Travel Florida The 10 Best Cities To Vacation In Florida For family vacations, romantic trips, mother-daughter getaways, and solo adventures. By Lisa A. Beach Lisa A. Beach Lisa Beach is an Orlando freelance travel/food/wellness writer whose work has been published in The New York Times, USA Today Go Escape, Good Housekeeping, Eating Well, and Orlando Magazine. Southern Living's editorial guidelines Published on July 4, 2024 Close Photo: Jessica Sample 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, 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. 11 Mistakes To Avoid On A Florida Vacation, According To A Longtime Floridian 01 of 10 St. Augustine Sean Pavone Photo/Getty Images 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. Explore St. Augustine 02 of 10 Anna Maria Island Jessica Sample 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. Explore Anna Maria Island 03 of 10 Orlando Getty Images 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. Explore Orlando 04 of 10 Amelia Island Courtesy of Omni Amelia Island Resort 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. Explore Amelia Island 05 of 10 Daytona Beach Sean Pavone Photo/Getty Images 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. 06 of 10 Key West Stephen Frink/Getty Images 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. Explore Key West 07 of 10 Miami Alexander Spatari/Getty Images 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. 08 of 10 Fort Lauderdale Pola Damonte/Getty Images 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. Explore Fort Lauderdale 09 of 10 Sarasota Robbie Caponetto Located on Florida's beautiful Sun Coast, just south of Tampa, Sarasota has all the essential ingredients for an unforgettable beach vacation. For one, you'll have 35 miles of beaches to explore in the area, including hotspots like Siesta Key and Lido Key Beach that both are renowned for their fine, sugar-white sand and turquoise waters. If you're able to peel yourself away from the crashing waves, take a walk or bike ride along the water at Bayfront Park. One non-waterfront, but still very worthwhile activity is exploring the 66-acre Ringling property that consists of a circus museum, museum of art, and Ca' d'Zan, the palatial Venetian-inspired home and gardens that circus tycoon John Ringling built for his wife Mable. 10 of 10 Naples Lots of destinations tout that they offer something for everyone, but nowhere lives up to that promise like Naples. Yes, you can explore the many public beaches at Naples Pier, Lowdermilk Park, and Vanderbilt Beach. You can just as easily climb aboard a boat to see dolphins, other wildlife, uninhabited beaches, and the surrounding barrier islands. But you can also find upscale shopping in the ritzy Third Street South neighborhood and a quaint downtown district along Fifth Avenue South. Accommodations range from the luxurious Ritz-Carlton to private beach homes. 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