Best towns for living/sailing in US/Canada-not liveaboard?

[Sailing_Duchess]

Hey all-not sure this is the best place to post this, but this is not really a liveaboard question . Long story short, my husband and I are planning to relocate part time to Annapolis MD from NJ in the next 3-5 years (I still need to travel back and forth to NJ on occasion for real estate business purposes) and have our boat and a small house/condo. We love Annapolis for all it offers in the town, as well as the Chesapeake sailing-the plan is to gradually move up to being about 70/30 liveaboard/land-based and more Caribbean/Europe sailing (although this might change, but I really like Thanksgiving/Christmas in my house!).

Question is, looking for other towns that offer a great mix of sailing conditions and good living conditions for those who might not be ready to be full time liveaboards. Good restaurants, access to healthcare, marinas/maintenance, and any other aspects that make somewhere "good to live" as well as having good access to sailing.

Working on compiling a database for a long term real estate related project-bonus, if you are an agent in any of these areas, please reach out- looking for potential long term referral agents.

[Wander4Wonder]

Ive heard Hampton VA, Onancock, VA, Washington, NC are all nice quaint areas. Occoquan VA is also nice but I am not sure there are a lot of options for liveaboard sailboats.