The Best Cities To Vacation In Florida

For family vacations, romantic trips, mother-daughter getaways, and solo adventures.

As a Florida resident for 25 years, I’ve traveled throughout the Sunshine State, sometimes flying but usually taking a great road-trip. From family vacations and romantic trips to mother-daughter getaways and solo adventures, I’ve hit sleepy beach towns, inland theme parks, charming small towns, and buzzing metro areas. Where do I recommend travelers visit when they’re planning a Florida vacation? While it really depends on whom you’re traveling with (BFF, little kids, parents) and what you want to do (visit craft breweries, build sand castles, go kayaking), you can’t go wrong in any of these Florida destination highlights. 

St. Augustine

History buffs flock to America’s oldest city for a glimpse into the past. Check out the 450-year-old Castillo de San Marcos, the oldest U.S. masonry fort, where you can witness live reenactments and the firing of cannons. Take an historic tour of Flagler College, visit the iconic Lightner Museum, and tour the Old Jail Museum and Oldest Wooden School House. Stroll along the famed St. George St., the walkable thoroughfare dotted with shops, eateries, and attractions. Then cross the Bridge of Lions to soak in spectacular birds-eye views at St. Augustine Lighthouse & Maritime Museum. Nearby, explore Anastasia State Park, a 1600-acre property brimming with wildlife, stunning beaches, maritime hammocks, and tidal marshes.

Anna Maria Island

For some charming, Old Florida hospitality, visit Anna Maria Island, which sits at the northern tip of a seven-mile island that also includes Holmes Beach and Bradenton Beach. Thanks to the daily free trolley, you can easily access the entire island. For incredible views of Tampa Bay’s iconic Sunshine Skyway Bridge, pop over to Anna Maria Bayfront Park. Amble along historic Pine Avenue to peruse local shops, grab lunch, or visit Anna Maria Island Historical Society Museum. Hit the surf at the family-friendly Holmes Beach. Spend the day in Historic Bridge Street area, where you can nosh on fresh seafood, peruse local shops, and book a dolphin tour through the Intracoastal Waterways.

Amelia Island

In the Northeast corner of Florida sits the lush Amelia Island beach town. Its 13 miles of uncrowded beaches lure travelers looking for a quiet, toes-in-the-sand respite. It’s also one of the few beaches where you can go horseback riding. But this island destination also boasts a walkable downtown, natural beauty, historical fort, top-notch golf courses, and a mix of both luxe resorts and quaint inns. Explore the Civil War era Fort Clinch State Park, “where history meets nature” to see the row of cannons lining the St. Mary’s River. Shop and eat your way along Historic Downtown Fernandina Beach, the 50-block Victorian seaport village dotted with local eateries and eclectic shops. And take a local-guided bike tour to learn about the city’s past.

Daytona Beach

With roughly 23 miles of expansive shoreline, Daytona Beach has been drawing tourists for decades. One reason? With a 500-foot-wide beach at low tide, you can drive your car right on the hard-packed sand! It tees up the perfect playground for throwing a Frisbee, fishing at the surf’s edge, playing volleyball, or building sandcastles. Stroll along the 1000-foot long Daytona Beach Pier, catch a concert in the oceanfront bandshell, or spend the day swimming, boating, or kayaking. Head inland for more fun, whether you want to take a mini-tour of the Angell & Phelps Chocolate Factory, race over to Daytona International Speedway, sip your way along the Daytona Beach Ale Trail, or shop at One Daytona.

Florida Keys

As Florida’s ultimate “chill” vacation, the Florida Keys tops the travel bucket list for many people. It takes about three hours to drive the 113-mile Overseas Highway from end to end. But instead of rushing through, drop anchor along the way. In the Upper Keys, visit Key Largo (Dive Capital of the World) with a can’t-miss stop at John Pennekamp Coral Reef State Park. Go scuba diving, take a glass-bottom boat tour, or paddle a kayak. On your drive, stop in the iconic Rain Barrell Village to buy kitschy souvenirs or handcrafted pieces from local artisans. In the Middle/Lower Keys, tour Pigeon Key (“the tiny island under the Old Seven-Mile Bridge”), visit some amazing craft breweries, and climb atop the old bridge at Bahia Honda State Park for incredible panoramic views. In Key West, grab a cold one at the famed Sloppy Joe’s bar, see the famous five-toed cats at the Ernest Hemingway Home, dive into history at the Mel Fisher Maritime Museum, and watch the glorious sunsets at Mallory Square.

Miami

If you’re looking for a more urban adventure, the Miami area won’t disappoint. Its thriving cultural scene, buzzing nightlife, and beautiful beaches draw millions of tourists every year. Don’t miss Miami’s funky Art Deco Historic District in South Beach and the colorful street art of Wynwood Walls. Stroll along the pedestrian-friendly beach promenade, visit the jaw-dropping Vizcaya Museum & Gardens, and savor al fresco dining on the waterfront.

Fort Lauderdale

With the nickname of “the Venice of America,” Fort Lauderdale boasts 165 miles of picturesque waterways and canals, making it the perfect playground for watersports, boat tours, and swimming. Get some retail therapy on Las Olas Boulevard, hike through Hugh Taylor Birch State Park, and tour the lovely Bonnet House Museum & Gardens.

Orlando

Known as the theme park capital of the world, Central Florida bursts with family-friendly fun. From Walt Disney World and Universal Orlando to SeaWorld and Legoland, kids and kids-at-heart can ride rollercoasters, learn about marine life, see live entertainment, meet favorite characters, and splash in waterparks for days of memory-making adventures. But beyond the theme park gates, you’ll find plenty to do in and around Orlando. Take in live improv at SAK Comedy Lab, learn to play pickleball at the U.S. Tennis Association campus, eat at Michelin-ranked restaurants, amble along the picturesque grounds of Leu Gardens, and take a swan boat ride in Lake Eola nestled in the heart of downtown.

The Panhandle

In the Northwest part the state, the Panhandle stretches for miles along Florida’s Emerald Coast. From the sugar-white sands of Santa Rosa Island and the popular Panama City Beach to Rosemary Beach and St. George Island, you’ve got your pick of charming seaside villages.

Get back to nature at Gulf Island National Seashore where you can explore maritime forests, fertile marshes, historic forts, and pristine beaches. Dive into the spectacular Underwater Museum of Art off Grayton Beach State Park. Check out the restored historic structures in the Civil War–era Fort Pickens in Santa Rosa Island. Cast your line off the Navarre Beach Pier—the longest fishing pier in the Gulf of Mexico at 1,545-feet. Or hit the greens at any of the four championship golf courses at Sandestin Golf and Beach Resort. 

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