15 favorite weekend getaways: Find the authentic and natural Florida

I’ve been planning weekend getaways in Florida for four decades. One reason I co-founded Florida Rambler with Bob Rountree was because I loved advising my friends on cool spots to go.

Now, a dozen years later, we’ve built a website with hundreds of weekend getaways. That’s a bit of a problem — it’s overwhelming, and even friends who dig through the website still ask for advice.

So this article is designed to help you make a list of weekend getaways in Florida for future adventures.

I can’t highlight them all – this article would be a book! – but I’ve selected some favorites, many of which are not on the usual “top 10 places to go in Florida.” Some of those top 10 places are truly wonderful, like Sanibel Island or Naples, and you’ll find links to Rambler’s guides to those additional destinations at the end of each geographic section.

If your favorite spot was overlooked, please use the comment box at the bottom to share it.

Weekend getaways in southeast Florida

Experience the Everglades at the last outpost – Flamingo

I fondly remember staying in Flamingo in cabins that were destroyed by both Hurricane Katrina and Wilma in 2005. Hotel-type accommodations are finally returning Nov. 1, 2023 with the debut of the new Flamingo Lodge. The lodge starts taking reservations Aug. 1.

Four lodging buildings have a mix of studio, one-bedroom, and two-bedroom units, all featuring kitchenettes, balconies, and views of Florida Bay. These buildings and a new restaurant are constructed of repurposed shipping containers. It’s not cheap; national parks never are. Rates begin at $259 for the studio. Here’s where to make reservations. 

I’ve enjoyed staying in the eco-tents at Flamingo. (To be prepared, read my story first.) I’ve also had a memorable but expensive weekend renting a houseboat there. There’s also a traditional campground here.

I like Flamingo as a weekend getaway because it is the essence of the Everglades, where we have reliably seen manatees, crocodiles, alligators, an osprey nest in the marina and flocks of gorgeous birds. I loved kayaking there and experiencing Florida Bay. Avid adventurers will want to canoe/camp to Cape Sable from Flamingo. Here’s our guide to visiting Flamingo

A closer Florida Keys destination with much to offer – Islamorada

Too many people think Key West is all there is to the Keys and drive right past the interesting destinations along the way. Islamorada is one of my favorites because there are picturesque waterfront tiki bars; my favorite kayak trip in the Keys, to the ghost-town island of Indian Key; a nice stretch of bicycling on the Florida Keys Overseas Heritage Trail, plus a well-executed and fascinating history museum, the Florida Keys History and Discover Center. You’ll read about that and more in my story on things to do in Islamorada.

Jupiter has it all: Hiking, biking, kayaking, wildlife and more

Years ago, I started going to Jupiter to paddle the Loxahatchee River in a section that is federally designated as a National Wild and Scenic River. It’s spectacular! Every time I visited, I discovered more special places – Jonathan Dickinson State Park, which has great camping, cabins, extensive hiking, history and biking; Blowing Rocks Preserve, a dramatic Atlantic beach; Riverbend Park, with excellent family biking trails, and the beautiful Jupiter Lighthouse, which you can climb for a breathtaking view. There are also great restaurants and bars, and more. You’ll find it all in my story on things to do in Jupiter.

Vero Beach is a charming beach town not overrun with development

There is just enough to do in Vero Beach to keep you stimulated and amused without making you feel like you have to do a whole lot. It is a beach town, after all, and if you don’t spend time walking on these beaches, swimming or just staring into the blue, you aren’t doing it right. I love the McKee Botantical Gardens, the historic downtown and dining at the iconic Waldo’s at the Driftwood Inn. (We liked staying at the Driftwood Inn too.) There are other beautiful spots to visit in this story on things to do in Vero Beach.

More great weekend getaways in South Florida: Delray Beach, Lower Keys, Marathon, Key Largo, Fort Pierce

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Weekend getaways in southwest Florida

Everglades City: Explore the Everglades, Ten Thousand Islands and a historic fishing town

Everglades City has seen a lot. And you can see a lot if you use it as your base for exploring this wild and wet corner of Florida. It’s a small town at the end of the road surrounded by national and state parks in all directions. We’ve stayed at both the historic Everglades Rod and Gun Club and the eco-resort The Ivey House, which arranges many kayak and other outings.

My favorite Everglades paddling trip is here, on the Turner River, and I recommend getting in a boat to see the Ten Thousand Islands. You can book a tour at the Everglades National Park headquarters here or rent kayaks to do-it-yourself and paddle to Sandfly Key. In winter, you can feast on stone crabs next to the boats that bring them in. And don’t miss the historic Smallwood Store on nearby Chokoloskee Island.

Venice: Bicycling, beaches, history, even shark teeth

We went to Venice to bicycle the Legacy Trail, one of Florida’s best paved bike trails. But we discovered so much more to do here. Our ride took us through Oscar Scherer State Park, which is a gem and an excellent place to camp. On that visit we stayed on an unspoiled barrier island – Casey Key, and enjoyed digging for shark’s teeth in the gorgeous Venice beaches.

One thing that’s special about Venice is it history: Buildings in the Venetian style line the boulevards of this carefully planned city, built in the 1920s by a railroad union seeking investments for its members. Historic Spanish Point is a lovely Bayfront spot that tells the story of Bertha Palmer, a member of a founding family. Here are five things to discover in the Venice area.

Pass-a-Grille and Fort DeSoto Park are throwbacks in time

There are hidden gems on the barrier islands on the southern end of the peninsula occupied by St. Petersburg. The Old Florida beachfront community of Pass-A-Grille has no highrises and tons of charm. From there, you have a great base for discovering all the Old Florida ambiance in St. Petersburg.

Just south of Pass-a-Grille is the award-winning Fort DeSoto County Park, an outstanding place to camp with great beaches and a historic fort. From Fort DeSoto, you can take a ferry to Egmont Key, a wild island in the mouth of the bay with a picturesque fort in ruins and lots of wildlife – birds and gopher tortoises are guaranteed.

More weekend getaways in southwest Florida: Anna Maria Island, Sanibel Island, Fort Myers Beach, Naples, Punta Gorda, Pine Island, Boca Grande, Matlacha

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Weekend getaways in Central Florida

Visit the Lake Wales Ridge for hiking, kayaking, history and small towns

An often overlooked region of Florida hugs US 27 for 150 miles between Lake Okeechobee and Orlando. It’s a ridge, the part of Florida that was above water when the rest of the state was submerged several million years ago. Its highest point is 312-foot Sugarloaf Mountain.

There are a series of small towns to explore — Sebring, Avon Park, Lake Placid, Lake Wales – and several terrific state parks and preserves —Highland Hammocks State Park,  Lake Kissimmee State Park and Kissimmee Prairie Preserve State Park – that are good for hiking and camping. We especially recommend bringing your kayaks and discovering Arbuckle Creek, which passes along the Avon Park Bombing Range, ensuring there is no development and lots of wildlife. In the region, we also love Bok Tower and Gardens. But we’ve only begun. Here’s the whole story on the Lake Wales Ridge.

Winter Garden has a great downtown built around an excellent bike trail

Living several hours away, I had not heard anything good or bad about Winter Garden. (In fact, I always got it confused with Winter Haven and Winter Park.) So I was surprised when we visited to bike the wonderful West Orange Trail what a neat spot it was.

We loved staying in the old downtown hotel, the Historic Edgewater Hotel, now a bed and breakfast, and then biking and walking everywhere. We ate well, drank well, bicycled in both directions, stopped in the Oakland Nature Preserve and browsed the museums downtown. Here’s how to have a similarly great weekend in Winter Garden.

More weekend getaways in Central Florida: Mount Dora, Winter Park

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Weekend getaways in northern Florida

For kayakers, Ocala is a terrific base for clear springs and wild rivers

If you love to paddle, this is your spot. Based in Ocala, you can experience four of Florida’s most beautiful rivers and have a good chance of seeing wildlife — from manatees to bald eagles to alligators and even wild monkeys. All four rivers are well-served by outfitters from whom you can rent gear and livery service. You also can launch your own kayaks.

Our favorite place to stay is in a cabin in Silver Springs State Park, which also has a nice campground. (You’ll have to plan ahead to get a reservation or get lucky with a cancellation.) You have the vast Ocala National Forest to explore, too, with outstanding hiking (and more camping.) Here’s a story on Ocala for kayakers.

New Smyrna Beach is one of Florida’s best little beach towns

With the long and wild Canaveral National Seashore on its southern edge, New Smyrna Beach offers extensive beachfront. The beach here is not only long, it’s also very wide. It’s walkable, bikable, drivable and great for surfing and surf fishing. You can even build a bonfire on this beach (permit required.) There are numerous natural and historic spots to explore in the vicinity.

We particularly like Ponce Inlet, with its trails, boardwalk and the stunning Ponce Inlet lighthouse, the tallest lighthouse in Florida. There’s also a great bike trail here, the boringly named but excellent East Central Regional Rail Trail. Here’s a guide to visiting New Smyrna Beach.

Near Gainesville, explore Micanopy, Cross Creek and Paynes Prairie Preserve

With a location right off I-75, it is surprising that these authentic Old Florida locales take you so far away from the modern day. This is gorgeous countryside, with sprawling live oaks decorated with moss and tree-lined country roads. We love the little town of Micanopy, founded in 1812, and especially staying at its great bed and breakfast, the Herlong Mansion. From there, it’s a short drive to Cross Creek, home of Pulitzer Prize winning author of The Yearling, whose Cracker home is now preserved as Marjorie Kinnan Rawings Historic State Park.

Also within minutes is Payne Prairie Preserve, an expansive state park where you have a chance to see wild horses and a herd of bison. Bring your bike and a pedal the scenic Gainesville-Hawthorne State Trail. Here’s a roundup on Micanopy and the region.

Amelia Island: Historic town, evocative fort, great beaches and paddling

If you love history and nature, you will find more there than you can possibly do in a weekend getaway. The Amelia Island region boasts eight state parks and a national park. There’s a walkable and appealing small historic town, Fernandina Beach.

And history! Here you can visit the oldest continually operating bar in Florida, Florida’s oldest hotel and the state’s oldest active lighthouse. Whether you hike, bike, fish, camp or enjoy beaches, you’ll find many options. Here are 11 outstanding outdoor things to do in Amelia Island.

More weekend getaways in northern Florida: Flagler Beach, Dunnellon, Tarpon Springs, St. Augustine, Cedar Key

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Weekend getaways in the Panhandle

Stay in the historic lodge at Wakulla Springs and explore a less-visited Florida

The Big Bend region of Florida is unspoiled and full of wild and natural places. It’s a long way from the most populated places in Florida, but it makes a great stopover if you driving north. We’ve stayed at the historic Wakulla Spring lodge in Wakulla Springs State Park twice separated by 20 years, and each time it was memorable.

The park, with its spring, its swimming hole, its guided boat trip and its trails, is a treasure. But there’s so much to explore here – St. Mark’s National Wildlife Refuge for birding, hiking and a scenic lighthouse; the Big Bend Scenic Byway; tiny St. Marks with its historic sites, plus good opportunity for kayaking and biking on Florida’s first rail-trail, the Tallahassee-St. Marks Historic Railroad State Trail. This story about the Big Bend Scenic Byway covers all these places and more.

Florida’s ‘canoe capitol,’ Milton is way off the beaten track

North of Pensacola, Milton is in a part of Florida where towns are scarce and rivers run clear. There are two rivers here that have long been popular with canoers and kayakers – Blackwater Creek and Coldwater Creek. The peak time for these rivers is summer, when they are filled with people on tubes enjoying the cool spring-fed waters.

This area has two eco-resorts with camping and cabins. We stayed in one, Adventures Unlimited, and heard good word-of-mouth about the other, Coldwater Gardens. We also enjoyed a rail-trail here, the Blackwater Heritage State Trail. All the details are in this story on Milton, FL.

More weekend getaways in Florida’s Panhandle: Apalachicola

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More Florida Rambler guides for planning your weekend getaways in Florida

• Florida’s best state parks
• Florida’s best bike trails
• Florida’s best kayaking
• Florida’s best historic sites
• Florida’s best camping
• Florida’s best small beach towns
• Florida’s best gardens