Overview
Escape the winter chill and treat yourself to a tropical cycling adventure on the Florida Keys Overseas Heritage Trail. Spanning over 140 miles of paved paths with breathtaking ocean views, this 4-days and 3-nights tour offers the perfect blend of sun, sand, and serenity. Starting in Key Largo, you'll pedal south through the stunning Florida Keys, where every turn brings you closer to the vibrant culture, pristine beaches, and the warm embrace of island life. You will have the chance to explore the unique charm of each Key, with stops at laid-back beaches and casual, local eateries where you can enjoy the flavors of the Keys. This tour offers the ideal balance of adventure and leisure, giving you the satisfaction of earning your rest as you unwind with your toes in the sand, watching the sun dip below the horizon in the Florida Keys. Whether you’re soaking in the sun or savoring the fresh seafood, this tour is the perfect way to wash away those winter blues and recharge your spirit in paradise. This ride is meant for people who ride on roads as you are on the shoulder for 30% of the ride. If you would like a longer time in the Keys, you can have additional days in your favorite locations at the beginning or end of your tour. Consider flying out of Key West instead of having a return shuttle to Key Largo and then drive to Miami for your flight. Give us a call or email to have our tour specialists design your perfect vacation. What’s included in your tour: * 3 nights in hand-picked inns & B&Bs * Digital maps, voice navigation & electronic itinerary * Trail T-shirt & patch Need any extras? * Luggage shuttle — your bags moved each day * Bike Rentals – Hybrid (manual), Road and E-bikes available * Extra Night Accommodation before or after the tour to spend more time in Key West or Key Largo * Shuttle back to Key Largo Trail: Florida Keys Overseas Heritage Trail - paved Mileage: 140 miles – 35-mile daily average Tour timing: All year long You ride — we handle the rest.
Schedule
4 day Tour Schedule
Previous
Next
Day 1 - Key Largo Loop - 40 miles
Start your adventure in Key Largo with a scenic loop ride exploring the northeastern part of the keys. This out-and-back route along Highway 509 offers the warm Florida air and many trees on the quiet road ride.
After your ride, return to Key Largo for a peaceful evening. You can unwind with a stroll along the beach or relax at a local venue, soaking in the Key Largo's laid-back charm.
Day 2 - Key Largo to Long Key - 35 miles
Set out on a southbound ride along the Florida Keys Overseas Heritage Trail. Today’s route takes you through the Upper Keys, showcasing spectacular views of both the Atlantic Ocean and Gulf of Mexico.
Stop in Tavernier for the Bird Sanctuary and then Islamorada to explore unique features of the area, such as seeing the large lobster statue, visit the history of Diving museum and go swim with the dolphins. You can also visit the 2 breweries in town, one having a distillery as well. Spend the night in Long Key and stay on the water.
Day 3 - Long Key to Big Pine Key - 34 miles
Continue your ride southward towards Marathon and their Dolphin Research Center, the Turtle Hospital (need reservations) before crossing the iconic Seven Mile Bridge. This part of the journey is renowned for its breathtaking views of the open ocean and is a standout feature of the tour. Soon after the bridge you could see the Key Deer near the Big Pine Keys where you will spend the night again by the water.
Dates (other dates available)
September 2026
- Sun
- Mon
- Tue
- Wed
- Thu
- Fri
- Sat
1 queen room - 2 people
06 - 09 September 2026
FROM$600.00/pp
2 Beds in room - 2 people
06 - 09 September 2026
FROM$700.00/pp
1 queen room - 1 person
06 - 09 September 2026
FROM$1,100.00/pp
1 queen room - 2 people
08 - 11 September 2026
FROM$600.00/pp
2 Beds in room - 2 people
08 - 11 September 2026
FROM$700.00/pp
1 queen room - 1 person
08 - 11 September 2026
FROM$1,100.00/pp
1 queen room - 2 people
13 - 16 September 2026
FROM$600.00/pp
2 Beds in room - 2 people
13 - 16 September 2026
FROM$700.00/pp
1 queen room - 1 person
13 - 16 September 2026
FROM$1,100.00/pp
1 queen room - 2 people
15 - 18 September 2026
FROM$600.00/pp
2 Beds in room - 2 people
15 - 18 September 2026
FROM$700.00/pp
1 queen room - 1 person
15 - 18 September 2026
FROM$1,100.00/pp
1 queen room - 2 people
20 - 23 September 2026
FROM$600.00/pp
2 Beds in room - 2 people
20 - 23 September 2026
FROM$700.00/pp
1 queen room - 1 person
20 - 23 September 2026
FROM$1,100.00/pp
1 queen room - 2 people
22 - 25 September 2026
FROM$600.00/pp
2 Beds in room - 2 people
22 - 25 September 2026
FROM$700.00/pp
1 queen room - 1 person
22 - 25 September 2026
FROM$1,100.00/pp
1 queen room - 2 people
27 - 30 September 2026
FROM$600.00/pp
2 Beds in room - 2 people
27 - 30 September 2026
FROM$700.00/pp
1 queen room - 1 person
27 - 30 September 2026
FROM$1,100.00/pp
1 queen room - 2 people
29 September - 02 October 2026
FROM$600.00/pp
2 Beds in room - 2 people
29 September - 02 October 2026
FROM$700.00/pp
1 queen room - 1 person
29 September - 02 October 2026
FROM$1,100.00/pp
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