Pacific Northwest & Mexico
My ideal retirement would be summers & fall in Puget Sound and winter & spring in Baja Mexico. Sailing out of Anacortes or Bellingham, Washington, you have easy access to a wealth of beautiful sailing areas such as the San Juan Islands, Gulf Islands of Canada, the Sunshine coast of British Columbia, Vancouver Island, Desolation Sound in B.C. and even more on up to Alaska. Summer weather is warm days & cool nights, low humidity, light to brisk winds, some fog. There are a myriad of state and provincial parks with docks, mooring buoys and anchorages;fuel and provisions generally available, although less so the farther north you go. Add bald eagles, seals, dolphins, killer whales. Oh, crabbing too. I don't think you would run out of cruising destinations too soon. But..in winter, I'd migrate to Baja. La Paz on the Sea of Cortez would be a great winter port. Winter temperatures are much more bearable than the summer, the water is still warm for swimming, and there's generally at least some wind. Provisions including the necessary tequila and cerveza ( and water)are available in La Paz. I have only sampled a few of the cruising grounds in the Sea of Cortez, but they're beautiful (i.e., rugged) uncrowded and unspoiled. Fishing and diving are great, and although I'm not into those things, I enjoyed snorkeling and feasting on BBQ-d dorado caught by others. The pace is much slower than the NW, which suits my basically lazy style of cruising.I haven't yet figured out how I would pull off this dream crusing combo, but I've got 5 more years before I can take off. Tick, tock.