We did the USVI in November and I was very disappointed with Simon Scott's new edition that is allegedly Post Irma/Maria. The information was very dated and having done a land based trip last February, I knew more going in than the book helped me with.

Provisioning and water is a bit different in the USVI and the sails are definitely shorter. We honestly did not do much sailing but we were with our kids ranging in age from 21-25 so it was more about the destination than the sailing. We went clockwise around St. Thomas and also clockwise around St. John. I swear to God it didn't matter what direction we were going in, the wind was almost always against us! It is more difficult to find places to fill your water tanks. Luckily, my kids have been trained to use as little water as possible and we were able to go 9 days with 6 people on 100 gallons of water. If you think you will need water try to plan your trip in a way that allows you to be near a marina (St. Thomas) in the middle of your trip. There are tons of places to provision on St. Thomas and it is pretty inexpensive. We stock up at Cost U Less. Most provisioning on St. John has to be at Cruz Bay and it is quite a bit more expensive.

Flying out of St. Thomas on a Saturday is a nightmare! I was there last weekend and had to fly out on a Saturday. I heard people talking about being in line for over 3 hours. Luckily I have Global Entry and so went to the entrance to security, asked a guard where I should go and she escorted me to the front of the line. I was the first person in the Global Entry line. I am sure there were Global Entry people ahead of me but they didn't think to ask or assumed it just wasn't available.

Have a blast! We loved the USVI!