12 Small Florida Getaways That Are Perfect for a Winter Weekend
Florida in winter feels like a secret the rest of the country hasn’t figured out yet. While snow piles up elsewhere, small towns across the Sunshine State offer warm breezes, festive lights, and peaceful escapes without the summer crowds.
Whether you’re craving historic charm, Gulf Coast sunsets, or a chance to swim with manatees, these hidden gems make for the perfect quick getaway.
1. St. Augustine
America’s oldest city transforms into a glowing wonderland every winter, thanks to millions of twinkling lights draped across Spanish colonial buildings. Cooler temperatures make exploring St. George Street and the old fort way more comfortable than the sticky summer months.
Start your weekend at Castillo de San Marcos, where thick stone walls and ocean views tell stories from centuries ago. Hop on a trolley tour to cover more ground, then finish with a sunset stroll through the illuminated historic district.
The whole town feels like stepping into a postcard that came to life.
2. Mount Dora
Picture a lakeside town straight out of a storybook, complete with antique shops, cozy cafes, and festivals that pop up all winter long. Mount Dora’s downtown glows with string lights after dark, giving off serious Hallmark movie vibes without the cheesy script.
Spend Saturday browsing quirky boutiques and vintage treasures, then take a relaxing boat cruise across Lake Dora. Wind down at a wine bar or grab dinner at one of the farm-to-table spots. Everything you need is within walking distance, so you can leave your car parked and just wander.
3. Cedar Key
If you’re hunting for that old-school Florida fishing village vibe, Cedar Key delivers in spades. Winter here means fewer tourists, calmer waters, and sunsets so vivid they look Photoshopped. It’s the kind of place where the biggest decision is which seafood shack to hit next.
Kayak through the wildlife refuge in the morning when the water’s glassy and birds are everywhere. Spend the afternoon doing a clam chowder crawl—yes, that’s a thing—and sampling different recipes at waterfront spots. End your day on a porch somewhere, doing absolutely nothing, and loving every minute of it.
4. Fernandina Beach
Amelia Island’s charming downtown feels like a Victorian-era postcard, especially in December when holiday lights add extra magic to the tree-lined streets. Winter brings calm, romantic weather that’s perfect for long beach walks and outdoor dining without breaking a sweat.
Explore the historic district on foot, popping into galleries and gift shops along Centre Street. Fort Clinch State Park offers trails, history, and coastal views all in one spot.
Cap off your evening with fresh seafood at one of the waterfront restaurants where you can watch boats drift by as the sun sets over the marsh.
5. Tarpon Springs
Tarpon Springs feels like a little slice of Greece dropped onto Florida’s Gulf Coast, complete with sponge divers, baklava shops, and waterfront tavernas. Winter offers mild beach days and fewer crowds, making it ideal for a laid-back coastal escape with a Mediterranean twist.
Start your morning with flaky pastries and strong Greek coffee along the sponge docks, then watch divers bring up natural sponges the old-fashioned way. Stroll the waterfront, browsing shops filled with handmade goods and olive oils.
Head to Fred Howard Park in the afternoon for a quiet beach day where the sand stretches out like a ribbon into the bay.
6. Venice
Venice offers all the Gulf Coast charm without the tourist chaos that hits nearby Sarasota. Downtown is walkable, friendly, and dotted with local restaurants and boutiques that give off serious neighborhood vibes. Winter weather here is absolutely perfect—sunny, breezy, and just right for beach time.
Caspersen Beach is your weekend mission: it’s famous for fossilized shark teeth that wash up along the shore, so bring a small mesh bag and start hunting. After a few hours of beachcombing, head back to Main Street for dinner at one of the patio spots. The whole weekend feels easy, unhurried, and refreshingly low-key.
7. Micanopy
Micanopy is basically a time capsule wrapped in Spanish moss and tucked under ancient oaks. This tiny town near Gainesville is packed with antique shops, vintage finds, and a slow-paced energy that feels like stepping back fifty years. Winter is the best time to visit—cool enough to wander without melting.
Spend your morning treasure hunting through dusty shops filled with everything from old books to vintage furniture. In the afternoon, head to nearby Paynes Prairie Preserve for hiking and wildlife spotting—wild horses and bison roam free here. Book a cozy bed-and-breakfast for the night and soak in the quiet, moss-covered magic.
8. Apalachicola
Apalachicola sits on Florida’s Forgotten Coast, and honestly, that’s part of its charm. This historic oyster town moves at its own pace, with riverfront shops, fresh seafood joints, and a vibe that’s equal parts salty and sophisticated. Winter keeps things calm and cool, perfect for long meals and slow exploring.
Hit the oyster bars first—raw, steamed, or fried, they’re all incredible here. Stroll the riverfront district, checking out art galleries and quirky boutiques housed in old brick buildings. If you need a beach fix, nearby St. George Island is just a short drive away and offers empty stretches of white sand.
9. Seaside
Seaside and the other towns along 30A look like someone designed them specifically for Instagram, but they’re even better in person. Pastel cottages, bike paths, and sugar-white sand make for a dreamy winter escape. December brings holiday lights and parades, adding extra charm to an already picture-perfect setting.
Start your day with a sunrise bike ride along the coastal path, stopping at food trucks for breakfast tacos or fresh smoothies. Spend the afternoon on the beach, where cooler temps make it comfortable to lounge without frying. End your night with a bonfire on the sand, roasting marshmallows and watching stars come out.
10. Crystal River
Winter in Crystal River means one thing: manatees. These gentle giants flock to the warm springs when Gulf temperatures drop, making it one of the best places in the world to see them up close. The whole town is geared toward nature lovers, with paddleboard rentals, eco-tours, and waterfront tiki bars everywhere you look.
Three Sisters Springs is your main stop—snorkel or kayak alongside manatees in crystal-clear water that stays a cozy 72 degrees year-round. Afterward, grab lunch at a riverside spot and watch more manatees drift by. It’s a weekend that feels both adventurous and totally chill at the same time.
11. Key West
Sure, Key West is technically a small city, but for a winter weekend, it’s pretty much unbeatable. Everything is warm, festive, and within walking distance, from conch fritter stands to sunset celebrations at Mallory Square. The island vibe is laid-back but lively, with live music spilling out of every corner bar.
Spend Saturday wandering Duval Street, popping into quirky shops and grabbing frozen drinks along the way. Join the nightly sunset celebration where street performers, artists, and locals gather to cheer as the sun sinks into the Gulf.
Sunday can be a beach day at Fort Zachary Taylor—clear water, good snorkeling, and way fewer crowds than you’d expect.
12. Sebastian
Sebastian flies under the radar compared to its flashier neighbors, and that’s exactly why winter here feels so refreshing. This quiet Treasure Coast town offers solid surf, calm lagoon paddling, and riverfront seafood spots where the fish is so fresh it practically jumps onto your plate. No crowds, no lines, no stress.
Spend your morning surfing or bodyboarding at Sebastian Inlet, where winter swells bring some of the best waves on Florida’s east coast. In the afternoon, paddle the Indian River Lagoon and keep your eyes peeled for dolphins and manatees.
Finish your day at a waterfront restaurant, eating grouper sandwiches while the sun sets over the water.
