In early January 2026, I was recapping my 2025 adventures, longing once again for the outdoors. For the past 5 years, I’d begun my hiking season earlier and earlier, to the extent that I started my Desert Winter Thru Hike at the end of January, nearly 1 year prior. While I didn’t really want to repeat a 1500 mile winter thru-hike again this year, a mini staycation / thru-hike seemed like the perfect way to satisfy my immediate wanderlust. So I began studying the logistics of hiking the Florida Keys Overseas Heritage Trail, which lies conveniently in my backyard. Pretty quickly, I added more ambitious plans to also paddle my sea kayak to Key West, making it a paddling / walking yo-yo adventure: Key Largo to Key West to Key Largo i.e. the “KL2KW2KL.”
I intended to complete the FL Keys kayaking trip for nearly 20 years, ever since moving to South Florida in 2006. In that time, I paddled the 100 mile Everglades Wilderness Waterway, over 70 miles from Miami to Flamingo via Florida Bay, Shark Valley to Flamingo (across 26 miles of sawgrass), 60 miles of the Peace River, 150 miles of the Suwanee River, and countless other shorter rivers, creeks, and springs throughout Florida, but never the entirety of the Keys. I was inspired to combine my passions for kayaking and thru-hiking when I did a version of this multi-sport adventure on the Suwanee River and Florida Trail back in 2020. Thru-hiking the Oregon Coast Trail in 2023 further made me yearn to incorporate my sea kayak into my long distance adventures. I figured my 20 year South Florida anniversary was the perfect time to finally achieve this goal.
After just a few weeks, the many logistics of this multi-sport trip started to fall into place. Namely, how I would get my kayak from Key West to Key Largo, while I walked back. But I’ll describe all these these logistics further in my daily blogs. I’ve added a map here to help readers gain a geographical idea of the journey I undertook. In the end, I paddled about 105 miles along the length of the Keys and walked just over 100 miles along the overseas highway.
A bit more context, the Florida Keys are a part of several “officially” designated, long distance, self-propelled adventures routes. The first is the Florida Circumnavigational Paddle Trail (CT), a 1500 mile route encompassing the entire Florida Peninsula…and yes, I hope to maybe someday tackle this in my sea kayak. Running parallel to the CT is the Florida Keys Overseas Heritage Trail, a state-designated walking and biking corridor, utilizing over 90 miles of multi-use paths, including several of the original Henry Flagler railroad bridges. Unfortunately there are still about 15 miles where a thru-hiker or biker has to walk directly on the shoulder of busy US1, most notably across the entirety of the 7 mile bridge, west of Marathon. This “trail” has recently gained popularity in the long distance hiking community as being a leg of the 5000+ mile Eastern Continental Trail, which goes from the southernmost point in Key West to the northernmost point (either Quebec or Newfoundland in Canada, depending on who you ask). While I have no aspirations of completing the ECT as a thru-hike, I am interested in doing large sections of it. Thus far, I’ve walked the Appalachian Trail, Benton Mackaye Trail and now the OHT sections. Over the summer (2026), I hope to complete the 1500 mile International Appalachian Trail (IAT) section from Katahdin Mountain, Maine to the northern tip of Newfoundland…but that’s for another blog.
Day 1: Thursday January 22, 2026. Distance: 10 miles. John Pennekamp State Park, Key Largo to Harry Harris County Beach Park, Tavernier. Stops: a small breakwater and Dove Key.
Despite a very wet forecast, I drove to Key Largo early in the morning and parked at my friends’ Mary and Shane’s house. Shane just so happens to be the park manager and they enjoy the small perk of living in staff housing, with their own private boat basin. They invited me to park my car there for the day and launch from the small ramp, which was just perfect for a kayak. The only catch was that I needed to be on the lookout for their resident crocodiles. South Florida is the only place on earth where both the American crocodile and American alligator overlap habitats. But in the Keys, it’s pretty much only crocs. After paddling in Florida for over 20 years, I’m used to both, so I confidently slid my kayak into the water and paddled out the basin. I was indeed looking closely for the crocs, but only so I could start off my animal sightings list with a ringer. Crocs are actually quite rare/endangered, especially compared gators, which I see almost every time I’m paddling. A croc sighting is a lucky privilege, as they are shy, timid and basically harmless to humans, especially those taking the form of a 16′ kayak. To both gators and crocs, I appear as a very large animal and they want nothing to do with me. Alas, there were no crocs to bid me Bon Voyage (but I’d get to see one on my return 2 weeks later).
Below are some of the many warning signs you’ll see throughout Florida…usually when the warning is specifically about crocs, it’s actually a gator that’s pictured (as in the first sign). But the second sign is by far the worst rendition of a gator? croc? I’ve ever seen…seriously, who drew that? It cracked me up!
It began to rain just as I paddled past the Pennekamp beach and into the mangrove tunnels. It was pretty neat paddling the tunnels in the rain, giving the lush setting a very tropical feel. I also had the tunnels all to myself, which almost never happens in this very popular state park. It could rain all day, as long as it wasn’t also windy. All my wx apps assured me that the winds would be light this day. I’d been eyeing the forecasts for weeks and the next 5 days were the best I’d seen, at least in terms of fair winds. Jan-April are typically the windiest months in the Keys, but also the best in terms of not being oppressively hot and buggy. Doing this trip in the summer or fall would ensure generally calmer days, but also extreme heat, bugs and the risk of thunderstorms. Camping during those time frames is also usually a miserable experience, mainly due to the no-see-ums. Thus I’d aimed for a January trip, fully aware that I’d have to time my days on the water in-between winter fronts. The next was due to arrive by late Monday, bringing the wind up to 30 kts, so I needed to paddle fast!
Upon reaching open waters, I was relieved to find that it was indeed calm, just as the forecast called for. I paddled all morning and into the early afternoon through bouts of rain, at times pretty heavy and more than I’d expected. My weather app said it was supposed to stop after only an hour, so I hadn’t bothered to put on any rain gear. So hours later, when I was still getting dumped on and thoroughly soaked, I started to get a little chilled. But the temps were still in the 70s, and so long as I kept moving, I was fine. I’m pretty used to being wet all the time in my kayak anyway, it just goes with the territory. Plus, wearing a PFD, a neoprene skirt, and sun clothing, I was pretty well insulated. Usually the challenge in Florida is to stay cool while paddling, not warm. There were hardly any other boats on the water, but the few that I did see were thankfully a good distance away. I was leery of the low visibility and speed of the powerboats…not a good combination when you’re in a small self-propelled watercraft on the open ocean. But the closest I came to any vessel was of my own design, as I spied a wreck in the distance. It was the first of many sunken sailboats that I passed on my journey, a sad outcome of life on the water.
I saw some cool wildlife along the way. A sizable loggerhead sea turtle surfaced very close, as well as many smaller green sea turtles. They always appear very surprised to see me. Unlike a powerboat, I make no noise and can creep up on the critters pretty close. Speaking of creeping, at one point I just happened to glance over my shoulder to get a bearing and glimpsed a shark fin in my wake! It seemed to notice me noticing it and immediately peeled off. Perhaps it was following me or equally likely, I just happened to turn around as it was passing. I don’t really worry about sharks while paddling my kayak, but have heard a few personal accounts of sharks “tasting” kayaks…I even saw the toothmarks left by one on a friend’s yak. So I do know they can occasionally get a little bold. Shark sightings were almost an hourly occurrence in the shallow waters in days to come, but all appeared to be harmless nurse or lemon sharks. Birds were also plentiful, namely cormorants, herons, terns and a few mergansers.
I made only 2 stops all day: one at the edge of a breakwater (just to pee, by far the worst part about kayaking!) and a second on Dove Key, a small offshore island. I paddled all the way around and finally found a tiny opening in the mangroves. Clearly locals visit the spot with very small skiffs, and there was just enough dry ground to potentially pitch a tent. Camping in the Keys is a real challenge due to all the luxury private property. Beaches are rare and coveted and most of the small, undeveloped islands are completely covered by mangroves. Thankfully, this night I’d arranged a stay in the backyard of some friends, Monica and Frank. They are long-time residents and former owners of Florida Bay Outfitters, the primary kayaking store in the Keys. They’d been supporting paddlers for over 20 years, and so it was an honor and privilege to be able to include them in my adventure. In fact, they were absolutely crucial to it! Monica solved the problem of how to get my kayak back from Key West by offering to drive my car down to pick it up. I was also able to leave my car parked at their house for the rest of my trip (except for this first day).
I reached Harris beach park around 2 pm and easily wheeled my kayak to Frank and Monica’s house a few blocks away. I didn’t load my camping gear this first day, since I’d be retrieving my car at the end. I was essentially slack-packing, though I barely notice the weight when it’s not on my back but instead inside my kayak. Still, it was nice to not have to lug the extra weight on my cart. Speaking of which, this was my first time experimenting with carrying the cart on my back deck. My Kayak Cart KC7 is a low profile cart with a capacity of only 120 lbs. The small wheels don’t do great in sand, but it works in a pinch and weighs only 3 lbs. I regret that it won’t fit inside one of my hatches but I discovered a pretty stable spot for it by strapping it upside down to my deck rigging. I was so pleased with this set-up that I decided to bring it along for the rest of the trip, which proved to be a good call!
Monica and Frank greeted me and gave me a tour of their lovely home. I set up my tent under their chickee (a classic keys campsite) and then was able to take a hot shower and change into dry clothes. After such a wet day on the ocean, oh how great this felt! Then we went to fetch my car, stopping off for happy hour at the local pizza place, C&C wood fire eats, which had an amazing pizza and beer deal for only $10. We left just as the sun was about to set, and being with 2 local Keys experts, they knew just where to go. We went to Snook’s Bayside restaurant for drinks and took in one of the most amazing sunsets I’ve ever seen! The gloomy clouds gave way to some stunning effects. It was a wonderful way to end my first day in the Keys.
Day 2: Friday January 23, 2026. Distance: 16 miles. Harry Harris County Beach, Tavernier to campsite on the DL. Stops: Kalteux Key, Islamorada sandbar, Indian Key.
A surprise rainstorm hit around 4 am, dumping more tropical moisture, but I woke up dry thanks to the protection of the chickee! I really thought the rain was done the day before, but I guess when you’re surrounded by water, there’s always a chance. I donned all my wet stuff and drove my kayak on top my car to the beach…yeah, I could have carted everything but why not use a motor while I had one? Monica saw me off, taking the only good shots of me and my boat of the whole trip. Thanks for the awesome pics! (Gear pictured: vintage ’00 16′ Impex Montauk, name: Pepper, Kayak Cart KC7, and my new favorite, a 2 piece carbon Gearlab Kalleq greenland paddle…I grew to absolutely love this paddle on this trip).
It felt really good to be back on the water and the day was full of promise atop the perfectly glassy water. The rain clouds gradually gave way to clear skies, making for dramatic vistas. I paddled a 3 mile warm-up to Kalteux Key. It’s a tiny island off Plantation Key with just enough high ground for a swing. The scene felt like it came straight from a polished Instagram influencer’s post. I took a nice snack break there, wishing I could spend the whole day. An island all to myself…one of several more to come.
I paddled on for miles across glassy shallow waters, a sea kayaker’s dream. I saw a few turtles and sharks. A gathering of boats in the distance drew me offshore a ways, and before I knew it, I was joining the powerboat revelers at the popular Islamorada sandbar. I really needed a pee break, so I simply swung my legs over the side and hopped out into the crotch-high, crystal-clear water. I couldn’t believe there was an anchored food boat #thepinchobarge serving hot eats and treats (think food truck only on the water). I just had to buy an ice cream for the novelty, since it was my first time encountering one of these on a paddle. The only vessel even more odd was mine. I could almost hear the thoughts of the power boaters: What’s a kayak doing all the way out here? But I’d like to think I had the sexiest boat of the flotilla.
By this point, I only had about 6 more miles to go. I paddled calm waters to Indian Key for a quick stop, a spot I’d visited several times before on day paddles. Unfortunately, just as I was about to call it a day, one of the most alarming episodes of the whole trip occurred. The perfect weather and easy conditions may have lulled me into a false sense of comfort and security, and I guess I let my guard down. Within half a mile of Indian Key, as I was crossing the last major boat channel, I made the mistake of crossing in front of an incoming power boat. It was sizeable too, a proper offshore fishing yacht. Previously, I’d waited for powerboats to pass in front of me at the other channel crossings, as regardless of who has the right-away, this is always the smart and conservative thing for a kayaker to do. But this boat looked to be so far away, I didn’t initially judge it to be a threat, or even noteworthy. What I didn’t realize was just how fast the outgoing current was pushing me offshore, towards the boat, and how much the channel curved to the northwest, away from me, effectively increasing the distance I had to go to get across.
As I neared the far edge of the channel, the powerboat was suddenly RIGHT THERE and keep turning left, almost as if it was trying to hit me. I quickly had to decide whether to keep paddling frantically to reach the channel edge, only yards away, or to stop, wave and yell frantically. I did the latter and thankfully they heard me (my whistle was tucked into my PFD pocket at the time, but after this, I had it and my air horn out, at the ready). The boat came off a plane and steered away. The guys on the boat seemed to be in total shock, waving their arms and yelling at me, probably profanities. I didn’t bother trying to decipher what they were saying because I didn’t want to get further unnerved. I absolutely did have the right-of-way, both because they were seeing my port side and also because I’m a paddle craft. But I can’t get caught up in that, because in the end, I will always lose a battle with a power boat. And I certainly wasn’t going to win a shouting match…Floridiots are usually packing heat. I simply ignored them and paddled as fast as I could into the nearby shallow waters, where I knew I’d be safe. Thankfully this was my only close call the whole trip, but it certainly woke me up to the need to constantly be on guard when paddling deep waters. My friend Flex, who paddles offshore and solo even more than I do, now flies a 6′ tall flag and wears an orange cone sombrero so as to be more visible. I’m considering a flag, as well.
The stop at Indian Key was clutch in letting my nerves settle. I did a quick tour along the old grid streets and then carried on to my secret campsite for the night, a few miles away. Enjoy these cool pics of Indian Key in the late afternoon. The island has an amazing history I won’t go into here (you can read for yourself at the link), but it’s deservedly one of my favorite places in the Keys. Best of all, visiting during the late day, I had it all to myself!
