Researching a Gay Multisport Tour From Miami to Gay Key West (Part 3)

This is Part Three of the research expedition that inspired the our fabulous South Beach to Gay Key West multi-sport tour. Click here to read (Part 1), Click here for (Part 2)

Day 3: Begin the Kayaking

OMG!!! We stayed up way too late last night celebrating our 100+ mile bike ride to get from Key West to Key Largo … aurgghhh such a headache! Was this the best way to start 120 nautical miles of kayaking? What were we thinking??

We enjoyed a breakfast of dried meat, fruit and watery oatmeal. (Why watery? Because Daisson made it, and straight guys don’t need to follow directions. He can make anything with his Colombian machismo …*eye roll*)  …Daisson also made some more of his burned coffee. But he made our breakfast and I didn’t have to, so l gracelessly accepted the fruits of his labor.

Moving the Kayaks

After a befuddled morning spent packing and repacking the kayaks, Daisson and I wrapped up our preparations and launched around 10:30 am. From here we paddled out into the mangrove channels of John Pennekamp State Park. It was an amazing maze of twists and turns that eventually led out into the open ocean.

Mangrove Maze

The water was a perfect aquamarine, and as smooth as glass. We made good time on our first day. Daisson and I made no stops whatsoever, because we had been so relaxed about our launch time and now needed to paddle like super humans in order to make it to our campsite for the evening.

My favorite part of the kayaking was when we would stop paddling while on the open water between islands to take potty breaks. It was a brief interlude where I could cool off, and take in my surroundings. We had to execute strange acrobatic maneuvers to accomplish this necessary task, resulting in a good number of capsizings. There are few things funnier than watching a grown man try to relieve himself while standing in a kayak in the middle of the open ocean.

Open Ocean

Our eating stops were so much fun too! We would link up our kayaks and make jokes about our ridiculous undertaking, “Why, oh WHY did we schedule 20 miles a day??” By the time we got to Coconut Cove, I was so sore and tired that I decided I would pay the extra money in order to sleep in the hotel room instead of camping for the night. It was wonderful: soft sheets, plush pillows and a nice hot bath. Daisson tried to tease me for pampering myself, and I just decided that I didn’t care what he said – I would treat myself to the same quality my clients would expect. It was heaven – no wonder our guys love 5-star lodgings!

ending a day

Day 4: The Paddling Comes to an End (so soon?!)

Daisson woke me up at 6:15. I would have happily slept until noon, but I was on a trip with Mr. Military, and we needed to get up and have a flag ceremony.

We got on the water by about 7:30 am for a beautiful crisp morning paddle. We crossed under the bridge to the gulf side, then zigzagged between islands. I decided I wanted to have more fun today, so I pulled right up into the mangroves. I got a great picture of a dragon fly that decided to land on my water bottle.

into mangroves


We paddled between mangrove islands, and even eventually made our way to Shell Island, where people are not allowed to set foot since it is a wildlife sanctuary. I paddled into the beautiful mangrove tunnels and did indeed attempt to set foot on the island until some huge prehistoric bird scared the living Sh** out of me. From that point on, I followed all the rules.

Shell Key

From Shell Key we paddled on and eventually landed on Lignumvitae Key, an island that is still home to an original, intact keys tropical forest. Then we paddled on to Robbie’s Marina. At this point my shoulder had started to give out from an old climbing injury and Sara was waiting to pluck me, my kayak, and my bruised ego from the water.

Daisson paddled on while we went out to lunch. As the rest of the day wore on, I began to realize that my shoulder injury was going to prevent me from continuing. I didn’t want to tell Daisson, and I asked Sara how on earth I was going to get out of tomorrow’s kayaking. She advised me to “Cry, Zach. Just bring on the tears.” We met Daisson at the campsite on Long Key and watched him set up camp. I told him that my shoulder just couldn’t take more of this journey and I suffered through his mockeries before I headed home to Key West for a wonderful night’s sleep in my own bed.

Day 5: The End of the World Brings an End to the Trip

Our intention had been to party hard at Knight’s Key, since it was the last night of the Mayan Calendar (yeah, remember when the End of the World didn’t happen?). If the Mayans were wrong, and the world continued the next day, we would paddle parallel to the Seven Mile Bridge and bee line it to Bahia Honda State Park. We had already bought a netted mosquito enclosure and more honey whiskey to celebrate the world ending.

daisson on his own

That morning, the wind started picking up really heavily and I saw that the Coast Guard had issued a small craft advisory. Safely at home, I started to worry about Daisson out on the water with no support. Around 1:00, he called me and told me he was going to have to call it quits on the trip. The weather was turning too foul and he no longer felt safe continuing with the Kayak portion of the trip.

I drove out to Curry Hammock to pluck Daisson out of harm’s way. On the way out there, the wind was blowing so hard that I feared I would lose the kayak once it was loaded on top of the truck. As I drove over the Seven Mile Bridge, I understood why he had decided to call the trip. The usually calm waters of the Florida Keys were raging into 4- and 5-foot swells.

Daisson looked exhausted and broken. We loaded up his kayak, then headed back to Key West to celebrate the world’s end (and the end of our adventure) at Irish Kevins in Key West.

loading to go

As we sat out the storm in a warm, dry pub, Daisson was clearly in a glum mood from not completing the trip that he had dreamed of for so long. I reminded him that plenty of expeditions or extreme sports get canceled or delayed because of injury or natural forces. I still loved the adventure! Getting out on my bike and on the water all along the Keys reenergized my love for my island paradise, and I came home with a lot of great ideas for making a Keys Adventure Tour that our clients would really love.

Below are some highlights from our Adventure Tour of the Fabulous Florida Keys and Gay Key West coming up in November/December, 2013. For more details, please click here.

Explore gay South Beach, enjoying the public art, architecture, & eye-candy of this trendy, gay-friendly island city.
Delve into the delicious tropical flavors of the local fruits and specialty wines of southern Florida.
Zip through the unique Everglades ecosystem on an airboat.
Scuba or snorkel to see Christ of the Abyss, a bronze statue submerged in the crystal clear water off of Key Largo.
Kayak through quiet tunnels of mangroves and underneath the bridge to nearby Indian Key.
Bicycle southwest along the Overseas Highway, through areas of native plant life as well as immaculately landscaped subtropical gardens.
Marvel at the expanse of shallow, shimmering water dotted with hundreds of islands and mangrove stands from the tiptop of the Seven Mile Bridge.
See endangered Key Deer in their native habitat (just a few of the thousands of islands host this rare species).
Wind your way through back-country scenery on a private, clothing-optional, gay paddleboarding tour.
Experience one of Key West’s famous drag shows and dive into the gay club scene with a local guide who can introduce you to everybody!
Live it up aboard a catamaran which sets sail for an all-day adventure full of jetskiing, parasailing, snorkeling, and just goofing off in the water.
Eat, play, and stay at gay-owned and gay-friendly restaurants, bars, and businesses throughout the tour. The Keys and especially Key West are tremendously welcoming of gay visitors who come from around the world to enjoy the warm, accepting atmosphere in addition to the amazing natural beauty of the island.
*For those who’d like to spend another day in paradise, we are offering an optional extension to visit Dry Tortugas National Park, a pristine island 70 miles west of Key West, and site of 19th century Fort Jefferson.

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, Hiking, Kayaking, Men's Tour, Men's Tour, Multi-Sport, Travel, Uncategorized, USA, Women's Tour, Writings, Zachary Moses and tagged , , , , , , , , , , , , , , , , , , , , , , . Bookmark the permalink.

2 Responses to Researching a Gay Multisport Tour From Miami to Gay Key West (Part 3)

  1. dave mckenna says:

    Hi Zach,
    The adventure tour of the Keys sounds like it has everything included in it. And the “dry” run sure exposed some practical problems and the backup needed to respond to changes in the plan. Good for you. How is your shoulder? Though clearly not a tour for me – flying into Miami, over night in South Beach, starting the tour (with all its’ different offerings), and ending with, say two days in Key West is a good package. And the exit airport is right there! Kudos. d.

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