1. Anna Maria Island
Anna Maria Island might be Florida’s best-kept secret because the postcard-perfect beaches here are rarely crowded. Celebrate the sun, sand and surf in November during the Symphony on the Sand festival, an exceptional beachfront concert series.
2. Historic Downtown Fernandina Beach, Amelia Island
Rumored to once be a haven for pirates and other colorful characters, Historic Downtown Fernandina Beach is an enchanting seaside village chock-full of elegant Victorian architecture on Amelia Island. Go during the Isle of Eight Flags Shrimp Festival in May and enjoy a festive parade, great local seafood, and a pirate invasion by sea.
3. The Ultimate Guide to Seaside, Florida
South Walton’s Seaside neighborhood features a whimsical collection of pastel-colored homes, a great farmer’s market, and an eclectic combo of local shops and restaurants. Listen to some of the best musical artists in the country during the annual 30A Songwriters Festival in January.
4. Pier 60, Clearwater Beach
Jutting out from one of the most gorgeous stretches of sand on the Gulf Coast, Pier 60 is home to a nightly sunset celebration featuring local artisans and loads of entertainment on Clearwater Beach. Go during the annual Pier 60 Sugar Sand Festival, a 10-day celebration every spring that pays homage to the beach and features the most amazing sand-sculpted works of art—way more impressive than the average sandcastles.
5. Miami’s Perfect Weekend Itinerary
Made famous in old-school movies like Scarface, Ocean Drive and the South Beach Art Deco District are home to fanciful pastel structures decked out in neon accents. Celebrate that iconic Art Deco architecture during the Miami Design Preservation League’s Art Deco Weekend that takes place each January.
6. Worth Avenue, Palm Beach
Perhaps the most affluent area in the entire Sunshine State, Worth Avenue has an impressive collection of high-end shops and swanky cafes. While you should never need an excuse to go on the ultimate shopping spree, the Palm Beach International Boat Show in March is a great time to go because you can haul your loot away on a mega yacht.
7. Atlantic Avenue, Delray Beach
Brimming with funky live music hotspots, lots of local art, and a calendar of events that will keep you entertained all year long, Delray Beach’s Atlantic Avenue is a fun place for the whole family. One of the most popular events of the year is the lighting ceremony of the 100-foot Christmas Tree each December.
8. St. Augustine Historic District
Not only is St. Augustine one of the nation’s oldest cities, it’s brimming with Spanish colonial architecture inspired by the arrival of European explorers more than 500 years ago. Visit the historic district during the annual Nights of Lights (runs from Thanksgiving through the New Year) when the city is decked out in more than three million tiny white lights.
9. Las Olas Boulevard, Fort Lauderdale
Stretching all the way to a gorgeous beach and lined with a variety of local boutiques, art galleries, and outdoor cafes, Las Olas Boulevard is Fort Lauderdale’s best place to see and be seen. Go during the Annual Las Olas Art Fair, which has become so popular that there’s three editions every year in January, March and October.
10. Historic Downtown Stuart
And last, but certainly not least, it’s Coastal Living’s Happiest Seaside Town of 2016! Offering a relaxed, flip-flop approach to life combined with Old Florida charm, Stuart’s historic downtown is the ultimate Florida destination. Enjoy year-round live music during the Rock’n Riverwalk free open-air concert every Sunday.
11. Captiva Island
Renowned for its sugar white sand and excellent shelling, Captiva Island is an oasis where the best mode of transportation is via golf cart and the most useful itinerary is to beach, eat, sleep, and repeat. Seashell collectors unite during the annual Sanibel Shell Show taking place on both islands every March.
12. Fifth Avenue South, Naples
Glamorous shops, pedestrian-friendly promenades, and a great collection of Italian bistros, Fifth Avenue South in downtown Naples oozes with timeless charm. The annual Naples Festival of the Arts draws a well-heeled crowd of art enthusiasts who also happen to love the beach.
13. Duval Street, Key West
For the ultimate bar crawl, there’s no better place in Florida to throw back a cold one (or two) than at the many watering holes that line lively Duval Street in Key West. The biggest street party of the year happens every October during Fantasy Fest, when fun-loving revelers descend on Duval wearing funky costumes for a wild extravaganza.
14. Beach Drive and Downtown St. Petersburg
Nestled next to the sharp blue waters of Tampa Bay, Beach Drive and the surrounding area of downtown St. Petersburg has gone through a renaissance with a host of new local eateries and artistic mainstays like The Dalí Museum. Visit during the annual Ribfest in the fall on the waterfront for a delectable combo of barbecue and rock bands.
15. St. Armands Circle, Sarasota
A lushly landscaped hub of stylish shops and local eateries, St. Armands Circle on Lido Key is a posh place to visit in Sarasota. Springtime is the perfect time to go, when the annual Sarasota Film Festival is in full swing, and you can catch an indie flick or an artsy up-and-comer during the when you can catch an indie flick or an artsy up-and-comer during the annual Sarasota Film Festival.