Looking for a winter bike tour? Pack your flip-flops and let’s bike the paved trails of the Pinellas Peninsula and Keys of Bradenton/Sarasota with sun on our face and coastal breezes at our back. It’s hard to beat Florida’s relaxed riding and lovely warm temperatures. There aren’t many hills, but the spectacular bridges will take you 45-72 feet above mooring sailboats for the trip’s best views, plus give you an effortless burst of speed on the other side.
The Pinellas Trail (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 not uncommon to see dolphin or a manatee while cruising causeways and bicycling along the bayfronts. And 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 a just stroll on beach.
Fred Marquis Pinellas Trail
Clearwater Beach Bridge
Cultural Downtown St. Pete
Safety Harbor Spa & Resort - Night 1
Fenway Hotel - Night 2
Hotel Indigo - Night 3
Postcard Inn on the Beach - Nights 4 & 5
Your cycle tour starts with a 10-mile ride across the open waters of Tampa Bay on the Courtney Causeway Trail and then on to 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 night’s lodging 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 north 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.
Climb the highest bridge of the trip (72 feet) and experience the award-winning Clearwater Beach, spinning along its ocean-front promenade. It’s just another lovely day on the Pinellas Trail! This stretch has two cultural little cities, and add in the trailside town of Gulfport, which is reminiscent of old Key West. The Pinellas Trail officially ends in the heart of downtown St. Pete (the “Burg”) with time to explore its art and history. Don’t miss the iconic Dali Museum.
Tonight’s accommodation is the Hotel Indigo and we have an extra 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. A 15-minute shuttle drops us at the Sunshine Skyway for an afternoon ride on a bike path out toward the spectacular twin golden spires. Three more bridges await along the Bayway Trail as we wrap up the day and head to our 1950s renovated motor lodge on the beach: The Postcard Inn. This hip oceanfront motel with surfer-themed rooms is just steps from the Gulf and exudes classic Florida charm.
Hop in the van for a shuttle south over the Skyway Bridge. A string of barrier islands awaits so narrow in places you can see Sarasota Bay and the Gulf of Mexico from the same point. The route is full of variety–twisty miles through a nature preserve, beachfront riding, a historic community that exudes old Florida, and impressive real estate and well-manicured tropical landscaping before reaching the upscale St. Armands Circle, famous for its fine boutiques.
Back in St. Pete Beach, we’ll celebrate our last evening with a sunset dinner cruise and another night at the Postcard Inn.
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.