Very interested in your travel decision from WA. to FL. My wife and I are traveling to WA. in late June to look at the Helmsman and Bracewell. We were considering doing the same thing as you.
Here are my questions to anyone debating the trip.
1. Do you expect to get to the west coast again?
2. Do you have somewhat unlimited time to make the trip. It can include flights to and from home, but can you make it at a pace to truly enjoy the areas you visit. If you're going to do it like a delivery run then no reason to do it. Just ship the boat, but if this is your chance to see some great places, then do it.
In our case, we'd never spent time on the West Coast. So, it was all new and exciting from Alaska to Washington to Portland to San Francisco to Los Angeles to San Diego. We left Washington the final time on September 30 and didn't leave San Diego until January 8.
Then from there we spent time as follows. Not showing our travel times as those would vary widely between boats. But these are the places we spent time.
Ensenada-2 Days
Cabo San Lucas-4
La Paz-3
Mazatlan-3
Puerto Mallarta-4
Acapulco-2 (Definitely not recommended today)
Huatulco-1
Quetzal, Guatemala-3
Costa Del Sol, El Salvador-2
Chinendega, Nicaragua-3
Liberia, Costa Rica-1
Puntaneris, Costa Rica-1
Quepos, Costa Rica-1
Golfito, Costa Rica-2
Panama City, Panama-4
Christobal, Panama-3
Bocas Del Toro, Panama-4
Now a bit of a detour
Cayman Islands-7
Port Antonio, Jamaica-5
Now back to the coastal cruise
Bocas Del Toro, Panama-3
Belize City, Belize-6
Puerto Aventuras, Mexico-4
Cancun, Mexico-6
We did cross from Cancun to Key West, but had we not already cruised the gulf coast often, we wouldn't have short cut that.
You very well may make more stops than we did and stay longer times. Just no calendar. Be free to stay longer due to weather or just desire to enjoy more. Just don't rush through it.
When I was in the corporate world, I traveled a lot of places in the world, but never saw them. Retired, I make a point to see them all.
Corporate life was funny in that respect. I had cities that all I'd ever seen was the airport-Los Angeles, Buffalo, Denver, Houston, Manchester, UK. When I retired, I guess I could say I'd traveled the world, but seen virtually none of it. I could count a great list of places I'd been. Lots of places for one day meetings.
So, only make this trip if you truly plan on seeing all the places along the way.