This Underrated Florida Town Is A Quiet Retirement Paradise With Miles Of Uncrowded White Sand Beaches

If you start in St. Petersburg — the bustling beach town with award-winning beaches just 23 miles across the bay from Tampa — and drive up the long, slender barrier island that fringes the coastline all the way to Clearwater, you'll pass through several charming beach towns tucked between the Gulf and Boca Ciega Bay's intercoastal waterway. These include vibrant St. Pete Beach, laid-back Treasure Island, underrated Madeira Beach with its beachside boardwalk, and — if you blink before you get to Indian Shores, you'll miss it — Redington Beach, a peak retirement town boasting a median age of 60. "Redington" is sometimes used as a catch-all term for three tiny locations along Gulf Boulevard: Redington Beach, North Redington Beach, and Redington Shores, three Pinellas County neighborhoods that share a wide, white sand beach. Redington Beach itself is about 1 square mile in size, abutting North Redington, which merges with Redington Shores to cover about 2.5 miles of beach total. Redington's beaches blend seamlessly south with Madeira Beach until it ends at John's Pass Bridge and continues north along Sand Key– 15 miles of connected coastline.

Hurricane Helene wreaked havoc on the area in 2024, followed closely by Hurricane Milton. Much of Redington and its fellow coastal communities were flooded and destroyed, and for weeks, the streets were piled high with sand, soaking couch cushions, broken building materials, moldy mattresses, and lifetimes' worth of personal items as devastated home and business owners dealt with storm cleanup and rebuilding. Cruise Gulf Boulevard today and you'll still see empty lots and boarded-up buildings. Yet Redington has resiliently bounced back, slowly reopening businesses and beaches, holding tight to its reputation as a delightful destination for retirees, tourists, and anyone else seeking sun and respite.

Florida's one of the best places to retire, and this stretch of Pinellas County's Gulf Coast, conveniently located 14 miles from St. Pete-Clearwater International Airport, may be the best of the best. Still marked by sleepy coastal charm and limited development, Redington's often overlooked between its bigger neighbors, but it's far from no-man's land. It's no Miami Beach — not yet anyway — nor even Clearwater Beach, which has morphed from a coastal village into a skyline of beachfront condos and concrete jungle. Meanwhile, Redington keeps its simple, unpretentious charm — where most bars are dives and the nicest restaurant in town welcomes flip flops.

One such spot is Conch Republic, which is a favorite for lunch, dinner, and weekend brunch. Known for its specialty fried conch and all-day happy hour, the menu includes crab legs, seafood gumbo, rum flights, tableside bananas foster, and occasional prime rib specials. Nearby, The Frog Pond Café re-opened in September 2025, a year after Hurricane Helene destroyed it. The popular daytime joint has retained its signature frog-related decor and serves hearty classics like the Key West Omelet and apple waffles, until 2 p.m. daily. 

Some motels are rebuilding post-hurricane, but Redington still has charming places to stay. Sand Vista is a historic, old-Florida style Gulf-front motel, and Island House Resort is a colorful, beachfront spot with a pool and tiki bar. The Hilton DoubleTree sits right on Redington Beach, offering decent beachfront rates. Its waterfront restaurant and tiki bar, Coconut Charlie's, is ideal for a sunset cocktail or casual dinner, and open to non-guests.

Redington's big draw is its beaches. Wide swathes of powder-white sand and six beach access points along Gulf Boulevard make it easy to spread out. Redington Shores Beach Access Park is one of the largest, with showers, bathrooms, and ample parking. You can rent beach chairs and umbrellas from WTF Rentals, though they don't handle set-up or tear-down. Several grassy parks with benches and shade along Gulf Boulevard add to the area's appeal, and the Suncoast Beach Trolley runs along Gulf Boulevard from St. Pete Beach to Clearwater for $2.25 per adult (or $5 for a day pass), making it easy to beach and bar-hop. After a day at Redington Shores Beach access, walk across the parking lot to Broke N Bored Grill for dinner and drinks. For a quick-and-easy post-swim meal or sandy picnic, Beach Pizza and Coastal Pizza Kitchen are both solid local picks.

Redington also does breakfast well. At Sweet Sage, a charming, eclectic breakfast and lunch spot and boutique, you'll find scrambled eggs, seafood wraps, and Bloody Marys among vintage decor and beachy knickknacks. Ask for a seat in the shaded garden patio and bring your pup for the special doggie menu. There's also My Happy Place, a charming outdoor lunch spot nearby. Kenny's Korner is an under-the-radar gem — if country-fried steak is on special, get it. The Eggs Benedict variations will excite even the most bougie brunch-lovers, especially paired with a mimosa or beer. For a relaxing morning coffee with water view, head to Coastal Souls Coffeehouse on the intercoastal, where you can nibble pastries and sip espresso while watching boats cruise by.