Welcome aboard. There is a company in SW Florida that charters trawlers. It depends on how often you will be using the boat. If it is only once or twice a year then chartering may be the way to go. If you are going to buy then there are lots of things to think about. Insurance is a big one, age of the boat and experience of the owner. Chartering would help some with the experience part. Also being an owner in Colorado and the boat being in Florida you will likely have to have someone contracted to check on the boat regularly. If you are only going to be using it infrequently then dry storage may be a possibility. They launch when you need it and block it ashore when you are gone. Maybe take a vacation and visit some brokers and look at boats to get an idea what you want. Maybe a TrawlerFest. Good luck.
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