Small Old Florida towns that are charming and close to hiking, biking, kayaking and historic sites

One of the most picturesque Old Florida towns: Historic Fernandina Beach on Amelia Island.
One of the most picturesque Old Florida towns: Historic Fernandina Beach on Amelia Island. (Photo by Bonnie Gross)

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

Clear water and a pristine beach await you on a kayak trip to Atsena Otie Key.
Clear water and a pristine beach await you on a kayak trip to Atsena Otie Key just off shore from Cedar Key. (Photo by Dave Clausen.)

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 the East Coast’s biggest producer of 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:

Sebring & Avon Park: Exploring the Lake Wales Ridge

Lobby, historic Hotel Jacaranda in Avon Park
Lobby of historic Hotel Jacaranda in the Old Florida town of Avon Park. (Photo: Bonnie Gross)

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:

Brooksville: The Withlacoochee and Weeki Wachee and more

Cypress forest along Withlacoochee State Trail in the Croom Tract of Withlacoochee State Forest.
A splendid bike path passes through a cypress forest. It’s the Withlacoochee State Trail in the Croom Tract of Withlacoochee State Forest. The trail is near the Old Florida towns of Brookesville and Dunnellon. (Photo by Bonnie Gross)

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.

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.

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:

You could spend an hour just browsing all the stuff at the Grumbles Antique and Garden Shop in Dunnellon. (Photo: David Blasco)
You could spend an hour just browsing all the stuff at the Grumbles Antique and Garden Shop in Dunnellon, one of the Old Florida towns that dates to the 1880s. (Photo: David Blasco)

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

Here’s a Rambler guide to Punta Gorda.

Sunset over the Amelia River at Fernandina Beach on Amelia Island.
Sunset over the Amelia River at Fernandina Beach on Amelia Island. (Photo by Bonnie Gross)

Fernandina 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 fascinating 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.

Here’s a Rambler guide to Fernandina Beach.

Everglades City

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 mangrove islands, hike in several different state and national parks and eat stone crab in funky riverfront restaurants. Here’s a Rambler guide to Everglades City.

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.


  1. Brooksville’s best lodging: the Chinsegut Hill Retreat and Conference Center. Bonnie, you have to check out this wonderful venue with trails, cottages for rent and a gorgeous manor house that is open weekends for tours. I have stayed here several times and highly recommend it!

  2. George Martinez

    I will retire in two years, and my wife and I love to drive to all these little towns in our state. It’s gratifying to know how much we can do and see without leaving our backyard. Thank you so much for your articles. I will be following them from now on.

  3. Christy Cherry

    Thanks so much Bonnie for all of your backroad wisdom! We love exploring Florida with all of its personalities and use your suggestions often!

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