We have been using VRBO to travel in Europe, USA and Canada for several years and have never once had a bad experience. Although this was an unusual experience for us and it did not disappoint. We are not sailors and have only once stayed on a much larger sailboat, and approached this with a mix of excitement and intrepidation. While wearing high heals along the dock to get onto the boat was likely not the wisest choice, I did not fall in, and that was a good thing. We were greeted by the friendly neighbouring slip captiain who quickly toured us through the ins and outs of the boat, being sure to note the obligitory safety features (lifevests, fire extinguishers, etc). Good to know and absolutely never needed. After the tour, he provided a list of his favourite restaurants and interesting sights along the Upper Keys and their marker location along the Overseas Highway.
If you love camping, this is a wonderful upgrade. All the amenities you need, and very comfortable for two. If you are used to a 5-star hotel, you might not enjoy the somewhat closer quarters of a sailboat.
We spent two wonderful weeks in the Upper Keys and were quite easily able to travel to Key West and Miami Beach for day trips. Before our first outing to Key West, our neighbour again provided some suggestions for us to visit. We loved it so much, we went twice. Some days we decided to stay closer to home base, and there were several beaches within walking or biking distance. We borrowed some fishing gear and were able to fish right off the back of the sailboat. We were quite excited that we easily caught several fish each time we fished.
For the adventurous, there are snorkel, scuba, kayaking and paddleboarding rental places nearby. For a romantic getaway, there is nothing like sitting on the back of a sailboat enjoying a beautiful moonlight evening, while listening to some soft jazz with a glass of wine and gently rocking as the waves brush along the side of the boat.
All in all, a wonderful experience. I'm hooked!