Explore Florida’s Cutest Small Cities On This Affordable Train Adventure
If you think you’ve seen all that Florida has to offer, try exploring it by train instead of car.
Brightline and Amtrak routes weave through small cities that most travelers drive past without noticing — places full of historic streets, cozy downtowns, waterfront charm, and surprisingly affordable local eats.
Last summer, I ditched my car keys, skipped the highway traffic, and boarded a train to see what these communities were really like.
The result? One of the most relaxing, budget-friendly trips I’ve ever taken in the Sunshine State.
Below is everything you need to know if you’re planning your own Florida train adventure — including which towns to visit, what to eat, where to walk, and how to make the most of each stop.
A Scenic Route That Makes Florida Feel Brand New
Riding through Florida by train feels completely different from driving.
You’re not stuck behind brake lights or trying to merge across six lanes of traffic.
Instead, you glide past moss-covered oak trees, quiet neighborhoods, silver-sparkling rivers, and stretches of farmland that look nothing like the busy coastal cities Florida is known for.
Brightline connects major stops like Miami, Aventura, Fort Lauderdale, Boca Raton, West Palm Beach, and Orlando, while Amtrak’s Silver Service line rolls straight into some of the state’s most charming small towns — places like DeLand, Sanford, Winter Park, Kissimmee, and Winter Haven, each offering its own little world to explore just steps from the station.
As the train moves, you watch Florida unfold scene by scene: rows of palm trees, tiny towns with old water towers, wetlands glowing green in the sun, and quiet marshes that seem untouched by time.
Traveling by rail turns the journey itself into part of the adventure — a moving window into parts of Florida most drivers never notice.
And best of all, you arrive refreshed instead of stressed.
Small-Town Stops Packed With Big Personality
DeLand was the first town that made me stop, wander, and think, “Why don’t more people come here?”
Tree-lined streets stretch past vintage lamps and brick storefronts, creating a setting that feels cozy and creative at the same time.
Antique shops fill entire blocks, murals brighten old walls, and cafés buzz with students from nearby Stetson University.
Then there’s Mount Dora, one of Florida’s most charming small cities.
Although you reach it with a quick rideshare from the nearest train stop, the detour is worth it.
With a lakeside promenade, weekend festivals, and independent boutiques, it feels like the set of a quaint movie.
Street musicians perform on corners, and almost every shop offers something handmade.
These towns prove that Florida isn’t just beaches and theme parks.
It’s the little pockets of community life — where locals greet you with a smile, and every corner reveals something quietly magical.
Charming Downtowns Perfect For Budget Travelers
If you love exploring without overspending, these downtowns are perfect.
Many offer free walking tours led by local volunteers who genuinely want to share their town’s stories.
You’ll find tree-shaded parks that are ideal for picnics, historic courthouses that look straight out of another era, and galleries that let you browse with no pressure to buy anything.
Window shopping is half the fun.
You’ll see hand-poured candles, vintage records, thrifted outfits, and artwork from local creators — all at prices far more reasonable than big-city boutiques.
Most towns hold free concerts in their central parks or gazebos, where families spread blankets and enjoy live music as the sun goes down.
And because everything is close together, you can walk everywhere instead of paying for parking or rideshares.
A $3 coffee on a shaded bench becomes an afternoon well spent, especially when you’re watching small-town life unfold like a living postcard.
Hidden Local Eats You’ll Want To Try Immediately
Forget the flashy restaurants and overpriced menus.
The best food on this train route comes from small, unpretentious places that have served locals for decades.
In Kissimmee, I found a tiny barbecue spot where the pulled pork tasted like it had simmered all morning just for me.
The owner said the recipe belonged to his grandmother, who used to cook for church fundraisers.
The entire meal cost less than a movie ticket — and tasted better, too.
Over in Winter Haven, Cuban bakeries fill the morning air with the smell of fresh pastelitos.
The pastries were so flaky and buttery that I bought several for the train ride, then bought several more “just in case.”
Family diners offer classic Southern breakfasts — eggs, grits, thick-cut bacon, and biscuits drowning in gravy — for under ten dollars.
These aren’t Instagram hotspots; they’re local favorites with generations of loyal customers.
If you ask residents where to eat, they’re more than happy to send you to hidden gems you’d never find on your own.
Historic Streets That Tell Florida’s Story
Some of Florida’s oldest towns are located along these train routes, and their streets still carry traces of the past.
In Sanford, historic buildings from the late 1800s stand proudly along brick-paved streets.
Many were built during the era of steamships and citrus barons, and today they hold shops, breweries, and coffee houses that preserve the city’s heritage.
St. Cloud, founded as a retirement community for Civil War veterans, maintains its frontier charm.
You’ll spot wooden storefronts, preserved homes from the early 1900s, and courthouses that survived hurricanes long before modern construction methods existed.
History in these towns isn’t hidden behind glass — it’s alive in the architecture, quietly woven into everyday life.
Simply walking these streets becomes a mini time-travel experience.
Cozy Coastal Corners Made For Slow Travel
Not all of these towns sit deep inland.
Some of the most peaceful stops are found right along Florida’s waterways.
Stuart, often called the “Sailfish Capital of the World,” offers a quiet waterfront dotted with benches and shaded paths.
Pelicans glide past boats drifting lazily down the river. It feels like the Florida of another era — slow, gentle, and deeply relaxing.
In New Smyrna Beach, the train drops you close enough to reach the coast with a quick rideshare.
Once there, you can wander from boutique-filled streets to sandy shores in minutes.
Surfers bob in the waves, families build sandcastles, and the entire town moves at a pace that encourages you to slow down, breathe, and simply enjoy being present.
What struck me most was how peaceful and affordable these coastal pockets are compared to Florida’s larger beach destinations.
Nature Spots Just Steps From The Train Tracks
One of the most surprising parts of this trip was discovering how close nature is to many train stops.
From the DeLand station, you can walk or take a very short ride to Blue Spring State Park, a gathering spot for manatees whenever the weather cools.
The water remains a steady 72 degrees, drawing dozens of gentle giants each winter.
Watching them glide through the spring is something you’ll never forget.
Other towns offer boardwalks through wetlands, birdwatching trails, and preserves filled with wildlife. Lake Monroe, near Sanford, features beautiful shoreline paths where you can spot herons, alligators, and turtles.
No car needed — just comfortable shoes and a bit of curiosity.
Affordable Activities Worth Every Penny
Museums in these small towns usually cost around five dollars — not fifty — yet many offer surprisingly rich exhibits about Florida’s quirky past.
I visited a citrus museum that showed how oranges shaped the state’s entire economy, complete with vintage packing tools, historic photos, and hands-on displays that kept kids busy while adults geeked out over old agriculture equipment.
Farmers markets are another highlight.
Rows of tables overflow with local produce, handmade crafts, and live music that turns an ordinary morning into a mini festival without the festival prices.
If you feel like getting on the water, kayak rentals average about twenty dollars for two hours, and you might even spot dolphins cruising alongside you.
Historic home tours, community-run cooking classes, and low-cost sunset cruises round out the experience — all far cheaper than anything you’d find in Florida’s big tourist hubs.
The best part? These activities connect you with real Florida culture.
You’re supporting family businesses, learning local traditions, and creating memories that don’t involve long lines, overpriced tickets, or crowded theme parks.
Why This Train Trip Belongs On Your Florida Bucket List
After years of Florida road trips that left me tired, stuck in traffic, or hopelessly circling for parking, this train journey reminded me what travel is supposed to feel like.
Relaxed. Spontaneous. Full of genuine local moments.
You’ll meet business owners who actually talk to you, residents who love their town enough to share its secrets, and communities that feel far removed from the commercial rush of Florida’s biggest attractions.
And the affordability is unbeatable.
Train tickets cost far less than gas, tolls, or rental cars, and once you arrive, you can enjoy entire afternoons of fun for just a few dollars — or nothing at all.
This trip reshapes how you see Florida. It’s slower. Softer. More authentic. And absolutely worth adding to your travel plans.