January 19-26

"Short days. Big fun.
Very little adult supervision..."

Click on map to view stops


January 19 - 26, 2024

Arrival Day /Bonita Bay

Arrive by plane in Fort Myers with transfers to our overnight hotel in Bonita Bay and check in, get your wristband, jersey and other information for the week ahead. Go grab dinner and mingle at will at the pool bar and pool. We will not have a formal get-together as we anticipate riders arriving at various times in the afternoon and evening.

Ride Day / Bonita Bay to Everglades City

Morning departure for a waterfront route led by our friends at a locally renowned bike shop, Naples Cyclery, including a stop at the shop to pick up supplies like CO2 cartridges and other items. You will then ride on to Everglades City with an exciting stop at a legendary bar, Gator Crossroads, for refueling before the last 20 miles to Everglades City. We will gather for a happy hour that evening at the HavAnnA Cafe, a local tiki bar.

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Ride Day / Everglades City to Miami
56 mi

This is your EVERGLADES day. We depart from Everglades City and ride across the Everglades toward Miami with two memorable stops: Clyde Butcher's home photo gallery, and Everglades Safari Park for a one-hour private eco-adventure airboat tour and nature walk, followed by lunch before transferring via shuttle to our Brickell Miami hotel.

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Ride Day/ Key Biscayne and beyond

24-mile minimum

Just miles from famous South Beach, we will embark on a tour of Key Biscayne, one of the most popular biking routes in the US with a memorable visit to its Lighthouse and incredible views of Miami. Mack Cycles will lead the ride and finish with a loop ending with coffee and lunch at a Cuban cafe. You will then have the afternoon to explore. We recommend a trip to South Beach for dinner and a stroll through the famous Art Deco district of one of the world's most famous beaches.

Click here for Key Biscayne loop
Ride Day/ Miami to Key Largo via Robert is Here
78.6 miles

This exciting ride led by Mack Cycles will take you through the back streets of Miami where you will feel and see the Cuban influence and quaint neighborhoods of Miami before arriving at one of the most famous "fruit stands" in the World--Robert is Here. Bustling with local fruit and smoothies and an abundance of shade and interesting things to see, it's the perfect stop before riding the original railroad route to the Keys on Card Sound Road with a lunch stop at the infamous Alabama Jacks restaurant and bar. There will be an option to shuttle directly to Robert is Here and start the Key Largo ride here. This eliminates riding through Miami and reduces the mileage roughly in half. However, the route through Miami is a popular one and a fun way to experience the Cuban-influenced neighborhoods.

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Ride Day / Key Largo to Marathon
57 mi

Morning departure for the ride along Highway 1 to Marathon, our next overnight. Our first aid station is an iconic venue for parties and weddings, and for you, a Rum Runner Drink to start the day. Relax a bit before continuing on Highway 1 south to Marathon. Post-ride suggestion... a visit to the Turtle Hospital and Sanctuary in Marathon before a complimentary sunset catamaran sailing cruise.

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Ride Day / Marathon to Key West
46 mi

Our last ride to the Southern most point in the United States, Key West. With stops at Bahia Honda State Park and Baby's Coffee, you will arrive in Key West with time to explore this historic city. That evening we will have a happy hour awards ceremony and let you pick your cuisine at one of many fine restaurants.

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Departure Day / Key West to Miami (or Naples or Fort Myers)

8:30 departure via the RUM RUNNER TOUR van to the Miami Airport (transfers included) or departure to the Naples or Fort Myers Airports for a late afternoon or evening flight or transfer to a Fort Myers hotel. (additional transfer fee to Ft. Myers--$100).

Click here to view all the RUM RUNNER TOUR daily routes.

*Times and events subject to change.