I am hoping to do a self supported ride from either Santa Monica or better yet, Santa Barbara to San Diego in May. Although it would be nicer to escape the winter months here, that is also when there is more rain there. I already have one person who is likely to accompany me (not from EBC). It is roughly 250 miles from Santa Barbara to San Diego and it is not super hilly despite being California since it close to the coast though of course there are few. The plan is to stay in some decent motels and only ride a moderate distance each day since we will be carrying things. The ride is supposed to be fun after all. A touring / gravel bike with a rack for panniers would be ideal though a sturdy road bike with a Tailfin rack would be OK too. I will probably be taking the train to the starting point from San Diego. The train from there or from LA allows bikes and it is recommended to make reservations on the train for the bike as they only have a limited number of spots for bikes. If we ride through through Camp Pendleton instead of on Intersate 5 (hopefully), you need a "Real ID" or similar to get on the base for a short distance before exiting in Oceanside. Just as we get to San Diego is probably the worst long hill (Torrey Pines) but it is never more that 6% and there is a double wide bike lane there.
Contact me if interested.