street view in Key West, Florida

7 of the Most Welcoming Towns in Florida

The Sunshine State is a friendly place, known for its Orlando theme parks, year-round warm weather, and beautiful wrap-around beaches. Beyond the Disney scene, its small towns host unique and welcoming local attractions, along with a local food scene that creates a trusting atmosphere. Nightlife can be found in Key West, the southernmost point in the continental US, or in Williston, the “Gateway to the Nature Coast,” which offers the best southern soul food on this side of the Mississippi.

These Florida towns offer quaintness, personality, and serenity. Take Apalachicola, for instance, a charming fishing village known as the Oyster Capital. In Jupiter, you and your pup can enjoy the Grill Berry Fresh Cafe Dogs on the beach, along with a designated 2.5-mile stretch of beach and a stroll to the Jupiter Inlet Lighthouse. St. Augustine transports you nearly half a millennium back with its military forts, castles, European architecture, trotting carriages, and firing cannonballs.


Street view of the Dixie Theater in Apalachicola, Florida
Street view of the Dixie Theater in Apalachicola, Florida

In Apalachicola, built on the timber and fishing industries, you'll find a blend of Cape Cod charm and southern hospitality. With its shallow bays, excellent fishing, and acres of national and state forests, Apalachicola attracts tourists with its natural beauty. Here, you'll find some of the country's finest seafood, like at Up The Creek Raw Bar, and local hospitality at places like the top-rated Gibson Inn or the charming Riverwood Suites. From the vibrant old Florida Panhandle downtown to the lovely waterfront parks, the friendly locals share the beautiful Gulf of Mexico waters for your enjoyment.

This charming fishing village, dubbed the “Oyster Capital of the World,” is home to countless cafes and restaurants serving family meals with a variety of sea delicacies. Its enchanting inns and structures date back to the 1830s, and the modern waterfront culture is inviting. A short trip to the pristine beaches on St. George Island is easy, and a pub drink at a local favorite, like Oyster City Brewing Company, makes for a memorable experience in Apalachicola.


 The coastal town of Gulfport, Florida.
The coastal town of Gulfport, Florida.

Gulfport, brimming with "Old Florida" charm, is a town known for its traditional friendliness. Visitors are welcomed to explore its historic brick-paved streets from the early 1900s and colorful cottages along the shore. The town boasts independent businesses, free of large chain stores, and parking meters, enhancing its quaint atmosphere. The local food scene contributes to this welcoming vibe. Gulfport, known for being homey, eclectic, artsy, and progressive, is picturesque, with Beach and Shore Boulevards offering scenic views of Boca Ciega Bay in the heart of the historic downtown area.

The Gulfport History Museum is the home of the Gulfport Historical Society
The Gulfport History Museum is the home of the Gulfport Historical Society, By Beyond My Ken - Own work, CC BY-SA 4.0, Wikimedia Commons

Ideal for trips of any length, Gulfport offers unique shopping experiences with boutiques, local artisans, and markets selling books, home decor, gifts, and antiques. It features over a dozen restaurants offering a variety of cuisines, often paired with live entertainment. Visitors can enjoy spas, salons, and massage parlors for a relaxing getaway. Local rentals and accommodations like the Peninsula Inn and Sea Breeze Manor offer distinct experiences, with rooms themed after exotic locations like Marrakech, Serengeti, Jamaica, and Aruba.


Waterfront homes in Jupiter, Florida.
Waterfront homes in Jupiter, Florida.

Jupiter, located north of West Palm Beach at the Intracoastal Waterway along the Loxahatchee River, is known for its friendly atmosphere and attractive tourist destinations. A favorite Southeast Florida destination, Jupiter boasts stunning beaches like Jupiter Beach and Ocean Cay Park, along with trails and parks ideal for hiking and biking. Visitors can experience turtle sightings on beach walks, climb the Jupiter Inlet Lighthouse, and catch spring training at Roger Dean Chevrolet Stadium, home to the Miami Marlins and St. Louis Cardinals. Other attractions include Carlin Park and Dubois Park, with their beaches and interactive exhibits at the River Center at Burt Reynolds Park and Loggerhead Marinelife Center.

Jupiter caters to outdoors enthusiasts, families, and adventurers with a range of casual to luxury amenities. It's a place for surfing, paddling, and fishing in the waterways. Downtown Abacoa offers specialty shops, sidewalk dining, weekly events, and live music, while Harbourside Place has shopping and dining with views. The town is rich in arts, featuring the Town of Jupiter Gallery of Art, Harbourside Place Amphitheater, Palm Beach Shakespeare Festival, and Maltz Jupiter Theatre. Pet-friendly outdoor adventures are aplenty, and dogs are welcome at many hotels and restaurants, including Grill Berry Fresh Cafe Dogs on the beach, as well as a designated 2.5-mile stretch of beach for dogs.

Key West

The famous Sloppy Joe's Bar on Duval Street where American author and journalist Ernest Hemingway frequently attended in Key West
The famous Sloppy Joe's Bar on Duval Street where American author and journalist Ernest Hemingway frequently attended in Key West, via Fotoluminate LLC /

Key West warmly invites visitors to its location at the southernmost point of the continental United States, nestled far in the Florida Keys. It offers a Caribbean-like atmosphere and traditional hospitality. Key West is unique, boasting pristine beaches and a vibrant heart with neon lights, iconic pastel-colored houses, café culture, and a historic downtown, complemented by a lively nightlife. The town is both cozy and exciting, with a friendly crowd that makes newcomers feel at home and in eager anticipation of what comes next, such as the famous Key lime pie!

Key West is rich in history and nature, with attractions like the Truman Little White House and the Hemingway House and Museum, where Ernest Hemingway lived and wrote. Visitors can enjoy the beaches and scenic Mallory Square, a plaza adjacent to the port, perfect for strolls. Boat trips around natural attractions like Zachary Taylor State Park and Dry Tortugas National Park, as well as nearby Sunset Key and Wisteria Island, are popular. Activities like snorkeling, parasailing, and kayaking trips are encouraged, with locals offering tips, advice, and a helping hand, leaving a lasting impression on visitors.

St. Augustine

People shopping in St. George Street in Saint Augustine, Florida
People shopping in St. George Street in Saint Augustine, Florida, via Andriy Blokhin /

St. Augustine, the oldest city in the US, is infused with European charm and over 450 years of history. The city offers a blend of unique scenery and a quaint atmosphere, featuring centuries-old buildings, hidden courtyards, military forts, stately castles, and Gilded-Age hotels. It's a journey through time, with enough sites to fill both quick getaways and longer vacations, including scenic nature trails and tranquil beaches. Visitors can explore museums, the spiraling lighthouse, and enjoy views from atop.

Rated the fourth friendliest city in the US by TravelAwaits, St. Augustine, with a population of just over 15,000, embraces its rich heritage in a dog-friendly environment. Its spirit of friendliness and Southern hospitality is evident along the cobblestone streets. Whether visiting for the first time or returning, everyday life here feels extraordinary, with activities delighting all ages, such as horse-drawn carriages along brick-paved streets and thundering cannon fire. The city's heritage unfolds before your eyes with historical monuments, ghost tours, and numerous bars and pubs where local stories of the bygone era are shared in a welcoming atmosphere.


Aerial view of Stuart, Florida
Aerial view of Stuart, Florida

Stuart, nestled along Florida's Treasure Coast between Palm Beach and Vero Beach, is renowned as "The Sailfish Capital of the World." It has earned several accolades, including being named “America’s Happiest Seaside Town” by Coastal Living Magazine. Additionally, its pristine, landscaped streets, lack of skyscrapers to obstruct views, and beautiful beaches have been highlighted by the Huffington Post as one of the “Top Ten Beach Towns in Florida.” Despite these prestigious awards, Stuart maintains a humble atmosphere with its friendly locals and rich culture, evident in working studios, art galleries, and museums. Highlights include the Stuart Heritage Museum, the Road to Victory Military Museum, and the Elliott Museum, as well as antique shops and the weekly Green Market.

Tourists are enjoying at a beach in Stuart, Florida.
Tourists are enjoying at a beach in Stuart, Florida. Editorial credit: Klimamarina /

Stuart offers abundant nature for adventure enthusiasts, with excellent kayaking, hiking, fishing, and bird watching opportunities. Couples often enjoy the pristine trails of St. Lucie Inlet Preserve State Park and its often deserted beachscape. The seasonal Sailfish Splash Waterpark is a hit with families, and Stuart’s Riverwalk is perfect for romantic strolls and sunset views. Roosevelt Bridge has been recognized as one of the “Spectacular Bridges Around the World” by Travel and Leisure. The weekly Rockin’ RiverWalk Music Series offers entertainment in the fresh air along the beautiful St. Lucie River. The historic, pedestrian-friendly downtown is ideal for strolling, featuring the Sunday Market on Main near City Hall and a variety of accommodations, including the colorful Old Colorado Inn, close to dining and recreational activities.


Aerial sunrise view of downtown Williston, Florida
Aerial sunrise view of downtown Williston, Florida

Williston's locals describe their town as a small-town paradise, ideal for outdoor adventurers. The community, with a strong spirit, enjoys activities like fishing, canoeing, kayaking, and hiking, and delights in sharing its natural beauty through nearby preserves, wildlife hikes, and photography opportunities. The town's Old Florida charm is evident in its ivy-covered buildings, antique shops, delicious restaurants, and unique boutiques, which invite visitors to relax and feel at home. Here, you can find some of the best Southern soul food on this side of the Mississippi, particularly along the festive streets during events like the annual Peanut Festival in October.

Williston offers a range of experiences, from vintage train rides to elephant encounters, and from exploring botanical gardens to diving into underwater caverns. Striking a balance between adventure and leisure, Williston, known as the “Gateway to the Nature Coast,” preserves a piece of Old Florida. Nearby Gainesville, just a half-hour drive away, offers additional attractions, including the prehistoric hot springs of Devil’s Den and Blue Grotto. The area is also known for its rural charm, with local production of peanuts and watermelons, showcased at the Williston Peanuts factory outlet store, and the presence of cattle ranching and horse farms.

Florida's approachable locals are known for opening their doors and hearts, offering valuable advice to ensure a memorable experience for visitors following any travel itinerary in this long and narrow state. In St. Augustine, you can climb the spiraling lighthouse, while Stuart, located on Florida's Treasure Coast, is home to the Roosevelt Bridge, recognized as one of the “most spectacular bridges around the world.”

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