Re: Our first bareboat charter BVI 2014
You are good to go, man; stop worrying.
I've bareboat chartered all over the Caribbean with far less experience than you have and no sailing lessons/certifications at all. The BVI is extremely sailing-friendly. Get the bigger boat!
Here are my tips:
1) Try to share the charter with a couple of friends. Having two more pairs of eyes and hands aboard will relieve a lot of work/stress on you and your wife. Sometimes my friends and I play captain-of-the-day. One person is the captain and must make the sailing decisions. In return, the crew serves the captain at his command, including making sandwiches, serving cold beers, etc.
2) The charter company will have a meeting with the captain. Have at least one other person beside yourself there. Even though you are eager to leave the marina, PAY ATTENTION. Also, have all of your crew PAY ATTENTION during the boat walk-through.
3) Don't worry, you'll have a blast!