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The Key West Wedding Run

Updated: Mar 23

Some much needed positivity....


Don’t let life get in the way of your passion. Find a way to weave the two together. This is often easier said than done, especially during “the Rona.” But now more than ever that’s exactly what is needed.


Regardless of what your experience has been over the past year the themes of uncertainty, fear and frustration are pretty common in a lot of us. Oddly enough for me, they haven’t been my primary drivers. With social activities limited, many people working remotely and the constant messaging to “social distance” I saw the perfect storm of opportunity.


The reduction in commuter traffic has made the roads much more motorcycle friendly. With Katie working remotely we had more time to ride than just weekends. And what activity could be more fun while being socially distant than winding your way down a twisty back road! As a result, Katie and I have seized this opportunity and have been riding multiple times each week for nearly a year. The only downside being that most of my bikes now need tires. But that’s a good problem to have.


What could possibly make this even better? …marrying Katie!



While motorcycling could fit rather nicely into the Rona environment we are experiencing, planning a wedding really does not. Obvious questions like. What venues are open? Will friends and family be able to travel? How many guests will we be allowed to have? And the list goes on. So much so that we quickly dismissed the idea of trying to plan a traditional wedding.


But putting our life on hold was also not an option. So how do we create a fun, memorable event without the restrictions we have become accustomed?


We started with the thing that has brought us the most joy over the past year. Riding! If a motorcycle is involved, how can it not be fun? Plus, we felt our wedding could be reason to inject some positive energy and adventure into a world that desperately needs it.


Once we committed to a two-wheeled wedding the pieces began rapidly falling into place. With a few text messages and google searches we had answers to our most important questions:

Q: Where is there good weather for riding and weddings during spring break?

A: Florida

Q: How restricted are activities in Florida?

A: Very little

Q: Can we rent a bike there?

A: Yes

Q: Where do people get married in Florida?

A: On the beach in Key West sounded like fun

Q: Where do we have friends in Florida?

A: Fort Myers

Q: Will Fort Myers to Key West make for a memorable ride?

A: Yes

Q: Will our friends go with us?

A: Yes

Q: Katie are you up for this?

A: YES!!


It’s funny how infectious things that are fun, spontaneous and adventuresome can be. When our friends began learning of our plan several started wondering if they could fit this into their schedule to join us. Darin and Jen in particular, jumped on board and rented a Harley to ride along. Our friends in Fort Myers, Greg and Barb would join us in their convertible. And with that we had our wedding party.



Greg and Barb met us at Fort Myers airport and drove us to the Eagle Rider rental location. Arriving on Easter Sunday presented our first travel challenge. The rental office was closed. But Anna, our helpful customer service person learned of our wedding plans and was willing to accommodate us. Per her instructions she left the bike outside and hid the keys in the tour pack of a different bike. The plan worked flawlessly, and she even included a just married flag and some zip ties to mount it!



I rode my “new to me” Road Glide Ultra back to Greg’s where we loaded the tour packs for our Key West adventure. There is Something freeing about having limited space for extra stuff. On the motorcycle it is just about the experience and making do with the few key things you can bring along.



The next morning with the top down on the convertible and the rumble of the big 114 ci Harley, we departed. Traffic was heavy but the weather was cool and sunny making for a comfortable start. Anticipating the ride on Rt 41 through the Everglades made the initial traffic much more tolerable.



Leaving the congestion behind in Naples and entering into the undeveloped Everglades was an amazing transition. Miles of wetlands, with birds and alligators and odd-looking trees like something from Dr. Seuss’ Lorax. And miles of straight road. I must admit the Harley was a great choice for this ride. Comfort, wind protection and music selection all made for a much better straight-line experience than my Ducati. All the more reason you can’t own just one bike!

After nearly 70 miles of Everglade riding, we worked our way south around Miami. The smell of the salt air let us know we were approaching Key Largo and the gateway to the Keys, Alabama Jacks. A celebratory stop here seemed like a must to kick off our experience in the Keys, before spending the night in Key Largo.



Day 2 of riding would all be in the keys. Crossing the 42 bridges on the overseas highway building the anticipation for the seven-mile bridge connecting the middle keys to the lower keys. Skimming along pristine blue / green water on a motorcycle was scenic and not something I had done anywhere else. The road is nearly all two-lane and the 50mph pace makes it easy to enjoy the views. The only real hazards were on the island sections where we would dodge the occasional Key Deer.



Our pace to Key West worked out perfectly with us arriving at the Marriott Beachside resort at 1:00 and receiving an early check-in. Time for a shower and change and on to the best idea of the trip. A six passenger golf cart to shuttle us around the island. The six of us hopped on board and Darin chauffeured us off to Smathers Beach for our 3:00 ceremony. We waited only a few minutes until our officiant, Josh showed up on a rented scooter. Very appropriate for the laidback vibe of Key West. We found an open space in near the water, and he performed the ceremony in the sand. It was simple, fun and exactly what we wanted.



The rest of the day we enjoyed our new celebrity status of what we had just done by making friends in traffic from our golf cart, receiving complimentary champagne toasts and experiencing the bars and restaurants along Duvall Street. A simply perfect day.



Our second day in Key West allowed for some quality time touring in our golf cart taking in the sites along Duvall Street, the Southernmost Point and Mallory square. Then hanging out by the pool at our beachside resort. This made for just enough recovery time before getting back on the bikes for a single day ride north to Ft Myers.



The beauty of traveling on the bike is you don’t feel sad to leave because your next ride is just beginning.


An early 7:00 am start with the sun rising over the water made for a fabulously scenic ride for the first few hours on the bikes. Our long single day ride was nicely broken up with stops at local coffee shops in the Keys and seeing all the alligators that seemed to be waiting for us on our return trip through the Everglades.



Perfect sunny conditions made us just want to keep riding even after making it back to Ft Myers.



After returning the bikes we celebrated our successful beach wedding and adventure ride to the keys with a day on Sanibel Island and a Tiki bar sunset cruise from Ft Myers.



So how do you plan a fun, memorable event during a pandemic? I would suggest its possible and just follow your passion. Doing it this way resulted in 6 days of fun!


Below is more info on what it took to make this ride a reality:


· The Bikes – We opted for comfort and luggage capacity as driving factors in our bike choices. I rented a Harley Davidson Road Glide Ultra and Darin opted for the Ultra Classic. Both bikes had the 114 ci motor, providing plenty of torque to move these big bikes away from a stop. The only difference in the two models is the handlebar position and the fixed front faring on my Road Glide vs the handlebar mounted faring on the Ultra Classic. So, the model you chose is just personal preference in appearance.

The storage in the boxes was perfect for our needs with my rather large carry-on roller bag fitting inside the top box. The only downside to the Harley boxes is they remain fixed to the bike rather than being quickly detachable like the panniers on many Adventure bikes. The quick detach option is a nice feature for carrying your luggage, if your ride requires overnight stays.



· The Gear- Safety is important to me and I am typically an “all the gear all the time” rider. However, given the heat of south Florida, the slower pace and the lack of twisty roads I opted to forgo the riding jacket and full-face helmet and enjoy the comfort of our ride. Despite the lack of a helmet law, I wore a DOT half helmet, snug fitting sunglasses, Ugly Bros riding pants with knee and hip armor, First Gear fingerless gloves, Cortech riding shoes and lots of sunscreen.


· Skill Level – On a scale of 1 – 10 this is probably a 4. This is not a technical ride, but I would suggest having some experience operating large touring motorcycles before learning in South Florida traffic.

· Travel logistics – We rented our Harleys from Eagle Rider in Fort Myers. We opted for Marriott Beach Resorts in both Key Largo and Key West. Both were motorcycle friendly with covered parking available and all amenities within walking distance.


· Greatest challenge – The large size of my bike. I typically ride a Ducati Monster or a dual sport bike. The Road Glide Ultra is more than twice the weight of my Ducati. Weighing in at just over 900 lbs. In addition, I would guess that anyone shorter than 5’9” will not be able to touch the ground flat footed. That certainly was the case for me. Now add six gallons of gas, forty pounds of luggage, and a passenger. This bike can be quite a handful at stop lights and when parking. I will give Harley credit the added mass does make for a really nice ride, and the 114 ci motor is plenty strong enough to accelerate this beast through traffic. But be aware of the slow speed and parking challenges if you are considering renting our buying a touring bike.


(Notice my heels do not reach the ground.)


· Cost – Airfare from Washington DC to Fort Myers $445 (per person.) Four-day bike rental with insurance was $910. Hotels vary widely due to the timing of your trip. Our trip was over Spring Break and two-bedroom suites were approximately $800/night. We liked the Marriott Resorts because a single suite could accommodate all of us and included kitchens, living rooms and patios.


· Time Required – This trip was 7 days total including travel with 4 days on the bike.


· How physically demanding is this ride – On a scale from 1 – 10 this is probably a 5 due to the length. The total distance each way was approximately 285 miles. We comfortably completed this in one day on our return in eight hours including stops.


Who will go with me – We are fortunate to have good friends who live in Florida and who shared our excitement for a destination ride and wedding. A huge thanks to Greg, Barb, Darin, Jen and of course Katie for making our “Fueled themed” wedding a reality!



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