Cycling Key West to Universal Studios


Offered: May 1–October 15

From the famous Key West Florida, the southernmost point in the continental U.S., we begin our 400-mile challenge at the home of famous writers such as Ernest Hemingway and Tennessee Williams.

Riding up the coastal highway through quaint towns, we breathe in the sea air of the Atlantic coast, which punctuates our days and fills our minds with memories to last a lifetime.

After some long and rewarding, challenging miles on the bike, we bask in the glow of the famed Miami Beach skyline, keeping our sights set on the remaining miles into Orlando, home of Disney heritage and the charity we have worked so hard to support.

We are not listing the elevation change for each day of cycling because Florida is relatively flat. We will discuss route details before each ride. Overall elevation change on the trip is +2,269/-2,273 with maximum grade +2.1 percent. Don’t be fooled, but keep your legs strong for the occasional greetings by the coastal headwinds.



Day 1 marks our arrival in Miami, one of the state’s—and the world’s—most popular vacation/cycling challenge spots. Though many destinations are said to offer a little something for everyone, the Miami area offers multiple enticements for everyone.

Upon arrival, you will be met by your local guides. You will be treated to a relaxing, three-hour transfer down to the Florida Keys and Key West, where there’s a lot to love. Rich in history, arts, and culture, the Key West area is also perfect for outdoor types, with eco-tours, snorkeling, scuba diving, sport fishing, and more. The 120-mile island chain is home to the only living coral barrier reef in the continental U.S., an amazing place to start our cycling challenge!

Driving: Three-hour airport transfer in motor coach/mini coach to Key West

LODGING: Key West Best Western Hibiscus

MEALS: On your own



Free day to explore Key West.

LODGING: Key West Best Western Hibiscus

MEALS: Breakfast, lunch, and dinner



We begin our cycling challenge with a bike fit and pre-trip briefing. We will cycle through the town of Key West, where the written name is as revered as the descendants of Hemingway’s six-toed cat. “Papa” Hemingway and a host of other literary luminaries, including Tennessee Williams, Elizabeth Bishop, and Shel Silverstein, once called this island home. Our challenge today will be to keep hydrated and keep our eyes on the road while cycling up the beautiful coast on Route 1. Our route over the panoramic Seven Mile Bridge sometimes likes to welcome you into Marathon, our stop tonight, with a strong head wind.


LODGING: Marathon Holiday Inn Express

MEALS: Breakfast, lunch, and dinner

RIDING: 54 miles


This morning we continue up Route 1 toward our destination tonight, Miami Beach, located above the Tropic of Cancer and known for some of the hottest nightlife in the U.S. While Miami might be known for nightlife, the biggest part of your life today will be your ability to deal with calf-burning miles and humid, salty air while not getting sand in your eyes! You will feel the sweat drip down your face as you hit your 110 miles today. You will be rewarded with the famed Miami skyline, amazing ocean views, and a nice, soft, therapeutic piece of beach to sit on while enjoying the sunset.


LODGING: Day’s Inn Miami Beach Oceanside

MEALS: Breakfast, lunch, and dinner

RIDING: 110 miles


When you wake up today, you will realize you have muscles you didn’t even know existed—until after having completed 164 miles. Well done! We begin our ride by saying goodbye to Miami Beach and saying hello to Jupiter, Florida. We will ride through some of the most expensive real estate in Florida—and the U.S.—home to celebrities and professional golfers. While riding 90 miles today, you will encounter coastal winds that come up late in the afternoon to push your thighs and calves to a nice medium level of burn. Hopefully, by now you are getting comfortable on your bike saddle, but don’t settle in too far and let your beach dreams distract you from our goal of reaching Universal Studios!

LODGING: Jupiter Waterfront Inn

MEALS: Breakfast, lunch, and dinner

RIDING: 90 miles


Our ride begins along the twin coasts 1 and 1A heading toward Cocoa Beach, home to world-class surfing and 75 miles closer to our final destination. As we ride today, we will get our first glimpse of coastal habitat that is a cross between spooky and adventurous. You will need to keep your pace up as you encounter the amazing sites of mangroves, strangler figs, and gumbo limbos, just to name a few species of trees. Along with that, several bridges in sight will test your cycling cardio ability before crossing the Banana River into the quintessential beach town of Cocoa Beach.


LODGING: International Palms Resort and Conference Resort

MEALS: Breakfast, lunch, and dinner

RIDING: 110 miles


On our final ride today, with 364 miles in the saddle behind us, we will be feeling it. But with Universal Studios in our sights, we will be motivated to stay focused and in the saddle. We will ride inland today towards our final goal of Universal Studios! We will see some of the first views of the famous Florida everglades and maybe an alligator to keep us pedaling to the finish line!


LODGING: Best Western Buena Vista Suites, Orlando (near Universal Studios)

MEALS: Breakfast, lunch, and celebration dinner

RIDING: 75 miles


After a well-earned night of rest, we have free time to enjoy Universal Studios and the surrounding area before we board flights home. Well done!


MEALS: Breakfast


What’s Included in the Cost? 

  • Airport transfers.
  • Vehicle support for the duration of the trip.
  • Professional, knowledgeable, friendly, and safety-certified guide(s) and support staff.
  • Hotel lodging for six nights (double occupancy).
  • Aid stations throughout the rides every 10–15 miles, depending on terrain and weather.
  • Meals: breakfast on day 2 through breakfast on day 8.
  • Bicycles: type of bike TBD.
  • Local taxes and dining and housekeeping gratuities.

Group Size

Min: 20 | Max: 60

CONTACT US for a customized itinerary and costs.