My Next Great Retirement Adventure is to Cycle Across America

One of the reasons I retired from medicine at age 54 was so I would still be young enough and healthy enough to enjoy adventures and travel. Many people we see on our travels are simply too old and frail to fully enjoy their adventure and we didn’t want to miss out on having big adventures in life due to our age.

Big adventures often necessitate a large time commitment away from home, which most working people do not have. There are, however, times during our working years that allow for a large chunk of time to be away from home, such as between jobs or when on a sabbatical.

I recently wrote about The Family Board Meeting book, in which is described how to have meaningful time with your children. I wanted what was described, so I spoke with my youngest son about scheduling small one-on-one activities a few times a year to bring us closer together. I asked him if he had anything in mind that would fit the bill. He suggested we ride our bicycles across America!

That was quite a bit bigger than my idea of spending the afternoon at the family fun center. But we discussed it at dinner and over the next few days investigated the logistics to determine if this would be possible right now. Everything lined up, so we decided we could go for it. We now had five weeks to prepare for a 3,000-mile bicycle ride averaging almost 70 miles a day. 

How did this crazy idea come to fruition?

My youngest son, Keith, will celebrate his 30th birthday during the ride. Keith is in the process of changing careers. As a prerequisite for his new job, he is taking a month-long course that will end the last week of March.  Since there is no requirement for him to apply for the new job immediately upon completing the course, he has a chance to take an extended vacation between jobs. This large block of time is a rare, but wonderful opportunity for a big adventure.

I will celebrate my 62nd birthday a few weeks before the adventure begins. At which time I will become eligible to collect social security. I am fortunate that I am still in good enough health to tackle a 3,000-mile bicycle ride. Looking at my schedule this spring, the few things that were already booked could be easily rescheduled. I therefore also have a large window of time that matches Keith’s window. Perfect timing!

My brother-in-law, Paul, who is also retired and just a few years younger than I, has previously expressed the desire to cycle across America. We contacted him to see if he might like to join us on this once in a lifetime adventure and after thinking about it a few days, he agreed to go with us. He previously joined us on a bicycle ride across Oregon several years ago with my other son, Brian.

My wife, Carolyn, cleared her schedule and will be driving the sag wagon. A sag wagon is the vehicle that travels with us on the journey carrying our luggage, food, water, and spare bicycle parts. In the event of a catastrophic breakdown of either man or machine, the sag wagon provides an emergency ride. She will strategically meet us a few times a day to replenish our water, food and anything else needed from the car, and spend the evening with us when we are done riding. We can take advantage of the car for sightseeing if we find we are near something interesting. The sag wagon also provides our transportation to our starting point in San Deigo, California, 850 miles from our home, and will take us back home after we finish, another 3,000+ miles.

Cycling is not new to any of us. We have all ridden thousands of miles over the years. I have been on Cycle Oregon several times which is a weeklong trip of about 500 miles. Paul and I cycled across Oregon, which was about a 400-mile trip with Carolyn supervising Keith driving the sag wagon with his new drivers permit.  Both Keith and I have been on bicycle racing teams as well as winning Oregon’s Best All Around Rider awards for our age groups in 2009. Keith raced for the University of Oregon cycling team. Carolyn and I logged thousands of miles on our tandem bicycle and enjoyed a guided weeklong bicycle tour of Acadia National Park. This new adventure is a longer version of many of our other cycling achievements so we will be starting with minimal need for additional training.

The adventure will begin April first (No this is not an April Fool’s joke) when we drive to San Deigo, California in the sag wagon. There we will mount our bikes and head East until we reach the Atlantic Ocean about eight weeks later. The actual route is still under construction.

Our ride will be about 50% longer than the Tour de France. The professional racers finish that race in three weeks. We estimate it will take us eight weeks to complete our ride.
The pros ride in a group (a peloton) of 160 riders and average about 28 MPH. We will be in a paceline of three riders and expect to average about 14 MPH. 

You all are invited to join us on this adventure though my social media outlets. Every Thursday I plan to publish a recap of our prior week’s ride on my blog. If you are not already a subscriber, sign up using the box in the upper left side of my web page so you will receive my blog in your email inbox and you won’t miss an update. I plan to also record a short video on my Facebook Page each day. Be sure to follow my Facebook Page to catch each of these daily videos. 

Throughout my career, I enjoyed many short adventures. Three-week motorhome trips every summer, multiple one-to-two-week river or ocean cruises, five weeks exploring France and Italy, and timeshare weeks all over the country to name a few. 

So far, my longest adventure was taking three months off after residency before starting my job as a surgeon. Like my son is doing now, I recognized a rare opportunity to take a large block of time off at the end of my training. Those opportunities don’t come around very often. If you are playing your cards right financially, and not living paycheck to paycheck, you can afford to take extended time off a few times during your working years. 

Often, we pass up opportunities like this when they appear because we think we can’t afford to take unpaid time off work or that our job can’t function without us for so long. Neither of these are likely to be the case. We will regret opportunities we miss much more than we will enjoy continuing our regular work schedule. 

Seize opportunities for adventures so you will look back and say, “I can’t believe I did that.” Don’t reach the end of your days thinking, “I wish I had done that.”

Since I retired with good health, I have been able to take longer adventures: Two-month motorhome trips, a 450-mile hike across Spain, 30+ day cruises, four weeks of timeshares linked back-to-back and more. 

Life is short. Look for an adventure and take it. Don’t live your life on the premise that all the fun will begin after you retire, or reach FIRE, or have generated sufficient passive income. Take an exciting adventure every year. Start right now by taking one item off your bucket list and putting it on the calendar. Life is too short for regrets. I hope you will follow us on this journey and it will spark an interest for you to do a great adventure of your own.

Bon Voyage!

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7 thoughts on “My Next Great Retirement Adventure is to Cycle Across America”

  1. Loved “ In the event of a catastrophic breakdown of either man or machine, the sag wagon provides an emergency ride.”
    Good luck and happy pedaling!

  2. Sounds like a fun time of riding, and bonding, with family and your bikes. The southern tier is a very doable route. I am planning a Northern tier crossing in 2026. It’s also great to have the SAG wagon! Don’t forget to get a Texas flag, or shirt while riding through Texas! It seems to appease the locals!


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