We have normally picked out the starting point of a cruise based on the proximity of launch ramps and truck and trailer storage. In 2011 we started out in Ft. Pierce, launched close by and left our truck in a locked yard a the Harbortown marina. Cost about 100 dollars in was a secure arrangement. We cruised 350 miles down to Key West in 13 days and got a rental car (Enterprise) to go back up and get our truck and trailer. We sat for a few days on the way down waiting on weather as March can be a windy month in the keys. We were going to cruise back north and a couple bad weather days is what caused the decision to waste less time by getting the boat back on the trailer and heading back to Key Largo with the boat on the trailer rather than sitting out the weather for a couple days. For us we decided that this year it made better sense to pick spots than we could enjoy for a week at a time doing day trips or even run somewhere and anchor for a couple nights if you wanted.. This way you avoided expensive overnight transcient fees and got weekly rates which are usually half of the daily rate. The real plus was you always had a vehicle and the trailer near the boat. That in itself if you is great if the weather works against you. Then after a week we trailered the boat to a new place sometimes only 50 miles away. Then put the boat back in and ran day trips. This allowed us to buy fuel on the hard instead of paying marina prices. And the freedom of always having a vehicle for land based excursions. So parts of the country are safer than others. No fun coming back to find your trailer is gone. To each his own. The cruising with one night transcient dockage and marina gas prices can get expensive. This year we went to four different locations each for a week long stay and while we liked cruising this worked out better for us.
D.D.