After I retired in 1995, my girlfriend and I left Annapolis and did the ICW on my Hunter legend 35 with a 4.5' draft. No dinghy, no dodger, no bimini. yes to a portable generator, coffee maker and microwave. Eventually got to the Virgin islands and 2 years later went back to Ft. Lauderdale, sold the boat and bought 51 footer in Tortola.
The 2 years gave us an idea of what we wanted. Cruised and race Chesapeake bay. We felt we were ready to go big. The 51' became our home for the next 12 years. Cruise from Trinidad/Venezuela to Maine, down to the keys, Cuba, Isla Mujeres, Honduras, Guatemala, back up and across the islands and St. Croix. JUST DO IT!