Small Old Florida towns that are charming and close to hiking, biking, kayaking and historic sites
Rambling around Florida, I’ve found a few spots that I consider outstanding places to stay while enjoying areas that are rich in natural beauty and history.
When I’ve visited them, I found myself saying: “Well, I can’t do everything here; I’ll have to get back here again soon.” Some I have visited over and over. Others are on my list of places I hope to return.
Each offers a variety of activities within an hour’s drive.
As you plan your travels and outings in Florida, consider these Old Florida destinations:
Cedar Key: Out of the way, and better for it
Despite the natural beauty of its location, Florida’s second oldest town (after St. Augustine, of course) has avoided too much commercial development. Cedar Key has been named one of the 10 coolest towns in America and is often compared to a Key West a half century ago. Of all the Old Florida towns on my list, it has the most charming downtown, the longest history and the most artsy ambiance.
We loved staying in the historic hotel on the main drag, the Cedar Key Island Hotel, and as a leading producer of farmed clams, Cedar Key is a great place to eat seafood.
In the area around Cedar Key, there is an abundance of natural resources. I want to return to kayak around the nearby islands, some of which have excellent beaches. One of those islands, Atsena Otie, is a ghost town with an old cemetery and a few ruins — just the sort of place I live to explore!
It’s a top birding location and there are many hiking and biking options. And after dark, gaze at the skies: There is little light pollution here and the night sky sparkles with stars.
Resources for visiting Cedar Key:
- A Florida Rambler guide to Cedar Key.
- Kayaking to a ghost-town island, Atsena Otie
- Cedar Key Art Festival April 6-7, 2024
- Cedar Key Seafood Festival in Oct. 21-23, 2023
Lake Placid, Sebring and Avon Park: Exploring the Lake Wales Ridge
A million years ago, the only part of Florida poking out a vast ocean was a stretch of high ground in Central Florida along what is now U.S. 27. (And with rising sea levels, maybe that’s the place to invest in Florida real estate today!)
Like an island, the high ground that remains has some vegetation you won’t find elsewhere.
Florida’s Turnpike sucked most of the traffic off the old route along 27, leaving a few of these Old Florida towns intact along the Lake Wales Ridge. They’re charming, with old hotels that were once grand places to winter in Florida and are now atmospheric and affordable.
What I like best are the many park and preserves where you can hike, kayak, camp and explore. There is a funky Florida winery with colorful free-range chickens, a state park that preserves huge ancient trees and a wild and pristine creek that is safe from development because it forms of the border of an active bombing range.
We’ve been back to this area several times, and still haven’t explored it all.
Here are resources for exploring these Old Florida towns and the Lake Wales Ridge area, which contain details and many links to other places to explore:
- Lake Placid charms with clowns, caladiums, good eatin’ and great stories
- 7 fun and funky things to do in Lake Wales
- An affordable historic hotel: Jacaranda Hotel in Avon Park
- Exploring the Lake Wales Ridge
- Scenic drive through Florida’s cow country
- Ancient trees preserved in one of Florida’s first state parks, Highland Hammocks
- Terrific hiking at Tiger Creek Preserve, Babson Park
- More great hiking at Lake Wales Ridge State Forest
- Beautiful kayaking river along a bombing range: Arbuckle Creek
Brooksville: The Withlacoochee and Weeki Wachee and more
An hour north of Tampa, surrounded by beautiful rivers and forests, the Brooksville area makes a good base for exploring a part of Florida that is rural and wild.
It’s an Old Florida town with a statue of a Confederate soldier in front of its courthouse and blueberry farms in the surrounding countryside. The downtown is a walk back in time, with historic buildings and grand live oak trees.
Nearby, Chinsegut (pronounced ChinSEEgut) Hill Historic Site in Brooksville is a well-preserved pre-Civil War plantation that looks like your stereotype of the grand white-columned Gone with the Wind mansion. But that period is just one chapter in a story full of colorful characters, as the estate becomes the home in the 20th Century of suffragists and labor union activists. You can take guided tours on weekends.
The reasons I love Brooksville are many, because of all the natural features nearby: The Withlacoochee is a pristine river full of wildlife and scenery, the 46-mile-long Withlacoochee Trail is the best paved bike trails I’ve pedaled in Florida, and the quiet and shaded Dade Battlefield Historic State Park is eye-opening and thought-provoking. There’s also good hiking at Chinsegut Wildlife and Environmental Area.
Brooksville is also a good base for exploring some of Florida’s most beautiful springs: Weeki Wachee springs and river and its kitschy historic Weeki Wachee mermaid show plus, a little north of there, the Chassahowitzka River.
There’s even more. There are a few mom-and-pop motels in Brooksville, but most places to lodge are flavorless hotels along I-75. Campsites are plentiful. A great place to eat is the Florida Cracker Kitchen.
More about exploring the Brooksville area:
- Chinsegut Hill: One of Florida’s most fascinating historical sites
- April Blueberry Festival in Brooskville
- Paddling the Weeki Wachee and seeing the mermaid show.
- Withlacoochee State Trail, one of the best paved bike trails Florida
- Paddling the Withlacoochee River
- The lovely Dade Battlefield Historic State Park
- The Chaz (Chassohowitzka) River for kayaking, scenery and wildlife
Dunnellon: Two rivers plus outstanding bike trail and hiking
You’d never know it now, but the little town of Dunnellon in northwest Florida was once so prosperous that its nickname was Boomtown. Today Dunnellon’s fame – and fame probably overstates it – is as the home of the spectacular Rainbow Springs and Rainbow River. In summer, thousands of people come here every week to float down the Rainbow River on inner tubes.
But there are more things to do in Dunnellon than kayaking or tubing the Rainbow River. It’s also a great place for hiking trails in the Halpata Tastanaki Preserve and bicycling on the Withlacoochee State Trail.
For a small town, Dunellen has a surprising number of good restaurants too.
The historic town makes a good base for exploring this unspoiled region, especially in cooler months. It starts with kayaking the Rainbow, but we also recommend six more things to do.
Punta Gorda: Kayaking, biking, charming downtown
Punta Gorda is a fun little town devoted to bicycling with all sorts of hiking and birding. There is both terrific saltwater mangrove kayaking as well as one of the best paddling rivers I’ve “discovered” – Shell Creek.
Many things to do in Punta Gorda revolve around the water vistas along the wide Peace River, including parks and walking/biking paths along the waterfront, historic neighborhoods with cobbled streets and stately old homes. In winter, Punta Gorda’s calendar is full of festivals and its downtown buzzes with pedestrians on weekends.
We loved the Peace River Botanical Garden too.
Here’s a Rambler guide to 11 things to do in Punta Gorda.
Fernandina Beach: Historic plantation, fort and “Boneyard Beach”
Up in the farthest northeast corner of Florida, Fernandina Beach has all of my favorite things, from old forts to bike trails to exceptional beaches and kayaking. The historic town has one of the best traditional downtowns around, with well-preserved Victorian architecture and many places to dine.
One of the most interesting historic sites in Florida is near here — the Kingsley Plantation, which is part of a little known national park. The beautiful site tells stories of slaves and slave holders that may surprise you.
Another historic highlight is Fort Clinch State Park, which preserves a stunning landscape of sprawling oak trees and a broad beautiful beach. The fort itself is fun to visit because there are re-enactors present to bring history alive.
Big and Little Talbot Island State Parks are two adjacent state parks near Fernandina Beach offering a wealth of recreational possibilities. Little Talbot Island is one of the few remaining undeveloped barrier islands in Florida. It has five miles of white sand beaches, but also maritime forests, dunes and salt marshes.
“Boneyard Beach” here, bleached driftwood on a pristine beach, is popular with photographers.
Here’s a Rambler guide to Fernandina Beach.
Everglades City: Old fishing village for stone crabs, great paddling
Everglades City, at the end of the road on the Gulf Coast, is an outstanding place to make a base for exploring the Everglades and Ten Thousand Islands.
You can kayak what I consider the most beautiful river in the Everglades (the Turner River), paddle in the Ten Thousand Islands, hike in several different state and national parks and eat stone crab in funky riverfront restaurants.
Ten minutes away, on the island of Chokoloskee, you can visit the 1906 general store, Smallwoods Store, an exceptional slice of history in a beautiful setting. It’s listed on the National Register of Historic Places and it is still owned by the original family.
The historic fishing town hosts the very popular Everglades Seafood Festival every February.
Here’s a Rambler guide to Everglades City.
Mount Dora: Might as well be Mount Dorable
Mount Dora has a lively restored downtown and historic district that have been landscaped and beautified to maximize the inherent charm of this small town 40 minutes northwest of Orlando.
Mount Dora overlooks Lake Dora and spreads out over rolling hills under a canopy of live oak trees that have been loved and cherished by residents for years.
For kayakers, there is the exquisite nearby Mount Dora canal and within a half hour you can reach Rock Creek Run, the Wekiva River and Lake Norris and Blackwater Creek.
We brought our bikes and loved biking along the shores of Lake Dora to another cute town, Tavares.
One thing that has kept Mount Dora full of restaurants and lodging is a series of very popular festivals that bring thousands to the town. Check the festival calendar if you want to enjoy one — or avoid them!
Here’s Florida Rambler’s 12 things to love about Mount Dora.
Sanford will surprise you with beer, food & nearby biking, kayaking
I’ve seen this historic riverfront town a half hour from Orlando called a “hidden gem” or “Central Florida’s best kept secret.” When I visited recently for a long weekend, I was surprised how lively and fun Sanford is today.
There are tons of things to do in Sanford, Florida.
There’s a beautiful riverfront where you can walk or bicycle for miles. Within a half hour, there are two wild and wonderful rivers to kayak and numerous hiking trails. Sanford has a charming brick-paved downtown filled with preserved historic buildings enlivened with restaurants, breweries and bars.
The nearby residential historic district is a splendid neighborhood shaded by hundred-year-old live oaks arching over carefully restored homes where golf carts are used to buzz around town.
Here’s Florida Rambler’s 10 reasons I fell in love with Sanford.
And there’s more:
Even with this list, I haven’t exhausted the possibilities. We also recommend these outstanding destinations. Each of these Old Florida towns are the subject to a profile on Florida Rambler with things to do and places to camp or stay.
- Flagler Beach
- Winter Garden
- Delray Beach
- Fort Pierce
- St. Augustine
- Vero Beach
- Lake Wales
- Winter Park
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The author, Bonnie Gross, travels with her husband David Blasco, discovering off-the-beaten path places to hike, kayak, bike, swim and explore. Florida Rambler was founded in 2010 by Bonnie and fellow journalist Bob Rountree, two long-time Florida residents who have spent decades exploring the Florida outdoors. Their articles have been published in the Sun Sentinel, the Miami Herald, the Orlando Sentinel, The Guardian and Visit Florida.