Caribbean Coming of Age

I cried like a baby when our son was born. I bawled my eyes out when he rode his bike without training wheels for the first time. And since I was a skier before I became a sailor, I burst into tears when our cute little begoggled-toddler rode a chairlift for the first time. In fact, that’s why I wear white sunglasses all the time—to hide all the blubbering!

But none of those tears of gratitude-inducing moments will ever compare to waterfall of emotion that washed over me when I witnessed our 7-year-old drive a RIB for the first time in the BVI last February.


The sun was hot. The air was soft. The water was BVI-tourist board blue. The mooring field at Manchioneel Bay on Cooper Island was crowded with charter boats. He and I had already done a couple of dingy training runs around the marina at the Sunsail charter base in Roadtown. And he’d helped me steer our ultra-comfortable Sunsail 454 catamaran in 20 knots of breeze across the Drake Channel the day before. But we’d agreed that this was going to be his maiden voyage as “Dingy Captain.” I was the teacher/passenger. He was in command.

Not a bad spot to learn how to drive a dinghy.

You guessed it. I welled up almost as soon as he gunned the engine sporting the widest smile I’ve ever seen. It was a smile of confidence, innocence and openness I wish every parent could see in their children. The only thing missing was the front tooth he’d lost the day before! And that’s when the significance of his maiden voyage really hit me.

Seven years before, my wife and I sailed into Manchioneel Bay with our 6-month old baby boy who literally cut his first teeth on that trip (check it out in the April 2013 issue). Now I’m helping him cut his teeth as a sailor. Talk about coming full circle. Makes you want to cry, right? That’s just the beginning.

2013 issue of Sailing Mag!

Chartering during school vacation week has its advantages, but, um, an empty mooring field in the one of the most popular charter stops on the planet—the Baths—is not one of them. But, honestly, that was okay with us. In fact, we opted to keep sailing up to Virgin Gorda’s North Sound instead of stopping there and our only complaint was that we went too fast! We had our happy catamaran reaching along at almost 10 knots before we made the turn past Richard Branson’s Mosquito Island into calm waters of North Sound.

Pi in North Sound was oh so superyachty.

Even though it’d been years since I’d sailed in there, felt like coming home. We buzzed the 250-foot-long superyacht Pi that was at anchor there and tried to guess who was sitting by the pool in the bow. And we got ready to go for a swim as soon as we pulled up a mooring up by the Bitter End Yacht Club that was devastated by hurricane damage a few years ago and is in the process of rebuilding. But, as we did at the Baths, we decided to keep moving because of the mooring situation. Not because it was too crowded. We turned into the narrow channel between Saba Rock and Virgin Gorda bound for the new yachting-friendly Oil Nut Bay Marina because the moorings haven’t been maintained (yet!) and field was eerily empty. It was sad to see the devastation and we look forward to visiting the rebuilt BEYC 2.0 soon!

Veteran charterers know it’s impossible to discover a sweet new spot in the BVI simply because it’s all been discovered already. And we hardly “discovered” the brand-new Oil Nut Bay Marina that’s just around the corner from the BEYC. But we all loved it because it’s way more than just another marina. It’s part the super-luxe Oil Nut Bay residential resort development so it also has huge deck, a fantastic pool and plenty of comfortable places to chill in addition to gourmet restaurant and chic bar. I highly recommend it weather you have kids or not.

We spent two days there. Our little one lived in the pool and he loved throwing darts in the game room. “Kids movie night” (viewed from comfortable seats on the beach near the marina) was a big hit. If that wasn’t enough, they also hold regular talks for marina guests. Dustin Rey ( spoke about sailing around the world after he lost his arm and his foot in a motorcycle accident while we were there. In fact, we may have never left if we didn’t have an invitation that no one could refuse—a chance to visit Necker Island while it’s famous owner—Richard Branson—was there.

Unfortunately, we didn’t end up meeting with Sir Richard during our visit. He was busy working with a group on climate change. But we did get a tour of his island that’s a combination of an exclusive resort with multiple tennis courts and a spa, a nature preserve, a think tank, and watersports paradise that’s unlike anyplace else on Earth. We marveled Necker’s large flamingo flock and various sustainability projects. But the highlight of our visit was getting to feed Necker’s famously endangered (and ridiculously cute) Lemurs that Richard is trying to help bounce back from the edge of extinction. Just look at our little one with a Lemur on his head. Could there be anything better? Um, no. And the 360-degree view from the top of Necker’s Great House may just be the best view in the entire Caribbean.


As anyone who has ever cruised with kids knows, frequent beach, snorkel and swim stops are essential. And unlike many charters who gravitate to the party atmosphere of the Soggy Dollar and Foxy’s on Jost Van Dyke, we were looking for a less active beach to spend our last couple of nights aboard. We knew Guana Island’s White Bay would be exactly what we were looking for. And since we’d stayed at the perfectly exclusive resort on Guana before (the entire 850-acre island is privately owned), I was able to arrange a tour so our little one could see how their innovative “orchard” produces many of the fruits and vegetables their chef serves the guests.

We loved learning about island agriculture, sustainability and farm-to-table cooking. And we were grateful to be reminded of our simple connections to the earth and each other when we tasted the fresh-picked produce that Vernon and Jamal grow with such care. But after a while, the boy just wanted to swim. And so did we. And that’s where the tears of gratitude started to come back into play.

Our sunglasses-sporting, pink-visor-wearing, two-front-teeth-missing dingy captain he drove us back to the boat with style and swagger. The trade winds that had been honking all week subsided a bit. We plunged into the water off the back of the boat like the charter pros we were becoming. And then we loaded up for some serious beach time on what may be one of the softest, whitest and most soothing beaches in the BVI.

The boy was off like a rocket as soon as we hit the beach. He’d spotted some kids off another boat digging a hole.

“I’m going to see if I can help,” he said as he walked up the beach.

“Have fun,” was all we needed to say. Kids need other kids, especially on a sailing charter.

There wasn’t a cloud in the sky. The sun was hot but hardly oppressive (especially since it was 5 degrees back home in New England) and refreshing dips were a regular occurrence. The view from the beach provided some of the best yacht watching I’ve seen anywhere. The 250-footer Pi that we saw in North Sound was there. The crew and guests from the superyacht Vibrant Curiosity were frequently shuttling between the 280-footer and the beach. And the majestic 137-foot-long sailing yacht Rebecca dropped anchor while we were there as well.


Surprisingly enough, I managed to hold back the tears, even on our last official dingy ride back from the beach. Refreshed and energized after a calm nights sleep, the last 10-miles we had to cover on our last morning to get back to the base were bittersweet. The wave of gratitude I felt for the role that sailing has played in my life, and now the life and legend of my family was humbling. In my opinion, a sailing vacation in the BVI (or other tropical locale) may just be the best family adventure there is. Were else can a young family learn teamwork, and understanding, and respect for the environment, and practical skills that build confidence and self-esteem in such beautiful and restorative place?

Our little one who was only 6 months old when he first sailed in the BVI is now a bonafide veteran now. And we all cried a little when it was finally time to go home.

[Editors note: This story first appeared in the April 2020 issue of Sailing Magazine. Please check it out there too!]

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