7-Night Harley-Davidson Self-Guided Tour: Miami And Key West Loop

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Tour Information

Key Details

  • Mobile Voucher Accepted
  • Hotel pickup Available
  • Free Cancellation
  • Duration: 8 Days
  • Departure Time :
    Flexible; contact the local service operator before travel to arrange your preferred airport pickup time
  • Departure Details :
    15th Street, central Miami
  • Return Details :
    Return to your original departure point


See Florida from the saddle of a Harley-Davidson, the beloved American motorcycle, on a 7-night self-guided tour from Miami! The 895-mile (1440-km) round-trip route from Miami to Key West takes in all the must-visit east and west coast cities, as well as iconic roads such as the Overseas Highway. Enjoy overnight accommodation in 3-star, biker-friendly hotels in Miami, Key Largo, Key West, Florida City, Naples and Orlando, and discover the tranquil wilderness of areas such as Everglades National Park. All thats needed is a valid US motorcycle license, at least a year of heavyweight motorcycle experience, and a sense of adventure!

Know More about this tour

This exciting 7-night Harley-Davidson tour is self-guided, meaning youll be given suggested directions and details of your hotel accommodation before leaving Miami. Besides riding, any activities outlined below are to give you an idea of the variety of things to do in Florida and are not included; any entrance fees, meals and activities are at your own expense.


Day 1: Miami International Airport – Miami
Start your experience with an airport transfer (own expense) from Miami International Airport to your hotel in central Miami. Check in to your hotel and relax overnight before the motorcycling fun begins.

Overnight: 3-star Best Western, Holiday Inn or Courtyard by Marriott hotel in Miami

Day 2: Miami – Key Largo
Make your own way to the rental shop in downtown Miami and, after a quick safety and orientation briefing, put on your helmet and choose your Harley-Davidson motorcycle. Models include the Electra Glide Classic, Street Glide, Road King, Heritage Softail Classic, Softail Fat Boy and Low Rider, and the rental staff will help pick out a bike that suits you best.

Then, jump on board and hit the road! Your tank is prefilled and you will be given a lock to use throughout your tour. Pass alongside Miami Beach, and then avoid any heavy traffic with a ride around South Beach. Once a mangrove swamp, the area was transformed when developers dredged sand from the ocean floor to turn South Beach into a tropical-esque getaway.

Head on to the famous Overseas Highway that passes above the Gulf of Mexico, and take a break in Florida City if you wish; both destinations are convenient stop-offs along your route. Ride along the southernmost section of Highway 1, and stop in Key Largo: your final city of the day. Check in to your hotel and spend the evening doing whatever you please.

Overnight: 3-star Best Western, Holiday Inn or Courtyard by Marriott hotel in Key Largo

Day 3: Key Largo – Key West
Leave Key Largo for a ride on another stretch of the Overseas Highway and see the color of the water shift from an emerald green to deep, azure blue. Around mile marker 59, why not make a diversion to the Dolphin Research Center? Famous faces such as Arnold Schwarzenegger and Jimmy Carter have swum with dolphins at the center, and it makes for an unforgettable Florida day out.

Continue over dozens of bridges, pass around harbors, and ogle views of the Atlantic Ocean to one side, framed by Florida Bay on the other. The Florida Keys are as Caribbean as Floridian, and it’s impossible to feel so far away from mainstream America without leaving the country itself.

Work your way into Key West, the southernmost US city, and discover its bohemian ambiance and Caribbean-influenced cuisine. Famously laid-back, Key West has long attracted a bohemian crowd and it’s a great place for partying and sightseeing alike. Attractions to look out for include Ernest Hemingway’s former home, the famed Sloppy Joe’s bar and the iconic end-of-the-road photo stop at the US’ southernmost spot. Check in to your hotel and relax overnight.

Overnight: 3-star Best Western, Holiday Inn or Courtyard by Marriott hotel in Key West

Day 4: Key West – Everglades National Park – Florida City
Leave Key West and return to Highway 1 for a visit to Florida City, gateway to Everglades National Park. Spread over 1.5-million acres (607 hectares), the park protects the largest subtropical wilderness in the US. Take a detour through the park to check out the scenery and wildlife. Home to some 300 species of birds (and that’s not even counting the animals), Everglades pulsates with life and is the perfect hideaway to find your peace with nature.

Continue into Florida City, check in to your hotel and then spend the evening at leisure.

Overnight: 3-star Best Western, Holiday Inn or Courtyard by Marriott hotel in Florida City

Day 5: Florida City – Everglades National Park – Naples
See some more of Everglades National Park after leaving Florida City, and then power north along Highway 997 to Highway 41. After turning off, enjoy the ride to Naples, the pearl of southwest Florida that’s nestled on the Gulf of Mexico’s shores. Popular with water lovers and recreationists alike, Naples is a great place to kick back and relax. Check in to your hotel, and then make the most of the balmy evening temperature with a stroll downtown, ice cream in hand.

Overnight: 3-star Best Western, Holiday Inn or Courtyard by Marriott hotel in Naples

Day 6: Naples – Florida West Coast – Orlando

Introduce your Harley-Davidson to the delights of Florida’s enticing west coast, with a ride along Highway 41. A host of exciting towns — Fort Myers, Cape Coral, Venice, St Petersburg and Tampa, to name a few — are dotted around the shores, and the highway makes for an exciting day of exploration. Discover buzzing urban areas rising behind sleepy fishing villages; scout out lively vacation strips just minutes from barren swampland; and switch between world-class art collections and theme parks for equal measures of culture and knuckle-biting fun.

The scenery along the route is set to make you swoon, and if you ride to a Gulf of Mexico vantage point around sunset time, you are in for a treat. Turn onto Highway 4 after Tampa, and continue to Orlando where your overnight accommodation awaits.

Overnight: 3-star Best Western, Holiday Inn or Courtyard by Marriott hotel in Orlando

Day 7: Orlando – Florida East Coast – Miami
Perhaps pay a visit to one of Orlando’s magical theme parks, such as Disneyland, Universal Studios or Sea World, and then make your way to Florida’s east coast for your journey to Miami. Cruise back along the lovely Highway 1, savoring your last glances of the Florida Keys’ scenery, and then work your way back into the fast-paced city of Miami.

Fill your tank with fuel, drop your bike back at the rental shop, and then make use of a transfer to your Miami hotel. Check in, and then enjoy the last night of your independent tour doing whatever you wish.

Overnight: 3-star Best Western, Holiday Inn or Courtyard by Marriott hotel in Miami

Day 8: Miami – Miami International Airport
Your 7-night Harley-Davidson experience finishes with a drop-off at Miami International Airport (own expense).


  • Hotel pickup and drop-off
  • VIP check-in at rental location
  • Harley-Davidson rental (Honda or BMW if preferred)
  • Orientation of operation, laws, maintenance
  • State mandatory liability insurance
  • Use of helmet for driver and passenger
  • Unlimited mileage
  • Hotel accommodation as per itinerary
  • Road book with a detailed day-by-day itinerary and scenic routing designed specifically for motorcycles
  • Maps and suggestions for local touring and visiting sights
  • One-way fees (when applicable)
  • Environmental surcharge of 6.5%
  • Local sales tax
  • Hotel taxes


  • Food and drinks
  • Fuel and oil
  • Airfare
  • Airport pickup and drop-off
  • Parking fees, park entrance fees, toad or toll charges
  • Theft and damage waivers, vacation interruption protection (VIP) and supplemental liability insurance (SLI)

Additional Info

Confirmation will be received at time of booking

Driver must be 21 years or older, possess a valid drivers license that qualifies him/her to operate a motorcycle in the country, state or province of origin

Minimum one year of heavyweight motorcycle riding experience is required

Motorcycles can accommodate an additional passenger; this passenger may be younger than 21 years provided this passenger will not be driving

Hotels are typically 3-star motorcycle-friendly properties that are booked according to availability; exact property names cannot be released until after booking

Hotel pickup and drop-off service is provided to and from hotels within a 7-mile (11-km) radius of the start point. Alternatively, take a taxi and you will be reimbursed up to $15.00 (provided the receipt can be shown)

Storage is available for excess traveler luggage and other items free of charge; however, this is at the traveler's risk

Customer orientation: every participant will receive a full orientation to the motorcycle. The participant orientation will cover safe motorcycle operation, the participants maintenance responsibilities, as well as some local and state traffic laws

Release and waiver policy: every participant is required to accept and sign a rental agreement and liability release waiver before the tour starts

It is recommended that you take out adequate travel, health and accident insurance as well as trip cancellation insurance. Please ask your booking agent for further information on the theft and damage waiver, as well as supplemental liability insurance

Any alterations made to the itinerary while on tour will be at the participants expense. This includes, and is not limited to, changing hotels, destinations, adding/subtracting tour days, etc. Any unused hotels on tour will not be refunded

No refunds will be granted for any unpleasant and unsuitable weather conditions

Tour may be cancelled without cancellations fees if the tour is cancelled 30 or more days prior to your tour start date. However, cancellation fees and refund amounts will be determined on a case by case basis. Any cancellation fees may be applied to a future tour booking anytime within a 12-month period following the cancellation date

Optional accessories such as GPS and motorcycle jackets are available for rent, payable direct to the supplier at time of pickup