USVI, BVI and it’s a wrap…for now

It’s been some time since I last wrote, and there have been some amazing adventures, and some not so great events in the last 6 months. It’s been hard to get back into it as so much time as passed, but I woke up this morning ready to share my story.

As I write this blog on a sweltering June day in Toronto, I am reflecting on an incredible sailing season, and then an unexpected turn of events that brought me home early. I’ve been back since exactly 3 a.m. on March 11, 2025—a full month ahead of schedule—cutting short my Caribbean adventure, but I’ll get to that a bit later.

When I last wrote we had just finished a wonderful family Christmas in Puerto Rico and were heading east to explore new islands. First up – Charlotte Amalie, U.S. Virgin Islands.

Charotte Amalie, the capitol of USVI, has a huge, sheltered harbour with room for at least 100 boats. Allen and I visited here about 16 years ago enroute to a charter vacation, and much was still the same despite the city being devastated in September 2017 by two Cat 5 hurricanes, Irma then Maria, hitting the USVI just two weeks apart. As Charlotte Amalie is popular cruise ship destination, I wouldn’t be surprised if cruise companies helped restore it—rebuilding countless duty-free shops selling luxury goods and enough jewels to outfit royalty. It’s touristy, but still pretty and charming.

Sixteen years ago, we hadn’t noticed the marina for mega yachts. We took the dinghy for a ride and got a close-up look. With Google’s help, we identified several of them, including the stunning, blue-hulled Kismet, owned by Jacksonville Jaguars’ owner Shadid Khan, and the smaller Bad Romance,sadly not Lady Gaga’s, but Dr. Phil’s. Despite the flashy yachts, no celebrity sightings.

Next stop was St. John, the smallest USVI island with a very interesting history. In 1718, Denmark claimed the island and several plantations were established, growing primarily sugar cane and cotton. Eventually the island was home to 109 plantations, with the Annaburg plantation becoming one of the island’s largest sugar producers.

In 1917, the United States bought the U.S. Virgin Islands from Denmark for $25 million (and agreed to recognize Denmark’s claim to Greenland as part of the deal). Private investors later purchased properties and transformed the island into a luxury tourist destination that it is today. Conservationist Laurence Rockefeller, purchased 5000 acres of pristine land, built an “eco resort” and later donated it to the US government to create the Virgin Islands National Park, which today covers 60% of the island. Today the park offers miles of hiking trails, pristine beaches and the preserved ruins of several plantations, including Annaburg.

In mid-January we moved on to neighboring British Virgin Islands, BVI, perhaps the best-known Caribbean sailing playground famous for stunning views and gentle sailing conditions. In this land of yacht charters and luxury resorts, you can find striking mountains, calm turquoise water, white beaches and very expensive bars and restaurants.

BVI have a similar history with the USVI and many other Caribbean islands, historically bouncing from empire to empire, from Dutch, French, Spanish, Danish and finally the British claiming the prize in 1672. Like their US neighbors, the BVI prospered from sugar cane production until 1834, when slavery was abolished. Today the BVI remains a British Colony and is one of the wealthiest Caribbean island nations with booming tourism and financial services industries.

We love hosting guests on our boat, but unpredictable weather makes scheduling tricky. Since many people don’t have the flexibility to change vacation dates and flights on short notice, we’ve had just a handful of guests join us in past seasons. However, the BVI changed all that.

The BVIs consist of over 50 small islands, only 16 of them inhabited, spread across just 25 miles. We can easily sail from one island to another in just a few hours, making airport pick-ups almost effortless. As a bonus, there is a secure mooring ball field right next to the airport – our guests simply exit the airport, walk 10 minutes to the dinghy dock for a quick 2-minute ride to the boat.

Highlights in the BVIs:

Tortola is the largest island and home to Road Town, the capital and largest city in BVI and I recommend you avoid it. Unlike many other Caribbean capitals, Road Town has no charm and there is no reason to go there unless you are catching a ferry, buying groceries, hardware, boat supplies, or need medical care (more about that later).

Two places worth visiting on Tortola are:

Soper’s Hole – a deep protected bay offering many mooring balls and marina for dockage. It has a grocery store and few small shops, restaurants, including the famous Pusser’s Rum restaurant and bar, featuring their signature BVI cocktail, The Pain Killer.

Cane Garden – A huge bay with plenty of mooring balls as well as good holding for anchoring. A casual village with several bars and restaurants, the Callwood Rum distillery and the best laundromat in the BVI made this a frequent stop for us.

Jost Van Dyke is perhaps the best-known island in the BVIs, thanks to it being home to the bars that put BVIs on modern maps, Foxy’s and Soggy Dollar. When we visited 16 years ago, we swam to shore, drank reasonably priced Pain Killers, added some graffiti to the wall and swam back to the boat. Today both bars have been rebuilt after devastating hurricanes and have become booming commercialized party destinations for cruise ship and charter boaters. Both now have huge gift shops, expensive drinks and have lost some of their charm, but if you’re looking for the party, this is the place.

Norman Island – you can’t write about the BVI without mentioning the famous Willie T, floating bar and restaurant. It’s a decommissioned tanker, parked near shore and features a bar, kitchen two decks for drinking enjoyment. Although there is a sign stating “No Diving No Jumping”, of course, it’s the main attraction of the Willie T!

Virgin Gorda is my favourite island in the BVIs because of its diversity. At the southern end are The Baths, a stunning maze of giant granite boulders and hidden rock pools where waves crash dramatically through the gaps. It’s a must-see—just be sure to arrive early to beat the cruise ship crowds.

On the north side of the island is The Sound, home to Bitter End Yacht Club, Saba Rock and Leverick Bay, where it’s not unusual to bump into Sir Richard Branson having an afternoon refreshment when he takes a break from his private island next door. The Sound offers tons of safe, protected anchoring, ample room for water sports and a variety of bars and restaurants for happy hour and dining.

Anagada isn’t as much an island as much as it’s an atoll. Starkly different from the rest of the BVI, it rises only 28 feet above sea level and is made up of coral and limestone. Surrounding reefs are responsible for many shipwrecks, making it a favourite snorkeling, spearfishing and diving destination. These same reefs also make sailing there quite challenging, especially in unsettled weather. Long, flat and sandy, the best way to see this island is by renting a Moke and using plenty of sunscreen.

Our BVI season was special mainly because we shared our adventure with friends, some there for the first time, some seasoned BVI-ers. However, my sailing season came to an abrupt and early end due to a medical emergency – a detached retina.

I started worry when I started seeing a sudden increase of “floaters” in my left eye. I searched for a local ophthalmologist and learned there was only one who visited the island about once a month. I booked an appointment about 10 days out and hoped for the best. Unfortunately, things got worse, and I could not wait any longer.

An optometrist in Road Town diagnosed a vitreous detachment, that is not dangerous but needs to be monitored. Thirty hours later my vision turned black and I phoned Toronto’s Sunnybrook Hospital and was advised to get home immediately.

The next 24 hours were a blur of ferries, taxis, and flights, ending in a middle-of-the-night arrival at home and surgery the next day. I then spent a week face down, 23 hours a day—eating, sleeping, reading. Unfortunately, the first surgery failed, I had a second, a vitrectomy, followed by two more weeks in the same face-down position.

While I was going through surgeries and recovery, Allen was left to single-handedly bring the boat back to Puerto Rico and prepare it for the upcoming summer heat and hurricane season. It was a very, very hard time for us, both physically and psychologically, with both of us feeling guilty for leaving the other yet being helpless to help one another.

But we made it. My family and friends all jumped in to help, from shuttling me to doctor appointments, shopping for groceries, making meals and just keeping me company. And Allen received offers from friends to come help with the boat, though at the end he chose to do it by himself with a bit of hired help at the marina.

Meshuggana² is safely tucked in at the marina in Puerto Rico, Allen is home and endlessly busy with other boat projects. My retina has healed, but I’ve permanently lost most of my vision in my left eye and I am learning to navigate the world with vision impairment.

But life and adventure must go on. We are starting to plan our next sailing season starting at the end of November. This year we will skim through the USVI and BVI quickly, as there so much more to experience in the islands beyond.