Day 3: Saturday January 24, 2026. Distance: 20 miles to near Duck key. Stops: Anne’s Beach-toilet/shower/replenish water, Long Key–lunch/replenish water, paddle through interior canals of Duck Key.
I got on the water much earlier this day (7 am), as I knew I had a long way to paddle. After just a bit, I stopped at Anne’s beach to replenish my drinking water. I also enjoyed a luke-warm beach shower and bathroom break. Thankfully there are numerous beach parks with these nice amenities throughout the keys, making logistics easy. I paddled on along the causeway for a bit, then made the crossing to Long Key. I stopped to check out some remote beaches and was sad to see just how much trash was washed up on the shores of this otherwise beautiful State Park. These areas were only accessible by boat and thus hard to clean.
On the way to the more developed part of Long Key SP, I saw some dolphins fishing in the shallows, being followed by a small boat of dolphin researchers. I waved but they seemed to not even notice me, they were so focused on following their targets. I also saw 2 rec kayaks, but didn’t get very close. I’d only seen a fishing kayak launching from Anne’s beach earlier in the day and another kayak the day before, near Tea Table Key. My sit-inside sea kayak was an anomaly among all of them, as there aren’t many that treat the sport as a means of serious travel and long distance adventuring.
I stopped at a picnic area on Long Key beach, enjoying a table and later a presentation about horseshoe crabs, thanks to the friendly rangers. I planned to camp at Long Key on my return as a backpacker, but it also serves as a viable camping option for paddlers, as do the other 3 state parks: Pennekamp, Curry Hammock, and Bahia Honda. All have walk/bike/paddle in sites that are left open for such patrons until the end of the day…but it’s best to call a day ahead of time to let them know you’re coming, so they don’t give the sites away to other visitors the day-of.
There was a decent breeze by the afternoon, which I noticed as soon as I set off to cross the Long Key Bridge, the second longest in the keys at 2.5 miles. This is also the longest span of the old Henry Flagler railroad bridge that’s still intact, so pedestrians can enjoy this stretch independent of the newer bridge, which is designated for busy US1 traffic. I quickly discovered that the current was pushing me into the bridges, towards Florida Bay, so rather than battle it, I slipped under to paddle the bayside for the first time this trip. But the wind, current and bridge infrastructure resulted in pretty choppy conditions. I had to paddle at an angle to counteract the current, constantly having to adjust as I zigzagged between the spans. In retrospect, I should have tried to stay farther offshore, away from the bridges. They can be very hazardous in that they attract fishing boats, which tend to zip in and out. The supports also reduce the visibility of my boat and others. Additional hazards include hanging fishing lines/hooks and falling debris. I was nervous about all this, but thankfully it was a pretty quiet day. On the upside, if you can maintain your heading perfectly parallel to the bridges, they provide a nice shade canopy!
I bounced my way along for almost an hour, then encountered another significant challenge of my trip: RIP TIDES! To resume my planned route, I needed to paddle back under the bridges, fighting the strong current, and then along the causeway. Going under was fine but the minute I set my course paralleling the causeway, I realized the wind and current were being funneled (the venturi effect) in a way that created chaotic 2′ haystack waves. I had to paddle with all my might (unfortunately greenland paddles are ideal for efficiency, not power stokes), trying to stay upright, all the while staring at the rocky shore only 20 feet away. It taunted me, as I could see that I was making almost no headway, and also worried me, knowing it would be a treacherous spot to get dashed upon by the current and waves. When paddling in normal wind swells, the waves are at least predictable in way that I can brace for them. But these waves were coming from every direction simultaneously. A couple hit me hard from opposite ends and directions, corkscrewing me around so that I almost went over… definitely the closest I came to capsizing in a long while. Again, I would have been much better off if I just stayed a mile offshore. Live and learn.
After what seemed like hours, but was probably only 10 minutes, I escaped the rip tides into calmer waters. I reached a breakwater off Walkers Island and was able to take a rest in the lee. Two small sit-on-top kayaks casually passed by, out for a leisurely paddle. None of the occupants were wearing PFDs, or even shirts, and were all holding their euro blades upside down (greenland sticks are symmetrical, therefore this is never an issue.) I laughed to myself, recalling the challenging conditions I’d just experienced less than a mile away, now seeing these unprepared tourists nonchalantly paddling the calm waters. The keys are a dynamic and constantly changing paddling area for sure! Then again, just about any adventure on the water can go from tranquil to life-threatening pretty fast, that’s how you get to Gilligan’s Island! It’s a 3 hour tour…
I decided it was the perfect time and conditions to paddle a little alternate route I’d spied when planning weeks before. Nearby Duck Key had a series of canals running through it, which seemed like a nice change of pace and escape from the wind. Sure, it added some distance to my day, but I was yearning to experience something other than open waters. I entered the canals at the north tip of the island and paddled past the loud speakers and tents of an outdoor expo that was taking place in the harbor, apparently for flashy outboard motors and sport fishers. I worried that I might regret entering the canals, as there could be a lot of boat traffic. Thankfully I only passed a few underway and they were all confined to no wake speeds. It was actually really nice and peaceful in the canals, so I was able relax and chill in the late afternoon.
I also passed by a semi-open dolphin enclosure, which was a surprise. All that was separating me from the dolphins was a chain link fence. I nosed up to it so I could watch the trainers throw beach balls for the dolphins to fetch. I could feel their whistles and squeaks vibrating through my hull, I was so close. Only after I started paddling away did I notice a sign warning boats to keep a 10′ distance off the fence, but I doubt they minded my quiet and non-polluting little kayak coming in for a closer visit. I read in a local newspaper days later that the facility was bankrupt and the dolphins were to be transferred to, you guessed it, Sea World in Orlando. Apparently one of the dolphins had spent her whole life in this ‘natural’ seawater enclosure and they were worried that she would have a hard time adjusting to her new enclosure (prison). Perhaps we just shouldn’t capture and/or breed captive dolphins and whales period, how about that idea?
I zoned out paddling the next few miles through the canals, pondering all the millions of dollars tied up in houses and boats that I passed by. The Florida Keys are the ultimate example of mankind’s hubris. These tiny islands, built up with mega-mansions and resorts, connected only by a network of relatively delicate bridges… it’s all such a fantastical and brash construct. There are interesting historical placards along the Overseas Highway describing Henry Flagler’s brazen endeavors and accomplishments, followed by the repeated devastation caused by hurricanes in the 1910-30’s. The more I read, the more I questioned the futility and absurdity of it all. I guess it’s easy to feel small and fatalistic when paddling a 16′ fiberglass kayak. But I preferred my vagabond existence at the moment, grateful I didn’t have to worry about insurance premiums, maintenance, repairs and evacuations plans.
My only goal for the rest of the day was to find a piece of sand to pitch my tiny tent for the night. My options in this area were limited. I could paddle another 4 miles to Curry Hammock, arriving after dark and not knowing if they would have a site left for me. This was a last resort, as I was really hoping to find a secluded spot on a nearby island. I also knew it was private with a mansion situated right in the center, so it was a gamble. I cautiously paddled by, looking for signs of current occupation. I didn’t see any, which was promising. I paddled half a mile further, out of sight of any surrounding areas, and spied a little spot with some Australian pines. Although they are a terrible invasive tree, I also know they provide secluded flat and dry spots that are ideal for camping.
The tide was very low in the late afternoon, so I had to drag my boat a ways to reach the small beach. But this was a good thing, as it meant that power boats couldn’t get in here and therefore I didn’t have to worry about anyone bothering me. It also meant the island owners wouldn’t expect any visitors in this location. I investigated to find a perfect spot under the trees, just I suspected. I dragged my boat partially out of sight (from a distance it just looks like debris), enjoying another peaceful night under the stars. As with all my stealth camping, I set up late in the day, left first thing in the morning, didn’t make a fire or any noise, and didn’t leave any trash or trace. It’s pretty easy for a solo traveler like me to go unnoticed.
Alas, I did attract the attention of some locals. Thus far, I hadn’t experienced any mosquitos, but the no-see-ums finally made a minor appearance this night. So I simply had my dinner on the beach, thankful for the stiff breeze, then sought the sanctuary of the bug netting from my tent. The next morning, I also found sandy footprints all over my kayak…the raccoons and/or rats worked it over pretty thoroughly, so it’s a good thing I secured all my food and water inside the hatches. Unfortunately they did get my mascot and bow decoration, a red pepper that I found floating the day before. It was a proper sacrifice to the locals in payment for my campsite I guess, and also the inspiration for christening my kayak with her first name: Pepper (I’m still trying it out).
Day 4: Sunday January 25, 2026. Distance: 23 miles to Molasses Key (mid-way along the 7 mile bridge). Stops: Curry Hammock SP, Keys Fisheries for lunch!, Pigeon Key.
The wind was even stiffer in the early morning and unfortunately out of the southeast, annoyingly hitting me on my port beam. But when you have a vessel with a 3″ draft and 3′ canopy, the diversity of route options in the Keys are astounding: from quiet canals amongst the most lavish real estate to shallow seagrass flats to open ocean, with every shade of green and blue in between. I’d planned to paddle the whole day on the ocean side, but earlier had scouted an inside route behind Deer Key, Coco Plum and Key Colony Beaches, then bayside through Vaca Cut. Knowing this would give me a nice lee from the wind all day, I decided on this route instead. The biggest advantage was that it would take me right past the Keys Fisheries restaurant around lunchtime…Sold!
I made a few early stops to check out future potential campsites, finding a couple prospects, then ducked in behind Deer Key to enjoy some easy paddling. I followed some canals, made a friend with a floaty toy on the water, and slid under a few tiny bridges that only a paddlecraft or skiff could manage. I even amused myself with paddling under a large catamaran that was docked. So I guess I did finally get run over by a boat, very slowly and without injury. I posted the video on my Instagram.
I easily rode the current through Vaca Cut, pleased that I finally timed something right, even though it was unplanned. After telling someone of my route, they were shocked I’d gone through the cut, as apparently it can be quite difficult. I surfed some fun wind swell around a point, then counted down the last few miles to lunch. All the while, planes, jets, and helicopters buzzed around, utilizing the nearby Marathon Airport. The bayside was also pretty busy with power boats as well as my mostly just annoying nemesis, jetskis! I kind of have to accept the fact that only being able to move at 3-5 kts top, there’s just not much I can do to outmaneuver the power boats, therefore I must let the waves break around me. But paddling in the shallowest water I can find, of which there is plenty in the keys, is the one trick I have up my sleeve. Unfortunately, these buzzards with their shallow drafts are able to penetrate my inner sanctum. It would hurt to get hit by one but an impact would also hurt them, so I’m always hopeful it’s in their interest to look out for and avoid me. But they tend to be the most brain-dead and distracted of all boaters, then combine that with high speeds and that’s what worries me about them.
There was plenty of space for all boaters this day and I made it unscathed to my well-earned lunch destination. I’d been visiting this low-key (what an appropriate pun) waterfront establishment since I worked for NOAA, 15 years prior and it hadn’t changed a bit…except of course for the steeper prices. Still, it’s one of the best deals for fresh local seafood and is famous for their lobster reubens. First I had to figure out a place to land, as the nearby boat basin was only suitable for large boats. I scrambled ashore along a jetty, fighting off the pelicans and iguanas for space and navigating the slippery seaweed and rocks to maintain a delicate balance. Luckily I’m pretty good at such feats, but I did lose it for a second, gouging a hole in my knuckle that took weeks to heal. At least I didn’t have to worry about anyone messing with my boat…who would go to the trouble? The idiots that stole a boat from Big Pine to “invade” Cuba weeks later wanted a fast panga, not a sea kayak. Very few enjoy a boat with no motor. But at least all my paddling built up an appetite for fried food! I ordered way too much between the mahi tacos and conch fitters. Mmmm. I was going to buy some run cake or key lime pie for take-away, but I was so stuffed, I passed.
Paddling the final 6 miles to Molasses Key was tough on such a full stomach. I also wasn’t looking forward to the exposed waters along the 7 mile bridge, especially with the wind blowing so strong. The conditions I’d encountered the day before along the Long Key bridge made me nervous about the crossing. But at least I could break up the distance with a stop at historic Pigeon Key, where I had the pleasure of visiting the gift shop to replenish my fading energy with a few cans of sugar water and caffeine. Like Indian Key, the stories about it go way back, more than I can summarize here. But I definitely recommend a stop and tour during any keys visit.
Thankfully the wind died almost completely as I paddled my last couple miles, crossing under the 7 Mile bridge(s) and across the shallow flats. Most think that this is the longest and potentially most treacherous open water stretch when paddling the Keys, but I’d beg to differ. The section I paddled the next day, from Big Munson Island to Lower Sugarloaf Key, was was over 8 miles and through much deeper water. But I guess it’s optional to do that crossing, as I’ll explain in my next blog. There is no alternate route when it comes to this 7 mile stretch, but it’s surprisingly shallow much of the way, and therefore the waves not as large even with a fair amount of wind. I suppose a small vessel could also get some protection from the bridge supports, if needed. Pigeon Key and the Molasses Keys also provide stepping-stones for a paddler. There are even a few smaller islands on the west end that I’ve never checked out, but could also serve as rest stops.
Given my plans to stop half-way across for the night, this crossing was actually quite easy for me. The last mile to Molasses Key was absolutely delightful, through tranquil waters, softly cast upon by the late afternoon sun. I landed around 5 pm and immediately set about getting my tent erected, seeing as how the no-see-ums had already started attacking me. I’d camped on this island once before, back in June 2023, at the invite of Frank and Monica, the previous owners. They had since sold the islands but were in touch with the new owners and had secured permission for me to camp there. This was such a relief, as I was free to go about my business without worry of someone ‘discovering’ me or chasing me off. With knowledge of some of the primitive amenities there, I made a beeline for the shower house, eager to rinse off the salt water. I had to supply my own fresh water, so I’d carried extra from my lunch stop. I then took some time to explore the island, say hi to the hermit crab community (Monica’s little babies), and take lots of sunset pics.
Everything looked pretty much the same as when I’d visited before. The only difference was the lack of my friends, as during my previous visit, Frank and Monica had been there, as well as 5 of my best paddling buddies. While the island was beautiful and peaceful this night, for which I was most grateful, I was feeling rather lonely and sad. A little less than 1 year prior, my paddling community lost our beloved friend and fearless leader, Rick Poston. Rick was one of the first sea kayakers I ever met in Miami and over 20 years, he’d also become a close friend. Readers of this blog may have even seen some of his encouraging comments on my posts. He loved reading about my adventures and I was always motivated to write about them, knowing at least someone was reading.
Pictures from my 1st visit to Molasses Key. RIP Rick, we love and miss you.
When I lost my own father in 2020, I looked to Rick, inspired that he was the same age as my dad but still going strong, paddling all over Florida, being cantankerous and a prankster, but also kind and inviting to all that knew and met him. The paddle to Molasses Key was one of our last paddles together. His absence was deeply felt as I tried to settle into my tent, having made an early retreat due to the fierce no-see-ums. The wind had shifted to the south and was nearly still. It was also incredibly humid, with a thick, sticky mist settling on everything as soon as the sun went down. After dinner, my unease forced me out to take a walk along the tide line in the dark. The sea had retreated a long ways out, exposing some pretty cool tide pools. I found a nice sea star and many other critters. My foray helped me work off some uneasy energy, but I still slept fitfully. The noise of US1 had been ever-present thus far, but especially this night, a far cry from the silence I normally experience on my thru-hikes. I was also nervous about the front moving in by the end of the next day, knowing I had a long ways to paddle. I was resigned to getting a very early start.
