Itinerary
The 6-Day Master Itinerary
Standard daily rides depart promptly at 9:00 AM and average 4 to 5 hours of relaxed ride time, inclusive of curated history and hydration stops (excluding Day 1).
Custom Fittings & Coastal Elegance
Your luxury tour kicks off in the charming town of Dunedin. Between 9:00 AM and 12:00 PM, we will meet all riders at Kafe Racer, our premier local bike shop partner.
Historic Trails, Coastal Towns & Vintage Luxury
At 9:00 AM, riders enjoy a seamless shuttle to Demens Landing Park, a beautiful waterfront peninsula nestled in downtown St. Petersburg.
Majestic Bridges & Historic Springs
Following morning yoga at the historic Fenway Hotel, we start the day’s ride by tracing our path back along the beautiful, waterfront Edgewater Trail.
White-Sand Yoga, Island Escapes & Greek Heritage
Your day begins with a morning luxury transport to the world-renowned shores of Clearwater Beach, where we kick off the morning with an unforgettable pre-ride yoga session on the sand, listening to the calming rhythm of the Gulf waves.
Wilderness Canopies & Historic Springs
Departing north from our morning retreat, riders hit the smooth asphalt of the northern Pinellas Trail, continuing across the county line into the beautiful Starkey Gap Trail.
Historic Rail Corridors & The Grand Finale
The final day of your cycling tour starts with a luxury morning shuttle to Brooksville to visit the historic Good Neighbor Trailhead located on Russell Street.
Six Days. Countless Memories.
Discover Florida at a different pace. Over six unforgettable days, we’ll follow scenic coastal paths, explore charming historic towns, and ride beneath the shaded canopies of Old Florida.
With thoughtfully planned routes, comfortable accommodations, and a friendly support team handling the details, you’re free to enjoy the ride—and the friendships made along the way
Day 1 — A Coastal Welcome
Just under 10 miles | St. Petersburg to Gulfport
Your Sunny Spokes adventure begins in charming Dunedin, where we’ll get everyone comfortably fitted with their bicycles and equipment before heading to St. Petersburg.
Our first ride is an easy introduction to Florida’s beautiful Gulf Coast. Beginning along the waterfront at Coffee Pot Park, we’ll follow scenic pathways and the Pinellas Trail toward the colorful seaside community of Gulfport.
Along the way, enjoy gentle coastal breezes, waterfront views, and the chance to get acquainted with your fellow travelers.
After settling into our boutique accommodations, we’ll gather for a relaxed welcome dinner at a carefully selected local restaurant.
In a welcoming outdoor setting, you’ll have the chance to meet your fellow travelers, share stories, and enjoy your first evening together.
Overnight: Gulfport
After stretching and getting centered, riders will set off along the North Bay Trail, a picturesque coastal path offering sweeping waterfront views and refreshing marine breezes.
As we leave the bay behind, we’ll transition smoothly onto the famous Pinellas Trail, a protected greenway ideal for relaxed cycling. From there, the route takes a scenic detour along the Gulfport Spur Trail, leading directly into the vibrant and artistic waterfront community of Gulfport.
After a leisurely, flat afternoon ride of just under 10 miles, we’ll arrive at our home for the evening: the exquisite Peninsula Bed & Cocktails.
Following a post-ride recovery yoga session on the beautiful grounds, riders will have plenty of time to unpack, freshen up, and relax.
As evening approaches, the group will gather for a casual yet refined dinner meet-and-greet at Gulfport Brewery + Eatery. To celebrate the beginning of the tour, dinner and two premium craft drinks will be fully provided.
Approximately 26 miles | St. Petersburg to Dunedin
Today we’ll discover the character of Florida’s Gulf Coast as we ride north from downtown St. Petersburg along the celebrated Pinellas Trail.
Our route winds through welcoming communities, shaded pathways, and neighborhoods rich with local history.
Along the way, we’ll share stories about the places that make this region so distinctive, with plenty of opportunities to stop, explore, and enjoy the scenery.
We’ll finish along Dunedin’s picturesque waterfront, where lunch and a little relaxation await.
The afternoon is yours to explore this delightful town, known for its independent boutiques, galleries, and inviting restaurants.
Enjoy an evening at your own pace before another beautiful day on the trails.
Approximately 31 miles | Dunedin to Safety Harbor
Today brings one of our most memorable rides as we follow scenic trails toward the sparkling waters of Tampa Bay.
Shaded pathways and waterfront views lead us to the Courtney Campbell Trail, where we’ll cycle across the bay with sweeping views in every direction.
It’s a wonderful place to appreciate Florida’s natural beauty—and pause for a photograph or two.
With time for refreshments and stories about the places we pass, the journey is every bit as enjoyable as the destination.
Our ride concludes in charming Safety Harbor, where a catered lunch and optional restorative stretching await.
Spend the afternoon exploring its walkable downtown or relaxing at the historic Safety Harbor Resort and Spa.
Overnight: Safety Harbor
Day 4 — Island Breezes & Greek Traditions
Approximately 26 miles | Clearwater Beach to Tarpon Springs
We’ll begin the morning beside the Gulf’s beautiful white-sand beaches before setting out on another spectacular coastal ride.
Crossing the Memorial Causeway, we’ll join the Pinellas Trail and make our way toward Honeymoon Island, where coastal forests, open skies, and refreshing sea breezes provide a wonderful setting for our journey.
After enjoying lunch surrounded by natural beauty, we’ll continue north to Tarpon Springs, a town celebrated for its Greek heritage and historic sponge-diving industry.
We’ll explore the famous Sponge Docks, hear stories of the families who shaped this remarkable community, and soak up its lively atmosphere.
Later, we’ll settle into our resort accommodations, with the evening free for relaxation or an independent dinner.
Overnight: Palm Harbor
Day 5 — Into the Heart of Wild Florida
Approximately 26 miles | Starkey Wilderness Park
Today we leave the bustle of the coast behind and discover a quieter side of Florida.
Our ride takes us along the Starkey Gap Trail and into Jay B. Starkey Wilderness Park, where peaceful paved pathways wind through pine forests, cypress wetlands, and landscapes that have changed little over generations.
Keep an eye out for deer, gopher tortoises, and the many birds that call this beautiful preserve home.
With fresh air, shady stretches, and the sounds of nature surrounding us, this is Florida cycling at its most peaceful.
After our ride, we’ll travel to historic New Port Richey for lunch and a relaxing afternoon.
Explore the charming downtown, stroll beside the river, or simply unwind.
Overnight: New Port Richey
Day 6 — A Grand Finale on the Rail Trails
Approximately 32 miles | Brooksville to Inverness
Our final ride takes us into the heart of Florida’s scenic countryside, beginning on the historic Good Neighbor Trail in Brooksville.
We’ll pedal beneath leafy canopies and through peaceful natural landscapes before joining the renowned Withlacoochee State Trail, one of Florida’s great rail-trail treasures.
Along the way, we’ll enjoy the easy rhythm of the ride, share a few final stories, and reflect on the places we’ve discovered together.
Our journey concludes in the welcoming town of Inverness, where everyone will have time to freshen up, shower, and change into comfortable clothes before gathering for a leisurely farewell lunch.
Over a delicious meal, we’ll celebrate six wonderful days of cycling, share our favorite memories, and enjoy a little more time together before our comfortable return transportation to Dunedin.
You’ll leave with beautiful memories of Florida—and perhaps a few new friends you’ll be planning your next adventure with.
