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Discovering the Classic “Old Florida” Town for Your Retirement

Category: Best Retirement Towns and States

May 2, 2014 — In Florida’s golden days in the early 20th century a group of inspired visionaries created many graceful towns. They produced magical communities that attracted hundreds of thousands of retirees from the north. Other towns somehow became classics just because of where they were situated or their economic success in their past. Moving forward to this century, most of these towns still have the great bones that made them attractive back in the day. This article will review some of our favorite “Old Florida” towns that make great places to retire right now.

Planning pays off
Many, but not all, of the classic Florida towns we know about were carefully planned. As a result they have symmetry and plentiful public spaces that make for graceful living. Many had wealthy residents who built lovely houses and paid attention to how their town was developed. Contrast any classic town built around public squares versus one with endless strip malls and frontage roads, and the quality of life differences are obvious. Although most Florida towns have gone through boom and bust periods over the last 100 years, the careful planning that went into their development remains an asset. Their charm persists, and people are attracted to it.

A tradition of big thinkers
Florida seems to attract developers who have big dreams and plans. Chief among Florida’s developers was Henry Flagler, a sidekick of John D. Rockefeller. Flagler sunk a major part of his considerable fortune developing Florida railroads, hotels, and towns. There were many others with big plans then; the desire to create special new communities continues to this day. Witness some of the grand developments started within the last 10 to 50 years: Palm Coast (ITT developed), Seaside (the new urban community, Celebration (Disney’s planned community), Port St. Lucie, Ave Maria, Abacoa. Some of the larger active communities like The Villages, On Top of the World, and Sun City Center continue that tradition.

Classic Florida towns
Not all of Florida’s classic towns had a single genius whose careful planning made them instant favorites. Some grew organically, blessed by a seaside location or wealthy residents who cared. But what makes them classics in our book is their balance, beauty, and grace. They tend to have real streets and stores where it is a pleasure to walk around. Beautiful plantings and parks abound. And the architecture is not fake and “strip mall modern”.

Classic, “Old Florida” Towns to retire to:
Below is a list some of our favorite classic favorite towns in Florida. We could have kept going, as there are many more where these came from. See our Florida Directory for more ideas. The towns we have chosen come from all over the state: on both coasts, north and south, and Central Florida too. Many have gone through tough economic times and represent a range of urban renewal – some are still struggling, while others are so affluent only the wealthy can afford to live there. A few have a combination of classic parts and other sections that are not so nice.

Appalachicola. We love this charming little fishing village in the Panhandle. Its earlier wealth is quite apparent, and this slow-paced town seems to be doing well now too.

Fernandina Beach. Fernandina Beach is an classic old Florida town just above very affluent Amelia Island. It has a charming downtown with an artsy feel and many quiet neighborhoods featuring Victorian homes. There are cute shops and many interesting restaurants.

Englewood. There is a collection of classic old Florida towns around Englewood, a beach town on Florida’s southwest coast. While it has a lovely downtown area, just to the south is an even classier community, Boca Grande. This small island and its stately Gasparilla Inn is where old money goes to relax and play.

Gulfport . Beach Boulevard is a wide boulevard along a park that leads off to a smaller and somewhat charming district. Down this street you will find a handsome library, a quite large senior center, kitchey shops and restaurants, and at the end – The Gulfport Casino Ballroom, one of the busiest dance halls in Florida.

Key West. Back in the 1970’s Key West was on the edge of ruin. All of its extractive industries like ship salvage, turtles, and sponges were exhausted, while the cigar industry had moved to Tampa. They brought in consultants to recommend new industry. The conclusion: Key West’s supply of beautiful Victorian homes, ocean, and wonderful climate make it a natural tourist destination. The rest is history.

Lakeland. Lakeland was an important town during the Florida land boom. Many of its historic structures date from that period including the Terrace Hotel, New Florida Hotel (Regency Towers), Polk Theatre, Promenade of Lake Mirror, and the former Lakeland Public Library. Frank Lloyd Wright’s “A Child of the Sun” project for Florida Southern College is the largest one-site collection of Frank Lloyd Wright buildings in the world. (photo of Lakeland skyline courtesy of Wikipedia).

Lake Wales Lakes Wales has a beautiful Historic Corridor where you can visit the restored Rhodesbilt Arcade, The Depot Museum and The Scenic Theater. Many of these buildings are on the National Register of Historic Places. Plus you will find plenty of interesting shops and art galleries.

Mt. Dora. Here is what the New York TImes said about Mount Dora in 2011: “… tiny little vintage town with gorgeous Victorian-era homes, great restaurants and a square where they play live music.” It also raved about Mount Dora’s Live Oak trees and the Spanish Moss.

Palm Beach. Founded by Henry Flagler to provide a luxury destination for his railroad, Palm Beach proper is one of the wealthiest and prettiest communities in the world. It lies on the Atlantic Ocean just above Miami and straddles the Intercoastal Waterway. Fancy shops and elegant estates abound in the beautiful downtown. Enormous estates go along the ocean and the Intracoastal. If you spend an hour on Worth Street and don’t see 2 Rolls Royces, you are not looking hard enough.

Naples. Surrounding the walk-able downtown are beautiful residential streets, conveniently situated next to the white coral beach that goes for miles, with condominiums and homes lining much of it.

Stuart. It has a lovely downtown that is fun to walk around in, with interesting shops and restaurants in a small town feel. There is a very ample coastline thanks to the bays and ocean that surround the town. There is much to do in this community of 16,000.
Some say that Stuart is the most northerly place on the Florida Coast that is positively affected by the Gulf Stream.

Downtown Venice

Venice. Originally developed in 1925 by the Brotherhood of Locomotive Engineers as a planned retirement community, Venice is named after the many canals and rivers running through it. Thanks to its central planning, Venice is a top rated community for adults over 55. In many ways Venice is similar to Naples, except with less traffic and far lower prices. The town has wide boulevards lined with palms and banyan trees. Much of the town is in the northern Italian renaissance architectural style. The lively downtown has many interesting shops and restaurants.

Winter Park. Winter Park was the first centrally planned city in Florida. It claims it has the most parks per capita of any Florida. Several U.S. Presidents including Chester Arthur, Grover Cleveland, and Franklin D. Roosevelt visited the city.

Bottom Line
Most of Florida’s classic towns have had their ups and downs. But many of the ones that are so appealing a long time ago have the charm and features that make them great places to retire today. You can find our reviews of 100 cities and towns in our Florida Directory.

Comments? Please share your comments below. Do you have a favorite Old Florida town we should have mentioned? One we should have forgotten about out? And what are some of your favorite things about old towns, anywhere?

Further Reading:
The Wall Street Journal wrote an entertaining article on the same subject, “Finding the Old, Classic Florida“, with some of the same picks as ours. Their classic Florida is, not surprisingly, a bit more upscale.
What is the Best Place to Retire in Florida – Interior or the Coast
Sunshine State is More Diverse Than You Think (a 2 Part article)
Florida Retirement Guide

Posted by Admin on May 3rd, 2014


  1. Florida is a great place to live, wake up and it is another Saturday pack a small lunch and you can be off for another day vacation! Many places to see and enjoy, life is good. Just take time to see and do. That’s what it is all about.

    by Brad — May 4, 2014

  2. Florida taxes, insurance costs,home prices and temperatures were way to high for us. We prefer 4 seasons. Winters are mild in East Tennessee. There are no hurricanes here. We left Florida after living there for 29 years and retired to Morristown TN. Knoxville nearby with better health care than FL. No state income taxes and lower real estate taxes and home insurance.

    by Sue — May 5, 2014

  3. 😎 We have very low monthly income & find Florida not much different than anywhere else for living costs. If you don’t relocate to the ocean or Bay sides & don’t move to the upscale locations, Florida homes cost no more than anywhere else – nor does home/car insurance. Again, I would urge people to check on the history of sink holes or flooding in the area they want to visit for further consideration before ‘buying’. There is no state income tax. For sure, it’s hot & humid in the summer but if you have your own pool or go to the ‘Y’, you can usually be swimming all thru the year except for a few in January. I have no experience nor know anyone who lives in Tenn so can’t comment on the health care. They’ve gotten us thru & past cancer for each of us so … what can I say. My only gripe is what I pay for water. Just sayin’ … everyone has their own financial considerations, health issues & scenery preferences. I’d rather be in Wisconsin – yes, I know it’s cold & it snows – a lot – some years. Enjoy your life today 🙂

    by Jeanne C — May 5, 2014

  4. We plan to retire to the Tampa area. If that doesn’t work out, east Tennessee is our Plan B. We live in west Tennessee now. We definitely will not be retiring in west Tennessee. We will spend our summers in Maine, where we were both born and raised.

    by Norma — May 6, 2014

  5. To Sue – why Morristown TN?? Curious. We are also looking at Eastern Tn, I am a motorcyclist and love the Smokey Mtns – just aren’t sure where to look.
    We have a down payment (refundable)on a modular home in homosassa Fl but r still open minded to some other destinations. As Seniors we are on a very limited budget and my wife needs to be near excellent medical facilities. tks, Robert

    by Robert — May 7, 2014

  6. All these “top retirement” sites and all the comments of the people are really wonderful and informative BUT it’s like loving Ice Cream and visiting a shop with 150 different flavors/lol. I think I am getting more confused as where to live upon exiting Pa. I am not criticizing this wonderful informative site = I guess it’s just me = DUH

    by Robert — May 7, 2014

  7. Norma,
    Where a bouts in Maine will you be staying in the summertime? We have a rental camp on the west shore of Sebago Lake. Drop me a line privately if you would like more info.

    We are focusing on the Venice – Sarasota stretch on the West Coast of Florida. Would love to return to the SF Bay Area but the costs and politics are a big turn off. 🙄

    And th journey continues . . . 😆

    by Jane — May 7, 2014

  8. We lived in central FL for 32 years. Not long after moving there I made my husband promise we’d retire further north because I missed a fuller change of seasons and wanted a shorter summer. We moved last November to Sun City HH. It’s as far north as he would go. The amenities were a factor. It was a good compromise. We still have our beach condo in FL which he loves more than I.

    by MarjieW — May 7, 2014

  9. A place that’s seldom mentioned is Safety Harbor, FL, in the Tampa Bay area near Clearwater and Dunedin. Now that’s real classic old Florida!

    The reason is that for many years in the mid-20th century the town of Safety Harbor couldn’t grow like the rest of Pinellas County due to limitations on sewerage and water. So the town center and nearby stayed about the way it was in the 1950s — brick streets, small and affordable houses shaded by old live oaks, an old-fashioned Main Street, with a small marina and fishing pier on Tampa Bay. You often see manatees off the pier. Although the areas around Safety Harbor have now exploded with growth, the town itself is still low-key, even quaint.

    My family spent winters there when I was growing up, and I still revisit every year or so to see what the old Florida Gulf Coast looks like. I’ve owned houses in Safety Harbor and Dunedin, but it’s too hot there in the summer for me. I prefer Asheville and the NC mountains.

    by Lan Sluder — May 7, 2014

  10. Robert,
    The Knoxville TN area is great for retiree’s. Knoxville has University of TN Medical Center there along with other good hospitals, low property taxes, no state income tax and the Smoky Mountains right there. Great area for motorcyclist called the Dragons Lair in Smoky Mountains. Lots of small towns around Knoxville, like Marysville, Lenoir, Lake Tellico, Townsend, ect.

    by Linda — May 7, 2014

  11. We lived in Key West in the 1970’s and I disagree. It was NOT on the verge of ruin. It was a wonderful place to live and raise children with lots of affordable places to live. You could buy a house there for a few thousand dollars. There was a wonderful community of people there from all walks of life. I am still in contact with many of my old friends. Almost all of us had to move on due to the absurd cost of living now. I bought my house in 1987 for $90,000. Recently that same house sold for over a million dollars! It is horrible there now. In fact it was voted the top most ruined place to live. Do your homework about Key West.

    by Roberta — May 7, 2014

  12. Tennessee is great but not entirely true about no income tax. If part of your retirement income is from
    investments i.e., dividends and interest, you will pay 7 percent tax on it.

    by John — May 7, 2014

  13. If you don’t know what you’re looking for, any place will do. Before retiring, you should have made a list of the things that are important to you and identified towns where you might be happy. I love Sarasota. It’s like a sleepy little town in the summer and a buzzing, cultural oasis in “Season”. Culture, proximity to the water, a diverse population and opportunities for continuing education were important to me. I found my paradise. Perfect? No. But ideal for what’s important to me? Yes.

    by Ava — May 7, 2014

  14. Ava: Sarasota is on my short list. I love Siesta Key but no way can afford it. Would love to find an affordable place not that far away. Any and all suggestions would be greatly appreciated.

    by Stacey — May 7, 2014

  15. I’m curious about the cost of pool maintenance in FL, if you buy a home with a pool and one of those mosquito cages. Does anyone use a pool service (I’m finding it difficult to take care of my pool and would need to outsource the work)? Typical weekly cost? And are those cages around the pool really useful for keeping bugs out? What happens to them during a hurricane or other storm?

    by Sharon — May 8, 2014

  16. After 51 years of our combined military service, my husband and I decided to retire in Venice two years ago. It has that wonderful small town feel we both enjoy. We are close enough to the big cities without having to worry about all the negatives that come from big city life. Sure, it gets hot in the summer but you spend the hot times of the day in the pool, inside or at the beach. Our monthly pool maintainence runs $60 and is serviced every Thursday. The only downfall is all the ‘snowbirds’ who invade the area from October through April. 😯 Aside from that, I can see us staying here until I convince him to move to Ireland or England! 😆

    by Elizabeth — May 8, 2014

  17. Hi Elizabeth, myself and my better half are also relocating to Venice in August. We will be renting for 6 months to a year before buying a condo or small home. In your thoughts what do you think of the Inglewood area (close to the beach) or Nokomis beach area? And did you find it hard to get insurance on your place? I am pleases to hear you to thought Venice is a wonderful. Thank you

    by CB — May 8, 2014

  18. CB, you will not have any issues finding insurance here. I will yell you, home prices are on the rise. Englewood and Nokomis will get you more for your money than Venice. Englewood has beautiful beaches; we go there more than we do Nokomis. Come on down, the weather is FINE!

    by Elizabeth — May 8, 2014

  19. You neglected to mention Cedar Key-a wonderful off the beaten path like Key West

    by John — May 9, 2014

  20. Thank you Elizabeth, if you think of any information that you might think would be helpful I am open to any suggestion, areas communities to look at, or non ones, rentals, great restaurants to try, seafood/fruit markets, items of interest to travel/see/do.
    If I am also ask how far inland do you live from the Venice beach, and what are thoughts on leaving a few blocks from the beach. We to enjoy the Florida weather, even in the summer.

    by CB — May 9, 2014

  21. Wondering what is a nice middle class city in Florida to retire to with the following criteria:
    Near pretty water
    Middle class to upper middle class retirees
    Diverse retirees in terms of ethnicity

    by Edie — June 9, 2014

  22. […] (adsbygoogle = window.adsbygoogle ||[]).push({}); For further reading Prettiest Town in Florida Classic Old Florida Towns College Towns Make for a Great Retirement 5 Big Reasons Why Small Towns Are Great Places to Retire […]

    by » Where Are the Prettiest Places to Retire? - Topretirements — October 28, 2014

  23. Note from Editor: These comments were moved from another Blog. Some of the info Valerie is looking for are in the article and comments above:

    From Valerie: This is an extremely informative blog!We are interested in Lakes of Mt Dora 55+ community.
    Does anyone have any info or personal experience about Lakes of Mt Dora 55+ community?We have lived in south Florida for 60 years and have retired this year. Looking for a change but not out of Florida.
    From Laura: I have a friend who lives in the Lakes of Mt Dora. I have spent time staying with her many times. It is a pretty community and there are a fair amount of activities and facilities but not on a daily basis. You are also responsible for your own yard maintenance and most homes are on fairly large lots. What are your specific questions?

    by Admin — June 15, 2018

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