It’s More Than Just a Bike Tour—It’s a Florida Keys Experience!

Join us for BubbaFest Florida Keys at the end of October and embark on a once-in-a-lifetime adventure from Key Largo to Key West, crossing 41 bridges along the scenic Florida Keys Overseas Heritage Bike Trail. This unforgettable journey combines stunning views, fun, and the laid-back charm of the Keys.

Pedal through scenic routes that immerse you in the natural beauty of the Keys while avoiding most traffic. Don’t miss the Seven Mile Bridge—quite possibly the most breathtaking seven miles you’ll ever ride.

Not into long bridges? We’ve got you covered!

If long bridges aren’t your thing, we’ll shuttle you and your bike over, so you can still enjoy the adventure without the worry.

Why BubbaFest Florida Keys is Different:

Our tour stands apart due to careful planning and long-standing relationships with some of the best venues across the Keys. From delicious meals to luxurious accommodations, we take care of the details so you can just ride, relax and soak in the incredible beauty of these islands.

Indulge in the Keys' diverse cuisine and explore the vibrant local culture—this truly is a paradise for cyclists and adventurers alike.

2026 Enhancements: More Pampering, Less Hassle

We’ve listened to your feedback and kept the 2025 upgrades, plus added even more ways to make your experience easier and more enjoyable:

• Sunday night accommodation and dinner are included.

• We’re offering four nights at the Fairfield Inn by Marriott in Marathon, cutting down on room changes and giving you more time to relax by the pool. Plus, if you drive down, you'll have more access to your car to explore the local sights at your leisure.

• New for 2025 and continuing in 2026—no more doubling back against the wind from Key West to Key Largo! Instead, we’re offering new routes that include Sombrero  Beach, Pigeon Key, a loop around Key West, and an exploration of Big Pine Key’s Blue Hole, Key Deer Refuge, and No Name Key.

Ready for the Keys Experience of a Lifetime?

We can’t wait to welcome you to the BubbaFest Florida Keys Experience—where adventure, fun, and pampering are all part of the ride!

Host Hotel: Fairfield Inn by Marriott Marathon
13201 Overseas Hwy, Marathon, FL 33050

Rider Check-In at the Fairfield Inn by Marriott Marathon, 2 PM – 4 PM

Rider Meeting at the Fairfield Inn by Marriott Marathon, 4:30 PM

Pedal 47 miles from Key Largo to Marathon, soaking in the beauty of the Keys along the way. Your first SAG stop is in Islamorada, where you can take a moment to visit the 1935 Hurricane Memorial, a poignant historical site that commemorates the impact of the great hurricane.

As you move closer to Marathon, consider a stop to feed the Tarpon at Robbie’s Marina. Another option is a visit to Long Key State Park for a scenic visit to one of the Keys' natural gems.

End your day with a group dinner at the Sunset Grille on Knights Key, where you can enjoy a delicious meal and take in stunning views of the Seven Mile Bridge as the sun sets over the horizon.

This optional ride begins with a visit to Sombrero Beach, one of the few truly public beaches in the Keys. From there, you'll pedal across the original railroad bridge, which has been transformed into a bike and pedestrian path, offering stunning views of the water below. The ride takes you out to Pigeon Key, a small island with a rich history, where you’ll get a taste of what tomorrow’s ride over the iconic Seven Mile Bridge will be like. It’s the perfect opportunity to experience the bridge firsthand and get a feel for the breathtaking views and unique atmosphere that await you on the next day’s adventure.

Pedal over the Seven Mile Bridge, one of the most breathtaking stretches of road in the Keys, with stunning views of the turquoise waters in every direction. Stop at Bahia Honda State Park, considered the best in the Keys, and snap photos of the old railroad’s iconic camelback bridge. A well-earned SAG stop at Boondocks Grille and Drafthouse offers refreshing snacks and drinks. After passing the Key West Naval Air Station, you’ll roll into the Hampton Inn Key West, where luxury and relaxation await after a memorable day of cycling. 

We highly recommend starting your ride early (around 8:00 AM) to avoid the crowds at the Southernmost Point Marker. From there, we will continue on to visit more of Key West's iconic sights before the hustle and bustle of the day sets in. Be sure to stop for another great photo opportunity at Mile Marker 0, which marks the end of U.S. Route 1 and is the perfect way to commemorate your bike ride from Key Largo.

In the late afternoon, we will offer a shuttle service for a walking tour that includes a visit to Mallory Square to experience the famous sunset celebration, where local artists, performers, and musicians gather to watch the sun dip below the horizon.

On Friday, we take a break from the Florida Keys Overseas Heritage Bike Trail for a leisurely ride through Big Pine Key, where you’ll explore the Blue Hole, Key Deer Refuge, and No Name Key. These peaceful, quiet roads offer more views of the turquoise waters and unique wildlife encounters. You’ll likely spot the endangered Key Deer and, with luck, an alligator at the Blue Hole, a freshwater pond nestled in the heart of the island. For a refreshing stop, visit the No Name Pub, a local favorite known for its cool A/C and laid-back atmosphere. It’s the perfect place to unwind and cool off before continuing your exploration of the Big Pine Keys' natural beauty.