Looking for a winter bike tour? Pack your flip-flops and let’s bike the paved trails of the Pinellas Peninsula, downtown St. Petersburg, and the barrier islands of Ft. DeSoto with sun on our faces and coastal breezes at our backs. It’s hard to beat Florida’s relaxed riding and lovely warm temperatures. There aren’t many hills, but numerous bridges will take you 45-72 feet above mooring sailboats for the trip’s best views. Plus, they will give you an effortless burst of speed on the other side.
The Pinellas Trail (listed in the Rail-Trail Hall of Fame) is at the heart of this tour. This national recreation trail follows an old railroad line. The other routes provide variety with sections surrounded by water, lined with palm trees or shaded by live oaks dripping with Spanish moss. You’ll ride to and through state and county parks and along tidal waterways and stretches of coastline. Visit seaside communities, quaint trail towns, and two very cultural little cities.
Maybe spot a Roseate Spoonbill as you’re riding along. It’s also not uncommon to see dolphin or a manatee while cruising causeways and bicycling along the bay fronts. We have a variety of suggestions for post-ride activities each day, whether it’s gallery hopping or tapping into the craft brewery scene, paddleboarding or shuffleboard, visiting an aquarium, people-watching or just strolling on the beach.
Fred Marquis Pinellas Trail
Clearwater Beach Bridge
Cultural Downtown St. Pete
Safety Harbor Spa & Resort - Night 1
Fenway Hotel - Night 2
Hampton Inn & Suites - Nights 3 & 4
Sirata Beach Resort - Night 5
Your cycling tour starts with a 10-mile ride across the open waters of Tampa Bay on the Courtney Causeway Trail and then onto the canopied Ream Wilson Trail. We’ll enjoy a bayside picnic before riding into the charming town of Safety Harbor and exploring the brick streets and colorful 1930s bungalows. Our lodging for the night at the Safety Harbor Resort and Spa is an acclaimed spa built on the town’s historic natural mineral springs. Your day ends with a group dinner out on the town.
Today begins with a short shuttle from Safety Harbor to the northern terminus of the Fred Marquis Pinellas Trail. This Rails-Trails Hall of Fame trail is home to some fabulous trail towns, including the famous Tarpon Springs! The ride continues after lunch out to Honeymoon Island State Park, where sugar-white sand meets the emerald green water of the Gulf.
Tonight’s destination is Dunedin, Florida’s first officially designated trail town. This walkable seaside community is bustling with galleries, shops, and restaurants, plus seven breweries scattered around Main Street. Grab a bite to eat, and then finish off a great day with the nightly sunset celebration from the rooftop bar of our lodging, the Fenway Hotel.
Experience the award-winning Clearwater Beach, and climb the highest bridge of the trip (72 feet), which snakes along Clearwater’s ocean-front promenade. It’s just another lovely day on the Pinellas Trail! This stretch has two cultural little cities and officially ends in the heart of downtown St. Pete (the “Burg”), and we’ll arrive with enough time to explore its art and history. Tonight’s accommodation is the Hampton Inn & Suites only a block away from the water, and we have a special dinner plan for this evening!
Head north out of the Burg for a morning ride along the Bay’s seawall through green spaces, past yachts and sailboats, beach volleyball and lively outdoor cafes, then “lollipop” loop back to downtown with choices for lunch including a dockside bistro. The afternoon is yours to explore the pier, the Discovery Center, and other highlights of the Burg. Don’t miss the iconic Dali Museum! We’ll spend a second night in a row in downtown St. Pete.
We leave St. Pete today and backtrack a few miles on the Pinellas Trail before taking a detour into the trailside town of Gulfport, which is reminiscent of Old Key West. Then we’ll cycle through Clam Bayou, a unique nature preserve, and onto the Sunshine Skyway, a bike path reaching into the bay toward the spectacular bridge with its twin, golden spires. Three more bridges await along the Bayway Trail as we wrap up the day and head for the Sirata Resort on St. Pete Beach, just steps away from the Gulf of Mexico.
More to explore by bike on our final day, including a slice of wild Florida. The first stop is Pass-a-Grille and the shortest Main Street in the U.S. Then the highlight, five interconnected keys where Tampa Bay meets the Gulf. From the saddle, you can enjoy 1,000+ acres of mangroves, wetlands, palm hammocks and hardwoods. On foot, reach the saltwater lagoon, historic fort and unspoiled beaches bordered by sea oats and dunes. Wade out to the off-shore sandbar, look back and take it all in!
5 Breakfasts | 4 Lunches | 3 Dinners
PP Double Occupancy
*This is required if you are traveling solo or if you are traveling with someone but require separate beds.