MVWeebles, you're living my dream. We would do Colorado again in a heartbeat. Unfortunately we've gotten priced out of most anywhere we'd like to buy a home there. This is why we're looking at Flagstaff, or Utah, or even places like Couer d'Alene, ID or Montana. We have to have that sun in the Winter like you have in CO though.
My real question is about where to cruise in the winter though. It sounds like you've found Florida to be comfortable? And if you live in CO you'd definitely recognize the humidity if it was bad. I'm thinking possibly keep the boat somewhere like Beaufort, NC for the summer. Move aboard in the late fall, work our way down the east coast and into FL, then cross over to the Bahamas. I know it may be a little chilly starting out in NC in the late fall but for the rest of the winter would that be comfortable outdoors weather? Not too hot/humid/buggy?
I've been very fortunate over the years. I love being outside - always have: motorcycles, skiing, horses, boats, golf, whatever. I must have been a Golden Retriever in a prior life.
My place in Colorado is really modest - literally a cabin built in the 1920s on forest service property that I bought 30 years ago. I grew up in SLC Utah and have lived in Denver and Colo Springs. My first set of wheels was a motorcycle that I rode all over the Intermountain West - even spent a little time in Coeur d'Alene. Years ago I caught the sailing bug by crewing on Star Boats on Lake Dillon near Breckenridge. There was a pretty competitive class fleet there.
In my opinion, the west is mostly comfortable in summer but not always. The only places I've lived that needed no AC was San Francisco and my cabin (8500 ft elevation). Denver often reaches 100 with low humidity, my neck of Florida reaches 94 plus humidity, though I admit Denver cools off at night vs Florida where temps do not drop below 80 in July/Aug - ever.
Colorado has always been a bit pricey. We don't have kids and our tastes run pretty modest anyway so we can always find a niche that works. I really like the mountains west of Colorado Springs as the access to airports is good. But there are other area - outside of Steamboat - Kremling area is beautiful.
I've had a really twisted career path and have lived a lot of places, some via corporate apts. NYC, LA, San Francisco, Philadelphia, Washington DC, Charlotte NC, Houston, Dallas, Atlanta, and a few others that don't deserve mention (Detroit). When we decided to move from San Francisco in 2005, I could live anywhere I wanted as long as I could get on a plane every Monday morning and return every Thursday evening. We looked all over. Austin TX was a close runner-up but too hot in summer and too cold in winter. Jacksonville FL was a bit cold in winter too. So for us, NC was out - no reason to leave SF. I like NC a lot - Charlotte is probably my favorite Big City (defined as a having a hub airport). We looked at other parts of Florida and decided on the Gulf Coast as its a bit more laid back than the East Coast.
To my thinking, Florida is really three climates. North Florida is no cooler in summer, but colder and cloudier in winter. While temps are important, sunshine is as important to us. When you watch the macro winter storm patterns as they march eastward across the country, you realize that Florida often escapes - the further south in Florida you go, the fewer cloudy days. Houston, Charlotte, and Atlanta all have moderate climates, but can go for days in winter with gray skies.
Southern Florida is subtropical and is sometimes described as having two seasons: rainy, and dry. The rainy season will wrap up in the next few weeks, and the fever (humidity) will break shortly after. After that, it's mostly nice weather through April, with the occasional storm that Frosty mentioned. Pleasant days are beginning - yesterday was in the upper 80's with relatively low humidity. By mid-October, our AC will get used only sporadically through April (at least). When you live in these climates, you learn to live with bugs. I still shriek when I see a giant Palmetto Bugs. And I cite mosquitos as reason to question the existence of a Higher Power. But after a while, you realize mosquitos have a lifecycle - they are active in the hour around sun-down and if you're lucky, bats and dragon flies will appear to defend you. But you cannot be outdoors defenseless in late evening (in all fairness, I was in the mountains of Wyoming last summer and was chased-out by mosquitos there too). The drier, lower humidity climate of winter definitely reduces the bug problem.
Winter is perfect anything-outdoors weather in Florida. I have a small shop that is nothing but a carport covering a work area; and I'm slowly remodeling my kitchen so have been using our outdoor cooking area (not really a kitchen) 100% for a few months. Even in summer and even with this dang COVID thing, we've had a great time and spend several hours outside every day doing something.
Right now, my cruising is limited to hitching a ride on friends' boats, and I can tell you that the cruising isn't tremendously varied - Florida is pretty flat. But you could easily spend many seasons poking around the state (Keys) and over to the Bahamas. Even the Bahamas is a bit monochromatic - I have dozens of pictures of deserted beaches with gin-clear water that all look the same. Not complaining - we like anchoring and reading books. Just saying it's not like the Caribbean where each Island has a ton of diversity.
Our boat is being restored/refit in Mexico so will be shipped to Florida this winter. I have sights set a bit further afield to Yucatan (Rio Dulce). A friend wants to head to the BVI so maybe into the Eastern Caribbean.
In short, if you want to do the snowbird thing on a boat, you can either start in Florida or cruise to Florida. But in this country in wintertime, boat-based exploration means Florida/Bahamas. The humidity is manageable, the temps are comfortable, and there is an abundance of sunshine. Remove the boat from the equation and there are many options including the desert SW. But then I'd include Mexico. The Yucatan is not exactly beautiful, and it is humid sometimes, but is varied and culturally interesting and easy to get to via Cancun.
Find a way to spend some time in Florida during winter. I think you will be surprised at the weather. The summer isn't nearly what most think either, but winter is pretty nice.
Good luck. Don't wait too long to make a decision. Time passes very quickly.
"The days are long but the years are short"
Peter
