I've rented (chartered) in the Caribbean 4 times. Taking your own vessel there is completely different. IMHO. A bit like the difference between building a house and buying one already made. When we sailed TD through the Virgins we had to make a passage of 1,500 miles and 4 weeks of exploration to get there. For me the experience didn't relate to renting a boat already there. I couldn't just give it back to them and fly home, I had to get it back myself. Didn't do that though we just kept going.