Re: Best U.S. city for sailing, living aboard, working
San Diego or Annapolis. Both have decent transportation/walking, good to great sailing, and job markets. In Annapolis you could work in Baltimore or DC. If you can't find a job, you aren't looking.
Climate in both cities are very different. You can sail year round in San Diego but Annapolis gets pretty cold November through end of February with a risk to see the water freeze around you..Summers in Annapolis can also be very hot and humid, you'd definitely need AC in your boat.