Nick, here's a sequence I think you'd enjoy...
...and don't forget to look at the recent archives as this was recently discussed at length WRT a large Hunter owner (the boat, not him <g>...) who needed to relocate to Tampa from New England and some of the same advice will apply.June-August: final prep, shakedown & provisioning in Long Is. Sound, sightseeing in New York at the 79th St. moorings (washy but not expensive) and transiting the NJ coastAugust-September: transit Chesapeake Bay; it will still be hot, muggy and buggy but the Bay's a joy almost any time; arriving earlier will insure it's even hotter and more windless but you'll have more time to enjoy both the Western & Eastern ShoresOctober-November: transit down the ICW to FL's border while staying ahead of the increasingly deeper fronts with lower temps as you move SouthDecember-January: finish running FL's east coast and run either around to Ft. Myers via Marathon on Vaca Key or direct via the Okeechobee Waterway from Stuart.Most folks like to leave the Bay a bit later, so they can visit the Annapolis Boat Shows (sail, the power) in mid-October but you pay a penalty in shorter days, colder temps and more fronts further south for the rest of the trip.Jack