I am remembering our first BVI sail in January 1993. We too had a lot of Chesapeake experience. but this boat , a 36 foot monohull, was the biggest we had ever handled. It was just the two of us. We were terrified and the Moorings dockhands literally had to push us off the dock. They apparently had faith in us.

Then, once we had cleared Tortola we raised the sail we never looked back. Yes we made mistakes, but every evening, over our gin and tonics, we discussed what went well, and more importantly what we could have done better. The captain kept his log, very technical and accurate. I, the admiral, kept the social log. We only had the boat for 5 days, but since then we never looked back. We ended up owning two monohulls through the years, Silent Partner, and Bountiful, and spending all our vacation time in the BVI.

We read the BVI sailing guide from cover to cover, and were never too embarrassed to ask for advice or help. We now have of course aged out, but we both still have our logs and our memories.

Three pieces of advice? 1.Greet everyone courteously, they are after all sharing their waters with you. 2. listen to the weather reports every day and be honest about your ability to handle the boat in heavy weather. 3. Never, never sail while under the influence of alcohol.