Last Updated October 12, 2020 10/12/2020

12 Road Trip Worthy Charming Small Towns in Florida

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While Orlando and Miami typically garner all the attention from tourists, Florida is full of charming small towns just begging to be explored. These lesser known destinations are blessed with pleasant vibes, picturesque natural beauty, and off-the-beaten-path attractions away from all the masses. Pack a bag and take a journey through Florida’s most unique small towns filled with rich history, friendly locals, and unbeatable charm.

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Santa Rosa Beach Santa Rosa Beach
Santa Rosa Beach

Santa Rosa Beach

Named one of Travel + Leisure’s Top 5 Favorite Towns in America, Santa Rosa is a luxurious beach town on Florida’s Emerald Coast. Soak in the beauty of the pristine undeveloped beach decorated with quaint beach houses and sugary white sand.

Grayton Beach Grayton Beach
Grayton Beach

Grayton Beach

A funky area with Hemingway-style wooden homes and paved streets with crushed oyster shells, Grayton beach is a small artsy town full of character with beaches that consistently rank among the most gorgeous in the US.

Apalachicola Apalachicola
Apalachicola

Apalachicola

Apalachicola Bay and nearby Port St. Joe are friendly little fishing towns affectionally known for their friendly locals and fresh seafood. Try your hand at fishing, dive for scallops, or nosh on the tastiest oysters you’ll find in Florida.

St. George Island St. George Island State Park
St. George Island State Park

St. George Island

A quiet island with 28 miles of undeveloped beaches and powdery white beach, St. George Island is one of the last unspoiled barrier islands in Florida. Avoid the crowds and soak in the beauty of this peaceful beach community.

Amelia Island Amelia Island
Amelia Island

Amelia Island

Quaint B&B’s and pristine beaches make up this tranquil northeast coast town, where beachside horseback riding and wildlife viewing are popular activities. Soak in the southern charm of the historic downtown or browse through the delightful set of shops and restaurants.

Micanopy

Micanopy

Full of rich history, Micanopy is a Florida small town favorite because of its quaint ambiance, eclectic storefronts, and antique treasures. It’s also full of natural beauty, with towering oaks and nearby Prairie Paynes Preserve.

Mount Dora Mount Dora
Mount Dora

Mount Dora

A popular small town in the Sunshine State, Mount Dora is laid-back Old Florida decorated with alluring 19th-century clapboard houses, bed and breakfast inns, and charming cafes. Stroll along the quaint downtown shops and search for valuable antiques.

Dunedin Fred Marquis Pinellas Trail
Fred Marquis Pinellas Trail

Dunedin

Known equally for their annual Scottish celebrations and charming small town vibes, Dunedin has a picturesque waterfront full of activities for the whole family. Nearby Caladesi and Honeymoon Island are also some of the best beaches you’ll find in Florida.

Safety Harbor Safety Harbor
Safety Harbor

Safety Harbor

Away from big city neighbors Tampa and St. Pete, Safety Harbor is a laid back community with an Old Florida feel. Here you’ll find scenic brick-lined streets decorated with moss covered oaks, historical landmarks, and unique bed and breakfast inns.

Gulfport Gulfport
Gulfport

Gulfport

A small town with big heart, Gulfport is the quintessential charming small town popular for their year-round events. The small independent shops and welcoming locals of this artsy Old Florida community have a way of making you feel right at home.

Anna Maria Island Anna Maria Island
Anna Maria Island

Anna Maria Island

The speed limit in Anna Maria Island doesn’t exceed 35mph, and for good reason. This quaint laid-back barrier island is 7 miles of natural beauty, where life slows down and soaking in the pristine turquoise ocean views is the #1 activity.

Sanibel Island Sanibel Island
Credit: EricRi
Sanibel Island

Sanibel Island

Famous for the world-class shelling, Sanibel Island also offers stunning sunsets and a charismatic community devoid of fast food restaurants, street lights, and city noise. Enjoy the cozy ambiance and natural beauty of one of Florida’s most beloved gems.

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