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Where to settle after retirement?

Former Chicagoan, 60, living in Miami for last 35 years. Can never live in cold weather again. FL is low tax but other costs can be high, like insurance. No big rush to leave where we are, but would probably pick some nice college town in the SE like Asheville or Raleigh NC, but there are a lot to choose from. I have family in S. AL near Fairhope, it's also very nice. We have friends who have retired to AZ, NC and CO. I thought Chicagoans have to retire to Branson, MO?
 
My dad retired to Florida; I'm thinking maybe in the early nineties. Died there this year. Florida in the winter is OK. Florida in the summer is a nightmare. Florida year 'round is not my cup of tea, for the most part. I know I won't be retiring there.

The old Scotsman loved it, though.
 
I would make a list of the factors that are important to you and put them in a spreadsheet. There are all kinds of lists of retirement destinations online, but I don't know how objective they are.

One consideration we have is to live within a reasonable distance of a major airport. You may fall in love with Salt Pork, West Virgina, but not if it takes three flights and a goat ride to get there...
 
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I had some ideas about the Olympic Peninsula in Washington State, but that area does not meet your requirement about being close to a city the size you are wanting to be near. It would be an amazing ferry ride though.

-Mike
 
I would make a list of the factors that are important to you and put them in a spreadsheet. There are all kinds of lists of retirement destinations online, but I don't know how objective they are.

The problem with doing that is how do you weight each factor without it being an exercise is applying weights to get the answer you want to?
 
Honestly: the small townships and areas around Eminence Ky sound perfect for ya. Warm most times of the year. 20 -30 minutes from shopping. 45 minutes from Louisville Ky. There's a ton of nice houses and small mom and pop shops around it. A renaissance faire in the summer.
 
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One consideration we have is to live within a reasonable distance of a major airport. You may fall in love with Salt Pork, West Virgina, but not if it takes three flights and a goat ride to get there...

Good point. My parents retired to Tucson AZ, which has a very nice (albeit small) airport...but it's nearly impossible to get a direct flight from the east coast to Tucson! Unless we're willing to pay exorbitant rates, every flight involves a transfer/layover in Phoenix or Dallas or Chicago... (yeah, I know, First World Problems)
 
Honestly: the small townships and areas around Eminence Ky sound perfect for ya. Warm most times of the year. 20 -30 minutes from shopping. 45 minutes from Louisville Ky. There's a ton of nice houses and small mom and pop shops around it. A renaissance faire in the summer.

Kentucky has a lot going for it. I spent a summer in the Mammoth Caves area, and it was very, very nice.
 
I retired about a year and a half ago. Looked into moving to a warmer area. Problem is the better the year round weather the more expensive the COL is.

Looked at some places in the South, but truth is I'm not enamored of the southern culture, or at least my interpretation of it.

Ended up staying in Lincoln.

Reasons:
1: COL isn't that bad. More expensive than other places, less so than many others.
2: Quality, quantity, price of golf. To me this is important.
3: Music. Many places to hear original bands, cover bands, touring bands, orchestra, symphony. Has had a very active music scene for over 30 years.
4: Housing. Used to own the big house and everything that goes with it. Hated it. Now I rent a two bedroom in a fourplex for less than friends and family pay for half the space back east.
5: Pay no state taxes on my retirement money.
6: UNL. The university kinda dominates the state, but not the only state where that happens.
7: Nebraska consists of Lincoln, Omaha, and Who Cares. Once you get out of the two cities it's very rural, very conservative. But since I retired I never have to go there, so doesn't matter.
8: Access to shopping. About every store you can imagine is here.
9: Food. Many good to excellent restaurants. Every type imaginable. From vegan/vegetarian to steak & potatoes. From almost every nationality you want. Grocery stores. Within 2 or 3 miles of my house I have three Hyvee, Trader Joe's, Whole Foods, natural/health food/vege/local stores. Plus a bunch more grocers I never use.
10: Bike and running paths. Lincoln has spent a lot of time and money creating them. Soon the trail will run all the way from Lincoln to Omaha.
11: Transportation. Two airports. I 80 runs through it east to west, I 29 runs north and south. Kansas City less than 250 miles away. Denver, Chicago, St Louis, Minneapolis, all 500 or less away.
12: Weather. I have a hard time listing this as an asset. Winters can be cold, wet, windy, lots of snow. They can be also be relatively mild, just not often. Summers tend to be hot, windy and humid.

This is why I ended up staying here even though I'm not a native Nebraskan, and as many years as I've lived here still don't count myself as a Nebraskan at all.
 
I appreciate all your replies. Sorry to be so long in returning to this thread. I've learned that if you fail to respond to a single alert from a thread you are subscribed to, then you won't receive any more alerts on that thread. That is what must have happened, and I wasn't aware I had received so many responses. Thanks. I'll read them carefully.
 
My wife and I have recruited several people to move to Durham, NC. Awesome community on so many levels. The metropolitan area consists of three smallish cities (Raleigh, Durham and Chapel Hill) and there are many smaller towns within a short drive of those three cities. It gets a little hot around this time of year, but otherwise, I haven't complained about where I live since I moved here. (I lived in Chicago from 1993-98)