So…I’ll dream. I would live in San Diego from October to April, and in Kennebunkport Maine in the late spring to early fall.
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I can agree with this! I’ll be your neighbor. 
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@thumper1 - completely agree with this! I love Kennebunkport in summer/fall. Luckily, we live close enough that we can make a day trip there and back. It’s a must-do for us each summer. Marginal Way in Ogunquit is one of my favorites! San Diego in winter is also a perfect pick!
If I could, I’d have a place where I could sit on a balcony or a porch watching the waves - my happy place!
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@thumper1 my boss has a home here in San Diego and a home in Wells, Maine not far from Kennebunkport.
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@great_lakes_mom I already live in San Diego, but would love Steamboat or Telluride in the winter months since we love to ski!
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We have friend in Wells. But if I’m dreaming BIG with no money restrictions, I want Kennebunkport…or maybe Wiscasset.
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I go to Maine often, usually to the mountain/lake region in the southwest part of the state. I would be happy living there from mid-June through the end of foliage season. Only drawback is that you are pretty far from decent medical care - Portland is 90 minutes away and it’s three hours to Boston for anything major. I’ve only been to Kennebunkport a couple of times. My recollection is that it’s nice, but lots of traffic on two-lane roads (mind you I was there in the summer).
I have 3 possible retirement ideas. In no particular order.
Las Vegas (not on the strip) (I like playing poker)
No city - Live on 10-20 acres(wooded) about 30-45 mins outside a town of 25-40K population. Nice little 2 bedroom cabin. Need decent internet. Hopefully 2-3 hours from a decent airport.
RV life - I always be where the high temp was 68-78 degrees. Head North in the Summer and South in the Winter.
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Certainly I’d like to visit a place… or ideally rent for a while before deciding. But first pass in research would be a check of Weatherspark. Example - Boulder Climate, Weather By Month, Average Temperature (Colorado, United States) - Weather Spark
There are a few charts per location. (You can try entering yours - I just did mine as example). When planning vacation location/dates and packing, I like to start with the avg temp chart
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Has anyone visited Montana and had a city there on their list? I know someone who moved there. Looking for gorgeous mountain views/hiking and am wondering if MO life might be similar to CO…??
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I’ve been to Bozeman (attending conferences) in the past. Beautiful area. Nice little town. But… 
in the winters!
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Just as a comparison (for those wishing to winter in San Diego, remember that it’s a Mediterranean climate, not a tropical one). The temperature range in the Chicago suburb where we used to live over 27 years ranged from a low of -26 to a high of 108.
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True—my ex BF taught at MSU in Bozeman. I got snowed in at Billings airport, waiting for the plane to fill with passengers from another flight. We had to walk to school in a blizzard because school didn’t close and Ex BF had to teach (everything else was closed). Of course, none of the pupils showed up, so we had to trudge back in the freezing cold.
It’s quite near Yellowstone. It’s too rural for me.
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Thanks, Colorado_mom, BunsenBurner, Himom! I don’t super mind the cold but my hub is not a fan (even though we both love nature/mountains). Might not be able to convince him lol.
Marilyn - funny to see the weather contrasts between MO & San Diego! I’ve seen San Diego listed as “best weather in the USA”!
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WE live at 9200 feet, so we’re used to cold winters. Every year at about the end of February I start dreaming of places like San Miguel de Allende in Mexico, or maybe Valencia, Spain.
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LOL - Last night I thought “I should have used San Diego as an example - everybody likes it there”.
Another format chart from Weatherspark… quite appealing
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We started looking at the chart that shows how much time a place is “oppressive.” We’ve decided against moving to some places based on that.
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One person’s “oppressive” is another person’s treasure. I can’t stand cold weather (big no to Montana from me) but I don’t mind heat and humidity. Florida would actually be pretty ok weather wise for me if it weren’t Florida. I prefer heat and humidity to dry heat too. I find the desert Southwest a little bleak and oppressive but can handle the Southeast just fine.
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that’s true @Sweetgum. Friends of ours recently moved to Florida which is a non starter for us (weather is one factor, but we are not hot weather folks). We will be relocating to Minneapolis next year and they think we are nuts!
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