Overview: Jerry and Michael have spent the majority of their lives in the Midwest and have had it with the brutal winters. The distance to the ocean and limited months of warm weather have been a struggle since they love to sail. They've dreamed of pursuing this passion on St. Thomas by opening up a charter sailing business. Now ready to start a new life in the Caribbean, they're working with real estate agent Kerstin McConnell to find their oceanfront condo.