Chartering Rediscovered: U.S. Virgin Islands

Sail News

There’s plenty to do while cruising the pristine waters of the U.S. Virgin Islands

Steady breezes, clear blue water and plentiful bays where you can grab both a mooring and a good rum punch—the U.S. Virgin Islands are heaven on Earth for sailors of all stripes. They’re also the perfect place to get kids hooked on cruising, as our family recently discovered on a circumnavigation of St. John.

Cruising in the USVI has been a kind of nautical comfort food for my husband, Josh, and me, ever since the first time we sailed there in 2001. So three years ago, when our boys were 7 and 9, it was only natural that we head there again for their first charter. The week was fun, but also a lesson in the challenges of cruising with little ones. The first night, Luke, 7, nearly sleepwalked out on deck, thwarted only by the companionway panels we had installed as an afterthought before going to bed. The day after that we were treated to a stiff breeze that delighted Josh and me, but not 9-year-old Malin, who, despite already being a competent helmsman, was rattled when a puff hit and our 45ft monohull began heeling over more than he liked. Luke, on the other hand, saw the steeply angled deck as a kind of American Ninja Warrior course and promptly darted to the bow and back, hands-free, up and down the leeward side deck, no less. (He was confined to the cockpit afterward.)


Still, cruising—aka “forced family time”—remained a priority for Josh and me. And the following summer we purchased Moxie, a 35ft 1988 Beneteau Oceanis 350, which we put on a mooring in Newport, Rhode Island, and started sailing together regularly as a family. For the most part, the kids were onboard with the program. However, there were also some complaints about boredom and seasickness, not to mention a reluctance to leave friends and other activities behind whenever cruising weekends rolled around. The solution? Sea Bands for the queasy stomachs and the trip to St. John. Our hope was that a circuit of this idyllic island with its abundance of snorkeling, hiking and short, comfortable sails would hook our kids on cruising for good.

“This is a huge boat,” Malin said as we stepped onboard Caicu, the Lagoon 45 we’d chartered from Sail Caribe ( out of Red Hook, St. Thomas, and it was true. Seemingly the size of an aircraft carrier, Caicu boasted more square footage than many Manhattan apartments. As Malin and I toured the boat’s four berths and spacious saloon, Luke swung on a spare line he’d tied to an overhead handrail. It already felt like home.

After checkout and provisioning, we picked up an Optimist dinghy we were borrowing and set out under power across Pillsbury Sound to Francis Bay on St. John, about an hour away. As Josh slowed down on the final approach to our destination, I listened from where I was doing some unpacking belowdecks for him to call down for help with the mooring. The call, though, never came, and by the time I arrived back up on deck, Malin had already snagged the pennant with the boathook and Luke was helping Josh attach it to the bows with a dock line. Well, I thought, this is new.

With the boat secure, we spent the afternoon getting to know Francis Bay, which like neighboring Maho Bay, is a gem for cruisers with kids. There’s easy hiking, safe but interesting snorkeling, shelter from the prevailing easterlies, white-sand beaches and easy taxi access to the nearby town of Cruz Bay.

We could have spent the entire week in Francis, but were eager to visit the underwater snorkel trail in Trunk Bay as well. So the next morning, after Malin and Luke had had a chance to go for a quick Opti sail in the gentle breeze, we were on our way, quickly encountering a northerly swell that served evidence of just how sheltered the previous night’s anchorage had been. At Trunk Bay, we snagged another mooring, loaded up the dinghy with snorkel gear and motored toward shore. Most bays on St. John have well-marked “no boat” zones for swimming with a channel off to one side for dinghies. Entering the channel at Trunk Bay, we could see sizeable waves breaking on shore. However, we also spotted a dinghy tie-up close to shore, with room for four boats. With the boat secure, we put on our masks and fins and jumped in.

The author looks on while the crew enjoys some synchronized diving

The author looks on while the crew enjoys some synchronized diving

It was about a quarter-mile along the shore to the trail, and once there, we swam the length of Trunk Cay, reading the submerged signs labeling various species of coral and fish. It was an ambitious plan, but Malin and Luke were up to the challenge and then some. Such is the appeal of the Virgin Islands: kids can push themselves there much more than they might otherwise. Our boys would never, for example, go snorkeling in the murky lake back home. But the crystal-blue water of the Caribbean makes it feel like you’re swimming in an oversize aquarium. Same thing with boathandling. Unlike the crowded anchorages in New England, finding a parking spot in the USVI is a cinch. Missed the pennant on your first pass? No worries. Just swing around and try again. There’s plenty of room and plenty of moorings to go around.

Back on Caicu, we had lunch and headed over to Maho, where we picked up another parks mooring (moorings on St. John are all maintained by the National Park Service, which is also in charge of the more than 5,000 acres of park land and seabed there) and the boys played on the two standup paddleboards we’d also brought with us. After a siesta, we dinghied to shore and caught a taxi into Cruz Bay for dinner at the Longboard restaurant. Returning to the boat just before sunset, we decided to return to Francis Bay, which would offer better protection from the northwest swells.

Malin steers a steady course in the Sir Francis Drake Channel

Malin steers a steady course in the Sir Francis Drake Channel

The next morning, we had a contest: anyone who could find the incorrectly tied bowline (it was on the dinghy) and then tie his own bowline correctly would win a handful of gummy bears. Both boys succeeded. After that it was time for a cabin inspection—beds all made, belongings stashed—followed by another trip ashore to explore the Francis Bay Trail, a short hike featuring plantation ruins and a boardwalk amid the mangroves. Back at the beach, we spotted some sea turtles, and Malin and Luke snorkeled out to have a look before we all returned to Caicu for lunch and another siesta. We capped off the day with dinner and painkillers at the nearby Maho Crossroads bar and restaurant.

The following morning, Josh and the boys dinghied over to the floating pay station to settle our mooring bill ($26 per night), after which we motored over to Waterlemon Cay for a quick snorkel before hoisting sail for the trip through the Narrows—the legendary wind-and-current funnel between Great Thatch Island, just east of Tortola, and Mary Point. Two-to-three-foot waves lapped at the hulls as the wind blew a steady 12-15 knots out of the east. Still in mooring mode, I had forgotten to stow anything away, but as Caicu bounded upwind toward Sir Frances Drake Channel, I realized I didn’t need to. Half-full water glasses remained upright. Books remained on shelves. Ah, the beauty of cruising aboard a catamaran!

Watching as Malin steered and Josh trimmed sails, it occurred to me that if we’d had a catamaran our first time out, things like heeling angles and play space would have been non-issues. Add to that the fact that more room meant more systems for things like a generator (air conditioning, anyone?), watermaker, ice maker and a huge battery bank. True, we might have made better time sailing upwind had we been aboard a monohull. But our kids couldn’t have cared less. With little ones, the journey is the destination.

Arriving Coral Bay after a rollicking two-and-a-half-hour sail (during which Malin had Caicu going an impressive 7 knots), we were reminded that this well-protected anchorage on the east side of St. John is not really the best place for the more casual charter cruiser, with no guest moorings and little in the way of convenient provisioning—which is just the way the locals like it. Beached boats dotted the shore, and a number of weather-beaten hulks could be seen among the liveaboards. Motoring toward the edge of the mooring field, we pointed Caicu into the wind and, with the touch of a button, dispatched our anchor to the sandy bottom in preparation for a meal ashore at the renowned open-air restaurant known as Skinny Legs.

Skinny Legs did not disappoint, and we returned to the boat with four full bellies, two gallons of bottled water from the bar and a new sundress from the boutique. Weighing anchor, we then motored the mile-and-a-half to Princess Bay, where we picked up another mooring. After another swim and a fiery sunset, the kids performed a moonlit comedy act on the trampoline while Josh and I sat in the forward lounge. Soon afterward, we called it a night.

Setting sail the following morning, our plan was to stop in at Salt Pond Bay for lunch and then continue on to either Little or Great Lameshur bays, which offer access to trails leading to what are believed to be a number of pre-Columbian rock carvings. Arriving in Salt Pond Bay, though, a trio of sea turtles immediately swam over to greet us, which in combination with the impossibly blue water there convinced us we needed to stay the night. As we edged up to a mooring, Malin and Luke jumped into action. They now had a system: Josh would steer, guiding the starboard hull toward the mooring; Malin would snag the pennant with the boathook; and Luke would thread the dock line through the plastic eye at the end of the pennant and cleat it off to the starboard hull. The three of them would then combine forces to add a second line to control the swing of the boat. Another reason for the extra line, Luke said was, “‘Cuz if one broke, the other one would hold on.”

Exploring Francis Bay by dinghy

Exploring Francis Bay by dinghy

The boat secure, Malin and Josh promptly dove in to commune with the sea turtles, after which we had lunch and dinghied ashore to explore the hiking trails and jaw-dropping cliffs at Ram Head point. After that came another snorkel session—Salt Pond Bay has excellent snorkeling for all levels—followed by dinner and another peaceful night. No big surprise, Salt Pond Bay was soon one of our favorite anchorages.

The next morning it was time to return the Optimist, so after a quick breakfast, Josh and I did a roll call to make sure everyone was onboard and set sail for St. Thomas. Underway, I took the helm while Josh and Luke spun yarns out on the forward lounge, and Malin read in the saloon. Malin and Josh had done most of the steering so far, and I was glad to have a turn. The sky was cloudy with the wind blowing around 8-10 knots, and Caicu sashayed comfortably over the 3ft waves on an easy reach. More than 43 miles to the south, St. Croix was invisible. But the lush, conical peaks of St. John immediately to starboard more than made up for its absence. Mesmerized, I drifted away from the rhumb line a few times. “It’s easy to get distracted and fall off course,” Malin observed.

It took us just over an hour to get to St. Thomas and find an unoccupied mooring. As I hooked the pennant and pulled it aboard, I saw it was coated in seaweed.

“Slimy,” I said, struggling to maintain my grasp as I attached the dock line.

“Well, that’s what happens when you’re sailing,” said Luke, ninja warrior now turned seasoned mariner.

Next stop was Christmas Cove on Great St. James Island, where we anchored and ordered three large pizzas from Pizza Pi, a local food truck disguised as an aluminum motorsailor. After that, we motored back across Pillsbury Sound to St. John’s Honeymoon Beach, where Malin handled the entire mooring process. “It’s fun, and it’s not that hard,” he explained, as we dinghied into Cruz Bay for dinner and some more drinking water.

Returning to the boat, we dropped the mooring, and glided into Hawksnest Bay as the sun was setting, surprised to see that ours was the only boat there. Slightly groggy the next morning, we sailed in 10 knots of wind to Cinnamon Bay, carefully avoiding the yellow buoys marking Johnson reef. Once there, we walked the half-mile Cinnamon Bay self-guided trail, a well-labeled journey through the ruins of an 18th-century sugar plantation, then returned to the boat and motored over to Maho for one last snorkel—this one in the company of a nurse shark and several sea turtles—followed by burgers and another round of painkillers at Maho Crossroads.

That night, the mood in the mooring field was a festive one. Maho’s location makes it a popular stop for charterers on their first night out. Someone blew a conch shell to signal sunset, and lights and laughter flickered across the darkening bay. Aboard Caicu, things were a bit more subdued as we cleaned up the boat in preparation for our return to Red Hook in the morning. Nonetheless, our charter had clearly been a success. We’d not only staved off boredom and seasickness, but Malin and Luke now seemed to genuinely enjoy sailing. I felt confident that though our trip would soon be over, our adventures as a cruising family had only begun. 

From left, Josh, Malin and Luke out hiking on their way to Ram Head Point

From left, Josh, Malin and Luke out hiking on their way to Ram Head Point

Cruising Tips: U.S. Virgin Islands

The U.S. Virgin Islands offer an unparalleled combination of easy sailing, moderate travel costs and minimal hassle in general. Navigation is line-of-sight, rocks, reefs and other obstructions are well marked, and there’s nothing like the many moorings surrounding St. John to provide a good night’s sleep (and also protect the underwater sea life there).

In addition to Sail Caribe (which, has a bases in the Spanish Virgin Islands and British Virgin Islands as well) a number of other charter companies also offer boats out of both Red Hook and St. Thomas’s capital city, Charlotte Amelie. Although many people charter during winter here in the Northern Hemisphere, a “shoulder season” charter can also be a lot of fun, with smaller crowds, and cheaper flights and charter rates. The weather in June and July is typically no hotter than in the rest of the United States, and the winds are pleasantly moderate. Hurricane season is June 1 to November 30, and late August through early October can be dicey. However, a Thanksgiving cruise in late November can be truly spectacular.

October 2020

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