Charter: the Spanish Virgin Islands with an All Female Crew


Five years ago I was invited, as the token sailing virgin, to set sail with my girlfriends and explore the British Virgin Islands. Six women of a certain age ditched their husbands, picked up their ukuleles and had the time of their lives.

Fast forward to 2018, and I jumped at the opportunity when I got the call to join another all-female crew on a sailing trip to the Puerto Rico and the Spanish Virgins. This time around we were able to muster only four volunteers, but my enthusiasm remained undented—in the words of our charter company, Sail Caribe, “When Is the Last Time You Focused on You? Dive In, Relax and Disconnect. You Deserve It.” Darn right. I was onboard!


So what of our four-lady crew? Well, there was Captain Pip, an experienced skipper, and our equally experienced co-pilot, Dawn. I was therefore in safe hands. Our fourth sailing companion was Molly, a rather delightful sailing novice like me, and a bendy yoga instructor to boot.

Crew all present and organized, we were wondered how both the U.S. Virgin Islands and the Spanish VI around Puerto Rico would be faring after the devastation wrought by hurricanes Irma and Maria in September 2017. Our trip preparations yielded scanty information about current infrastructure and available amenities, and so we did not know what to expect when we landed at Cyril E. King airport in St. Thomas. Our rough plan was to spend a couple of days exploring the USVI, then sail across to Culebra and Vieques, the Spanish Virgins.

The 45-minute drive from the airport to the Sail Caribe base at Red Hook Marina revealed extensive structural damage. But it was carnival weekend and the island was pulsing and throbbing, alive and kicking. I got the impression these islanders may have been battered, but they were most definitely not beaten.

Red Hook Marina, too, was up and running. Despite the need for a bit of prettying up, it offered everything you could want to get sailing. Moe’s supermarket, in particular, offers a good selection of fresh provisions.

That same evening saw a top-notch technical and chart briefing by Jose from Sail Caribe—with the promise of a chase boat in case of any problems sounding like music to my ears. The printed itinerary for our one-way trip had us heading east from Sail Caribe’s flagship base at Puerto Del Rey on the east end of Puerto Rico and then finishing the week in Red Hook. However, not wanting to have to beat our way through a combination of open-water and tradewinds, we had opted instead to pick up our boat in Red Hook and sail westward—downwind. In the words of our captain, we didn’t want to be getting our butts kicked on Day 1.

Departing from Red Hook provided us with a range of lovely options in addition to just making a straight downwind trip to Puerto Rico. These included exploring the USVI or jumping over to the BVI, a hop, skip and a jump to the northeast. However, given our limited timeframe, we opted to only spend a little time among the USVI before hooking on to the trades and heading for the Spanish Virgins.

We were delighted with our boat, Azulita, a spacious Lagoon 450 catamaran. She was loaded, with solar panels, air-conditioning, not one but two fridges and a generator. It was the first time Molly and I had ever touched electric winches. Moreover, Azulita had a watermaker! Pip, whose reputation as a water tyrant is legendary, was very impressed. For the Brits on board, the only concern was that there was no kettle for tea-making.


First thing Sunday morning, we were off on a 90-minute sail to our first destination, Maho Bay on St. John. This was our first glimpse of the hurricanes’ impact on a destination holiday beach, and it was a sobering one, to say the least, with the tree canopies destroyed and mature palm trees were flattened. A middle-aged American woman on the beach, a frequent visitor, told us she broke down in tears when she first saw the damage to her beloved bay.

Still, sitting on our boat, we couldn’t help but marvel at the bountiful nature all around us, including sea turtles, cheeky black-headed gulls and pelicans perched like drunk chickens on our dinghy lines. (I’ve learned two things about pelicans. Pelican poop is rock hard when it dries. Get it off your deck quick. Also, pelicans eventually go blind from diving into the water at break-neck speed.)

The bay also offered huge fish—and I mean huge, great blue flashes of tarpon so big they set off the anchor depth alarm—which quickly put paid to me entering the water.

The morning after that we started sailing west and ducked into Magens Bay on the north side of St. Thomas, a picture-perfect heart-shaped beach that features in many honeymoon brochures, where we picked up a mooring in the hardest of tropical downpours.

Unfortunately, the bay had been hit hard by Irma, with the nearby Fairchild arboretum and an entire 500-strong coconut grove destroyed. Painted wood reclaimed from shattered houses made for a colorful, albeit somber, monument to the disaster. Fluttering in the breeze were half a dozen purple paper bows hanging from trees and posts. A local woman told us they commemorated the deaths of islanders who had succumbed to “stress and depression,” and who “couldn’t face the task ahead.”

That said, a Magens Bay Restoration project—dedicated to the people of Saint Thomas—was well underway, and the entire beachfront had already been replanted (a gift from the Royal Caribbean cruise line), so that palm tree saplings, propped up like delicate yet defiant souls, could be seen silhouetted against the pink sundown.


Later, with Azulita secure, it was time for an evening drink—an obligatory Pain Killer—a heady mix of crème de cacao, rum and nutmeg. As luck would have it, the beach bar had got its cable TV back that very day and was celebrating. We also saw a mongoose skittling around the sands. Softened by our cocktails, we were only mildly irritated by the “no-see-‘ems,” invisible biting flies.

The next morning, we were accompanied by the gentle hum of a chainsaw in the distance as we set out, a common occurrence in the hurricane’s aftermath. Still, the sky was clearing as we headed to the Spanish Virgin Islands…

The farther west we sailed, the less storm damage we saw, and after a choppy yet exhilarating three-hour broad reach we arrived at Culebrita, part of the Culebra National Wildlife Refuge. Culebrita more than lives up to its reputation as one of the top 10 Caribbean beaches and is, indeed, a paradise on Earth. To our delight, it had been virtually untouched by the two hurricanes.

In Culebrita there are also plenty day-only moorings, a rule we immediately decided to ignore. Nobody was going to drag us away from this gorgeous island without a girlie fight. Other attractions included a historic lighthouse, baths (“pozitas”), snorkeling and body-surfing, not to mention white sand and turquoise waters in every direction. We’d stepped into the center spread of an amazing holiday brochure. More amazing still, there was not just a strong mobile phone signal, but 3G!

You’ve heard of Eco-Travel? Well, we now entered the realm of the latest travel trend—Ego Travel—the narcissistic heart of modern millennial holidaying. Grabbing our phones, we put on our best selfie faces and blasted social media with all kinds of Instagram-friendly shots. After that, we climbed up to the lighthouse where we practiced our Natarajasana “Lord of The Dance” yoga pose on the rocks, spoke to our families and posted yet more photos.


The morning after that, we awoke still drunk on the beauty of the bay, to the sound of bleating goats. Yes, bleating goats. Wild, cute, bleating goats. What’s not to love about Culebrita? Then came a short hop to Culebra, a nice downwind sail from Culebrita via the southern channel to Ensenada Honda, Culebra’s main harbor—or in our case following a late start, an hour-and-a-half motorsail to the outer harbor where the ferries come in. Upon our arrival, we also had a nerve-wracking time anchoring due to 20 knots of wind and loads of unexpected weed, which made it tough to find good holding.

Leaving the experienced sailors on deck, Molly and I took the dinghy to gather provisions: a short jaunt through mangrove channels and inlets. There are pretty painted houses in Culebra, friendly locals, chickens and a much welcome store with air-conditioning. Chatting with the people there revealed they had endured an eight-week stint without electricity post-Maria, and the town hall still was providing free bottled water for the residents. The island is reportedly 80 percent recovered. “Business is returning, slowly, but surely,” they said.

Shocked at the size of the game fish calmly inhabiting the waters so far, we found a great snorkeling spot at Punta Tamarindo Grande—a sheltered bay with a coral reef. Here we enjoyed a good selection of fish, lovely little ones, the type I like. After that it was onward to Palomino, just a few miles off Puerto Rico proper for our last overnight. We had hoped to visit Vieques and its famed bioluminescent bay, but ran out of time. In any case, we heard that the bays had not recovered from the pounding they took from Maria.


Palomino, again untouched by the hurricanes, is Puerto Rico’s very own “Love Island,” a 100-acre private holiday complex with a lush bay full of happy locals floating in the warm waters, playing salsa music and generally enjoying their weekend. There are chickens on the beach too. We anchored there and took the dinghy to its delightful sidekick, Palominito, an idyllic picture-postcard perfect island that was featured in Pirates of the Caribbean 4.

Alas, after that it was time to head home, although when we arrived at Puerto del Rey, the biggest marina in the Caribbean, next morning, Jose from Sail Caribe was there waiting for us to help helm the big catamaran back into its slip. Following the hurricanes, Puerto del Rey played host to the Puerto Rican Navy; and praises were sung of the latter’s astonishing efforts, as the marina’s restaurants stayed open to feed people and the marina put plans in place for employees and families to get gas, food and water.

Our last day was spent at Loquillo, a busy and lively beach with restaurants and bars for a last day of relaxing and last-minute shopping. It was also a good spot to reflect on our recent trip.


In short, we loved the Spanish Virgin Islands. They are quieter and less crowded than the USVI or BVI. There are no mooring fees, and boat charter is, by all accounts, cheaper than in the BVI.

As for things that went horribly wrong, our list was surprisingly short. I didn’t realize my cabin had hatches and woke up one morning like a boiled salmon in a bag. Nobody explained that a dinghy comes with a deadman’s ignition, leaving Molly and me stranded on land in embarrassment for an hour. There were also some rather alarming zig-zaggy, Etch-A-Sketch designs found on our chartplotter’s recorded track history. But I promised not to mention those. (Spot-on mooring can be tricky for four girls in a crosswind.)

We found Puerto Rico’s magical islands to be a fantastic charter destination, and now more than ever they are in dire need of restorative tourist dollars. You should go there. But just remember, if you charter with the wonderful folks at Sail Caribe and fancy a cup of tea British-style, bring your own kettle! 

Sian Davies chartered with Sail Caribe (

Photos by Sian Davies

October 2018



VIDEO: Sailing Not just for Millionaires

Sailing and boating can come with a hefty price tag, but there are plenty of ways to get on the water without breaking the bank. In this episode of Boat Talk, SAIL's managing editor Lydia Mullan and Power & Motor Yacht's executive editor Charlie Levine share tips on getting out more


Elcano Challenge Resurrected

In late 2020, sailing legend Jimmy Cornell set off on his Elcano Challenge, a green-powered circumnavigation aboard the custom Outremer Aventura Zero. Unfortunately, shortly after setting out, the boat encountered major power-generation issues. "I took the decision to turn more


Book Review: The Figure 8 Voyage

“What is the color of the ocean that rolls beneath Pacific trades? How does a wave curl and crash at 47 degrees south? Can an albatross remain awing in the worst of weathers?” Randall Reeves has always found images to be the most compelling part of the stories we tell about the more


VIDEO: Capsize in the Prada Cup

American Magic's Patriot capsized during day three of the Prada Cup. If you haven't yet watched the catastrophe unfold with your own eyes, check out the above video or any number of others that are circulating on social media. It's truly a tip that has to be seen to be believed. more


Prada Cup: Brits Take First Two Races

Who saw that coming? After getting skunked in December, INEOS Team UK has swept the first two races in the Prada Cup elimination series of the 36th America’s Cup  Racing took place on racecourse “C,” sheltered between Auckland’s North Head and Bastion Point to take advantage of more


Hutchinson: 36th America’s Cup will be a Close On

On the eve of the Prada Cup challenger series, the official start of the 36th America’s Cup, New York Yacht Club American Magic skipper Terry Hutchinson says it’s anyone’s game. "As we've seen in the last week, everyone's gotten faster," said Hutchinson said at the event’s more


Sailing Docuseries Released Online

Endless Media's Reaching Reality is the story of three friends, a 24-foot sailboat and 1,200 miles. With candor and humor, this series proves that you don't need to be an expert or a millionaire to cast off on the journey of a lifetime. Produced by Emmy-award winner Barry more


Prepping for a Transatlantic

Growing up on the coast of northern England, I dreamed about crossing oceans on my own boat. Like most of us, though, education, a family and a career took precedence, and before I knew it, we had mortgages, young children and endless work obligations. We also became landlocked, more