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10 Funky Towns in Florida for Retirement

Category: Best Retirement Towns and States

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.

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!).



The funky towns of Florida
Some of these towns are very small, probably too small for many people’s tastes. But even if their size is a problem, they are interesting enough to be worth a visit while you are exploring Florida. Note that we have arranged these towns by geographic area for your convenience. The 10 in this article are in the Panhandle, West Coast, and Central Florida. In a followup article we will list some more beyond this original ten in the Southern and Eastern portions of the Sunshine State. Our definition of Central Florida is pretty broad; it includes basically any place not too far north or south that is more than 25 miles from the coast. Although these are numbered, that does not represent any attempt at ranking them. We are indebted to several native (or almost native) Floridians for their suggestions for this article: Ann Morrow and her husband Don, David Moynahan, Jeff Chanton, and Susan Cerulean. You might enjoy “Scenic Driving in Florida” by Jan Godown, which was very helpful. Most of the photos here are courtesy of Wikipedia, especially ebyabe, who contributed an astonishing number of them including DeFuniak Springs, Micanopy, and Sopchoppy.

Big Bend/Panhandle

Historic home in Defuniak Springs (Wikipedia)

Historic home in DeFuniak Springs (Wikipedia)

1. DeFuniak Springs, population 5,000, was established as a final-destination resort with the cooperation and aid of the Chautauqua Movement. The Chautauqua Hall of Brotherhood, an auditorium seating 4,000, was constructed on Lake DeFuniak in the center of town. It also contains various other historically significant landmarks such as the Walton County Library on Circle Drive, the oldest extant library in the state of Florida.

2. Cedar Key is about fifty miles south of Gainesville. This small and easygoing fishing village is one of the oldest ports in the state and a classic supplier of seafood. This charming village has historic streets and back bayous teeming with wildlife and gorgeous views. John Muir, founder of the Sierra Club spent a winter here after walking 1,000 miles from Indiana. There are 30 historic buildings in this town of 700, yet residents get around in golf carts.

Sopchoppy Gymnasium

Sopchoppy Gymnasium

3. Sopchoppy. Ochlockonee River State Park is nearby this small village of 465. To encourage people to settle here the railroad had a significant advertising campaign that exaggerated the quality of the soil and climate. Funky – yes: The town is home to the annual Worm Grunting Festival, a town celebration named in honor of a worm grunting — also known as worm charming — a method for driving worms to the surface for use as fishing bait.

West coast – north
4. Dunedin is one of the larger towns on this list. This old sailing port of about 36,000 enjoys a spectacular setting on the west coast of Florida, just above Clearwater. Dunedin (pronounced da-need’-in) boasts at least a mile of unobstructed views of Gulf beaches including those on Honeymoon Island and Caladesi Island State Park. The latter was named the best public beach in America. Its downtown is quaint but prosperous.

5. Dunnellon is located in north central Florida between Spring Hill and Ocala (it is part of the Ocala Metro area). It’s slogan is the “Treasure of the Nature Coast”, and it welcomes visitors with small-town charm. Dunnellon is a small town (population just under 2,000) in thoroughbred horse raising country. This was once a wild boom town created by miners attracted to the area’s rich phosphate deposits.



6. Micanopy, a very pretty small town south of Gainesville, is mentioned in the Tom Petty song “A Mind with a Heart of Its Own”. Micanopy’s historic district is a popular tourist destination and is listed on the National Register of Historic Places. It contains a number of antique stores as well as a large used book store and several restaurants. The town hosts a large arts festival every autumn featuring many artists which draws in many visitors. The population is quite tiny (population 600) but has a few interesting neighborhoods.

7. High Springs Voted the “Friendliest Small Town” in Florida and claiming to be the Antique Capital of North Central Florida, High Springs is halfway between Gainesville and Lake City. The area offers delights for the nature lover such as canoeing on pristine rivers and scuba diving in crystal clear springs like those in Ichetucknee Springs State Park. There are tree-lined streets, restaurants, and the still active Priest Theater. The High Springs Opera House and Train Depot Museum are more highlights.

Dog parade in DeLand (Wikipedia and Mwanner)

Dog parade in DeLand (Wikipedia and Mwanner)

8. Deland is a small town just west of Daytona Beach. It is the home of Stetson University, named after its early benefactor, the founder of the famous hat company. Stetson Univ. was the first private college in Florida. The campus is part of a National Historic District. Although the population is about 28,000 it is part of the Daytona metro which has a large population. It is the county seat of Volusia County. DeLand is justly proud of the lovely downtown area with its distinctive Mediterranean architecture.

9. Lake Placid is part of the Sebring Metro. The town has two nicknames—”Town of Murals” and “The Caladium Capital of the World.” Lake Placid has more than 40 murals painted on buildings throughout the town. Some 98 percent of the world’s caladium bulbs come from Lake Placid. Dr. Melvil Dewey, inventor of the Dewey Decimal system, founded a southern extension of the Lake Placid (NY) club here as a health resort. He was the one who suggested changing the name of the local lake to Lake Placid. Reader’s Digest named this “America’s Most Interesting Town”. The population is 1,800.

10. The 18th century utopian community of Palatka was founded by Denys Rolle (1725-1797), an English gentleman and philanthropist, who established Rollestown on the east bank of the St. Johns River at the head of deep-water navigation. His 78,000-acre plantation was a utopian commercial and humanitarian experiment, recruiting settlers off the streets of London, including paupers, vagrants, pickpockets and “penitent prostitutes.” Unfortunately the utopian community didn’t work out as planned. This relatively poor city struggles economically, but is actively working toward redevelopment of its riverfront and downtown area. The population was 10,500 in 2010, and the larger Micro Metro has over 72,000. The annual Florida Azalea Festival and the Blue Crab Festival bring in many tourists to Palatka. Several architectural styles are represented within the city: Victorian, Colonial Revival, Art Deco, Classical Revival, and Prairie School are all prominent building styles in the historical districts.

Other towns worth visiting in north Florida
These towns are worth a visit while touring, but are either very small or exist more as an area than a town. As such they would probably not make great places to retire for very many people. But we bring them to your attention as funky places you might want to visit in your explorations of Florida.

Cassadaga (a Seneca Indian word meaning “Water beneath the rocks”) is a tiny unincorporated community founded by George Colby, a trance medium, that is located in Volusia County just north of Deltona. It is especially known for having a large number of psychics and mediums, and has consequently been named the “Psychic Capital of the World”. Today, The Cassadaga Camp today features the Cassadaga Hotel, a central auditorium, The Colby Memorial Temple, a community library, the Caesar Forman Healing Center, a Camp Bookstore, and a welcome center. Also, there is the Andrew Jackson Davis Educational building, used for musical performances and gatherings.

Steinhatchee – This charming old town on the river of the same name is in the Big Bend near Perry and the coast. There are docks, seafood restaurants, fish camps, and homes. Its cedars played an integral part in the foresting industry, as well as fishing, crabbing, sponge collecting, and scalloping. Steinhatchee Falls is a local attraction. President Zachary Taylor spent time here when he was a General in the Seminole Wars.

Alligator Point is a small beach community made up of mostly beach homes and the Alligator Point Yacht Basin. Located on Florida’s “Forgotten Coast” near Appalachicola. Alligator Point is a small beach that boast mostly natural beauty without much development. Nearby attractions include Bald Point State Park and the St. Marks Wildlife Refuge. Alligator Harbor is known for its clam harvesting and was featured on Discovery Channel’s “Dirty Jobs.”

Grayton Beach This historic beach village is in the center of a 20-mile long stretch of coastal dune lakes that are so rare they are only found in Walton County and remote portions of Africa. Grayton Beach has a broad natural beach and is one of the few beaches in the Panhandle that issues permits that allow for the driving of vehicles on the pure white sand. Note that although this was an affluent village in the 1920s, it is a very small village today. It is part of the larger area of Santa Rosa Beach and Fort Walton Beach. While in the area you should visit the New Urban planned community of Seaside, one of the more successful of those.

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 2: More Funky Florida Towns to Enjoy
Florida 101: The Sunshine State is Bigger and More Diverse Than You Think

Posted by Admin on May 26th, 2015


  1. […] the tropical and bohemian paradise, are among the highest in the country. // // More Resources: Funky Towns of Florida: Part 1 (North and Central) Directory of Florida retirement towns and active communities Part 2: Best […]

    by » Florida Retirement 101: The Sunshine State is Bigger and More Diverse than You Might Think - Topretirements — May 26, 2015

  2. We’ve visited Cedar Key many times and love it! Friendly people, small mom & pop motels, artsy stores and several restaurants (Tony’s has the best clam chowder). We actually have clam chowder shipped to us at home – yes, it’s that good! We enjoy walking all through the town and enjoying water activities as well. We thought about moving there, but it’s so far from the big cities and decided it wasn’t for us. We will definitely continue to visit the area though. Admin, thanks for the list. Now we have more towns to visit while in Florida.

    by SandyM — May 27, 2015

  3. Check out Flagler Beach, south of St. Augustine. It’s “Old Florida” – on the ocean, easy to walk/bike on the sidewalks, a nice pier, no high-rises, and lots of restaurants – not upscale, and definitely funky.

    Jan Cullinane, author, The Single Woman’s Guide to Retirement

    by Jan Cullinane — May 28, 2015

  4. One of my favorite towns is White Spring, north of Lake City. It is home of the Steven Foster State Park and host the Fl Folk Festival every Memorial Day weekend. The Swannee River runs through the town, homes are quaint and people friendly.

    by JudyS — May 28, 2015

  5. You overlooked Safety Harbor, on Tampa Bay in PInellas County. It’s an unusual little town in that from the late 1950s or early 1960s until fairly recently few or no building permits were given inside the town, so it stayed pretty much the way it was 50 or 60 years ago — brick streets, small houses, “cracker” cottages, little shops and restaurants, etc. (there was one big spa that always remained more or less separate from the town). Although development occurred all around the town Safety Harbor remained an island oasis in a sea of strip centers and condos.

    When I was growing up, we used to spend winters in Safety Harbor. You could walk or ride your bike almost anywhere in complete safety, and to some extent that is still the case. Wish we hadn’t sold our property there. I like it much better than nearby Clearwater or even Dunedin.

    However, there are now some upscale shops on Safety Harbor’s Main Street, a few places to eat and drink, and the marina and pier have been redone, with expensive condos and houses along the bayfront. You often can see manatees off the pier.

    by Lan Sluder — May 28, 2015

  6. I lived in Florida from 1980 until 1997 and here are some small to medium towns and communities I recommend at least visiting.
    1. Bunnell, Fl. is just due west of Flagler Beach on hwy 100.
    2. Hawthorne, Fl. is just east of Gainesville and a stone’s throw from Cross Creek and the Marjorie Kinnan Rawlings house. Marjorie Kinnan Rawlings wrote the famous novel ‘The Yearling’ about this area and The Yearling restaurant in Cross creek first opened in 1952 and tries to capture the flavor & spirit of early 1900’s Florida.
    3.Tarpon Springs, Fl. on the west coast is a must visit destination in Florida. It’s located a few miles north of Clearwater and is an old Greek influenced town and the sponge capital of the world. The docks are a perfect place to start with shops and restaurants and boat tours.
    Also while in this area you should visit:
    4. Clearwater Beach
    5. Indian Rocks Beach
    6. Sand Key.
    7. Ybor City is a little Cuban area in Tampa but is a must see location with a Cuban heritage and restaurants that are just marvelous.
    8. New Smyrna Beach, Fl. is on the east coast just south of the Daytona area.
    You can Google any of these towns for more info on what they offer and specific directions to visit them.
    I loved Florida and plan to return there to spend the rest of my retirement days!

    by Phil R. — May 28, 2015

  7. […] 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 […]

    by » Part 2: More Funky Places to Retire in Florida - Topretirements — June 5, 2015

  8. I didn’t see any funky towns listed in Miami-Dade, Broward or Palm Beach Counties. But one town that could qualify might be Lake Worth. Its downtown is not exactly upscale (which makes it funky), but has good, comfortable restaurants that are generally affordable. There are also a number of “funky” stores and boutiques, as well as some galleries and a good live theatre venue.

    The beach area has a long wooden fishing pier open to pedestrians. The city is working on downtown improvements, but whether it becomes another Asheville is not clear, though not out of the question.

    by Clyde — December 30, 2016

  9. Decided to check Dunedin out to see what a funky town was about. We were lucky enough to visit while there was an arts festival happening, the town was very walkable and friendly and we were glad we stopped. Another town we visited just south of Dunedin was Gulfport which I think was pretty funky. It is small but had a beach and a small but walkable town. The Gulfport Casino is a large ballroom at the beach that is very popular for swing dancing from what I could gather but I was there during the day and it is probably a lot more lively at night.

    by Hatty — March 1, 2018

  10. Thanks for the information. We just bought a second Home in Maitland ( our daughter lives there) and this gives me some places to explore nearby.

    by Brooks — June 20, 2018

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