Boosting this post. To remind, with the exception of the 41/3, RT’s are 10’ beam or less. It is actually quite reasonable to ship your boat to different locations and mess with it there. We have shipped our R29CB from San Francisco to Seattle multiple times—and back. It is not hard and is a great way to get a quick jump into the next adventure. For west coast cruising I would recommend: a ship to Seattle with a full two months of cruising in the Salish Sea. Then a ship to Kennewick, WA for a full month of cruising the Columbia and the Snake, ending in Astoria. Then a ship to San Francisco, with at least a month to explore the Bay and the Delta. If you are feeling adventurous, it is not hard to take it out the Golden Gate and down the coast to Santa Cruz and Monterey, hauling it there and shipping it to Oxnard. From there, you will need a month to cruise the Channel Islands, Santa Bárbara, etc. Or less, depends on your goals. Then you can pretty much move it down the coast all the way to Mexico on its bottom providing you have a good weather window or two. This includes stopping in Marina del Rey, working your way to Long Beach, then out to Catalina (a must), then down to San Diego. All depends on weather, but things get more benign (generally) as you go south. The toughest west coast water in my view is from Neah Bay (Juan de Fuca Straight) to San Francisco. Best to just skip that. A friend of mine just moved his boat from Portland to San Francisco. What should have taken less than 10 days took over a month due to wind.
There, I have just planned your first year of retirement. Enjoy!