There’s No Crying on a Harley-Davidson, But I Did Anyway

New and Used Motorcycles for Sale at Bert's Black Widow Harley-Davidson in Port Charlotte, Fla.
Bert's Black Widow Harley-Davidson, Port Charlotte, Fla.
Bert’s Black Widow Harley-Davidson, Port Charlotte, Fla.

Just as there is no crying in baseball, there is no crying on a Harley-Davidson motorcycle. Yeah, well, I’m here to confess I did just that. Straddling 500-some pounds of hot metal between my legs on a cool December evening, I sat bawling because I accepted reality – I am not coordinated enough to drive a motorcycle and If I get the chance I didn’t get in a motorcycle accident. You hear about people getting into accidents and needing someone like these motorcycle accident injury attorneys in Texas or law firm more local to them to help with their cases.


I’m Old Enough to Ride a Harley-Davidson, Right?
Being in my mid-forties and living in Southwest Florida means I’m at a point in my life where my friends are either retired or nearing retirement. They’re engaging in what I consider fun experiences they’ve worked their entire lives for including many riding Harley-Davidsons, either as the driver or on the back as their boyfriend or husband drives. As I’m learning, Harley-Davidson is a culture, lifestyle and mindset. Easily, it’s a form of escapism and lately, I need a little bit of that in my life. Of course, it can be dangerous if you don’t know what you’re doing, it can be dangerous even for those who know what they’re doing. You do hear stories about riders surviving pretty horrific motorcycle accident injury or some near miss.

How do I look on a Harley-Davidson? Here I am with dealer owner Bert King of Bert's Black Widow Harley-Davidson, Port Charlotte, Fla.
How do I look on a Harley-Davidson? Here I am with dealer owner Bert King of Bert’s Black Widow Harley-Davidson, Port Charlotte, Fla.

I’m not really a tribe person, meaning, I honestly think I’m at my best doing things solo or with a partner in crime, or small, close group of people. I don’t have time or patience for drama that comes from large tribes. BUT, I really want to be part of the Harley-Davidson culture. I want to be a biker babe who hangs out at the local dealership (in my case, it’s Bert’s Black Widow Harley-Davidson in Port Charlotte, Fla.) on the weekends taking part in the music, camaraderie, and rides over Florida’s backroads to see and experience real America. I want to meet and get to know new people, explore backroads, and experience a new freedom.

Alas, I haven’t found anyone inviting me to ride with him so I thought, “Hey. I could ride by myself.” After all, many dealerships rent Harleys.

Bert’s Black Widow Harley-Davidson Riding Academy
This logic of thinking didn’t kick in until I realized a gift certificate I had for Bert’s Black Widow Harley-Davidson Riding Academy was for earning a motorcycle license/endorsement. Honestly, I thought the riding academy was something like driver’s ed, a class where you learned the basics then went to the DMV to take your test. Nope.

The Harley-Davidson Riding Academy is a three-day course where you learn in the classroom then on the road course with the end goal of earning your motorcycle license/endorsement. It consisted of a full day in a classroom setting with a prerequisite of reading the Basic Ridercourse Rider Handbook published by the Motorcycle Safety Foundation prior to class. Motorcycle safety is of course very important for anyone who decides they are interested in riding one. It could literally save your life, and yes, while accidents to happen, I would rather be alive and have a really good lawyer to take on my case, than anything else.

Entrance into the Bert's Black Widow Harley-Davidson Riding Academy.
Entrance into the Bert’s Black Widow Harley-Davidson Riding Academy.

On-the-Bike Training
After passing the classroom portion, the next steps are two, six-hour on-the-course classes where what was learned in the classroom is applied in real-life on modified Harley-Davidsons. I say “modified” because they have extended handlebars and something else to prevent the bike from fully tipping over. Now, other than riding on the back of a motorcycle less than a handful of times (including on the back of a motorbike in Vietnam last April), I went into this experience clueless on how a motorcycle functions.

The course, created by the Motorcycle Safety Foundation, was designed with a building concept meaning everyone in the course (up to six people) must pass each step in order to proceed to the next step. If a student cannot successfully complete the step, they are counseled out. Or, if a student does not feel comfortable advancing, they can pull themselves out. Safety comes first.

I passed the classroom portion! Here I am (on the far right) with a friend and instructor. Dec. 2016
I passed the classroom portion! Here I am (on the far right) with a friend and instructor. Dec. 2016.

Then the Waterworks Broke
I’ll spare you the details, but during my first go-around with the riding academy, I was counseled out on the second day of on-the-course maneuvers. I was tired, sore from the previous night (I underestimated the physical requirements of riding), hot and sweaty and could not concentrate.

The second go around at the Harley-Davidson Riding Academy, I took myself out not even midway through the first day of on-the-course training and that’s when the waterworks on a Harley began. I had more confidence this time but for some reason, I could not get the coordination of the whole shifting concept from first to second gear. Mentally, I played it over and over in my mind how it should be done, yet I just couldn’t get left hand and left foot in sync. I knew I had to give up which was frustrating, embarrassing and ego-busting.

The waterworks broke on this Harley-Davidson.
The waterworks broke on this Harley-Davidson

Don’t Take Riding Lightly
Harley-Davidson has a sexy, badass, patriotic appeal, and reality is, being on a motorcycle, whether driving or riding, is dangerous. This time of year (winter/spring), Southwest Florida roadways are congested with out-of-town visitors navigating their cars and trucks in unfamiliar territory which means they’re probably not paying attention to the road and others on the roads, including motorcyclists and bicyclists. Plus, motorists have other distractions such as smartphones, eating, other passengers, and whatever else. Here in Florida, we don’t have a helmet law and many riders can be seen sans headgear which makes me nervous. Although I am disappointed in myself for not passing, I know I am not ready to ride.

If I had a bike to practice on, I think that would make a difference. The first time I took the class, most everyone had a bike and the course seemed easy for them. The second time, only one student had experience on a bike. I later learned she was the last one standing, out of six students, on the final night. Everyone learns differently and for me, I need lots of hands-on practice.

Part of the Harley-Davidson Riding Academy included a tour of Bert's Black Widow H-D, Port Charlotte, Fla.
Part of the Harley-Davidson Riding Academy included a tour of Bert’s Black Widow H-D, Port Charlotte, Fla.

Bert’s Black Widow Harley-Davidson Riding Academy. Do It!
The rider coaches at Bert’s Black Widow Harley-Davidson Riding Academy are excellent. I was concerned they would be condescending and impatient but they were not. They were kind, patient and always have safety first in mind. The course is designed for beginners and maybe this spring or next fall I’ll give it another try.

One of the coaches, who commented on how I had improved from the first class to the second class, suggested I hire a tutor to work with me. Nice idea but I think a membership on one of those online dating sites may be cheaper. I’d just need to create a profile for a biker babe wannabe and hope I can find someone who wants to show me the ropes, err, the gears. Or, maybe I’ll stick to my mountain bike.

Bert’s Black Widow Harley-Davidson
2224 El Jobean Rd
Port Charlotte, FL 33948
Tel: (941) 883-8000

Disclosure: This post contains some affiliate links which supports this blog, my traveling habit and special needs dog.



Jennifer A. Huber is an award-winning travel and outdoor blogger and writer in Southwest Florida. Originally from Buffalo, N.Y., a hiking trail led her to a career path in the tourism industry for more than 30 years. She spent a decade with a park management company in Yellowstone, Death Valley, and Everglades National Parks. She founded the travel blog, with the goal of inspiring others to travel alone, not lonely. The unexpected death of her former husband in 2008 reminded her how short life is. His passing was a catalyst for sharing her experiences with the goal of inspiring and empowering others to travel solo. Jennifer holds a Travel Marketing Professional certification from the Southeast Tourism Society, is a certified food judge, member of the NASA Social community, and alum of the FBI Citizens Academy. When not traveling, she is either in the kitchen, practicing her photography skills, or road tripping with her dog, Radcliff.

9 thoughts on “There’s No Crying on a Harley-Davidson, But I Did Anyway

  1. Enjoyed your blog entry. Keep trying Jen, it will be worth it. Nothing compares to the wind in your hair and the bugs in your teeth! Now THAT’S freedom.

  2. Well if you try again let me know! I’d love to learn how to ride, and probably would also experience the Harley trail of tears. I am a huge klutz too ha!

  3. Not sure if I’ll do it again. I want to, but man oh man it’s SO exhausting! Maybe if we run across another $500 bike we can go halfsies and practice before trying again 🙂

Comments are closed.

One of the resident wolves at Shy Wolf Sanctuary in Naples, Fla., April 24, 2022.
Featured Florida Fun

Florida Travel: Meditate with Wolves at Shy Wolf Sanctuary in Naples

Wolves and Florida seem like an unlikely pair but in Naples, there’s a special sanctuary for wolves and wolfdogs. In addition to touring the facility and learning more about the residents, meditation sessions are sometimes available at Shy Wolf Sanctuary.

Continue Reading
"Caloosahatchee Manuscripts" at the Sidney & Berne Davis Art Center in Fort Myers, Fla., June 2022.
Destinations Featured Florida Fun Games

Fort Myers Discovery Challenge is a Passport to Fun in 2022

The Fort Myers Discovery Challenge is a new digital passport to help you discover fun things to do in Fort Myers and Lee County, Fla. The more places you visit and check-in, the more you’ll be rewarded.

Continue Reading
Daniel Lind-Ramos, sculptures made with debris caused by Hurricane Maria in Puerto Rico, Sept. 2017
Budget Travel Featured Florida Fun

6 Ways to Visit Florida Museums and Parks Free in Summer 2022

With rising gas prices and inflation, you’re probably wondering if you can enjoy a summer vacation. Here are six ways to visit Florida museums and parks free in Summer 2022.

Continue Reading