Frequently Asked Questions

1. When is the ride?  November 2nd – November 4th, 2018.
The ride will start at 7:00 am Friday morning, departing from a fenced in parking lot at 2080 Main Street, Ft. Myers Beach.  Key West is the final destination.

2. What is the cost of the ride?
Early registration starts at $289 per rider + a minimum fundraising per ride of $300 (See registration page – Click Here)

3. What does the registration fee include?
A custom made 72 Hours To Key West performance shirt , SAG support throughout the entire 3 day ride, homemade lunch provided all three days, hydration and unlimited snacks, victory celebration in Key West (food and drinks), motor coach return for riders and return transportation of bikes to Ft. Myers Beach. A portion of your registration fee will go toward feeding low income families with children through our partnership with the Tiny Hands Foundation.

4. What is the average speed of the ride?
We require that all riders be able to maintain a minimum average speed of 16-18 mph for the duration of the ride. Our SAG support is rolling and stops every 25-30 miles and if you are unable to maintain this average speed you run the risk of missing the SAG stops. If a rider falls significantly behind our support crew will provide two options. #1: Forgo SAG support for the remainder of the day. #2: Allow the SAG crew to transport you and your bike ahead to the rest of the group.

5. Will I be riding with a Group or alone?
You’ll find that 90% of the riders end up forming small groups with others who are riding at similar speeds. We strongly encourage to utilize the buddy system and ride with at least one other rider. When cycling on public roads there is safety in numbers and we highly recommend riding with others. 

6. Why Key West?
Key West is a picturesque ride from Ft. Myers Beach. The Florida Keys hold a lot of treasures for visitors. The islands offer a tropical blend of azure waters, lush foliage, fine dining, and accommodations for any budget, some with a history of notorious and notable. The city of Key West carries the creative torch of such former residents as Ernest Hemingway, Tennessee Williams and some past presidents. If you’re looking for things to do, there’s world-class fishing tours, snorkeling, jet skis, parasailing, glass-bottom boat tours, and sunset cruises available year round.

7. How do I get back from Ft. Myers Beach?
On Monday, November 5th at 10:30am, we will board a motorcoach for the return trip back to the original starting point in Ft. Myers Beach.  The trip takes approximately 7 hours with a stop for a late lunch (on your own).  

8. How far is the ride?
The total distance of the three-day ride is approximately 280 miles.

9. Who sponsored the Key West Bike Ride?
The ride is organized AND sponsored by Kevin Bupp Companies (Kevin Bupp & Joanna Bupp). Kevin and Joanna are ambitious, avid cyclists who enjoy sharing their passion for the sport of cycling and running. Through their business, they bring the community together to enjoy the celebration of camaraderie and positive energy! The ride will be an epic Florida adventure, and make a difference in our community.

10. Where did the idea for this event originate?
Kevin Bupp completed a 11-day, 1,100-mile solo bike ride from Florida to Washington, D.C. in April of 2011. During this journey, he was inspired to create a ride within Florida to enjoy with friends, fellow cyclists, and other athletes, while contributing to an important cause.

11. What is the mission of the Key West Ride?
1. To raise funds to be distributed to the Tiny Hands Foundation.
2. To provide an opportunity for individuals to engage in recreation and socialization.
3. To progressively grow the bike ride to reach a greater number of families in need.

12. What happens to money from the ride?
A portion of all proceeds from both riders and sponsors will be donated to help feed families through the Tiny Hands Foundation.

13. What’s the deadline for registration?
The registration deadline is October 31st, 2016.

14. What is the rider registration limit?
This ride will be limited to 70 cyclists. The goal of this year’s ride is to be safe, while maintaining a small “boutique” of riders along the route.

15. What if I can’t finish?
We’ve got you covered! A SAG vehicle will be following us and you can load your bike in the back of the van and call it a day.  The SAG vehicle is primarily for those who can’t finish the ride due to mechanical and/or emergencies.  Please note: You should only sign up for this ride if you feel you have the physical ability to finish a ride of this duration.

16. How far do the riders bike?
Day #1 – Ft. Myers Beach to the Miccosukee Indian Reservation. (120 miles)
The largest section by far is known as the Alligator Alley Reservation, which is located at the extreme western part of Broward County, at its county line with Collier County. Homeland of the Miccosukee tribe of Native Americans, and the Miccosukee Resort and Casino is on this site.

Day #2 – Miccosukee to Marathon. (105 miles)
Our Village of Islands is situated between the saltwater wilderness of Everglades National Park in one direction and North America’s only coral barrier reef and the deep blue waters of the Florida Straits in the other. Marathon is a city on Knight’s Key, Boot Key, Key Vaca, Fat Deer Key, Long Point Key, Crawl Key and Grassy Key islands in the middle Florida Keys.

Day #3 – Marathon to Key West. (55 miles)
This is the final stretch!  After a scenic ride over  the Seven Mile Bridge, the stunning gateway to the Lower Keys.  We finish at the Southern Most Point in Key West for a victory toast.

17. Are the roads open to traffic?
Yes. The Key West Ride takes place on roads open to traffic. While efforts have been made to select a route using less heavily trafficked roads, all riders should be aware of traffic and obstacles along the road and be in constant communication with their fellow riders. Rules of the Road do apply.

18. What type of support do the riders receive on the ride?
We are happy to provide SAG (Support and Gear) services to all registered riders who experience mechanical or other problems, such as being lost or unable to complete the ride due to a physical problem. If you need assistance, please call one of the cell numbers provided on your cue sheet. Please remember to provide your name, the nature of the problem, your location and your cell phone number. In the event of an emergency, dial 9-1-1.

  • Please use SAG service responsibly. If you are unable to complete the ride due to a mechanical or physical problem, the SAG vehicle will transport you and your bike to Key West. Please do not call the SAG simply because you do not think you will finish the ride on time.
  • Please carry some cash with you to cover the cost of parts. Our SAG vehicles are staffed by volunteers who may be able to assist with minor mechanical problems, such as flat tires. In order to keep our participant fees low, we ask that you be responsible for the cost of parts, such as tubes and tires.

19. Are there rest stops along the route?
This ride is “not” a race. We will be riding at a pace that’s comfortable and enjoyable and will stop for restroom and snack breaks at least once every 25-30 miles. The SAG vehicle will be stocked with snacks like fruit, nutritional bars and pretzels, as well as cold water and energy drinks.

20. What is the terrain like?
The terrain is flat to rolling with no major hills. At this time of year we may experience constant headwinds that may make cycling a bit more challenging. Welcome to Florida!

21. Is the ride rain or shine?
Yes. However, ride organizers will be “on the ground” evaluating conditions as they arise. Any decision to cancel the ride will be made at their discretion with the safety of the riders foremost. Riders must respect their decision. All riders should bring appropriate gear for all conditions, including sunscreen. November in Florida is absolutely beautiful, but it can get a bit chilly.

22. Can I wear my iPod or Bluetooth while I ride?
We strongly discourage use of headphones during the ride. For your safety and the safety of your fellow participants, we ask that you do not wear any personal electronic devices. We do recommend you carry your cell phone with you in case of emergency or if you become in need of SAG support. If you must use your cell phone, we ask that you stop safely on the side of the road to do so.

23. How do I become a sponsor?
Please click on the ‘Become A Sponsor’ link on the Home Page of the Web site. There are four sponsorship opportunities to choose from.  Please see the sponsor page for more info.

Nov 14th – 16th, 2019

Registration begins May 1, 2019

Eventbrite - 72 Hours to Key West - 280 Mile Charity Bike Ride

Benefiting the
Tiny Hands Foundation

Improving the quality of impoverished children’s lives in Southwest Florida.






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72 hours to key west


For someone who hadn’t yet explored southern Florida, this was an amazing and unique way to go about it – biking through the Everglades, next to the ocean, over long bridges, and ending in magical Key West! What an adventure! Even training for the ride was interesting. And to top it all off, I got to spend time with some great people.
Eric- St. Petersburg, FL
Kevin and Joanna are great even organizers. Their attention to detail made the ride even better than I could have ever expected. There is not a doubt in my mind that this ride will be on my calendar each year moving forward.
Leslie- Orlando, FL
The 72 hours to Key West ride is one of the best organized rides I have ridden. It was very well organized with SAG support and was a great opportunity to meet fellow cyclists. I thoroughly enjoyed every minute of it and cannot wait to do it again next year.
Craig- Naples, FL
Amazing experience, great course, and great finish into Key West.. Kevin and Joanna are awesome people and organizers. We made friends and had a chance for a great accomplishment.
Emily- Orlando, FL
Thank you for an awesome trip!!!! Highly recommend this bike tour; Kevin and Joanna are the best ride leaders!!!!
Katie- St. Petersburg
Amazingly fun, well organized tour ride through spectacular vistas of the glades and the ocean with a great group of riders and organizers. Do not leave this opportunity unchecked on your bucket list!
Ron- Palm Harbour, FL
This is the ride for those that want to push themselves just a little bit, enjoy great vistas, water, some of the best folks around and a weekend of fun.
Court- Ft. Myers, FL
I drove 10 hours south looking for a new cycling challenge and instead had the ride of my life. A true bucket list experience! I can’t wait to go again next year!
John- Atlanta, GA
This event is fun because it’s not too hard and not too easy – nicely balanced for both the serious or semi-serious rider (I wouldn’t recommend for casual riders). Day 1 is quite challenging because of distance, potential heat and winds, with a pleasant start but a rugged finish that sets you up for days 2 and 3, which gradually become more beautiful and enthralling. The last 50 miles into Key West are scenically delightful, the 7-mile bridge being a particular highlight, and are an excellent preparation for your entry to Key West, and a well-deserved evening of celebrations!
Eric- Iowa
I was a bit skeptical and concerned about safety on Tamiami Trail and Krome Ave at first. However, the road conditions were not that bad, Tamiami Trail was one of the mst scenic rides I’ve ever done. The group was great and no one was ever dropped, everyone was looking out for each other and the experience as a whole exceeded my expectations.
Tod Landess- Miami