Florida Keys
Florida Keys
- It's More than Just a Bike Tour, It's a Florida Keys Experience
- Cycle the Florida Keys Overseas Heritage Trail
- A scenic journey spanning 41 bridges
- Pedal, Be Pampered and Party in Paradise
Check Out Our Tour Brochure
Tour Video
Tour Map
It’s More Than Just a Bike Tour – It’s a Florida Keys Experience!
Join us at the end of October for our Florida Keys tour 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 that makes the Keys so special.
Pedal through scenic routes that immerse you in the natural beauty of the Keys. Don’t miss the Seven Mile Bridge, quite possibly the most breathtaking seven miles you’ll ever ride.
Not into long bridges? We have 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 this Florida Keys tour 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 well-appointed 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 listened to your feedback and kept the 2025 upgrades, plus added even more ways to make your experience easier and more enjoyable:
- Sunday night accommodations and dinner are included.
- Four nights at the Fairfield Inn by Marriott in Marathon, which means fewer room changes and more time to relax by the pool. If you are driving, you’ll have more access to your car to explore the local sights at your leisure.
- Two nights at the Hampton Inn Key West, just steps from the oceanside promenade. This wide, scenic, bike-friendly path offers safe, easy riding into the heart of Key West, with beautiful water views along the way.
- No more doubling back against the wind from Key West to Key Largo. Our new routes were a hit, so they’re here to stay. These include Sombrero Beach, Pigeon Key, a loop around Key West, and a cycling 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 Florida Keys Experience, where adventure, fun, and pampering are all part of the ride.
Day 0 - Fairfield Inn by Marriott Marathon
Florida Keys participants can enjoy special rates at the Fairfield Inn by Marriott Marathon on October 23 & 24 for one or two extra nights and/or October 31 & November 1, 2026 for one or two extra nights, both before and after the ride. The booking must be done online by no later than September 23, 2026. To qualify for this offer use the following links:
Book your group rate for Pampered
Pedalers – Oct 23 & 24, 2026
Book your group rate for Pampered
Pedalers – Oct 31 & Nov. 1, 2026
Day 1 - Key Largo to Marathon
- Monday morning, we shuttle riders and their bikes from our hotel to the starting location in Key Largo, where your journey through the Keys begins. From there ride toward 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 possibility is a visit to Long Key State Park for a scenic visit to one of the Keys’ natural gems. End your day with our group dinner at the Sunset Grille on Knights Key, where we’ll enjoy a delicious meal while taking in stunning views of the Seven Mile Bridge as the sun sets over the horizon.
Day 2 - Hotel to Pigeon Key and Sombrero Beach (Out and Back)
- 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.
Day 3 - Marathon to Key West
- 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 provides 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.
Day 4 - Optional Key West Loop Ride
- We suggest starting early (around 8:00 AM) to avoid the crowds at the Southernmost Point Marker. Afterward, enjoy a peaceful breakfast in the heart of Key West, before the hustle and bustle of the day sets in. Don’t miss another great photo opportunity at Mile Marker 0, marking the end of U.S. Route 1 and the perfect way to commemorate your ride all the way from Key Largo.
In the late afternoon, we’ll 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 sunset.
Day 5 - Big Pine and No Name Keys
- 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 Big Pine Keys’ natural beauty. If you prefer more than these 27 miles you have the option to ride back over the 7 mile bridge back to the host hotel for a just over 50 mile day.
Oct 25 to Oct 31, 2026
Miami International Airport is the best connected. It will be your responsibility to arrange transportation from the airport to the starting location. Prices for ride hailing apps tend to fluctuate. You can pre-book a ride day(s) in advance of your arrival \ departure.
Shuttle service can be arranged through Keys Shuttle. Check their web site for pick-up locations and pricing information. Make sure to inform them if traveling with your bicycle.
If you are flying out the ending Saturday, to assure making your flight, DO NOT book a flight before 5 PM if using the Miami airport and not before 7 PM if using the Ft. Lauderdale airport.
Free long-term parking will be available at the host hotel. The parking lot is secure and we have never had issues with security, that being said the tour does not take responsibility for any potential issues associated with your vehicle.
Riders must make their own arrangements for bike rental. These outfitters will bring the bikes to the hotel on Sunday for fitting, likewise they will be on site on Saturday to collect your bikes.
82240 Overseas Hwy, Islamorada, FL 33036 305.517.4177
2994 Overseas HWY, Marathon, FL 33050 305.743.3204
All bikes must be equipped with a front facing headlamp and a rear facing red blinking light, which must be activated at all times.
The trails are mostly paved and this bicycle vacation is suitable for any bicycle type. Historically, riders have favored hybrids, road bikes, and EBikes.
Each rider can bring two pieces of baggage, with each piece ideally not exceeding 30 pounds. Your bags will be taken care of in the morning by our staff, who will move them to your next lodging location and bring them directly to your room. That’s why PAMPERED is the name of the game.
Not a problem. That said, vegetarian is the only other dietary option available.
We welcome everyone. Non-riders will need to complete the same registration forms and pay the same fee as a rider. A non-rider will be part of every aspect of the tour except the riding if they so choose.
No problem. If you feel you cannot finish the day’s ride, our staff will assist you and your bike to get you to the ending location. No questions asked. Alternatively, each evening before the next day’s ride we offered shortened mileage variants where we will move you forward and this way everyone ends at the same point.
| Package | Price |
|---|---|
| Single | $3,300 |
| Double | $2,700 |
Please note that there is an expiration date associated with the early bird discount code. Pricing when redeeming a discount code is honored by the date your registration and deposit are received. Mail-in registrations paid in full must be postmarked by the stated discount code expiration date to qualify.
Note: To pass savings onto riders, we have moved to Double pricing base rates; for Triple & Quad rates please reach out to us by email. (pamperedpedalers@gmail.com)
It’s More Than Just a Bike Tour – It’s a Florida Keys Experience!
Join us at the end of October for our Florida Keys tour 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 that makes the Keys so special.
Pedal through scenic routes that immerse you in the natural beauty of the Keys. Don’t miss the Seven Mile Bridge, quite possibly the most breathtaking seven miles you’ll ever ride.
Not into long bridges? We have 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 this Florida Keys tour 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 well-appointed 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 listened to your feedback and kept the 2025 upgrades, plus added even more ways to make your experience easier and more enjoyable:
- Sunday night accommodations and dinner are included.
- Four nights at the Fairfield Inn by Marriott in Marathon, which means fewer room changes and more time to relax by the pool. If you are driving, you’ll have more access to your car to explore the local sights at your leisure.
- Two nights at the Hampton Inn Key West, just steps from the oceanside promenade. This wide, scenic, bike-friendly path offers safe, easy riding into the heart of Key West, with beautiful water views along the way.
- No more doubling back against the wind from Key West to Key Largo. Our new routes were a hit, so they’re here to stay. These include Sombrero Beach, Pigeon Key, a loop around Key West, and a cycling 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 Florida Keys Experience, where adventure, fun, and pampering are all part of the ride.
Day 0 - Fairfield Inn by Marriott Marathon
Florida Keys participants can enjoy special rates at the Fairfield Inn by Marriott Marathon on October 23 & 24 for one or two extra nights and/or October 31 & November 1, 2026 for one or two extra nights, both before and after the ride. The booking must be done online by no later than September 23, 2026. To qualify for this offer use the following links:
Book your group rate for Pampered
Pedalers – Oct 23 & 24, 2026
Book your group rate for Pampered
Pedalers – Oct 31 & Nov. 1, 2026
Day 1 - Key Largo to Marathon
- Start with a journey 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 possibility is a visit to Long Key State Park for a scenic visit to one of the Keys’ natural gems. End your day with our group dinner at the Sunset Grille on Knights Key, where we’ll enjoy a delicious meal while taking in stunning views of the Seven Mile Bridge as the sun sets over the horizon.
Day 2 - Hotel to Pigeon Key and Sombrero Beach (Out and Back)
- 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.
Day 3 - Marathon to Key West
- 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 provides 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.
Day 4 - Optional Key West Loop Ride
- We suggest starting early (around 8:00 AM) to avoid the crowds at the Southernmost Point Marker. Afterward, enjoy a peaceful breakfast in the heart of Key West, before the hustle and bustle of the day sets in. Don’t miss another great photo opportunity at Mile Marker 0, marking the end of U.S. Route 1 and the perfect way to commemorate your ride all the way from Key Largo.
In the late afternoon, we’ll 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 sunset.
Day 5 - Big Pine and No Name Keys
- 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 Big Pine Keys’ natural beauty. If you prefer more than these 27 miles you have the option to ride back over the 7 mile bridge back to the host hotel for a just over 50 mile day.
Oct 25 to Oct 31, 2026
Miami International Airport is the best connected. It will be your responsibility to arrange transportation from the airport to the starting location. Prices for ride hailing apps tend to fluctuate. You can pre-book a ride day(s) in advance of your arrival \ departure.
Shuttle service can be arranged through Keys Shuttle. Check their web site for pick-up locations and pricing information. Make sure to inform them if traveling with your bicycle.
If you are flying out the ending Saturday, to assure making your flight, DO NOT book a flight before 5 PM if using the Miami airport and not before 7 PM if using the Ft. Lauderdale airport.
Free long-term parking will be available at the host hotel. The parking lot is secure and we have never had issues with security, that being said the tour does not take responsibility for any potential issues associated with your vehicle.
Riders must make their own arrangements for bike rental. These outfitters will bring the bikes to the hotel on Sunday for fitting, likewise they will be on site on Saturday to collect your bikes.
82240 Overseas Hwy, Islamorada, FL 33036 305.517.4177
2994 Overseas HWY, Marathon, FL 33050 305.743.3204
All bikes must be equipped with a front facing headlamp and a rear facing red blinking light, which must be activated at all times.
The trails are mostly paved and this bicycle vacation is suitable for any bicycle type. Historically, riders have favored hybrids, road bikes, and EBikes.
Each rider can bring two pieces of baggage, with each piece ideally not exceeding 30 pounds. Your bags will be taken care of in the morning by our staff, who will move them to your next lodging location and bring them directly to your room. That’s why PAMPERED is the name of the game.
Not a problem. That said, vegetarian is the only other dietary option available.
We welcome everyone. Non-riders will need to complete the same registration forms and pay the same fee as a rider. A non-rider will be part of every aspect of the tour except the riding if they so choose.
No problem. If you feel you cannot finish the day’s ride, our staff will assist you and your bike to get you to the ending location. No questions asked. Alternatively, each evening before the next day’s ride we offered shortened mileage variants where we will move you forward and this way everyone ends at the same point.
| Package | Price |
|---|---|
| Single | $3,300 |
| Double | $2,700 |
Please note that there is an expiration date associated with the early bird discount code. Pricing when redeeming a discount code is honored by the date your registration and deposit are received. Mail-in registrations paid in full must be postmarked by the stated discount code expiration date to qualify.
Note: To pass savings onto riders, we have moved to Double pricing base rates; for Triple & Quad rates please reach out to us by email. (pamperedpedalers@gmail.com)
Florida Keys Memories
