We have been going south for the winter for over 2 decades. Not all of that with boating in mind, but we have traveled the entire Sun Belt many times, looking for warmth (when we lived in the Black Hills). 3 areas that are generally "reliable" for decent winter weather in the Continental US: San Diego (you can also toss in southern Arizona, but not much for boating there IMHO); deep south Texas (along the Gulf Coast); southern Florida (from Naples/Miami south). There are marinas and homes with canals or dockominiums in those areas.
There are pros/cons to each of those areas. Florida is crowded (and expensive), San Diego can be crowded (and expensive), south Texas isn't as crowded (but is becoming more expensive). You may have heard me refer to this area as "Mexico Lite." Some people don't care for the culture. Although you will find 55+ residential areas in all those places, if you are considering winters there, most of the homes (or rentals) with water access are going to be occupied by seasoned citizens during the winter.
The village we live in used to be an upscale owner-type RV resort. While there were (and still are) rentals, each lot is individually owned. Over time, most of those lots now have small homes built on them. Most of the places are second homes for people from up north. Many of the lots here are located on canals, so you can have your boat right out your door.
We have seen similar residential areas in Florida - some with all mobile homes, with river access, leading to the Gulf. Not sure what is available similar in the San Diego area.
Go north from us to Corpus Christi/Rockport area (where Brent and Dixie have spent winters), and you will find more homes/RV parks with canals and/or water access. It is a few degrees cooler in that area compared to the tip of Texas.
The best suggestion I can offer is to go to an area you think you might enjoy and see what the climate, population, and amenities are truly like. Rent something, visit with a real estate expert in that area to see what things sell for and what other expenses are involved.
In our resort/village, each residence has monthly owners fee (consider it like a condo fee) that includes water, sewer, cable TV, 24 hour gated security, lawn care, use of common areas (tennis courts, indoor and outdoor swimming pools, hot tubs, an exercise room, activities, etc). There is an 18 hole executive golf course that is very reasonable for owners (so I am told - never got into chasing a ball around a pasture). We bought here so we'd have a place for a boat, right out the door. The monthly fees for owners runs $250... and you pay that every month, whether you are here or not. Compared to condo fees in our area that do not have water access, that is a good deal. Add taxes and insurance to that.
The beauty of these places is year-round boating. Shirt-sleeves and shorts. Summers can be hot and humid (the sea breeze really helps). WAY more families with kids during the summer. When we owned up north, going south in the winter was our escape... now, going north in the summer is our preference. Those migrating birds really have it right. :wink:
We are in the middle of a norther currently: a cold front that generally blows in from the north to northwest, knocking daytime highs to the 50s. Cold wind. More typical: winter daytime highs around 70º. Plenty of sunshine.
We just got back from Dallas (Joan's Mother's birthday). It was 81º here when we left Saturday morning; 52º currently (thanks to the norther). But, it was freezing cold the whole time in Dallas!
Yes, we are in a hurricane potential area. Just like most places along the East and Gulf Coasts. Hurricanes in San Diego are rare, but not unheard of. We had a direct hit in 2008; it had been 28 years before that. Hurricane insurance (and flood insurance) is expensive. Homes have to be built to certain standards here to even qualify to buy that insurance. On the flip side of that, see the "plenty of sunshine" comment above - if we have 3 or 4 days in a row of overcast, people get cranky. I can only imagine what a bear I would be if I lived in an area where you might go weeks or months without regular sunshine. Different strokes.
It's interesting to talk to the "winter folks" in any of those areas... they will usually tell you that they endured the cold, snow, and gray... until the first time they went south. Then, no going back!
Good luck with the search.
Best wishes,
Jim B.