Back to the Florida Keys for Bubba Fest

When you come across a breathtaking aerial view of the Florida Keys, it almost always shows the Seven Mile Bridge, the longest by far in the Keys. About four times longer than the Golden Gate Bridge, it spans the blended blue-green waters of the Atlantic and Gulf of Mexico near the middle of this 126-mile-long island chain.

When Bubba Barron, founder of the Bubba Fest Florida Keys bicycle tour, hypes the Seven Mile Bridge as “the most beautiful 7 miles you have ever biked,” he exaggerates only a little. The midpoint may be the farthest out to sea you can get on a bicycle. The view from the top may be one of the most sublime you will ever see on bicycle. But what Bubba doesn’t tell you is that, especially for a first timer, the Seven Mile Bridge may be the most unnerving 7 miles you have ever biked.

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There is a not quite high enough concrete barrier between you and a gracefully long fall into some of the loveliest waters you have ever seen. There is a not quite wide enough shoulder separating you from all the cars and trucks blowing past just a few feet away. You need to focus ahead of you, scanning for obstacles and sharp debris on that seemingly endless shoulder, while praying that you don’t get a flat. Please God, not here.

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You get major bragging rights for biking across it twice: once on the way from Key Largo to Key West, with a fine subtropical breeze at your back, and again on your return, with a gusty make-my-day wind in your face.

My First Bubba Fest

Once described by someone as a rolling party, Bubba Fest Florida Keys is a week-long bicycle tour that begins and ends in Key Largo, the northernmost of the chain of keys (islands) that extend southwest like drips of coral and limestone from the tip of the Florida mainland. Over two days, you bike from Key Largo to the end-of-the-road city and island of Key West, about 100 miles away. You spend a couple of layover days at Key West and then retrace your route. I rode Bubba Fest in November 2009. It was my first bike trip in the Florida Keys, and a very mixed experience.


Me at Boyd’s Key West Campground in 2009.

I got off to a bad start. The reasons for this involved the timing of the trip, high winds and threatening weather, feeling like I was crashing a party where I didn’t belong, and an anxiety-roiled sleepless night just before the first day’s ride. By morning, sleep deprived and paralyzed by panic, I nearly decided to drop out of the tour.

But once underway on my bike, I cycled out of the panic and ended up having a great time exploring the Keys. They were among the most beautiful places I’d ever biked. But I biked alone for almost the entire trip. I never warmed up to the group, the festivities irritated me, and I ended up isolating myself. I was the first to leave the farewell party on the last night and the first to leave camp the next morning. I reached Key Largo before anyone else and quickly packed up and left.

Now 10 years later, I began thinking the time had come to bike the Florida Keys again. And I thought perhaps it was time to give Bubba Fest another try.

Back to Bubba

For my first Bubba Fest, I had flown down to Florida alone. This time I hoped to rustle up a companion to make the tour more enjoyable. I contacted my Michigan friend Bob, whom I met a couple of years ago on a Bike Florida bicycle tour. Even though this was something of a last-minute proposal, Bob was game. We considered various options for a Keys cycling trip (an Adventure Cycling tour, a trip with Keys cycling guide Earl Stine, and going it on our own) and concluded that Bubba Fest seemed the best fit. Surprisingly, registration was still open with the tour only weeks away. Because of a late-breaking dental issue I had to contend with, we registered only two weeks before the tour was set to begin.

Bob rendezvoused with me at my home in Maryland. We drove down to Key Largo in his minivan, taking just over two days and bringing with us his new motor assisted e-bike and my trusty touring bike.

Bubba Fest, Then and Now

The tour format had changed a bit. Last time, after a first night in a Key Largo hotel, we camped for the rest of the trip, at the town of Marathon (the midpoint of the Keys) and just outside Key West. We had one layover day in Marathon and two in Key West. This time, there was no layover in Marathon, which was still recovering from Irma, a Category 4 hurricane that struck the middle Keys in 2017.

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Many things remain the same.

Nearby Pigeon Key, a nice day trip by bicycle from Marathon via the old highway bridge, was now accessible only by boat tour. The campground in Marathon was gone, developed into a resort. So this time, we stayed in a hotel in Marathon on the trip down and back. Like last time, we spent three nights at Boyd’s Campground near Key West.

Bubba’s Pampered Pedalers provided everyone with roomy tents, air mattresses, and other amenities. Most breakfasts and dinners were included, along with the mechanical and emergency support you expect on a fully supported tour.

The Cult of Bubba

One of the reasons I felt like an outsider at some stranger’s week-long party 10 years ago was because, in a sense, I was. Bubba has a devoted following. Many of the riders on Bubba Fest have done Bubba tours before. While this comradery can make Bubba Fest feel just a bit clannish at times, everyone welcomes newcomers. This time around, knowing what to expect, I felt much more relaxed and sociable. I really enjoyed meeting and talking with people, and that made a huge difference in how much more I enjoyed the tour this time.

Most of the people who set up the tents, drive the support vehicles, and help out in many other ways are volunteers and veterans of Bubba bicycle tours. Bubba himself, a retired police detective from St. Louis, remains a commanding yet jovial presence throughout the trip. He began running Keys tours in the early 2000s and has since branched out and added a few others, including a fully supported cross-country bicycle tour. Bubba’s Pampered Pedalers also provides tent rentals and pampering service for several other bicycle tours around the country.

Bubba clearly relishes running these trips. His “pirates trolley tour” of Key West—required if you want a ride to that night’s catered dinner at a restaurant near Mallory Square—remains unapologetically juvenile and tacky, unless perhaps you’ve indulged in a couple of his pink and potent “Bubbaritas” in camp before heading out. You have to wonder how much all that pirate paraphernalia (bag, shirt, bandana, and a plastic sword you are encouraged to wave threateningly), along with all the other Bubba branded stuff he gives out, adds to the tour cost. But I did appreciate the stainless steel mug he provided each of us to fill at the coffee stand thoughtfully set up for us in camp by 6:30 each morning.

Biking the Florida Keys

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The bike ride follows the Florida Keys Overseas Heritage Trail, a multiuse trail that, when completed, will extend 106 miles from Key Largo to Key West. The trail website states that over 90 miles have been finished. Indeed, comparing the trail maps I have from 2009 and 2019 reveals great progress. Some of that progress was undone in 2017 by Hurricane Irma, which damaged trail sections in the middle Keys.

Note that “trail” does not always mean “bike path.” Lengthy sections of the Overseas Trail consist of paved paths separate from US 1, the main (and only) highway through the Keys. This is especially true in the Upper Keys. Many other sections consist of bike lanes alongside the highway, sometimes generously wide and separated from the traffic lane by rumble strips, and sometimes not. In a few places, you ride on narrow shoulders or sidewalks. Here and there, the trail switches sides of the highway. It’s not always clear which side of the road you should be on. There was little directional signage for the trail; we had to follow the small pink arrows Bubba laid down on the pavement to show where to turn or cross. But you can’t really get lost.

Through the Upper Keys, the trail is not especially scenic. But then you start crossing bridges. More than 40 of them link the islands of the Florida Keys. Some you barely notice. About 20 range from nearly 1,000 feet to over 2 miles long. And then there’s the aforementioned Seven Mile Bridge. Some are modern highway bridges completed in the decades after World War II. Many are historic railroad bridges later converted to highway bridges, relics of the short-lived railway built in the early 1900s that linked mainland Florida with Key West.

Many of the historic bridges are only open to bicycles and pedestrians; it’s just you and the folks fishing from them. A few in bad shape are closed altogether. Many are still active highway bridges, and you bike along the shoulder. In some places, as on the Seven Mile Bridge, you bike on the newer bridge, with the abandoned historic bridge a ghostly presence beside you.

It is from these bridges that you enjoy the most exquisite views in the Florida Keys: of the stunning range of colors in the waters around you, of the endless expanse of ocean and gulf extending to the horizon on either side of you, of the magnificent tropical cloudscape painted across the sky above and beyond you. There is no place I have ever been that is anything like it.

And at the end of the trail is Key West. We had two days to explore that compact city, and a bicycle is the best way to do it. The Overseas Trail splits into two when it reaches Key West. The upper branch runs past a long, generic commercial strip. The more scenic lower branch runs along the Atlantic shore, past the airport and several seaside resorts, and leads you into the heart of old Key West. From there you can cycle up and down the streets and past all the areas to which tourists and locals flock.

Throughout the trip, the winds were mostly gentle, and the temperature each day ranged only a few degrees, from the upper 70s at night to the mid-80s by day. Other than a refreshing sprinkle, we never got rained on while riding. Only on the last day, as we biked from Marathon back to Key Largo, was there any real threat of rain, but it held off. The headwinds grew stronger and gustier as the morning wore on. Along with many other riders, Bob and I decided to take the shorter riding option that day. We let Bubba’s helpers shuttle us by car for the last 18 miles to Key Largo, so we could get an earlier start for home.

The Future of Bubba Fest

Bob and I joke that we jinx bicycle tours. After we signed up for the 2018 Rails to Trails Pennsylvania Sojourn, the Rails to Trails Conservancy announced it was ending its popular series of rail trail tours. After we joined Bike Florida’s 25th anniversary spring tour this past year, Bike Florida announced it would not hold the tour in 2020. Now it appears there are changes in store for Bubba Fest too.

That Bob and I were able to sign up for Bubba Fest only two weeks before the start of the tour is revealing. Just over 70 riders participated in the tour—as I recall, about half as many as 10 years ago. The oldest rider was over 80. A significant number were in their 70s. Only two riders were younger than 40.

Not enough younger people are filling the bicycle touring ranks increasingly vacated by aging baby boomers. But that said, there were many first-timers at Bubba Fest this year. So maybe there’s hope for reversing that demographic trend.

At the farewell party, after handing out awards for oldest and youngest rider (and to Bob and me for being the last to register!), Bubba announced a significant change. Next year, Bubba Fest will be an all-hotel trip with no camping. Many Bubbafesters will cheer this change, given the inevitable discomforts and inconveniences of camping. Maybe this is a concession to Bubba’s aging clientele. Maybe it will attract new riders. It’s likely to change Bubba Fest.

I wonder how this will affect the social nature of the ride. Our camping area was centered on an open air pavilion, where we would hang out, share meals, and get to know one another. Will that be harder to do when everyone has a private, air-conditioned room to retreat to? The group meals at restaurants tended to be in noisy rooms with people seated in small groups at large round tables, where it was often hard to talk to anyone but the person next to you. I much preferred the rows of picnic tables in the campground pavilion.

Despite discomforts and inconveniences, camping has its delights too. Like pouring yourself a mug of hot coffee in the predawn darkness and walking over to the nearby shore to watch the sunrise. Or hanging out with fellow riders and getting to know them because you have nothing better to do. Or helping out a discouraged campmate who could use a pair of earplugs and some empathy. Or just enjoying the small pleasures of living a simpler and less connected life outdoors for a few days on a subtropical island.


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My first Bubba Fest 10 years ago was an experience I swore I would never repeat. This Bubba Fest turned out to be everything for me that the last one was not, a far better time than I expected. Much of that had to do with having Bob along to share the adventure. I was also in a far better frame of mind and therefore enjoyed the social experience more.

Having finally gotten to bike the Keys again, I doubt I’ll be tempted to do another Bubba Fest. But I’m really glad I did this one. Despite the unseasonable chill that greeted us after our return to Maryland two days later, I still felt a lingering warmth.

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David Romanowski, 2019

5 thoughts on “Back to the Florida Keys for Bubba Fest

  1. David – glad you had such a good experience! I enjoyed reading about the comparisons with your previous ride and this one. Besides Bubba Fest morphing a bit, we, as humans also change over time and our expectations and view points as well. Having done the trip with Earl Stine a few years ago along with friends, I was able to relate to parts of your adventure, especially riding back on the 7 mile bridge with the head wind, marginal riding lane, dodging misc items on the road, and the traffic rushing by. It took us 23 minutes heading south early in the morning and 70 minutes returning mid day, wind, and traffic! Thanks for the very well written narrative of your trip! Tad


  2. Thanks Tad! Bob and I were planning to get shuttled over the Seven Mile Bridge on the way back, but it turned out to be about as perfect a day as you could get for the return trip–sunny with light winds–so we decided to go for it. We stopped for ice cream in Marathon to reward ourselves!


    • Ah, the ice cream reward!!! No biking adventure is complete with out a nice ice cream cone, ice cream sundae, or best of all for a super reward, a classic banana split!

      Liked by 1 person

  3. Reading your diary, I was pleasantly reminded of our bike tour with Earl and the amazing Florida sunrises and sunsets. To this day, I miss these daily growing up sights.

    My favorite pics are the sandled crossed feet with a refreshing beverage at arm’s reach looking out at the water scene and the lizards. I remember coming upon a field of them on the bike path and swerving erratically to miss them. Do you remember where you were when encountering them?

    Happy Thanksgiving!

    Liked by 1 person

    • Hi Lea! Thanks for your comment. I saw iguanas all over the Keys, often darting across the trail in front of me. As for the big one in the pictures, I was relaxing by the water, right where I took that picture of my feet, when I looked to my left and noticed that lizard resting just a few feet away. He didn’t dart away when I circled around him and took about a dozen photos. I guess he was there to chill out too, and he wasn’t going to let me bother him!


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