Winter Travel and BVI
It’s been a week since 2025 waved goodbye, and three weeks since the CWS clan decided to trade rain and traffic for sun, sand and sail in the British Virgin Islands. Let's cannonball into our tropical tale, but first, let's gawk at what lured us back to BVI like moths to a tiki torch.
Way back in 2002, the Mrs. and I first dipped our toes into BVI and USVI. That adventure started as a budget-friendly escape—thanks to US Airways' 25k mile R/T fare sale to the Caribbean. We penciled it in for Thanksgiving week and sweet-talked my mom and her hubby into a week-long babysitting gig at our Pittsburgh pad. My wife was seven months pregnant, so we knew if we didn’t plan ahead, we’d be stuck at home watching the Macy's Thanksgiving parade on TV. We picked USVI and St. Thomas, clueless but excited. After booking a "just-in-case" resort, we stumbled upon a treasure trove of info about sailing vacations. Enter Shamu of Tortola, recommended by Sherry Yates at Yates Yachts. This was a spiffy 47’ catamaran captained by a couple of retired navy folks, Captain Bryan and Ann Petley. Their retirement plan? Sail the Caribbean, soak up the sun, and avoid hurricanes, all while entertaining others. My Mrs. isn’t quite sold on the idea… yet.
Every morning, I’d perform my ritual: shove the dinghy aside and snorkel the nearest reef. A barracuda, who apparently thought it was my spirit animal, followed me everywhere. The coral was dazzling, the water crystal-clear, and the temps were a dream for a guy from The Ohio Valley. Returning to Shamu, a fresh coffee awaited me right next to the warm freshwater rinse faucet and sprayer. Heaven, right? After drying off, breakfast was served, and we’d chat with the Petleys about our next escapade. The itinerary was simple: breakfast, adventure/snorkel at spots like the Baths, the Indians or Bubbly Pool, lunch, sail to the next anchorage with a cocktail, gourmet dinner, stargazing, sleep, repeat. What’s not to adore? After a week of this, I was hooked and fantasized about captaining my own ship next time.
Step one to captaining a pricey yacht: learn to sail. Our dads were lake fishermen, so we had water experience—mostly getting yelled at for tangled lines and bathroom breaks. After 20 years in telecom, I was gifted an early retirement (involuntarily downsized) in 2011. With almost a year’s salary and benefits to pad my way until gainful employment was attained, I spent two months diving into ASA 101-114 courses at Blue Pacific in Marina Del Rey. My training included classroom, hands-on, and overnight trips to Catalina. At our first hands-on boat training, we were welcomed by Yogaqua students (yoga on paddleboards) and a pod of dolphins. Spotting the Yogaqua crew became a regular delight, but dolphins? Never saw them in the marina again. I snagged a 1977 25’ Catalina on Craigslist for a cool $3k, learning the ropes on a aged yacht that tested my quick thinking regularly. Fingers crossed I never have to apply this on a $1.5 million Caribbean catamaran!
Fast forward to 2025, and I had my college crew home for winter break. In the months preparing for our trip, I donned my captain’s hat and doled out tasks via spreadsheet. The crew needed sailing basics—not from me—so they enrolled in a US Sailing course in San Diego. Other tasks: transport to/from St. Thomas and Tortola, meal plans, activities, onboard entertainment, knot-tying, some light reading, and YouTube watching. I mapped our float plan from Road Town to Norman Island, The Indians, Jost Van Dyke, Marina Cay, Virgin Gorda and The Baths and ending at Cooper Island with alternate spots. I’ll let the photos do the talking, but there’s no Caribbean vacation like waking up and falling asleep on your very own floating condo with unforgettable views. No alarms, no crowds (unless you want them), no buffet lines. The locals are the friendliest folks, ensuring you’re happy—from boat boys delivering ice and food to beach bars competing in friendliness. This time, it won’t be 23 years between trips. Those locals will know my face before I sail into the sunset.
Hope you enjoyed this latest post. It brought back memories that I thought were buried at sea. If you ever want to chat sailing or need a backup skipper, I’m more than willing to pay my way and help helm your next adventure. Find me here or wherever I dock in MDR (sometime before spring 2026). Next up: full skipper certification!
Fair winds and following seas, CC at CWS
(click on the photo below for a full sized slideshow)
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