Hi Rob, actually we have been bareboating in the BVI since the 80's and we have both given rides to people island hopping over the years and been invited along on someone else's bareboat when we did a land based vacation. I feel like if this is your dream... GO FOR IT! We had a full.boat of people and gave someone a ride from Anegada to Virgin Gorda because they had a party to go to. Made a new friend and dropped him off with a smile.You never know who you'll meet in life by being open, so don't let anyone rain on your dreams. Sometimes you just gotta take a chance and live on the edge to feel alive and appreciate every day. And if we run across you, you absolutely have an invite! 😎😎