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Have You Planned This Year’s Best Places to Retire Road Trips

Category: Best Retirement Towns and States

September 20, 2011 — Doing a great job of finding your best place to retire is a process. This article will focus on one of the last steps in a successful best places to retire quest – exploring different communities and forming perceptions based on what it is actually like to live somewhere.

But first, here is a quick review of the steps to help you successfully find your best place to retire (see helpful resources for each at end of article):
1. Identify your location priorities. If you have a significant other, find out and discuss how those match.
2. Work on a budget, which will help narrow your search to the best places that fit you.
3. Decide on broad areas of the country to which you would consider moving.
4. Identify priority activities and lifestyles that you want to focus on.
5. Review different communities online and over the phone to narrow down the possibilities. The reviews on Topretirements can be particularly helpful on this step. The maps on our States and Communities pages identify towns we have reviewed – click on the red pin to see the name and a link to each town.

After you have completed Step 5, you are ready to graduate to Step 6, making site visits to the communities on your list. In this article we provide you with a few different scenarios on how you might handle your visits, depending on whether you intend to find your best place to retire in the western or the eastern parts of the U.S., as well as how long you can spend on your trip. This is just a sample that might or not be right for you. The best way to find your own itinerary is to get out some maps and start planning.

When planning your visits please remember our mantra – the more places you visit the smarter you will be about selecting your new home. In this market renting is a lot safer than buying, so don’t be too eager to pull the trigger until you have seen what is out there.

East Coast
Short Trip: Assuming that you live on the East Coast and can’t spend more than 2 weeks on the road, here are a few options:
The Western Mountains of the East Coast. Fly to Asheville, NC. From here you can visit a lot of towns in western NC like Murphy or Mt. Airy, eastern Tennessee like Knoxville, northern Georgia like Blue Ridge, and northwestern SC like Clemson. When planning your tour be prepared, the mountains along the Carolina/Tennessee border are forbidding, particularly in winter. Depending on your preferences, you could adapt your tour in many different directions. You will find many great towns in this region reviewed at Topretirements. Read the reviews here and then plan on visiting the ones that grab you. If you have a chance to visit some active communities along the way, even better.
Eastern Coast Carolinas. If you fly into Wilmington NC there are a lot of coastal towns you could visit in both Carolinas and even northern Virginia. Places like New Bern and Myrtle Beach should be on your list. Or, fly to Charleston and explore the Beaufort and Hilton Head Island area, which not only have many interesting towns but hundreds of active communities.
Florida. Both coasts of Florida make for a pretty easy tour because they are so linear – just keep going and you will see a lot of towns! Don’t miss Sarasota in the west and Vero Beach in the east. But you might also consider the Central Florida region since it is home to so many towns and active communities, most of which are quite inexpensive. Flying into Orlando is easy; then go out and visit Ocala (don’t miss the tour at The Villages), Winter Haven, Mount Dora, and more.
Virginia and Maryland. You can drive to a lot of places in these states. Check out towns near the Chesapeake, the Potomac, and in the western mountains.
Other places. Don’t overlook a trip to Fairhope in Alabama. Many towns and places in Kentucky or Tennessee like Maryville or Tellico Lake are worth a visit.

Western U.S.
If you only have a week or 2 to explore, you might want to fly to a central point and then explore the region in a rental car. Another option, if you are close enough to a region that you can drive to in a day or two, is to explore towns in nearby states.

Arizona. From Phoenix you could cover most of the state. Tucson, Bisbee and Green Valley are in the south; whereas Sedona, Prescott, and Flagstaff are the north.

New Mexico. Albuquerque is a good place to start because it’s in the middle, with Santa Fe up north. Down south you might enjoy looking at Ruidoso, Las Cruces, and Alamogordo. You could even visit west Texas from here.

Utah, Nevada, Texas, and Colorado. The problem with almost all of the western states is that they are so big. It is hard to explore more than one of them at a time, unless you are either driving from point A to point B and cherrypick your stops, or you visit one which has communities that abut another state. Some of Utah’s nicest retirement towns are either in the south (St. George’s) or in the north (Park City), with not much in between. Most of the Colorado towns reviewed on Topretirements are in the central or north central part of the state.
California. A huge state with plenty of nice places to retire. Many of them can be discovered driving north to south.
Oregon and Washington. Although these are big states too, it is possible to tour a lot of the best places. Medford, Bend, Olympia, Portland – there are some terrific places to retire that are also fun to visit. In Oregon most of the best places are in the western half of the state, whereas in Washington they tend to be in the northwest.
Longer Trip: Lets say you just retired and this is your first winter without the pressures of a job. What a great opportunity! Here are some recommendations:

– Line up as many Stay and Play packages as you can in active communities that interest you. These discounted packages are usually for 1 or 2 nights, but are often longer. There is usually a little selling that goes along with these visits, but that is OK because it gives you a chance to learn more and ask questions. Call the communities to get details.

– Get a short term rental (usually hard to get for less than 1 month) in a community somewhere.

– Visit your friends and relatives who have a place.

– Rent for the whole season and use that time to thoroughly explore that region. If you go online or call communities directly it is fairly easy to find rentals, but it is much harder if you wait too long.

– B & B’s and hotels are nice, but they can get to be expensive and you might tire of living out of a suitcase.

Comments: What kind of road trips have you taken, or are thinking about? Do you have suggestions on a good route or place to visit? Let your fellow members know in the Comments section below.

Our Guide to Active Adult Communities
Baby Boomers Guide to Selecting a Retirement Community
Will We Have Enough Money in Retirement
5 Reasons Why We Should Move to Another State

Posted by John Brady on September 20th, 2011


  1. This is what we are looking to do this winter. We are looking for a winter place to escape the NW Indiana winters. Our game plan is to drive to central Florida and explore the region north of Orlando. We are interested in the Mt Dora area as it looks like a nice area without the traffic and crowds, yet close enough. Was not aware of stay and play plans, but will consider it.

    by Bill Yoder — September 21, 2011

  2. John, you overlooked your home region of New England! Where else can you find more culture; better medical care; close proximity to mountains, lakes, ocean, historic cities, and picturesque towns; and the beauty of four seasons? Not to mention the fact that New Englanders seem to live longer than those who live in the South! I took my first preretirement road trip this summer to the White Mtns of NH and while I decided that it is too remote for my tastes, I cannot wait to live within a few hours so that I can enjoy mid week jaunts without the weekend traffic jams that clog the highways and small towns up there. Next year, I will explore southern NH or the Berkshires. I still have a few years before retirement, but your advice to start looking was right on! BTW, I just saw an ad for a month-long escorted group vacation to Cuenca, Equador that provides a furnished apartment for a month and some hosted activities. Will this type of vacation travel catch on?

    by Mary — September 21, 2011

  3. Hello Florida going to see the sunsine state. I hope the sun is out and fun is waiting. The north west is getting ready for gray days, we have been blessed with some great weather but that will soon change. we plan to look at the villages and Lake Aston. Anyone been there, any ideas?

    by Brad — September 21, 2011

  4. hi Brad my wife and i just came back visiting both comunities.lake ashton is one of the best i have seen. very good quality homes excelent grounts nice open floor plans .the agent Barbara wiechment was excelent. you can get a nice house about 1700sqf for 259.000 lake view.the villages are very nice also with a difrend life style .my wife do not drive so villages is maybe better for the village squares you can find anything you like and you can drive anyware on a colf car.the homes are not as good as the Ashton lake.good luck on your trip.

    by chris dedes — September 22, 2011

  5. Brad, We have been to both places and I love Lake Aston. I just didn’t like the area outside of Lake Aston. the Villages is great, but you are only going to interact with senior people. Even going to church…. So, my preference is in Ocala just Northwest of The Villages. The community is Top of The World. Nicely built, 55+ community with lots to do and you have Ocala as a town to go to. Also, SummerGlen is there and is very nice and OakRun is a bit older but has lots to offer. If you are going to The villages, do yourself a favor
    and go to the 3 communities in the Ocala area. they are all listed on this site. Top of the world and SummerGlen have 3 day programs that you can utilize. that will give you a great view of the communities. Good Luck

    by sandy — September 22, 2011

  6. :grin:We are heading out to TN and western NC, combining a fall camping trip with looking at some potential relocation spots, mainly around Knoxville or Ashville. Have some time before retirement, going to look in South Carolina, mainly around the Charleston area next spring

    by Cathy Ahern — September 22, 2011

  7. We just bought a beautiful home in the Arlington Ridge 55+ community in Leesburg, Fl. D R Horton has just taken over the community over and is really doing some great things and with just taking overing, the pricing is more than reasonable The sales person, Laura Jaret 352-702-0244, is the best. We worked together for a couple of months before I made the decision to buy comittment and believe me she was very patient and easy to work with. The ammenities can’t be beat, the location is perfect with being close to several small town, many lakes, golf courses (one of them being in Arlinton Ridge). Orlando is about 45 minutes away, The Villages less than 30 minutes, Tampa 1 1/2 hrs away, the beaches less than an hour away. Check it out, I think you will see the potential.

    by Barb Waters — September 23, 2011

  8. We are checking out Woodside Plantation in Aiken, SC. Loooks like a great place to live – a little more on the upscale side. Large development, well established. Not just for seniors, families of all ages, although probably more seniors in proportion. Charleston is a great city to visit – city itself is expensive, and at certain times of the year, humid, swampy and buggy. So keep that in mind.

    by carole — September 23, 2011

  9. If you are looking for a four season location, you need to make two trips, one in the summer and one in the winter. We visited Fairfield Glade in Crossville, TN this August are are planning to go back in January or February.

    by Gary Fitch — September 23, 2011

  10. Sandy thanks for the ideas and input on areas to look at we will try to give them a drive by on this trip. Alot to see on this go around, I will look on line too. Brad

    by Brad — September 24, 2011

  11. Hi brad,
    Barb Water mentioned Arlington Ridge – that’s another area to check out From US4 North on Hwy 27 all the way up to Leesburg there are a TON of 55+ communities. We looked at a lot of them. My husband will only look at ‘stick’ built homes – he doesn’t like the ‘tie down’ method they use on manufactured homes. so we didn’t look at mfg home communities. If that isn’t a problem to you, you will find more communities to look at and not enough time. There’s one about 1-1.5mile south of Leesburg that was VERY nice. They had their own lake and you could have a boat and LOTS of activities – I just can’t think of the name – maybe Hamilton – not sure. It was wonderful, but mfg homes so no go with my husband. Plantation is there and very nice. The area is easy access to Orlando/airport, Disney, etc. And you are in the center of the state (higher elevation) and don’t need to worry about hurricanes, just the wind and the rain from them. There is a ‘tornado alley’ North of Leesburg – so watch for that – lots of bars etc named ‘twister’ etc. – interesting

    by sandy — September 25, 2011

  12. Sandy, was it Hawthorne at Leesburg? Sounds like it. We have written a review anyway . But let me know if it is not the one you were thinking of – it sounds like a great place.

    Thanks for all your contributions – including this one!

    by Admin — September 25, 2011

  13. Yup! That’s the one. It is a great and very reasonable community. I loved it. It just didn’t have the things that my husband needed, so it was taken off our “possibility list”. We do need to live together…..

    by sandy — September 27, 2011

  14. my husband is semi retired, works about 6 months a year, I will be working 5-10 years yet depending on circumstances like health and income. I would like to retire in a area that is mostly warm, little snow and near a major airport and a military base as we are both veterans. Now we are in the middle of Nebraska which doesn’t meet any of those criteria. Any suggestions? Thanks:smile:

    by LaRee — October 26, 2011

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