Over the winter my wife Ashley and I decided that we would like to go back to the Caribbean this summer. We felt like we were getting quite overdue since we haven't been on vacation in 3 years. When I mentioned the idea of chartering a sailboat, I got a rather tepid response but I didn't let the idea die since it has been one of my dream vacations for many years. My wife's first question was along the lines of "are you serious, do you realize how long it's been since you went sailing?" Good point, it had been more than 10 years since I went out and even longer than that since I have been on a bigger boat. I assured her that it was like riding a bike, it would all come right back to me and after all, I did have a USCG Master's license (back in the day). After several other questions such as "what about pirates" (I assured her that it was very unlikely that we would run into Mr. Depp), she seemed to start warming to the idea. Next hurdle was to find some willing co-conspirators. I initially approached two other couples, and they both jumped at the idea so the real planning was begun. The first question for me was would the charter companies be willing to let me charter without a captain. A quick phone call and online Sailing Resume let me know that there would be no problems on that front. Next up was picking a date. Since two of the couples have school age children, it was going to be either Spring break or end of School for us. The June time frame seemed to offer better sailing conditions, cheaper rates and more flexibility, so that aspect was settled. Somewhere along this time, one of the couples let me know that they were no longer interested, so I focused my research on a 4 person charter. After reading every article, blog, and trip review that I could find, I decided that we needed to go with a Moorings 35 or the Sunsail 36i out of St Martin. These boats seemed big enough to be comfortable and I liked St Martin because of the opportunity to visit a variety of very different islands and cultures. After talking to reps from both companies, it seemed like a real tossup, I really liked the rep from Sunsail, she was very helpful and knowledgeable, but the Moorings had offered to basically match prices and the boats are virtually identical. The only other factor was that Sunsail could offer a 39 footer that had 2 heads for only $300 more for the week. The women jumped all over that idea, so the decision was made for me! and the boat and airline tickets were booked. (continued)