Today posed another “first” challenge for us: anchoring & exiting a very crowded anchorage. We also got a lesson on “if you think you should reef, it’s already too late.”
The plan was to spend the morning in White Bay visiting Soggy Dollar Bar and then make the short crossing from Jost Van Dyke to Cane Garden Bay in Tortola.

Above: On our way to White Bay.
If you plan on going to White Bay, staying the night at Great Harbor JVD is perfect, as it is only about 5 min away (if you motor). You could technically leave the boat in Great Harbor and take a taxi to White Bay, but we wanted the experience of anchoring in those turquoise blue waters. So shortly after breakfast, we entered the White Bay channel and realized there were only two boats in the entire bay. Perfect! We decided to anchor at the western most section to stay away from the channel. This turned out to be a big mistake!

Above: Ahhh, so many anchoring spots to chose from! (reminder for next time: don’t anchor in the very “back”)
The anchoring process went well, and soon after that our crew was swimming to shore to enjoy mid-morning drinks at the Soggy Dollar Bar.
By noon, the anchorage was packed with all kinds of boats, from small power boats, to massive day charters, to cruisers. That’s when we realized that we were kind of trapped. Boats blocked our entire path to the channel, and two idiots (pardon the colorful language, but to this day I hate those boats) had anchored in a way that completely blocked the channel. It may surprise you that the idiots were not your typical charter boats, but were instead two private 50ft Oysters Yachts with US flags. It made me wonder if I was witnessing the boating version of the BMW phenomenon (Research suggests that wealthy drivers are less likely to obey traffic laws!).
Anyhow, by the time we were ready to go we had no (safe) way out. There is a channel in the western end of the anchorage, but it is unmarked and there was no way we would risk going that route. Our only hope was that the space between the boats furthest from the beach and the reef was deep enough for us to make it. We did not feel comfortable risking this approach without first confirming if it was deep enough. So we got on the dinghy and went on a mission. First, we tried using the dingy anchor to test the depth, but we abandoned that idea when we realized there was too much ground to test. But then we saw a hired-captain on a charter cat just waiting for his guests to come back from the beach, so we decided ask him. He confirmed that the path we wanted to take was completely safe for our cat, so we got back to the boat to get ready to go. On our way out of the bay, we asked another day charter captain the same question and he also said it was safe, so by then we were pretty relieved that we would be ok. And we were! Whew…

Above: Our path, cutting close to the shoal, to get out of the crowded anchorage.
The sail to Caine Garden Cay in Tortola was supposed to be a relatively easy close haul 6nm trip, but the predicted ESE winds became WNW and so we had an epic 15nm tacking festival up wind – with a lesson on reefing thrown in the mix.
The saying is, if you think you should reef, you are too late.
For our non-sailing friends, to “reef” is to shorten the amount of sail exposed to the wind, when the wind is blowing too strong/fast. You do this to prevent damage to the boat, or worse – capsizing. There are various levels of reefing. You put one reef when the wind is between 15-20knots and a second reef when the wind is 20-25knots, etc. We were already sailing with one reef as the winds were predicted to be 15-20knots, but at some point we saw a squall approaching from the east. Squalls always come with very high winds, so it is a good idea to reef again if a squall is approaching. The squall seemed far enough away that I told Yolanda that we could wait until after the next tack to reef (i.e., wait until we change directions). In this boat, it is easier to reef when the wind is on the starboard side of the boat because you can see the mast. We had the wind on our port (left) side so we decided to wait until we changed directions to tack. That was a rookie mistake!
We tacked just fine, and then immediately began going through the reefing procedures. Then it began to rain heavily, and before we knew it, the squall was on top of us. Suddenly the wind instrument was reading 35 knots of apparent wind! Forget reefing!
“DROP THE MAIN!!!” I yelled in the middle of the reefing process, as we were getting soaked and the wind was so strong we could barely see. Yolanda did not blink. She simply opened the main halyard cleat and the main came down in 2 seconds flat!
Once the sail came down, we were sailing comfortably under ½ jib alone. It was a good recovery from my late reefing mistake, thanks to a very attentive first mate!
We finally made it to Cane Garden Bay not knowing exactly what to expect. This is not a common stop for charter boats, and few people talk about this bay. Yet it was my favorite stop of the week. The place really feels like you are cruising and not chartering. Maybe it is because it reminded me of sailing in Guadaloupe, or because most of the boats around were cruisers. Whatever the reason, we simply loved this place.
So we took the dinghy to the beach, walked around for a while, and ended up having awesome pizzas for dinner at Paradise Club!

Above: Yolanda takes a picture of Nestor taking a picture of our crewmates Ashley and Seth; and behind them, our other crew mates Jason and Ellorie taking a selfie!

Above: Our crew walking on the beach at the amazing Cane Garden Bay.
Coming up in day 8: A masochistic tacking festival!
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I’ve really enjoyed reading about your sailing adventures. I am planning to enroll in ASA101, 103 and 104 sometime in 2016 and hoping to charter a sailboat (or cat) in 2018 for my 50th birthday. It will either be a coastal sail from Miami to the upper Keys or a trip to Bimini, Bahamas. My dream is to purchase a sailboat and spend the first two years of retirement in the Caribbean.
Do the ASA101,103 and 104 classes provide enough experience for a bareboat charter, or do you suggest something more? Thanks again for the great blog.
Hi Derek, some people do go charting after 104 but I did not feel comfortable doing so. It wasn’t until RYA Coastal Skipper and many many days racing as crew that I felt comfortable enough to do the BVI charter. Crewing on a racing boat during the local Wednesday night races was key in developing my skills and confidence. Definitely find a local yacht club and get some experience crewing on their boats. Thanks for reading!