Tips and tales for glorious sails
Story and photos by Lisa Player
A few years ago, I shared in Bella the story of my first sailing trip around the British Virgin Islands with friends. Back then, I was so nervous about being aboard a sailboat for a week — I get seasick, and I’m not adventurous at all. But the boat, the friends and the gorgeous scenery made me a convert, and this year we decided to go again.
With the nerves gone and new adventures to uncover, I had another fantastic trip, and I wanted to come back to share some details in case you want to try it, too.
LOGISTICS
Planning ahead for several months is helpful to ensure smooth sailing. We used The Moorings (moorings.com) to charter a bareboat sailing catamaran. For three couples, we chose a 50-foot Moorings 5000 four-cabin vessel (with our own separate cabins with en-suite baths), a spacious interior saloon with a fully stocked kitchen and an upper deck with a seating area. We didn’t need to hire a captain because our friend is already an experienced sailor, but The Moorings does offer skipper/chef packages. This boat has Wi-Fi, air conditioning and a nice sound system.
You can order food, wine, liquor and other sundries ahead of time from a Rite Way grocery store near the marina. We planned to make and eat a simple breakfast and lunch on board, while enjoying dinner out each evening. All provisions are delivered directly to your boat on launch day. Be ready for creative substitutions from the shoppers, though!
We booked flights from Pensacola to Miami to Tortola, as well as an airport transfer to The Moorings Yacht Club. Arriving on a Friday, we reserved hotel rooms at The Moorings for that evening. There’s a chart briefing for captains to learn about current conditions, and the property has restaurants, a spa, a pool and shops to enjoy for a relaxing afternoon and evening before you set sail.
The restaurant experience in the BVI is meant to be relaxed and unhurried. And it is. Get ready for “island time,” and don’t arrive at any restaurant starving.
While we tentatively planned our route, we left some flexibility based on sailing conditions and our own whims. One thing I loved on both BVI trips was a scheduled midweek stop at Scrub Island, where you can dock in a slip (reserve ahead), enjoy the pools, shops and restaurants, and take advantage of their showers. As much fun as it is to live on a sailboat for a week, showering with a tiny handheld showerhead that starts and stops to conserve fresh water can be a challenge.
HIGHLIGHTS
Necker Island Nature Tour: We booked this tour, which is often sold out, months in advance. It was the favorite part of the trip for all of us, and I highly recommend it. Necker Island is billionaire Richard Branson’s private retreat, where he has also built a luxury resort and a wildlife sanctuary. The nature tours are meant as an educational journey through the island’s gorgeous animal habitats, built to preserve some of the world’s most beautiful and endangered species.
Upon arrival, we were greeted by one of the wildlife sanctuary’s longtime caretakers. He explained that the original tour company we booked with was no longer managing the tours, and he would be doing ours himself. Thus began our three-hour-plus behind-the-scenes exploration of animals, residential and resort spaces.
It was a magical day and included personal encounters with lemurs, giant tortoises, flamingos and red ibis, kangaroos and parrots, as well as stops for drinks in some of the island’s many luxury, open-air bar spaces. We even trekked up many flights to the highest lookout on the island, with a driving mat on the way up for hitting biodegradable fish-food golf balls into the water.
To request this tour, email Vaman.Ramlall@virginlimitededition.com
Jost Van Dyke ATV tour: This was truly a thrilling, memorable experience — for the brave at heart!
We reserved three four-wheeled ATVs from Salt Life Adventures (saltlifeadventuresports.com) for an island tour over rough terrain. Our tour was just over two hours, and it was filled with breathtaking views and heart-stopping moments.
The culmination of the ride over the island was at Diamond Cay, where we parked the ATVs and hiked to the famous Bubbly Pool, nestled between huge boulders where the surf crashes in. Finally, we headed back to White Bay, this time taking paved roads the whole way.
Cooper Island Beach Club: We made an unplanned stop at Cooper Island and decided to check it out. According to its website (cooperislandbeachclub.com), the resort is “completely off-grid” and “self-sufficient in power and water.” It includes a solar-powered brewery, coffee shop, boutique and restaurant, so it’s enjoyable for day-boaters like us as well as its resort guests. All the cocktails, coffee, lunch dishes and ice cream we sampled were amazing, especially the chicken roti and fish and chips.
Peter Island: Another discovery was the Peter Island Resort, renovated and reopened in 2024. We moored in Great Harbour, beached our dinghy on the empty beach and hiked over to the resort. It’s an odd little path across the island, but the resort is beautiful, with a great bar. You can also head to the resort directly by boat instead of hiking from Great Harbour.
Dove Restaurant: A truly exciting discovery for us was Dove Restaurant in Road Town, Tortola, where we went on our final night after returning to port. It was pure joy to dock, take real showers in The Moorings resort, put on nice clothes and taxi to the restaurant in Road Town. From pre-dinner cocktails to appetizers to main courses, we were all thrilled with our last vacation dinner.
ONE WEEK IN THE ISLANDS
Here’s our full one-week itinerary in the British Virgin Islands.
Friday: Arrive; spend the night at The Moorings Yacht Club; dine at Charlie’s Restaurant.
Saturday: Provision the boat, complete inspections and depart; sail to Peter Island Great Harbour; hike over to Peter Island Resort for drinks; dine at Ocean’s 7 Yacht Club (we recommend the prawn linguine and baby back ribs).
Sunday: Snorkel at The Indians in the morning, sail to Norman Island and moor; hike up to the top of the island; take a quick dinghy ride over to the famous Willy T’s for a pre-dinner drink, then dine at Pirates Bight restaurant (recommend West Indian wings for lunch, baby-back ribs and chicken roti for dinner).
Monday: Stop at Cooper Island Resort for lunch (fish and chips are to die for). Sail to Bitter End/Saba Rock and moor; enjoy drinks on Saba Rock. (The restaurant on Saba Rock is outstanding! Be sure to make a reservation.)
Tuesday: Sail to Necker Island for the nature tour; sail to Diamond Cay/Little Jost; dine at Just Taboo restaurant.
Wednesday: Snorkel around the cay. (Become stranded when the dinghy engine dies and get rescued by some nice Brazilians in speedos who don’t speak English). Sail to Scrub Island and dock for the night; enjoy pools and showers; dine at the open-air Donovan’s Reef restaurant.
Thursday: Sail to Jost Van Dyke’s Great Harbour; dine at Ali Baba’s (see Page 33); enjoy drinks and dancing at Foxy’s.
Friday: Late morning ATV tour from White Bay to Bubbly Pool; enjoy lunch at Coco Loco and a drink at Soggy Dollar before sailing back to Tortola and The Moorings; dine at Dove Restaurant in Road Town.
Saturday: Travel home, exhausted, sated and smiling.
Ali Baba’s on Jost Van Dyke
My favorite vacation experiences are always the unexpected ones. Both times we’ve been to the BVI, we have enjoyed memorable moments at Ali Baba’s Restaurant on Jost Van Dyke. The small, open-air, family-owned place sits 20 feet from the beach and is named after its owner, the legendary Ali Baba. He will happily give you a lesson on how to blow into a conch shell (if you buy one), show you the handmade jewelry and crafts he makes and sells on the premises (do not touch unless you’re brave and buying), tell you a story (we heard about his 76th birthday party a few days before where there seemed to have been a wrestling match between Ali Baba and a regretful challenger), or get you a cab ride for the next morning with his friend (who will also tell you stories about the same birthday party).
This trip, Ali Baba’s equally legendary (though more low-profile) and likely very tolerant wife was playing bartender, host, waiter, bus staff and chef mostly by herself after the staff quit unexpectedly. No worries! What better time to offer to make our own drinks, clean up the bar, clear away dishes and chat with the other table of customers, who were growing grumpier by the minute. Extra tips and handshakes capped off a night to remember. Of course, bright and early the next morning, Ali Baba was right outside, helping us hail his friend’s cab and telling us to come visit again soon.
TRIP TIPS
Don’t sail after dark. Plan to reach destinations ahead of sunset.
Early each morning, you can attempt to book a mooring ball in many harbors throughout the BVI by using the Boaty Ball website (boatyball.com). They go live at 7 a.m. and fill up quickly. Be sure to learn the difference between bookable/reserved balls and first-come, first-served balls, which is based on color and sometimes shape.
Stay flexible and have backup itineraries ready.
Check with your doctor to get prescription anti-nausea ear patches.
If you wear glasses, go to MBT Divers in Pensacola before your trip and let them fit you for a dive/snorkel mask with corrective lenses.
Stock up on reef-safe sunscreen and a supply of Free Fly skorts and bamboo shade hoodies, which are lightweight and comfortable.
Finally — don’t laugh — I highly suggest a daily morning cocktail of Benefiber mixed with a sugar-free electrolyte-replacement packet in a 16-ounce water bottle.
