10 Most Fun Florida Cities to Visit

June 29, 2023

fun florida cities

With more than 8,000 miles of shoreline, diverse landscapes, and a nickname of “the Sunshine State,” determining what are the best places to visit in Florida can be a challenge. The southernmost U.S. state lies between the Gulf of Mexico and the Atlantic, but beyond the world-class beaches, there are also exhilarating theme parks, fascinating colonial Spanish historic sites, freshwater springs, rich culture, and wild and wacky adventures. The sheer number of picturesque road trips is astounding and keeps visitors returning to these fun Florida cities again and again.


Vizcaya Mansion, Miami

Here are our favorite fun Florida cities, and we are sure many of them will be yours too!

10 Gainesville

ginnie springs

  • Elevation: 177′
  • Area: 64.54 mi²
  • Population: 132,127

Located in Northern Florida, Gainesville is a city we love for its proximity to outdoor adventures and state parks. Gainesville doesn’t quite fit the mold of a stereotypical Florida vacation. There aren’t any beaches or theme parks, but instead, you’ll find college-town vitality and protected natural beauty with over 30 miles of hiking and biking trails, scenic rivers, a prehistoric spring, zipline over canyon waters in nearby Ocala, antiquing in the surrounding small towns, and more.

While the heat in some places in Florida is intolerable in summer, the cool, natural springs around Gainesville and Alachua County make for a very pleasant season and is why it is one of the best places in Florida to visit during the scorching summer months.


Be sure to check out the stately Victorian homes that sit along quiet streets lined with live oak trees draped with Spanish moss. They are within walking distance and you can even stay at some of the converted bed and breakfast inns, like Magnolia Plantation (see link below).

Here are the top 10 things to do in or around Gainesville:

  1. Ginnie Springs
  2. Paynes Prairie Preserve
  3. Juniper Springs
  4. Silver Springs
  5. Micanopy
  6. Downtown
  7. University of Florida
  8. Loblolly Woods Nature Park
  9. The Actor’s Warehouse
  10. Depot Park

Read more:

Magnolia Plantation: A Treasure in Every Way

9 Amelia Island

amelia island florida

  • Max length: 13.05 mi
  • Population: 36,395

Amelia Island is a barrier island on Florida’s northeast Atlantic coast, about an hour north of Jacksonville Beach and a short distance from the Georgia border. The island, named for Princess Amelia, daughter of George II of Great Britain, has a laid-back vibe, reminiscent of “old Florida.

Showcasing a history of Spanish, French, British, and American rule, Amelia Island is a popular weekend destination known for its 13 miles of shoreline, luxury resorts, golf courses, and antiquing.

Outdoor enthusiasts will love the dunes and boardwalk at Main Beach Park and swimming in lovely nearby Fernandina Beach, as well as opportunities for kayaking, horseback riding, fishing from Fernandina Pier, or climbing the lighthouse.

Here are the top 10 things to do in Amelia Island:

  1. Stroll Main Beach Park
  2. Farmer’s Market
  3. Historic Downtown
  4. Carriage Ride
  5. Fort Clinch
  6. Antiquing
  7. Sunset Dinner at Marina
  8. Fish Fernandina Pier
  9. Kayaking
  10. Lighthouse

Read more:

Things to Do at Amelia Island in Winter

Best Things to Do in Jacksonville Beach

8 Naples

fun florida cities

  • Elevation: 3′
  • Weather: 71°F (22°C), Wind E at 14 mph (23 km/h), 50% Humidity weather.com
  • Population: 21,812

Naples, located on the southwest coast of Florida on the Gulf of Mexico, is an upscale city with a population of a little over 20,000, much of which are transplants from cooler climates.

It’s known for the abundance of golf courses, fast, expensive cars, and high-end shops and eateries. Named Best US Luxury Destination in December 2015 by JustLuxe, the city boasts miles of white-sand aquamarine beaches, interesting eco-systems to explore, and year-round outdoor activities.

fun florida cities

Naples Bay is one of the most popular areas of Naples. On the bay is the Cove Inn, the Dock Restaurant, and the Tiki Hut Bar, all very popular. Visitors can rent bikes at the marina and there are more than 50 restaurants within walking distance of the marina. Sunset at the marina is not to be missed.

The Naples Pier, first erected in 1888, is the city’s symbol and is a popular fishing and dolphin-spotting destination. It’s flanked by miles of beaches with calm waters and fine white “sugar” sand, including those at Clam Pass Park and Delnor-Wiggins Pass State Park.

Here are the top 10 things to do in Naples:

  1. Stay on a Houseboat
  2. Sunset at Naples Bay
  3. Historic 3rd Street
  4. Lowdermilk Beach
  5. 5th Avenue
  6. Mercado
  7. Naples Pier
  8. Trolley Tour
  9. Naples Botanical Garden
  10. Tin City

Read more:

Boat Rentals Naples FL: How About a Houseboat?

7 Daytona Beach

daytona beach

  • Area: 68.19 mi²
  • Elevation: 13′
  • Population: 67,604

Daytona Beach, on Florida’s Atlantic coast, is best known for Daytona International Speedway, which hosts February’s iconic Daytona 500 NASCAR race. But that’s far from all the city has to offer. The beach has more than 20 miles of shoreline with hard-packed sand where driving is permitted in designated areas.

Near the boardwalk’s rides and arcades, Daytona Beach Bandshell stages free summer concerts. For outdoor activities, visitors can climb to the top of Ponce de Leon Lighthouse, one of the oldest lighthouses in the United States, kayak at Tomoka State Park, and hike at Tiger Bay State Forest.

hard rock hotel daytona

We recommend the Daytona Beach Hard Rock Resort! It is a hoot and gorgeous to boot!

Here are the best Instagram spots in Daytona.

Here are the top 10 things to do in Daytona Beach:

  1. Beach and pier
  2. Daytona Boardwalk
  3. Kayak at Tomoka State Park
  4. Daytona Surfside Historic Downtown
  5. Riverfront Marketplace
  6. Tiger Bay State Forest
  7. Richard Petty Driving Experience
  8. Ponce de Leon Lighthouse
  9. Beach Street
  10. Andy Pompano Beachfront Park

INSIDER TIP: Click here for the ONLY beach packing list you’ll ever need!

6 St. Augustine

st augustine

  • Founded: September 1565
  • Age: About 456 years
  • Elevation: 0′
  • Population: 14,515

St. Augustine, on the northeast coast of Florida, proclaims to be America’s oldest continually inhabited city. The historical and charming St. Augustine was founded in 1565 (four decades before Jamestown was settled and predating the Pilgrims’ landing at Plymouth Rock) and is also considered by many to be America’s most romantic destination.

Best known for its Spanish Colonial and Moorish Revival architecture, the city also has Atlantic Ocean beaches like sandy St. Augustine Beach on Anastasia Island. History buffs will be filled with glee at the rich historical sites such as the Castillo de San Marcos, a 17th-century Spanish stone fortress with views of the St. Augustine Inlet, the Old Jail, and Ponce de Leon Fountain of Youth Archaeological  Site.

The brick-lined streets are reminiscent of the old town districts of European cities. Horse-drawn carriages carry tourists past grand historical architecture. The pleasant, sometimes humid, subtropical climate and coastal location combine to create an alluring, warm and sunny environment.

Here are the top 10 things to do in St. Augustine:

  1. Colonial Quarter
  2. Old Town Trolley
  3. Old Jail
  4. Fountain of Youth Discovery Park
  5. Magnolia Street
  6. Climb the Lighthouse
  7. Castillo de San Marcos Fort
  8. Augustine Beach
  9. Lightner Museum
  10. Night of Lights Festival

Read more:

St Augustine in November: 11 Best Things to Do

The Datil Pepper Sauce Boss of St. Augustine

5 Miami

fun florida cities

  • Elevation: 6.562′
  • Population: 454,279

Miami is a coastal metropolis located in southeastern Florida popular for tourists looking for sun, surf, and…people watching.

Miami’s beaches and mojitos are just the beginning of what this fascinating city has to offer. From the legendary pulsating nightlife, high-end designer shops, and cutting-edge galleries salsa dancing, and museums, there are a lot of things for couples to do in Miami.

But there are also outdoor activities, too. Visitors can enjoy kayaking at Oleta River State Park and Crandon Park, as well as explore the dunes and mangroves at Marjory Stoneman Douglas Biscayne Nature Center, and the Fairchild Botanical Gardens.

miami beach

For beach lovers, head straight to famous (or infamous!) South Beach for shimmering turquoise green waters set in a backdrop of stunning Art Deco architecture. It’s one of the best beaches in Florida for couples.

There’s so much culture, too…Little Havana, the Ancient Spanish Monastery, Vizcaya Mansion, and the Wynwood Walls are not to be missed.

Don’t miss a day trip to nearby Everglades National Park.

Here are the top 10 things to do in Miami:

  1. South Beach
  2. Everglades National Park
  3. Little Havana
  4. Wynwood Walls
  5. Coral Gardens
  6. Ancient Spanish Monastery
  7. Bayfront Park
  8. Key Biscayne
  9. Viscaza Museum & Gardens
  10. Oleta River State Park

4 Panhandle

fun florida cities

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  • Width: 50 to 100 miles
  • Population: 1,407,925

Boasting unspoiled natural beauty and laid-back beach towns, the Florida Panhandle is in the northwestern part of Florida. The idyllic strip of land is roughly 200 miles long and 50 to 100 miles wide bordered by the Gulf of Mexico, Alabama, and Georgia.

The Gulf Islands National Seashore with impossibly iridescent turquoise water rivals anything in the Caribbean. With a staggering 320 days of tropical sunshine per year and 27 miles of shimmering emerald coastline, you’ll have an incredible array of fun things to do.

Culturally more like the US South than the rest of Florida, the locals are friendly and warm and eager to produce a great vacation experience.

Our picks for the best towns in the Florida panhandle are Panama City Beach, Pensacola Beach, and Cape San Blas. Yes, I know, I cheated as these are really three separate towns/cities, but they are cohesive as one.

panama city beach

Panama City Beach

Lined with swaying palms, Panama City Beach lies on one of the most gorgeous stretches of beach in the entire United States – the Emerald Coast. In fact, their tourism board insists that their little piece of the Gulf of Mexico contains “the world’s most beautiful beaches,” and yet has fewer tourists than other Florida beach destinations.

Here are the top 10 things to do in Panama City Beach:

  1. Shell Island
  2. Carillon Beach
  3. Russell Pier
  4. Andrew’s Park
  5. Helicopter Flight
  6. Camp Helen
  7. Sunset on the Beach
  8. Rainbow Houses
  9. Pier Park
  10. Dolphin Watching Cruise

Read more:

Panama City Beach Helicopter Rides: 3 Girls, 1 Bird

fun florida cities

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As you can probably guess, beaches in Pensacola FL are the biggest draw. A humid subtropical climate combined with shimmering turquoise water lapping onto impossibly white sand makes it arguably the prettiest beach in the U.S.

Pensacola is the largest metropolitan area between New Orleans and Tampa, yet still maintains a small-town vibe, especially around the beach area. It’s home to several annual festivals, events, historic tours, and landmarks.

Pensacola, originally inhabited by the Muskogean-speaking indigenous people, is the site of the first Spanish settlement within the borders of the continental United States. In 1559, predating the establishment of St. Augustine by 6 years, Spanish sailor Tristán de Luna led America’s first settlement attempt here. The settlement was abandoned due to a hurricane and not re-established until 1698 when the Spanish established a presidio in the area, from which the modern city gradually developed.

Here are the top 10 things to do in Pensacola:

  1. Gulf Islands National Seashore
  2. Pensacola Beach
  3. Fort Pickens
  4. Palafox Street
  5. Sunset Over the Pier
  6. Kiteboarding Okaloosa Island
  7. Pensacola Pedal Trolley
  8. Pensacola Lighthouse
  9. Seville Quarter
  10. Historic Pensacola Village

Read more:

Gulf Coast Road Trip: 10 Best Stops on the Emerald Coast

gulf county fl

Florida’s “Forgotten Coast” is a charming, quiet, and relatively undeveloped section in the heart of the Panhandle. Here, in Gulf County, you’ll find 43 miles of coastal bliss in Cape San Blas and Port St. Joe.

The coastal complex of Cape San Blas, St. Joseph Bay, and the St. Joseph Peninsula offer pristine white powdery sand beaches along the Gulf of Mexico shore, as well as the sheltered waters of the bay, ideal for water sports.

Cape San Blas is located on St. Joseph Peninsula, a 750-acre narrow stretch of land extending out from Port St. Joe and curving around St. Joseph Bay. The “Cape,” as locals call it, was named the best beach in America (2002) by Dr. Stephen P. Leatherman (a.k.a. Dr. Beach) for its unspoiled beaches.

Here are the top 10 things to do in Cape San Blas:

  1. Beach Bonfire
  2. Cape Palms Park
  3. Rock Wall Beach
  4. Stump Hole
  5. Eat Oysters
  6. Eagle Bay
  7. Joseph Peninsula State Park
  8. Cape San Blas Light
  9. Salinas Park
  10. Paddle Kayak

3 Orlando/West Volusia

fun florida cities

  • Elevation: 82′
  • Area: 119.1 mi²
  • Weather: 66°F (19°C), Wind E at 8 mph (13 km/h), 63% Humidity weather.com
  • Population: 280,832

There’s nowhere like Orlando on the planet. Located in central Florida, Orlando is a staple vacation destination for families and well-known to be one of the most fun Florida cities to visit. While it is home to more than a dozen exciting theme parks, there’s more to the area, particularly adventures in West Volusia.

Our favorite theme parks are Universal Studios and Islands of Adventure (love those rollercoasters!). There’s a lot to see there, so here are some Universal Orlando tips.  Walt Disney World theme parks of Epcot (drink around the world!), Magic Kingdom, MGM Studios, and Animal Kingdom are also a lot of fun.

Tip: If you are not staying at a Disney property (very expensive!) here’s a guide to the best Orlando hotels with a free shuttle bus to Disney and Universal.

skydive deland

To get away from the fun but commercialized theme parks, head to the secret gen of West Volusia for a different kind of grown-up fun. Conveniently located between Orlando and Daytona Beach, it is oozing with “old Florida” vibes, it is one with nature offering a plethora of outdoor adventures in unspoiled landscapes, as well as some quirky venues such as the Haunted Antique Store and a rage room. Instead of beaches, you’ll find freshwater springs, wetlands, and forests. There are so many unique adventures in Central Florida!

The West Volusia are is one of my favorite fun Florida cities! Here are the top 10 things to do in Orlando/West Volusia:

  1. Epcot
  2. Universal Studios/Islands of Adventure
  3. Skydive DeLand
  4. Airboat
  5. Clear Kayak
  6. Tubbing Blue Springs
  7. Magic Kingdom
  8. MGM Studios
  9. New Smyrna Beach
  10. Horseback Deep Creek

2 Sarasota

fun florida cities

  • Elevation: 16′
  • Area: 24.08 mi²
  • Weather: 71°F (22°C), Wind E at 12 mph (19 km/h), 50% Humidity weather.com
  • Population: 56,919

Sarasota is a city on Florida’s Mid-Gulf Coast that was once the winter home of the Ringling Brothers Circus. The city is known for its natural, historical, and cultural attractions. The town motto describes it as a town “where urban amenities meet small-town living.”

ringling museum

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While the Ringling palatial complex is still a big draw – and rightly so, the majority of things to do in the area are undoubtedly linked to nature. With more than its share of stunning turquoise beaches, Sarasota beckons sun-worshipers to its shores, especially world-renown Siesta Key, commonly listed as one of the best beaches in the world.

Sarasota is a nature lover’s playground. Hiking and kayaking at Myakka River Park is suburb, as well as strolling through Marie Selby Botanical Gardens. There are a ton of outdoor activities in Sarasota.

Here are the top 10 things to do in Sarasota:

  1. Ringling Complex Ca’ d’Zan
  2. Beer Can Island
  3. Marie Selby Botanical Gardens
  4. Siesta Key Beach
  5. Myakka Park
  6. Kayak Lido Mangrove Tunnels
  7. Spanish Point
  8. Armand Circle
  9. Lido Key
  10. Longboat Key

1 The Keys

fun florida cities

  • Area: 137.5 mi²
  • Population: 82,847
  • Number: 800 keys
  • Length: 180 miles

The Florida Keys are as close as you can get to the Caribbean. A string of tropical islands stretching about 120 miles off the southern tip of the United States, the tiny islands are connected by one of the most scenic causeway drives in the world making this road trip a must-do.

Overflowing with its own blend of bohemian/tropical charm, the Florida Keys are one of the few U.S. destinations that wield widespread magnetic appeal and is why it tops the list of best places to visit in Florida. The temperature ranges from Caribbean sultry to relatively mild, making it a popular and easy tropical vacation spot for Americans to travel without a passport.

fun florida cities

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Like its island neighbors just south in the Caribbean Sea, the Keys offer many of the same amenities, such as snorkeling in the warm turquoise water, sailing the open seas, kayaking in acres of mangroves, fishing, eco-tours in the state parks, and lots of one-of-a-kind restaurants and bars. Add to that killer sunsets and the best key lime pie in the world and it’s no wonder why many consider the Keys to be the best vacation destination in the contiguous United States.

mallory square

The southernmost city of Key West is one of the most fun Florida cities to visit. It is famous for Duval Street’s many bars, Mallory Square’s nightly Sunset Celebration, the Ernest Hemingway Home and Museum, and the southernmost point in the United States – just 90 miles from Cuba.

Here are the top 10 things to do in the Keys:

  1. Bahia Honda Beach
  2. Overland Highway
  3. Dry Tortugas National Park
  4. Key Largo Sunset
  5. John Pennekamp Coral Reef Park
  6. Fort Zachary Taylor Park
  7. Duval Street/Mallory Square
  8. Cheeca Fishing Pier
  9. Southernmost Marker
  10. Ernest Hemingway Home

Read more:

Florida Keys Photos: USA’s #1 Destination

Key West Holidays: Best Resorts for Baby Boomers

Three Hands Fish: Hands Down, The Keys’ Best Seafood

Beyond Disney: Enjoy the Florida Keys with Kids


fun florida cities

Florida is one of my top three U.S. states. Every time I go back (which is quite often) I find entirely new things to do, see, and eat.

Click below to PIN so you can find fun Florida cities again:

fun florida cities

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About the Author

Patti MorrowPatti Morrow is a freelance travel writer and founder of the award-winning international blog Luggage and Lipstick and southern travel blog Gone to Carolinas. TripAdvisor called her one of “20 Baby Boomer Travel Bloggers Having More Fun Than Millennials” and she was named one of the “Top 35 Travel Blogs” in the world.

She is also the star of the upcoming TV series “Destination Takeover” which is scheduled to premiere in the new few months.

Patti is the author of the book “Girls Go Solo: Tips for Women Traveling Alone,” and has over 150 bylines in 40 print and online publications, including The Huffington Post, International Living Magazine, Washington Post Sunday Travel, Travel Girl, Travel Play Live Magazine, and Ladies Home Journal. She has traveled extensively through six continents looking for fabulous destinations, exotic beaches, and adventure activities for her Baby Boomer tribe.


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