TOURS
DAY 1
Gulfport & The Peninsula Bed & Cocktails
Welcome to Gulfport, a small, artsy waterfront city on Boca Ciega Bay, defined by brick-paved streets, candy-colored cottages, and an independent “Old Florida” spirit. This laid-back enclave features no chain stores or parking meters, making it incredibly bike-friendly and easy to explore.
You can easily walk through the Historic Waterfront District to browse local art galleries and boutiques, or stroll down to the calm, uncrowded Gulfport Beach.
At the end of your first day on the saddle, you will stay at The Peninsula Bed & Cocktails, a meticulously renovated historic boutique hotel nestled in the heart of town. Merging classic Southern veranda elegance with a seamless, high-tech contactless check-in, this luxury retreat offers bespoke accommodations where each room is a tasteful homage to an iconic global cocktail.
After a rewarding ride, unwind in the picturesque Lobby Bar as master mixologists craft artisanal libations just for you.
Gulfport is very walkable, with many fine restaurants to choose from for an enjoyable evening.
DAY 2
Dunedin & Fenway Hotel
Pedal into Dunedin, a charming waterfront city celebrated for its vibrant Scottish heritage, bustling craft brewery scene, and direct access to the scenic Fred Marquis Pinellas Trail.
The town radiates a relaxed, community-first energy with its walkable downtown, local boutiques, and stunning sunset views over the Intracoastal Waterway.
Your home for the night is the historic Fenway Hotel. A proud icon of the Jazz Age that opened in 1927, this beautifully modernized boutique property perfectly blends musical soul with mid-century style.
After unpacking, head up to Hi-Fi, the hotel’s premier rooftop bar, to enjoy a refreshing drink while taking in panoramic coastal views of Honeymoon and Caladesi Islands.
DAY 3
Safety Harbor & Safety Harbor Resort and Spa
Roll into Safety Harbor, a peaceful, historic sanctuary nestled on the west shore of Tampa Bay, famous for its massive ancient oak trees and tranquil brick-lined streets.
This hidden gem offers a quaint downtown filled with unique eateries, folk art installations, and a serene pier that is perfect for spotting local marine life.
You will spend the evening relaxing at the historic Safety Harbor Resort and Spa. Built directly over natural, mineral-rich subterranean springs that have attracted wellness seekers for centuries, this sprawling waterfront destination is the perfect place to rejuvenate.
Treat your muscles to a therapeutic spa treatment or soak in the mineral pools to completely refresh your body after days of riding.
DAY 4
Palm Harbor & Innisbrook Golf Resort
Journey to Palm Harbor, a coastal community that perfectly balances quiet Old Florida charm with world-class recreation. Known for its historic downtown grid, excellent local seafood joints, and rolling parklands, it provides a peaceful and upscale escape along the trail network.
Your accommodation for the night is the expansive Innisbrook Golf Resort, a prestigious destination nestled among rolling, tree-lined hills.
Celebrated globally for hosting the PGA Tour’s Valspar Championship on its famed Copperhead Course, this luxury resort offers lodge-style condo rentals surrounded by pristine nature.
It is the perfect spot to enjoy top-tier dining, explore acres of beautifully manicured grounds, or lounge by the Loch Ness Monster pool complex.
DAY 5
New Port Richey & The Hacienda
Conclude your overnight stays in New Port Richey, a historic riverfront city undergoing a beautiful modern cultural revival. Built around the winding waters of the Pithlachascotee River, the downtown area features a lively, walkable layout filled with craft breweries, riverfront parks, and local theaters.
You will stay at The Hacienda, a brilliantly restored 1920s historic boutique hotel listed on the National Register of Historic Places.
Originally known as one of Florida’s “pink palaces” during the golden age of Hollywood, this stunning Spanish-Floridian oasis features its original grand fireplaces, striking chandeliers, and a lush courtyard fountain that has been operating since 1927.
Unwind with a handcrafted cocktail at the hotel’s reclaimed-wood bar and celebrate a phenomenal week on the trails.
DAY 6
Final Ride & Departure
On your final day, enjoy a smooth, flat morning cruise along the pristine paved trails as you bring your 6-day tour to a memorable close.
Take in the last of the beautiful Florida sunshine and refreshing coastal air before preparing for your journey home.
For those not quite ready to leave, you can also choose to extend your stay and enjoy more time in the sun-drenched Tampa Bay region.