Experience Florida Like a Local: The Best Ways to Discover a City Before You Move There

July 4, 2026

By

Dionne Aiken

Florida's cities each have their own personality, and one of the best ways to discover them is by experiencing them firsthand. From local 5Ks and cycling tours to festivals, farmers markets, and weekend getaways, here are some of my favorite ways to explore communities beyond the map.

When people ask me how to really get to know a city, my answer is almost never, "Drive through a few neighborhoods."

Instead, I encourage them to experience it.

One of my favorite discoveries this year has been local 5Ks. They may only be 3.1 miles long, but they have a remarkable way of introducing you to a community. You see neighborhoods you might have otherwise driven past, wave to cheering families, meet local business owners, and spend a morning alongside people who genuinely love where they live.

That's exactly how I felt during the Freedom 5K in Clermont.

Every time I'm there, I fall in love with Clermont all over again. The rolling hills, sparkling lakes, charming downtown, and welcoming community remind me that every Florida city has its own personality.

The more I explore Florida, the more I realize there are countless ways to discover a place beyond scrolling through listings or reading statistics.

Lace Up Your Running (or Walking) Shoes

You don't have to be a competitive runner to enjoy a local race.

Throughout Florida, you'll find:

5Ks and 10Ks
Charity walks
Holiday races
Sunset runs
Trail races
Marathon weekends

These events often take participants through historic districts, waterfronts, parks, and neighborhoods while bringing together hundreds or sometimes thousands of locals.

Explore on Two Wheels

Many Florida communities offer countless ways to explore on two wheels. From organized cycling events and charity rides to bike rentals, e-bikes, and electric scooters available in many downtowns, there's no shortage of opportunities to see a city from a different perspective.

Whether you're taking on Clermont's rolling hills, riding the West Orange Trail, cruising along the coast, or hopping on a scooter to explore a charming downtown, traveling at a slower pace allows you to notice the local architecture, parks, shops, public art, and neighborhoods that often go unnoticed from behind a windshield.

Paddle, Kayak, and See Florida From the Water

Some of Florida's most beautiful places aren't visible from the road.

Kayaking through crystal-clear springs, paddleboarding across quiet lakes, taking a guided boat tour like the Winter Park Scenic Boat Tour, or exploring Florida's rivers and waterways offers an entirely different perspective on the communities that surround them.

Stay Like a Local

Instead of booking a traditional hotel, consider spending a weekend in a neighborhood through a vacation rental.

Wake up where residents wake up.

Walk to the neighborhood coffee shop.

Visit the local farmers market.

Take the dog to the nearby park.

It's one of the best ways to understand what everyday life actually feels like.

Visit Festivals and Community Events

Every Florida town seems to have something worth celebrating.

Art festivals.

Food truck nights.

Wine walks.

Farmers markets.

Music festivals.

Holiday parades.

Craft fairs.

These gatherings tell you far more about a community than a demographic report ever could. They showcase the people, traditions, creativity, and small businesses that give each city its unique character.

Explore the Trails

Whether you enjoy hiking, walking, or simply being outdoors, Florida has an incredible network of nature preserves, boardwalks, state parks, and multi-use trails.

They're perfect places to slow down, observe wildlife, and see how residents spend their weekends.

Become a Tourist in Your Own State

One of the greatest gifts of living in Florida is that every weekend can become a new adventure.

I've found myself exploring places I had never visited before simply by saying yes to a race, a festival, or a recommendation from a local.

Each experience teaches me something new about the city and the people who call it home.

As a REALTOR®, these experiences help me guide my clients beyond square footage and price points. They help me understand the lifestyle each community offers, and that's often what people remember most.

Florida is filled with incredible places.

Sometimes all it takes is a pair of running shoes, a bicycle, a kayak, or an open weekend to discover your next favorite city.

Where should I explore next?