Well, to date I have sailed and spent time in S California (Oxnard to Catalina Island - San Diego), the Pacific NW (some time on the sound), and all overthe gulf from Texas to Key Largo.
South California is fun sailing, and Catalina Island is a fun place, but I found it devoid of great anchorages unless you want to go south to Mexico (which I did not). Good friends of ours did that and they fell in love with the locals in the Sea of Cortez. They were only going to visit and stayed there five years. But the actual area of Southern California was pretty busy with commercial traffic and I would probably opt for somewhere with warmer water and more destinations.
The PNW is gorgeous. I can see why it is considered one of the top destinations in the world for cruising (during season). The mountains literally go straight into the water and it is calm and protected for the most part. There are a LOT of parks and places to go - no shortage of them. Washington especially has done a great job of making them inviting and well kept. I wll also say that the PNW boasts the most friendly people I think I have ever met. And if you enjoy a variety of wines, microbreweries, and great coffee houses, you will fall in love with it. The huge negative for the PNW (and its a big one) is the winters, parts of fall and parts of spring SUCK!!! If you are a South Florida boy used to sun most of the year, you will be in for a shock. I was. I am not sure I could ever live there again or spend more than the summer months there. It was tough on me and the family. Also, the summers are generally pretty light winds. Kinda sucks for sailing.
We have spent most of our time in Florida. I do not care for Miami, and can only stay in Ft Lauderdale for short periods. Pensacola is beautiful but gets too cold for me in the winter. Same for Panama City. Certainly one of the most beautiful areas has to be the keys and Tortugas. Drop-dead gorgeous waters, super clear, warm weather, and Key West is a lot of fun for adults (and a bit for kids... a bit). Marathon pretty much is the hub for taking off anywhere you want to go. If you have not seen Boot Key during season, it is amazing and stuffed with hundreds of boats. Outside of that you can grab a ball at Sombrero light and snorkel the reefs, anchor
off Washer woman, or head out and east to one of many other great snorkeling/diving spots. The fishing is fantastic too. The negative of the keys is that it is expensive and there is a bit of a cultural clash. No offense, but Marathon itself has people that are insanely wealthy and those that barely get by (or don't get by at all). Compared to other small "cities", it is not as new and young and vibrant (and I am trying to be nice). The only real crime we have ever had was in Marathon (someone stole our credit card numbers), and I just found out that has happened to very good friends of ours too (their first as well). Another set of friends had their tender stolen, etc. Key West is a whole other country, and I found the people more enjoyable, but it is a tough place for kids and the bar scene gets old before long. Not to mention, Key West is insanely expensive for slippage.
One of the most fun, exciting, and beautiful places we have been has suprisingly been St. Petersburg. The people are some of the most friendly anywhere in Florida, the rates for slippage are ok, there are a lot of yards and competition which makes for good services at reasonable costs (half of the keys), you can get anything you want in St Pete or Tampa marine related, most everything is walkable, there are gorgeous beaches, there are a multitude of parks to go to and explore (Egmont, emerson, Desoto, etc, etc) with Emerson being the best I have ever been to anywhere in any state, and it is very young, new, historic and vibrant. Of all the places I have been, I would probably put St Pete on the top with the Keys a close second.