the littler beach cleared out too, and we decided to clear in. That night, we had Little Lameshur entirely to ourselves. We dinghied ashore, lit up the National Park-provided grill and sat around the National Park-provided picnic table to enjoy the serene sunset, pleased to be the only boat in the bay.

The next day, we grabbed a mooring in Caneel Bay on the western side of the island and enjoyed the Lind Point Trail, which weaves up and over the hill separating Caneel and Cruz Bays. In addition to being a pretty walk, this trail saves you the trouble of anchoring in bustling Cruz Bay when you need to clear customs on your way to or from the nearby BVIs.

Cruz Bay is best known for Mongoose Junction, a fun “downtown” district filled with good eats and dozens of small shops that sell crafts and souvenirs handmade on the surrounding islands. Best of all, Cruz Bay is home to the National Park office, where we found a nifty topographic map and a half-dozen Park Rangers itching to talk to us about island hiking. The next time I sail around St. John, I’ll be sure to stop here first.

Following this peaceful island experience—the lush hiking trails, tidy mooring fields, gorgeous beaches and deserted coves—we were far from ready for what came next…

“Too much meat in the hammock!” shouted a gaggle of British gents on White Bay as seven of their large manly friends crowded into one hammock between two creaking palm trees. They laughed hysterically, trying not to spill their Painkillers, until they toppled out on top of one another, a heaping pile of British giggles.

Nearby, a group of teenage girls lounged in tiny bikinis while Katy Perry blasted from the speakers of a massive powerboat that had come in from Tortola and cruised right up onto the beach. Ah, the Soggy Dollar Bar on Jost Van Dyke. This bar, and the spectacle that accompanies it, is a defining moment in any tour of the BVI. Just be sure you’re ready for it.

Later that night, we moored in Diamond Cay, had a drink ashore at Foxy’s Taboo, fulfilled our hike quota with a walk to the Bubbly Pool and enjoyed a delicious lobster dinner at Sidney’s Peace and Love followed by some dancing at Foxy’s. St. John had put us in a trance, and Jost Van Dyke did its best to snap us out of it.

On our next and final day, we took a turn back to nature with a stop at Sandy Cay, a tiny and tidy island just off Jost. Beyond the beach is a trailhead that leads into the wooded part of the island, up to the exposed hilltop, and around the bend, ending back on the beach. In no time, we were back in hiking mode, taking note of the plentiful hermit crabs crawling all around the soursops.

Apparently still in a daze from the night before, we’d foolishly left our shoes aboard and were tip-toeing across the hot and jagged rocks of the trail when an older gentleman passed us, performing some trail maintenance. His skin was leathered by the sun, and he laughed heartily at us and our amateur wardrobe selection.

We padded cautiously along, playing “hot lava” with ourselves and he looked back and said, “If you go slow, you will make it far.” I think we met the Caribbean Yoda.

We sailed back down toward St. Thomas, passing the bays of St. John we’d come to love: Francis, Cinnamon, Hawksnest, Caneel. From our sailboat, the island looked pristine and uninhabited, the bold turquoise water splashing against the crisp white beaches beneath the lush green hills.

We thought back on the steps we’d taken and figured that while we certainly hadn’t run a marathon, we’d at least walked more than we would have at home. We remembered the wildlife and the ruins, the beaches and the sunsets and especially the night we’d had the bay all to ourselves. And we agreed: we’d only scratched the surface and needed to visit here again.

Some of the creatures we encountered along the way (below)

Meredith Laitos is SAIL's Senior Editor

and the host of the Charter Channel at


Do you want to read about more charter destinations?

Try one of these stories.

• Thin-Water Paradise

• Baring It

• A Boat of Their Own



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