Day 7: Wednesday 28, 2026. Distance: 14 miles to Saddlebunch Keys.
I began my hike of the Florida Keys Overseas Heritage Trail this day. I woke early, intending to slack-pack some miles before Monica arrived with my car. I stashed all my gear inside my kayak and carted it over to the trailer storage area. The nice folks at Boyds let me keep it there for the morning, which was kind of them. I set out on foot, turning east instead of west, as first I wanted to visit the naval air station on Boca Chica. I hoped to register to camp at Sigsbee campground, which was situated on one of the nearby bases. They’d recently opened it to veterans and I was hoping to spend another night in Key West if I could camp at this much more affordable location ($24 a night). Unfortunately the rules stipulated that it was only available to veterans with a service-connected disability, so I was out luck. Thanks for your service, now go away. Oh well, I tried, and with the weather being so crappy, I kind of just wanted to start walking.
Lori, a local friend of a friend, gave me a ride from the NAS to down town, where I started walking back to Boyds, getting some more miles done. About the time that I made it there, Monica arrived with my car and her friend Sandy, so we went out to lunch. Then we drove back to the Southernmost Point so that I could take pictures with my backpack, then returned to Boyd’s, where it took another hour to load my kayak and get all my gear sorted and situated. During that time, it started to rain, which was mostly just annoying. I was sad to see my kayak go, but I was also relieved to simplify my gear. The weather over the next few days wasn’t good for being on the water, but it was decent enough for walking.
Finally, I was ready to hit the highway and Monica dropped me off at the 8 mile mark, the point I walked to in the morning. I still needed to make some miles to get away from the immediate radius of town, as I planned to stealth camp this first night. Monica, who used to be a promoter/manager for the Overseas Heritage Trail, pointed out a couple of prospective spots on the map. It’s funny that all the signs for the OHT explicitly stated “No tents or camping.” Unless you have hundreds or even thousands of dollars to shell out for hotels each night, the keys are not that welcoming to hikers and campers. Yet I hadn’t let this stop me. Perhaps the biggest advantage to kayaking versus walking was that I could paddle to some pretty remote and secure locations to camp. Stealth camping along the highway in the vicinity of so many houses and resorts would be a much bigger challenge.
I walked into the late afternoon, finally able to shed some layers as I dried out from the rain. I stopped to use the bathroom at a gas station and checked out a few stealth sites in the area…they would have worked but I had at least another hour before dark, so I kept going. Within 2 miles of my prospective stealth site, I saw 2 local women on the path ahead me, enjoying an early evening stroll. I caught up, calling out in advance so as not to scare them too much. They still jumped, but at least I wasn’t on top their heels as they turned around. Of course I struck up a conversation with them, as they were curious about my pack and where I’d come from.
We had a nice chat as we walked and about the time that I reached my prospective stealth site, Deanna asked me where I planned to stay overnight. I awkwardly pointed towards the bushes, behind the nearby kiosk. “Maybe there?” (it would have worked just fine, too. I think). But Deanna’s house just so happened to be off the next road, mere feet away. She offered to let me camp in her backyard, which I couldn’t have been more grateful for. It was a fantastic backyard as well, all soft grass and right on a canal. A luxury RV place was situated right across the way, charging hundred of dollars a night. After a few more minutes of talking, she also invited me to come inside to check out her spare bedroom. I must admit, the chillier temperatures and rain over the past few days, plus even colder temps coming up, motivated me towards a warm bed. It might be the last chance I got this trip, so I graciously accepted the offer.
I made my ramen dinner in Deanna’s kitchen that night while we had a really good conversation, lasting hours. While I’m accustomed to such random acts of kindness from strangers, since they happen to me pretty often on the trail, I always have to keep in mind that it’s usually the first time such a thing has happened to the other person. It’s quite a leap of faith to invite a complete stranger into your home and I was very appreciative of both my luck and Deanna’s generosity. Since her husband was away but they had cameras installed around the house, she had to give him a head’s up about me so he wouldn’t be alarmed. I bet that was an interesting conversation. I chuckled as I laid down in the bed because I could see the area where I’d planned to stealth camp from the bedroom window. What a fortunate series of events to wind up here as opposed to in the bushes.
Day 8: Thursday 29, 2026. Distance: 24 miles to Bahia Honda.
I departed my comfortable bed early, as I needed to hike a pretty long distance to make it to Bahia Honda. I felt bad about taking off before my host was awake, but figured she’d understand. I left her a small note expressing my gratitude and she later texted me some messages of encouragement. What a sweetheart. I was also eager to make a pit stop at Baby’s Coffee. I’d passed the cafe many times before but never visited. I’d been missing out, because it was the best coffee I had in all the keys, and at the most affordable price! I enjoyed a yummy breakfast pastry as well, then was back on the highway, pondering a number of curiosities that one will find when walking through touristy areas. I even took a 1 mile detour to check out an old bat house on Sugarloaf Key. It had fallen over but was still intact. The bats had long since departed.
This was my favorite day of the walk overall. The weather was perfect (upper 60s and partly cloudy, light winds) and there were heaps of fun stops and things to see. There were also lots of scenic bridge crossings, as I passed from Sugarloaf, Cudjoe, Ramrod, Torch and Big Pine Keys. Unfortunately, many of the old railroad bridges were in disrepair and closed along this stretch. Decades of saltwater exposure had eaten into the iron supports and caused severe spalling. But it’s really quite a testament to the original construction that these bridges remained largely intact after 100 years of exposure to such extreme conditions. In these places, the route followed the highway shoulder. I didn’t mind because it was really wide and the views were great.
For several miles, a really nice bike path utilized the old SR4 road, completely separated from the highway by mangroves. I had good views of 2 CBP aerostats (blimps) flying from Cudjoe Key, the first time I’d seen more than one. I guess they’d ramped up border surveillance operations. It was here, perhaps somewhat ironically, that I came across a sign “Taco Expess.” I guess they were so express that they left out the R…but hey, the trail provides! It was very smart of them to put a sign along the path and I just had to stop, as it was exactly noon. What a great call, as the tacos were indeed fast but also delicious. I almost went back for more but then glanced at my watch and realized I needed to quit dallying. Yet the afternoon brought even more distractions. I splurged on candy from a gas station, checked out lovely Pine Channel Nature park, posed with tourist signs, and laughed at all the kitschy keys stuff along the way. One of these staples was the manatee holding a mailbox (there are hundreds of these in the keys), but I’d yet to see a youngin’ holding a toothbrush!
The signature treat I had yet to check off my list by the time I was almost through Big Pine was a key deer. These charming critters are a subspecies of whitetail deer that migrated to the keys thousands of years ago and became stunted due to the lack of resources on the islands. They are about the size of a medium dog and are highly endangered and protected, being found nowhere else in the keys, or world, for that matter. Yet they are rather plentiful in this small area and I’d seen them several times before. Rare or not, I’ll never grow tired of interactions with them, they are just so cute. What a disappointment it would have been to walk 17 miles through key deer habitat without spotting one of these iconic residents.
Just as I thought I was going to have to settle with the painted statues in front of the visitor’s center, as if on cue, a deer walked right up behind me. She was obviously looking for a handout and actually caught me being naughty, as I was pretending to feed sour patch kids to the statue, taking gag pictures to send to a friend. But I did NOT oblige her wanton begging…you think I’d waste watermelon sour patch kids on a deer? Hell no, that amount of toxic processed sugar was fit only for me. After I denied her request, she still posed for some adorable pictures. It almost seemed as if she was lonely, especially seeing her sniff the baby statue. Awe. But as I hiked on only a few minutes more, I passed a little buck off in the mangroves.
After so many stops this day, the afternoon was suddenly slipping towards evening. I’d called the park earlier to let them know I was coming and they requested I arrive before the office closed at 6 pm. Now it was nearly 5 and I still had 4 miles to go! I blame it on the small detour I had to take due to road construction at the end of Big Pine, but really it was my own fault for not managing my time better. I did my best to walk/jog along a very scenic stretch of bridges, grateful for the easy path and cool weather. I made it just in time to check in and then hurry to catch the sunset over the old railroad bridge. It was pretty cool and I was quite proud of myself for cramming so much into one day.
But I wasn’t done yet. I still needed to walk over half a mile through the park, back under the causeway, to find my campsite in the dark. I followed the road all the way to the end to site 60, the very last in the park. It was situated near the water, which made it ideal for kayak campers. But it was also fully exposed to the north wind, which was blowing strong. I hate windy, exposed sites and immediately started looking around for alternatives. Having paid $50 for this tent site, I was at least going to sleep soundly, free of my tent flapping all night. Lucky for me, 3 of the nearby sites were still empty and I decided to risk that no one else was turning up this late. I picked a site with a big tree that I could slide under, not even utilizing any of the large gravel square meant to be a tent / vehicle pad. Had someone arrived later, they could have easily still fit. After I got set up, I yearned for a hot shower, but the bathhouse was way back over near the marina. I was too tired to go search for it so I made my simple dinner and went to bed. I needed an early start the next day in order to tackle the 7 mile bridge.