My wife and I are researching buying a single family canal home within a 10 minute bike ride of a nice beach. We are currently living in northern US and probably 10-15 years away from retirement. The finances are more favorable if we buy a retirement-quality home for $1M-$1.5M and place it in a weekly rental pool to help pay the mortgage since we would only use it a few times per year. We realize it will need to be refitted once we eventually retire. We are still trying to decide between south Florida: EAST vs. KEYS vs. WEST coast. I am hesitant to buy a home with a 45 foot seawall in case we want a 50 foot boat some day. The home should appreciate while the boat is an expense. I'm tempted to forgo the home altogether until the next housing crash(if there is one in the next 10 years) for the sake of adventure (but a boat is a poor investment while a home is not), and just explore the whole area by buying a 50 footer to be kept at a marina for a few years until the next crash. Or save and wait until retirement to buy the home and skip the rental pool? We love adventure and socializing, so the Keys are appealing, but we are concerned that the kids and eventual grandkids will be less tolerant of the 2-2 1/2 hour drive with rental car from MIA/FLL than a home on EAST/WEST coast. Marco seems too sleepy for us, so we are considering Naples, Bonita, Fort Myers Beach on the West coast. But I like the East coast for the flights, culture, waves and convenience of hopping over to the Bahamas. What are the cultural differences between EAST, KEYS, WEST? Where is the best fishing? I'm an occasional fisherman who wouldn't mind filleting and cooking. Like snorkeling and island hopping along with the usual sun, bathing suits, and beverages. We have a bowrider and 40 foot Express Cruiser up north. Buy HOME first? Or BOAT first? Thoughts?