Miami South Beach to Gay Key West Research Tour (Part 1)

By Zachary Moses

A gay multi-sport tour of the keys? Why didn’t we think of it before? Of course we should do a gay Keys and Key West tour! HE Travel has been headquartered on this sunny, gay-friendly island for 30 of our 40 years in the gay travel business.

Behind the scenes: Creation of an innovative new gay tour

In the office, we’ve never really been able to agree on the best way bring our own group of visitors to Key West, even though our town is world famous for being a great gay destination. The idea and jumpstart for the new tour came from my eccentric military buddy Daisson. His plan was to ride his bike from Key West to Key Largo, trade the bike for a fully loaded sea kayak, then paddle the entire way back to Key West … all 100 nautical miles.  And all of this in the EIGHT days before Christmas. He asked me if I wanted to be in on his harebrained scheme, and I thought “why not?”. I’ve been dreaming of a Keys tour for years, so why not get out and do a little research? Maybe take a little mini-vacation from my office and experience first-hand the beauty that makes the Florida Keys a famous destination for outdoor enthusiasts from all around the world.

Did I mention Daisson is a true-blue Army dude? I had no idea just what I was signing up for. This was no vacation, this was more like what I can imagine boot camp is like! Daisson had been planning his trip for about a year, and wanted to show me his notes. He took me onto the military base and he showed me his “command center.” Wow, it was like walking into mission control in a military movie. He had charts and maps taped to the walls, piles of outdoor gear, vacuum sealed bags of dried meat and fruit, notes, journals and logs, and every electronic military gadget he thought he might need. “This is an expedition,” he told me. “I want to be prepared for anything.” This was really a show of commitment… or a mental disorder… but I love Daisson, so I figured I would go with the former and trust his well-trained judgment.

Daisson poses next to the food we prepared for our 8 day research for HE Travel’s Gay South Beach to Gay Key West tour. Our rations included homemade beef jerky, every kind of raw nut and seed, and dried fruits and coconut.


We spent the week leading up to the trip frantically getting my supplies together and my bike outfitted with packs for the journey. We pre-packed our kayaks with our equipment and drove them up to Key Largo, where we stowed them in a storage shed at John Pennekamp State Park. On the drive south toward home, we took copious notes and GPS data points for emergency supplies, medical facilities, and most importantly, good Cuban restaurants and cheeseburgers.

Day 1: Key West to Curry Hammock by Bike

Phil, Zach, and Daisson in Key West getting ready to launch the research tour for HE Travel’s Gay South Beach to Gay Key West tour.


Daisson and I met at my house and prepped the last of our gear. Phil (HE Travel CEO) came by to bid us Bon Voyage. Phil really put the pressure on me when he stated to me that he was sure I would design the best gay vacation ever with this one.

We then rode from my house at mile marker 1 (MM1) to the famous MM0 sign for pictures. Mile Zero, we had decided, had to be the official start of our research tour, or the tour wouldn’t have that “authentic” feel to it.

We departed along the south side of the island and rode past the monument for the Southernmost Point in the continental USA. We then continued on the waterfront bike path past the beaches and airport and out onto the Overseas Highway. Leaving Key West and entering neighboring  Stock Island, we took a detour to have coffee with our friends Jess and Casey who live at the Golf Course.

Sara from the office sent us a text to tell us how great our GPS tracker was working, because she checked it and could tell that we were NOT actually doing our research ride, and she knew damn well that we were lollygagging, and by the way, “How are Jess and Casey?”… oops! Busted!

Gay Key West Tour

After our scolding, we downed our coffee and took off up the Keys. At one point we decided to cut across some grass and Daisson had the first and only flat of the trip, at MM10. I spent a good deal of time fixing his flat tire (Mr. Military Preparedness had overlooked this particular skill). Plus, he had just gotten a new pair of really tight fitting gator tires, and getting the bead to go over the rim was an absolute nightmare.

Luckily, I am a bike guide, and if there is anything I know tricks for, it’s changing a flat tire. I had to unpack my shaving soap and smear it all over the wheel: I was able to use this slickness to convince the tire over the rim. I only had a hand pump and could not get the tire pressure as high as I would have liked. I would have used a compressor at a gas station to make up the difference, but unfortunately when I went to grab it, I realized someone had stolen my the adapter right off my tire stem…grrrr. We rode a bit up the road to try and find a bike shop. When we checked at a visitor center to ask where the closest one was, they said it was either backtrack the 10 miles to Key West, or continue 20 miles to MM31 on Big Pine Key. I just about broke my hand trying to fill the tire as full as I could, so that Daisson could make it without having to backtrack. This is my level of commitment to non-backtracking.

When we pulled into Big Pine Key we stopped at the Good Food Conspiracy Health Food Store for snacks, directions to the bike shop, and a bottle of honey for quick energy replenishing. Next we stopped at the little bike shop and used their compressor to bring Daisson’s tire pressure up and bought some new adapters for any future flats.

From here we continued through the rest of Big Pine Key, which was a really beautiful stretch complete with a half a dozen endangered Key Deer sightings! We crossed the bridge and soon made it to Bahia Honda State Park, known for having the most beautiful beaches in the Keys. We stopped to take photos of the original bridge built by Henry Flagler for the overseas railroad. It was one of the few iron truss bridges of the original railroad and designed for a single rail track inside the bridge. When the Overseas Highway was built on the original railbed in 1938, the highway deck was actually built on top of this bridge.

From Bahia Honda Key we continued a short distance to neighboring Ohio Key where there is a resort and a gas station. We had been riding way too hard for the last two hours, due to the lazy start we had this morning. With the six or seven coffee stops that we’d made, and our tendency to dilly-dally, we were just running out of time. We were both suffering from blood sugar lows and we still had 15 miles left to go for the day! We entered the gas station and wolfed down a dozen chocolate bars and a half gallon of Gatorade. These are the sugary things I would normally never eat or drink, but they were so delicious and just what I needed! I felt re-energized and ready to tackle the Seven Mile Bridge.

A couple more tiny bridges, and we made our way to the entrance of the famous Seven Mile Bridge (shown being blown up in “True Lies!” with Arnold Schwarzenegger and Jamie Lee Curtis).

Gay Key West and the Seven Mile Bridge

We took a few pictures at the entrance to the Seven Mile Bridge, adjusted our rear view mirrors, then set off single-file. We were not really looking forward to this unbroken stretch of bridge, expecting the traffic to be bad and the ride boring. On the contrary, it turned out to be the most beautiful Keys view I’ve ever experienced. When we topped the high section of the bridge the view was absolutely spectacular, with visibility for miles in all directions. We got a true appreciation for the beauty of the 1700 or so islands that make up the Florida Keys.

At the peak of the bridge there was a plaque commemorating the life of a man Peter C Fancher the bridge tender who lost his life in a tragic accident on the old bridge in 1981. I never knew this sign was here. I’ve driven this route dozens of times and never saw the sign until now.

On the far side of the bridge we came to the unbroken bike paths of Marathon. It was lovely riding through Marathon on these winding pathways. We stopped to get dinner at the Publix (already tired of our rations of jerky), and darkness fell while we were in the store. We had to ride the last few miles to our campground at Curry Hammock State Park in the dark. Part of what I do in research is to figure out how much time activities take. This way my group never has to repeat my errors and ride in the dark.

We arrived at our campground exhausted, and still had to find the park ranger’s place. When we finally got our camp set up, I was sooo hungry. I had tied my bag of groceries to the back of my bike rack, and it was at this point that I discovered that that I had lost my orange…Damn It!!! I wanted that orange like nobody’s business. Plus, I would have killed for a bathtub to soak in. It was at this point I realized that, in designing our Gay Keys Tour, I would absolutely NOT be asking our guys to sleep on the ground, and there would be hot baths (or at least showers) at the end of every day! However, it was nice to know that one could sleep naked in a mosquito tent in December; the weather was lovely.

For more information about the tour that this research inspired click here!

Curry Hammock state park Gay Key West tour


About philsheldon

Owner of Hanns Ebensten Travel and Alyson Adventures.
This entry was posted in All Welcome Tour, All Welcome Tour, Alyson Adventures, Biking, Essays, Florida Keys & Key West, HE Travel, Kayaking, Men's Tour, Men's Tour, Multi-Sport, Philip Sheldon, Travel, Uncategorized, Women's Tour, Writings, Zachary Moses and tagged , , , , , , , , , , , , , , , , , , , . Bookmark the permalink.

5 Responses to Miami South Beach to Gay Key West Research Tour (Part 1)

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