Clearwater Beach is the hippy to its tri-city sisters Tampa and St. Petersburg. With its laid-back, come as you are style, this Gulf of Mexico tropical island is super chill, friendly and continually receives kudos as one of the best beaches in the country. Recently named USA Today’s 2013 “Best Beach Town in Florida,” Clearwater Beach is an everyman’s place and a microcosm of the world, from bankers to bikers, lawmakers to laborers.
1 The Ultimate Beach Town
Clearwater Beach sits on a barrier island sandwiched between the Intracoastal Waterway and the Gulf of Mexico about half way up Florida’s peninsula. Its 2.5 miles of white sandy beach and its average temperature of 73 degrees make it an attractive year-round destination. But what really earns it a ranking as one of Florida’s ultimate beach towns is its pedestrian-friendly Beach Walk. The 2008 beautification project introduced wide curvy sidewalks, sand dunes and tropical landscaping along the beach side of Gulf View Blvd. Cross over and the street is lined with swimwear boutiques, open-air cafes, bicycles shops and a marina, making this a great beach town where there’s more to do than just hang out on the sand.
2 Dolphins by Land and Sea
Follow the squeals of delight and chances are your fellow beachgoers have spotted one or more frolicking dolphin just offshore. Daily boat excursions from the municipal marina take passengers out in open water, creating dolphin-attracting wakes. On land, follow the growing trail of dolphin sculptures created by local artists, starting with the blue-and-silver sculpted wire trio near Clearwater’s landmark Pier 60, the gem-covered Jewel dolphin sculpture in the Hilton Clearwater Beach’s lobby, and Rush, Palm Pavilion Inn’s dolphin decked out in straw hat and tropical shirt.
3 Find Your Beach Style
Clear, shallow waters and super-observant lifeguards make Clearwater Beach ideal for families. Concessionaires sell ice cream and rent water-sports equipment, plus there’s a large beachfront playground to keep kids busy. Nearby restrooms and turtle-topped showers let you leave the sand at the beach. But for those in search of a little solitude, undeveloped Caldas Island sits just north of Clearwater Beach; here you can walk hours without seeing nary a soul. Anyone looking to rub elbows with the locals can head south and cross the bridge over Clearwater Pass to Sand Key, a more residential barrier island with a park and beach.
4 Life at the Pier
Pier 60 is the heartbeat of Clearwater Beach. With 1,080 feet jutting into the Gulf of Mexico, this public pier is populated with fishermen and sightseers. A bait house rents fishing gear and sells live bait so even if you didn’t plan ahead, you can cast a line. Nature lovers find this to be a good perch for spotting brown pelicans, long-legged waterfowl and an occasional dolphin. However, the best time to visit the pier is at dusk, when sunset celebrations happen nightly. Live bands and street performers, from fire eaters to break dancers, entertain while vendors sell everything from handcrafted jewelry to artsy photos of the pier. Parents with youngsters in tow find magicians and balloon artists to keep the little ones enthralled.
5 Beachfront Tiki Bars
Nothing says you’re in a tropical locale better than your toes planted firmly in the sand with a frosty cocktail—umbrella optional—in hand and the thatched roof of a tiki hut overhead. Clearwater has the beach and vibe that’s perfect for tiki bars, and there are plenty beach-bum spots to indulge in libations. Take in the sunset at Tommy’s Tiki Bar at the Hilton Clearwater Beach, then dance the night away at Shephard’s Backyard Tiki Bar, where live reggae and rock bands occasionally jam an ’80s tune or two. “Electric Slide,” anyone?
6 Resorts of all Sorts
Humble little bungalows, charming cottages and mid-century motels verging on historic add charm to this beach town. But you’ll also find condos and ultra-luxurious resorts replete with heavenly spas, fine dining and suites with full kitchens for a weekend or extended-stay. Newer high-rises like the Sandpearl and Hyatt Regency resorts provide aerial views of the Gulf and its shoreline. Best thing, all the properties skirt the beach or the backwaters of Clearwater Bay. Distances in Clearwater Beach are judged by steps to the shore.
7 On the Water
The turquoise Gulf water is one of Clearwater Beach’s top attractions—whether you’re in it, on it or soaring above. Concessionaires and charters at the municipal Clearwater Beach Marina offer ample opportunities for power boating, parasailing, dive excursions and fishing charters. If slow is more your scene, opt for a dinner cruise, dolphin tour or sight-seeing boat trip. For those who want to be on the water in a quiet, relaxed setting, kayaking mangrove tunnels surrounded by nature is an activity accessible at nearby Caladesi Island, where rental equipment is available.
8 Downtown Diversion
Clearwater’s bluff-top downtown is just a causeway bridge away and its oak-lined streets juxtapose the beach scene just to the west. Leave the sand and surf behind and walk the pedestrian-friendly Memorial Causeway to the Cleveland Street District. Here you can dine alfresco at a café, deli or all-day breakfast diner. Then browse boutiques offering home decor, sports gear and luxe men and women’s fashions or catch a concert or classic movie at the 655-seat Capitol Theatre, built in 1921 and one of the oldest operating theaters in Florida.
9 Sync your Smartphone Calendar
No matter the month, even the day of the week, there’s always a special event on the beach or downtown. Your activity barometer will register from laid-back to super-charged with an abundance of annual events. Foodies like the totally hip, slip-off-your-shoes and walk-in-the-sand Clearwater Beach Uncorked wine and food fest, along with visits during Clearwater Beach Restaurant Week when they can try new dining spots for a fraction of the regular dinner bill. Sports-oriented visitors come for the Iron Girl half-marathon, Swim Across America’s Tampa Bay Open Water Swim and the Super Boat National Championship & Seafood Festival.
10 Go Greek
Hop on board Clearwater Beach’s Jolley Trolley for a ride north to neighboring Tarpon Springs, a Greek community with a history of sponge diving. The main street Dodecanese Boulevard runs along the Anclote River, where shrimp boats proudly flying the Greek flag dock. The boulevard is lined with restaurants, bakeries, souvlaki stands and gift shops that are owned and run by local Greeks. The food is authentic so don’t hesitate to order a dish of moussaka and stop in the bakery for syrupy phyllo pastries like baklava and kataifi. Even the Greek-centric souvenirs, reminders of the mother country, make shopping here fun.