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Part 2: More Funky Places to Retire in Florida

Category: Best Retirement Towns and States

June 6, 2015 — This is part 2 of our series on the “Funky Towns of Florida”. Part 1 explored unusual towns of this stripe in the Northern, Central, and Western reaches of the Sunshine State. In this edition we concentrate on the Eastern and Southern regions, plus one additional town from Florida Central. As always we want to know your suggestions for more “funky Florida” towns, which we define as communities that are interesting, have potential but are perhaps a bit down at the heels, and cater to a slightly more bohemian crowd.

East Coast
Fernandina Beach is the biggest town on Amelia island at the northeastern tip of Florida. It has about 11,000 people with an average age of about 46. There is a charming downtown with an artsy feel, a bustling waterfront with shrimp boats, a working lighthouse, and many quiet neighborhoods featuring Victorian homes. There are cute shops and many interesting restaurants and bars. There is a 50 block area is listed on the National Register of Historic Places.

New Smyrna Beach New Smyrna Beach is a peaceful beach community of 23,000 located in the northern portion of Florida’s east coast. It prides itself on being a laid back coastal community, free of crowds and pollution. The city incorporates the city of Coronado Beach. New Smyrna Beach was the center of intense real estate speculation during the 1920’s; about 800 buildings from that era survive.

Indiantown, population 5,600, is part of Port St. Lucie. S. Davies Warfield, who planned on making Indiantown the southern hub of the Seaboard rail line, planned Indiantown as a model city, laying out streets and building a school, housing, and a railroad station. Warfield also built the Seminole Inn, which is now on the National Register of Historic Places. Unfortunately, the Seminole Inn is virtually all that remains of the 1920s boom. Payson Park is a top Thoroughbred racing facility.

Jensen Beach

Jensen Beach


Jensen Beach is a low key town on the Intracoastal that runs down Florida’s east coast. It is located just below St. Lucie and adjacent to much more affluent Stuart. People like the slightly funky Jensen Beach downtown for its restaurants, shops, galleries, and casual atmosphere. What is unusual about the town is the tremendous number of mobile home and RV parks that are situated right along the Intracoastal, which gives retirees a broad choice of affordable housing. There is a very big snowbird contingent here.

West Coast

St. Petersburg


St. Petersburg has long been a synonym for retirement community, which does not tell the real story. This city on a long peninsula has a lot going for it. For one, it has a bustling, big city downtown with thriving businesses and lots to do. For another, it’s a peninsula with beaches and water just about everywhere. Then it has many funky neighborhoods and villages, like definitely funky Gulfport and its famous dancehall Casino.
Great mural in Tarpon Springs

Great mural in Tarpon Springs


Tarpon Springs is a fascinating little town on the West Coast above Tampa and St. Pete. What makes it unique is its Greek heritage – descendants of earlier immigrants who came here for sponge gathering are still here fishing and operating Greek restaurants for tourists. Another unique feature of Tarpon Springs is that is has 2 downtowns. The main one has a nice area with shops, restaurants, and the old train station. It is charming, but a bit frayed around the edges like a funky town should be. The waterfront area a mile away offers an array of Greek restaurants and views of fishing and shrimp boats.

Boca Grande is hard to describe as funky because it is so wealthy, but it is extremely interesting. Located on Gasparilla Island on Florida’s southwest coast, it is hard to get to, which probably adds to the charm. There is the lovely old luxury resort, the Gasparilla Inn, which attracts notables like the Presidents Bush. There are beaches, quite canals, and plenty of water. The town is quite small but does have some good restaurants and high end shops.

Key West is by many people’s opinion the grandmother of all Florida funky towns, although it is less so than it used to be. Once the wealthiest city in Florida, it has created fortunes over the centuries from shipwreck treasures, turtles, sponges fishing, and cigars. Most recently its economy is based on the tourist trade and folks looking for a warm and bohemian place to spend the winter. “The Conch Republic” as it is known attracts artists, musicians, and gays – plus people of every type under the rainbow – for its relaxed atmosphere and beautiful setting among picture postcard Victorian homes.

Central Florida
In Part 1 we covered many more funky FL towns from the Central part of the state, but here is one more:

Lake Mirror


Lakeland is a larger town which has its passionate devotees. It was an important town during the Florida land boom and 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 There are plenty of lakes (hence the name!). 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. Many people think the nearby (and smaller) town of Winter Haven as offering a similar kind of experience, but it doesn’t seem to have quite the same level of funkiness that you will find in Lakeland.

Comments? Do you know some funky or interesting towns in Florida that we didn’t mention? By all means share them in the Comments section below, along with why you think they are interesting.

For further reading:
Part 1: 10 Funky Towns in Florida
Florida 101: The Sunshine State is Bigger and More Diverse Than You Think

Posted by Admin on June 5th, 2015

31 Comments »

  1. […] May 18, 2015 — When you think Florida, is your image one of a north-south string of strip malls, punctuated by boring developments full of old people? If so, you would not be alone. But we are about to show you that Florida has more than its fair share of interesting, offbeat, even funky towns – places that completely defy the stereotypes. While they might not be for everyone, they might be just the place for some boomers looking for a retirement location that matches their personality. This is Part 1 of a series; you can find even more funky FL towns in Part 2. […]

    by » 10 Funky Towns in Florida for Retirement - Topretirements — June 5, 2015

  2. Admin: I clicked on all four websites this morning and came up, each time, with “More Funky Places…”. Is there something that can be done to fix this problem? I am computer savvy, so no simple responses from well-wishers please. Thanks!

    Note from Admin: To fix this problem you need to clear your cookies/web history. Once you do this it should be fine. Sorry you had the problem.

    by ella — June 6, 2015

  3. Folks: What ever you consider for a retirement location, stay away from the City of Port St Lucie.
    The City has MASSIVE debt that is growing closer to 1 Billion. City just sold one City backed building for 13M but had around 37M invested. Big loss, more long term, debt. Another City backed business is failing and has not made latest mortgage payment.
    City has beautiful, expensive Civic Center but development around Center is a total failure. Latest owner, Chinese citizen, owes about 13M in back taxes for development property adjacent to Center. Owner has promised plans several times but nothing yet. City will probably have to take over property for back taxes. A expensive proposition. Another St Lucie mess!
    City politics is terrible. Just do search of local papers to confirm, Use Treasure Coast Newspapers.
    Better bet is Indian River County, Vero Beach and Sebastian. This is next County north of St Lucie County. Generally much less traffic and great beaches along with Sebastian Inlet for fishing, surfing, camping etc. City of Sebastian has little debt,has well run government and great park, golf and airport facilities. Beautiful waterfront with 10 restaurants and a “working waterfront” project in process.

    by ed herlihy — June 10, 2015

  4. I live in St. Pete Beach. I absolutely love it. I love being close to the beach, near Gulfport the other funky town and most importantly near a thriving revitalized St. Petersburg! It feels like a mini big urban city, but full of nice welcoming people. The new Sundial shopping area is fabulous. The Mahaffey theater has great shows, the Florida orchestra, and $5.00 parking! What city beats that! The Dali museum and the Museum of Fine Arts are wonderful. And to boot- they’re all on Tampa Bay! The sunsets are to die for and the people are the best!

    by Ellen Roux — June 10, 2015

  5. Another area South of St. Pete’s Beach is Pass-A-Grille. My family vacationed there every year for decades at Easter time. We stayed at Island’s End and have wonderful memories. My husband and I went back there last year and it still looks and feels the same as it did in the 60’s and 70’s. There are some million dollar homes a little North of P-A-G, but overall the one block downtown area is quaint and has some very nice boutiques. Love it there and the people are very friendly.

    by Jana Harrison — June 10, 2015

  6. Englewood, located a few miles south of Venice, is how old Florida used to be. With the real deal of Dearborn Street and it’s funky shops and several eclectic restaurants, wonderful Art Center, hometown theater, and beautiful views all around it’s definitely a mellow funky little gem. Then there are the 3 fab beaches, one even has free parking, lifeguard, big shower house and covered picnic tables to boot! There are really fancy neighborhoods and some just ordinary to lovely places too. Old, new and in between Englewood is just a little out of the way but doesn’t have that new busy touristy feel. It’s more like a hidden gem within 25 miles of all that Sarasota and numerous other more crowded & known places have to offer. A great place to live or vacation!

    by Dee Aller — June 10, 2015

  7. Regarding Englewood………Shhhhhhhhhhhhhhh, don’t let any more people know about it!!!!

    by Donna D — June 10, 2015

  8. Am no Florida expert and have only made a few trips in the last few years, but like Indian Rocks Beach and agree that Pass A Grille is an interesting Old Florida town. May never live there as am cool on being too close to the gulf and hurricane threat. Fla is nice for the beach and a winter break

    by Jeff — June 10, 2015

  9. From Ray:
    How about Dunedin Fl?

    by Admin — June 10, 2015

  10. Florida communities are much discussed here, but according to a story published by USA Today “The Best Place to Retire Isn’t Florida”. Bankrate.com published a survey with their top 10 list. The Phoenix metro area is no. 1–in fact, three of the ten are Arizona cities. Cape Coral, FL makes the cut at no. 9. The 10 worst places are also listed, NYC is no. 1. Here’s the full story:
    http://www.usatoday.com/story/money/2015/06/08/bankrate-best-cities-to-retire/28481565/

    by Celecel — June 11, 2015

  11. Why let some magazine or poll decide what is the best place to retire? In my view, the best place to retire is what works for you. Not everyone likes the same things. Phoenix didn’t work for me and I’ve spent a lot of time there–my son and my grandchildren and many of my relatives live there. I wanted to be on the water.

    by Linda — June 11, 2015

  12. William sent in this question:

    Query: I understand that Pinellas County has its own transit system so a retiree in St. Pete can take a bus to Clearwater and Dunedin. But what if a retiree in St. Pete wants to take public transit from St. Pete or Clearwater to Tampa on a daily or 3X a week basis? What public transit is available for a non-driver between St. Pete, Clearwater and Tampa and how frequent is the service? Thanks!

    by Admin — June 12, 2015

  13. I don’t think any of the above suggestions are “funky”. I am disappointed.

    by Karen — June 17, 2015

  14. somebody please tell me the definition of “funky”. I would imagine different people have different opinions.

    by Robert — June 18, 2015

  15. From Editor:
    Here is how we tried to define funky in Part 1 of this series (open to interpretation!):

    First of all let’s define what we mean by funky (and we realize you might have a different interpretation). We think of a funky retirement town as one that has good bones – an interesting downtown or layout – often because it was a wealthy or prosperous town in a past era. It should have some interesting restaurants, cafes, shops. It especially should have some colorful folks living there, the more local characters the better. It might a little run-down and perhaps a bit bohemian. And it should offer the tantalizing prospect that a big comeback right might be just around the corner, that maybe with a little luck it could be the next Asheville! Note that dictionaries like Merriam-Websters have different definitions of funky: an earthy unsophisticated style/feeling (especially some music), odd or quaint, unconventionally stylish, even having an odor (we promise the towns listed here don’t smell!).

    by Admin — June 18, 2015

  16. William: To help you with your question regarding transportation between Pinellas and Hillsborough Counties, please refer to this website. It is for the Tampa Bay Area Regional Transportation Authority. I hope it helps. http://www.tbarta.com/en/
    However, I will say that this area has been very adverse to additional taxes to pay for any type of light rail transportation system. This metropolitan area is the largest in the country without some type of comprehensive mass transit system (although TBARTA is trying), which is especially noticeable due to the lack of a light rail system.

    by Steve — June 26, 2015

  17. To those of you who are thinking of these funky places in Pinellas County, ie. Dunedin, Safety Harbor, Gulfport, Tarpon Springs, etc., etc. as quiet little towns in which to retire, please understand that while these are all small towns and do meet the “funky” litmus test, they are all part of a very densely populated metropolitan area. It is the 6th most populace county in the state at just under 1 million, and it is the second smallest in land area in the state. This makes for the most densely populated county in the state by far. It’s hard to turn around without bumping into someone. All of the towns border the next town as there are 24 municipalities in this small area. It is difficult to know when you have left one town and entered the other. I have lived in Pinellas County since 1957 and can attest to the fact that it is officially “overgrown”. I will not deny its beautiful beaches, or the ability to enjoy outdoor activities 52 weeks a year (except when a hurricane blows through), or a plethora of cultural outlets, or the beautiful parks that have been saved from the developers. The area has its benefits, but don’t expect to find any sleepy little funky towns here; they just don’t exist.

    by Steve — June 26, 2015

  18. We just came back from two weeks on the North Atlantic Coast. We looked at the area from Amelia Island to New Smyrna Beach. We liked Ormond Beach (Halifax Plantation) but we love Amelia Island/Fernandina Beach. Great downtown on the marina; wonderful restaurants and shops. Good beaches. On the pricey side, if you want to live “on the island”, $400K+. Good communities on the mainland, about 15-20 minutes away. Amelia National and North Hampton appealed to us the most.. We found good houses with water/golf views for $320-$390K. We’ll be focusing our search here.

    by Richard — October 20, 2015

  19. In my teaching career the term “funk(y)” was always fun to banter around with high schoolers. Of course if you don’t throw in James Brown’s music style the conversation would go to “getting stoned”! As an old hipster I relish my strut along Florida’s panhandle – 30a – in Walton County. The 26 mile paved path gets me to fun and frolic in a straw brim and dark shades. Uhhh, ain’t it funky now!?!? Good gawd!!!

    by Gregory — June 1, 2016

  20. In response to: Celecil. Cape Coral may be in the top 10 destinations in the country to retire; I’m not sure why it even qualified for that. But, it is definitely not a “funky” town by any stretch of the imagination. It is very large, a development city, and has little to offer beyond being a bedroom community.

    by Kathleen — December 29, 2016

  21. Having spent some time in Cape Coral and used a lot of that to consider it as a second home, I really can’t agree with Kathleen’s assessment. Large (or rather sprawling) yes. Highly developed, yes (surpise, surprise, South Florida!). Odd? Certainly. Consider a city built of interconnecting canals where most back yards have a dock. Consider a significant number of restaurants overlooking some part of an ocean/swamp and ranging from swank to casual (with the best sunsets around). Consider small bordering communities like Matlacha (MAT-la-shay) or the very different Pine Island for which “funky” is a barely adequate description. Go north a bit, east to Fr. Myers and you’ll find more “normal” environments. Some great opportunities for coastal waterway enjoyment. As for “bedroom community”, I suppose. More likely a retirement or vacation community.

    And yes, there are problems. Traffic — with only two major ways in/out, best to plan to stay awhile. Ripe for hurricane damage — better believe it. Economic issues — yes. Once badly over-built (or planned for overbuilding) there are a goodly number of repos and declining properties. Do your due diligence before commiting. But abslolutely no reason not to go down and enjoy a nice time relaxing or exploring.

    by Rich — December 30, 2016

  22. @Kathleen: Sorry you dislike Cape Coral. The reason it makes everybody’s top ten lists is that we have over 400 miles of canals. It’s a boating community. You can live on the water without paying a fortune to be gulf front. We also have a lovely beach. Very friendly people. And some funky spots.

    by Linda — December 30, 2016

  23. Anyone able to talk about Delray Beach.

    by Gary Luebbers — December 31, 2016

  24. Don’t know if Delray Beach is considered a Funky Town or not, but one way to find information about a town and state would be to go to the home page and find “Retirement Towns by State”. There you will find general info on the state and more specific info on the town and any communities you may be interested in. You can also check out the Forum under Delray Beach FL and post any questions you may have. There is also a “search” box where you can enter Delray Beach for any additional information on the site.
    Hope this helps!!

    by Moderator Flo — December 31, 2016

  25. Fernandina Beach which is reviewed below is a great example of a funky Florida town.

    by Staci — January 1, 2017

  26. I don’t think this is the right place to post this but I don’t know where else??
    Does anyone know where on the West coast of Florida we can find retirement areas where there would be a good amount of retired New York City Firefighters? My husband is one and I think we would have a lot in common?

    by Virginia — January 1, 2017

  27. This is a reply for both Virginia and Gary Luebbers. I’ve lived in the Deleay Beach/Boca Raton area for 25 years. The majority of transplants here are from the New York and New England areas. In fact we have New York City Firefighters march in our Delray Beach St Patrick’s Day parade. I’ve met many retired police force members from New York and also some Firefighters. Gary, I don’t know what you would like to know about Delray, but I’d be glad to answer your questions.

    by Laura — January 2, 2017

  28. Delray Beach is a bit too upscale to probably fit into the funky category. It has been involved in a successful downtown development plan for more than twenty years now and that has made the two miles of the main street, Atlantic Avenue, that run to the beach a very happening place with many restaurants from moderate-priced to high end, many with sidewalk eating areas. There are a good number of boutique-style stores and art galleries. That said, it doesn’t have (fortunately) the ultra-luxe feel of a Palm Beach, nor the attitude that goes with that. There are still stores downtown like a pharmacy, office supply, etc. The business district is highly walkable with a busy, but laid-back vibe. There are several blocks where the trees have formed a nice canopy.

    by Clyde — January 2, 2017

  29. Hi Virginia
    I would try posting your question to the Florida forum in the areas you’re interested in. You could also try the search box, although I’m not sure what you’ll find. Check back here to see if Admin has any further suggestions.
    Thanks!!

    by Moderator Flo — January 2, 2017

  30. Thank you Laura and Flo

    by Virginia — January 2, 2017

  31. Thank you to all who have posted opinions and to this website, Funky Places To Retire In Florida. How lucky I am to have stumbled upon this wonderful site. All of the information has has been extremely helpful, fun and easy to access.
    Sincerely, Coral W.

    by Coral — November 27, 2018

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