Trips & Routes

Small Towns

Trips & Routes
Small Towns

The Charming Florida Town Locals Hope Stays Off Tourists’ Radar

Located on scenic Gasparilla Island, Boca Grande, Florida, remains one of the state’s most relaxing coastal escapes for travelers hoping to avoid the crowds.

by Megan Todaro
on Mar 14
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Trips & Routes

4 Small Towns in Florida So Dreamy, You’ll Swear You’ve Seen Them on TV

by Mariana Zapata Herrera
on Jan 13
Pristine spring in central Florida
Trips & Routes

Discover the Americana Town in Florida So Charming You’ll Want to Keep It a Secret

by Melanie Johnson
on Nov 6
Several shrimping and fishing boats docked at the bay in Apalachicola, FL
Trips & Routes

This Tiny Town in Florida Feels Like a Living Time Capsule

by Megan Todaro
on Apr 3
View of downtown Micanopy, FL, with a street lined with palm trees, oak trees draped with Spanish moss, and historic buildings with cars parked outside.
Trips & Routes

Greetings From Destin, Florida: The Best of the Beach Town I’ve Loved for 25+ Years

by Kelly Carroll
on Apr 13
Okaloosa beach city sign for Harbor Boardwalk Pirate's Alley on sunny winter day in Florida panhandle Gulf of mexico

Latest Small Towns

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Small Towns

This Waterfront Town Will Transport You to the European Coast — No Passport Needed

Discover why Tarpon Springs, Florida, feels like a European coastal town. From Greek sponge diving heritage to Mediterranean architecture, explore its rich cultural roots.

by Megan Todaro
on May 8
the marina of the greek town of tarpon springs, florida
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Small Towns

Why Homestead, Florida the Gateway of Everglades National Park, Is Worth a Visit in Its Own Right

Beyond the Everglades: discover the culture, history, and charm that make Homestead, Florida a destination all its own.

by Megan Todaro
on Jun 23
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Small Towns

Skip Europe This Summer: This Town in Florida Is Just as Stunning as Greece

This Florida beach town may look like it belongs on the Aegean Sea, but Alys Beach blends Grecian style with Southern charm for a truly unique stateside escape.

by Megan Todaro
on May 8
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Small Towns
Unique Trips

Dunedin, Florida: The Perfect Stay-and-Play Getaway

This charming coastal town on the Gulf has a seemingly endless number of things to do. This easy-to-plan getaway is your go-to guide for exploration.

by Megan Todaro
on Feb 28
Decorated sign on the border between Dunedin and Clearwater welcoming the city of Dunedin Pinellas County, Florida, United States
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Small Towns
Unique Trips

Resilience and Revival: Exploring Fort Myers and Bonita Springs Post-Hurricane

Discover the enduring spirit of Fort Myers and Bonita Springs, Florida, as we explore top attractions, dining, and cultural gems that showcase the region’s resilience and charm after natural disasters.

by Marisa Roman
on Jan 3
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Small Towns

Florida’s Rising Star: This Underrated City Is Ideal for Any Traveler

Englewood, Florida, has experienced much change over the last couple of years and has massive potential for any traveler looking for a quiet beachfront escape.

by Chris Dodge
on Nov 25
A bird's eye view of Englewood.
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Small Towns

The Remote Town in Florida We Simply Can’t Get Enough Of

LaBelle Florida is a lovely small town that has the natural beauty of a river town mixed with the cowboy history which creates a unique small town we love.

by Chris Dodge
on Oct 28
A man walking his horse.
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Small Towns

The Best Small Town Getaway In Florida: Best Things To Do In St. Augustine

by Megan Todaro
on Jul 18
Aerial view of a coastal town at sunset, featuring colorful buildings, a marina, and a vibrant sky.
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Small Towns

I Visited The Coastal Town Of Hobe Sound, Florida And Here Are My Favorite Stops

by Marisa Roman
on Mar 26
A sandy path leads through lush greenery to a serene beach under a clear blue sky.
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Small Towns

The Cozy Small Town in Florida That Comes Alive During the Winter

Tavernier is the perfect cozy small town in Florida to visit during winter. Come enjoy soaking up the sun and waterside fun!

by Megan Todaro
on Dec 2
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Small Towns

This Charming Community Might Just Be The Most Peaceful Place To Live In Florida

by Megan Todaro
on Nov 23
Aerial view of a beachside restaurant at sunset, with lounge chairs, umbrellas, and a calm water shoreline.
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Small Towns

7 Christmas Towns in Florida That Will Fill Your Heart With Holiday Cheer

These 7 Christmas towns in Florida are filled with holiday festivities. Come enjoy a charming holiday adventure throughout the Sunshine State.

by Megan Todaro
on Nov 11
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Small Towns

The Remote Small Town in Florida Locals Don’t Want You to Find

Visit Keaton Beach, a secluded hideaway in Florida on the coast. Known for scalloping, fishing, and relaxing, this small town has a laid-back vibe.

by Megan Todaro
on Oct 8
Butterflies fluttering around wildflowers near the coastline at Keaton Beach, FL
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Small Towns

The Small Town In Florida That Comes Alive In The Fall Season

by Rachel Pfutzenreuter
on Sep 22
A red caboose with "Withlacoochee State Trail" written on it, set against a blue sky and green grass.
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Small Towns

The Charming Small Town In Florida That’s Perfect For A Fall Day Trip

Lake City, Florida, offers a unique fall experience with its natural springs, vibrant forests, and rich historical heritage.

by Megan Todaro
on Jul 25
A rustic wooden barn surrounded by lush greenery and trees, bathed in warm golden sunlight.
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Small Towns

The Most Charming College Town In Florida Is Home To Delicious Dining, Shopping, And More

Coral Gables, Florida, is a vibrant community known for its Mediterranean Revival architecture, upscale lifestyle, and the University of Miami.

by Megan Todaro
on Aug 25
Aerial view of a modern campus surrounded by greenery and a lake, with city skyline in the background at sunset.
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Small Towns

Enjoy The Simple Life When You Visit This Tiny Rural Community In Florida

Carrabelle, Florida, is a historic coastal town known for its maritime heritage, natural beauty, and outdoor activities.

by Megan Todaro
on Aug 4
A serene waterfront scene with a wooden pier extending into calm waters, surrounded by lush greenery and a cloudy sky.
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Small Towns

A Charming And Historic Small Town In Florida, Punta Gorda Is A Natural Wonderland

Punta Gorda, Florida, is a natural wonderland with rich wildlife, historic charm, and abundant waterfront activities.

by Megan Todaro
on Jul 27
Aerial view of a coastal town with waterfront, parks, and residential areas along the shore. Clear blue water in the background.
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Small Towns

The Sweetest Town In Florida Is One Of The Most Charming Small Towns You’ll Ever Visit

Clewiston, Florida, known as America’s Sweetest Town, is famous for its sugar cane crops and annual Sugar Festival.

by Megan Todaro
on Jul 11
A gravel road winds through a misty field at sunrise, with vibrant pink and purple clouds in the sky.
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Small Towns

Here Are The 10 Most Dangerous Towns In Florida To Live In

Lists the most dangerous cities in Florida based on recent crime rate statistics.

by Victoria Winkler
on Jun 29
Colorful buildings line a palm tree-lined street, with outdoor seating and a sign for the Betsy hotel.
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Small Towns

You’d Be Surprised To Learn That Flagler Beach, Florida Is One Of The Country’s Best Coastal Towns

Flagler Beach in Florida is a charming coastal town with retro vibes, natural beauty, and various attractions.

by Megan Todaro
on Jun 14
Aerial view of a beach pier with colorful buildings and waves, surrounded by greenery and a coastal town.
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Small Towns

You Could Spend Forever Exploring This Florida Small Town, But We’ll Settle For A Weekend

Jensen Beach, Florida offers a charming small-town experience with beautiful beaches, surfing, and family-friendly activities.

by Rachel Pfutzenreuter
on Apr 23
A serene beach scene with soft sand, gentle waves, and a clear blue sky dotted with clouds.
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Small Towns

This Peaceful Florida City Feels Like a Hidden Escape (You Might Just Want to Move)

Oldsmar is a suburb of Tampa with very few full-time residents.

by Marisa Roman
on May 5
View of the long dock at R.E. Olds Park in Oldsmar, Florida
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Small Towns

Paddle Through Mangrove Tunnels, Then Dine At A Funky Eatery On This Delightful Adventure In Florida

Experience a day of kayaking through Robinson Preserve's mangrove tunnels followed by a seafood meal at The Ugly Grouper in Bradenton, Florida.

by Marisa Roman
on May 2
A wooden observation tower stands amidst lush greenery and a calm water body under a cloudy sky.
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Small Towns

Few People Realize How Much Maritime History Is Preserved In The Small Town Of Cortez, Florida

Cortez, Florida, is a historic fishing village known for its maritime history and laid-back lifestyle.

by Marisa Roman
on Jun 3
A serene waterway lined with lush greenery and boats docked along wooden piers.
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Small Towns

Straddling The Florida-Alabama Border, The Town Of Perdido Key Is One Of The Most Unique Places You’ll Ever Visit

Perdido Key, Florida, is a unique barrier island known for its pristine beaches, wildlife, and laid-back coastal community.

by Marisa Roman
on Apr 12
A wooden walkway leads through sandy dunes to a serene beach under a blue sky with scattered clouds.
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Small Towns

The Friendly Small Town In Florida That’s Perfect For A Spring Day Trip

Fernandina Beach in Florida is a historic small town perfect for a spring day trip with its rich history, local attractions, and festivals.

by Megan Todaro
on Apr 4
Aerial view of a coastal town with a river, industrial area, and historic buildings along the waterfront.
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Small Towns

The Tiny Town In Florida That’s Absolute Heaven If You Love Antiquing

Micanopy, Florida, known as the "Antique Capital of Florida," offers a rich antiquing experience with numerous shops and historic charm.

by Marisa Roman
on Mar 23
A horse-drawn carriage in front of a grand mansion, surrounded by lush greenery and people enjoying an outdoor event.
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Small Towns

Take A Lovely Day Trip To Mount Dora, A Fascinating Town In Florida

Mount Dora, a charming small town in Central Florida, offers historic sites, unique shops, and numerous festivals year-round.

by Victoria Winkler
on Mar 20
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Small Towns

This Funky Little Town In Florida Is A True Hidden Gem

Cassadaga, Florida, known as the Psychic Capital of the World, offers a unique and eclectic small-town adventure with spiritual and supernatural attractions.

by Marisa Roman
on Mar 22
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Small Towns

Here Are The 8 Most Beautiful, Charming Small Towns In Florida

Explore the charm and history of Old Florida by visiting these eight small towns.

by Victoria Winkler
on Jun 13
View of a waterfront with palm trees, a park, and a building in the foreground during sunset.
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Small Towns

Plan A Trip To This Underrated Historic Town In Florida

by Marisa Roman
on Mar 1
A vintage steam locomotive and red caboose displayed on tracks, surrounded by greenery and a cloudy sky.
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Small Towns

The Perfect New Smyrna Beach Day Trip Itinerary – Not Your Average Bucket List Episode 3

New Smyrna Beach, Florida, is a charming coastal town known for its surfer's paradise and small-town charm.

by Marisa Roman
on Feb 21
Aerial view of a beach with a jetty, cars parked along the shore, and buildings in the background under a clear sky.
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Small Towns

This Enchanting and Historic Town in Florida is the Perfect Day Trip Destination

Cedar Key is both an enchanting and historic town in Florida. Come explore this small coastal town and see what there is to do.

by Megan Todaro
on Dec 30
A red mid-century building with a large porch surrounded by oak trees draped with Spanish Moss at Cedar Key Museum State Park in Florida.
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Small Towns

This Tiny Amish Town in Florida is the Perfect Day Trip Destination

Discover Pinecraft, a charming Amish community in Florida known for homemade food, peaceful streets, and a unique day trip experience.

by Marisa Roman
on Apr 8
Horse and buggy replica from a tiny Amish community in Sarasota, Florida
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Small Towns

Few People Know This Charming Small Town In Florida Is The Halfway Point Between Jacksonville & Key West

Hobe Sound, FL, is a picturesque coastal town halfway between Jacksonville and Key West, known for its pristine beaches and natural beauty.

by Marisa Roman
on Feb 13
A scenic road lined with tall, bare trees creating a natural canopy overhead on a sunny day.
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Small Towns

This Enchanting Town In Florida Is Unlike Any Other In The World

Key Largo, the northernmost of the Florida Keys, is renowned for its stunning natural beauty, world’s largest artificial reef, and enchanting sunsets.

by Marisa Roman
on Feb 1
A sunset view over a calm lake, with people on a wooden pier and boats in the distance under a colorful sky.
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Small Towns

You Won’t Find A Soul In This Abandoned Town In Florida

by Sophia Mitrokostas
on Sep 24
Abandoned row of single-story houses along a quiet street, surrounded by lush green trees and overgrown grass.
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Small Towns

Visit These 12 Incredible Charming Small Towns in Florida, One for Each Month of the Year

Discover 12 charming small towns in Florida, each offering unique attractions for every month of the year. Start planning your trips today!

by Marisa Roman
on Dec 18
Two vacationers sitting in folding chairs on the sand shores of a beach in Florida, surrounded by two trees curved with branches.
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Small Towns

The Unassuming Town Of Cocoa Beach, Florida Is One Of America’s Best Hidden Gems For A Weekend Getaway

Cocoa Beach, Florida, is a hidden gem perfect for a weekend getaway with its surf breaks, beaches, and family-friendly activities.

by Marisa Roman
on Jan 9
A colorful pier at sunset, with restaurants and shops illuminated against a serene ocean backdrop.
Trips & Routes
Small Towns

This Friendly Town In Florida Is The Perfect Day Trip Destination

Boca Grande, Florida, is a charming and historic day trip destination known for its beaches, fishing, and relaxing atmosphere.

by Megan Todaro
on Dec 21
Aerial view of a coastal landscape with turquoise waters, sandy beaches, and a winding shoreline.
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Small Towns

15 Towns In Florida With Extremely Strange And Hilarious Names

Celebrates Florida's quirky town names with a list of amusing and unique places.

by Victoria Winkler
on Dec 27
A colorful sign reading "Welcome to Yeehaw" with a sun, dolphin, and tropical theme, surrounded by trees.
Trips & Routes
Small Towns

The Historic Town In Florida That Comes Alive During The Winter Season

Plant City, Florida, comes alive in winter due to its renowned strawberry season and the annual Florida Strawberry Festival.

by Marisa Roman
on Jan 10
A colorful water tower shaped like a strawberry, labeled "Plant City," surrounded by green fields and baseball fields.
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Small Towns

10 Up And Coming Cities In Florida Ready To Explode

Florida is home to some of the fastest-growing cities in the U.S., driven by population growth and a booming economy.

by Victoria Winkler
on Dec 22
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Small Towns

This Florida Christmas Town Is Straight Out Of A Norman Rockwell Painting

New Smyrna Beach transforms into a picturesque holiday town with festive events and activities during the Christmas season.

by Marisa Roman
on Nov 23
A festive street lined with trees adorned with lights, leading to palm trees, under a twilight sky.
Trips & Routes
Small Towns

This Charming Florida Town Transforms Into a Christmas Wonderland Each Year

Discover the enchanting Nights of Lights in St. Augustine, Florida, a top holiday destination with millions of lights, historic charm, and festive tours.

by Marisa Roman
on Oct 22
A historic hotel in St. Augustine, Florida dotted with lots of sparkling lights during the annual Christmas festival.
Trips & Routes
Small Towns

Florida Just Wouldn’t Be The Same Without These 7 Charming Small Towns

Discover charming small towns in Florida that are rich in history, hospitality, and exciting activities.

by Marisa Roman
on Oct 21
Aerial view of a coastal town with water, trees, and buildings under a blue sky with scattered clouds.
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Small Towns

10 Magical Christmas Towns in Florida to Explore This Holiday Season

Discover 10 enchanting Christmas towns in Florida that offer unique holiday celebrations and festive events.

by Victoria Winkler
on Oct 28
A beachside scene featuring a striped lamp post with a bow, surrounded by palm trees and a cloudy sky.
Trips & Routes
Small Towns

This Is The Absolute Best Town In Florida To Visit During The Halloween Season

Delray Beach transforms into a top Halloween destination with numerous festive activities for all ages.

by Marisa Roman
on Oct 12
A vintage red fire truck leads a parade down a tree-lined street with people watching.
Trips & Routes
Small Towns

20 Small Towns In Florida Where Everyone Knows Your Name

Discover some of the coolest and most historic small towns in Florida that deserve more attention.

by Victoria Winkler
on Oct 7
A street view of Dixie Theatre and nearby buildings under a cloudy sky, with palm trees lining the sidewalk.