Looking forward to living aboard

[emeraldprinting]

My husband and I plan to live aboard as snowbirds in about five years to explore Gulf Coast Florida, escaping these cold Missouri winters. We enjoy a 26' cruiser now but are considering 'practicing' in the meantime by upgrading to 32'-40' or larger in the Ozarks. We are planning to rent a yacht for a week in the spring of 09 from either Jung Charters in Sarasota or Southwest Florida Yachts out of Ft. Myers. We figure this is a great way to get a taste of the cruising lifestyle before making a permanent investment. We would love to hear suggestions from this experienced audience as to what things we should consider, if we should be concerned about making a $50,000+ investment in a boat at this time, what marinas/dock restaurants/sites are not to be missed on our rental next year, etc. We appreciate your input and enjoy living vicariously through your experiences in the meantime!