Sometimes life really doesn't go your way. I'm not talking about hitting every red light on your drive home from work. I mean something insurmountable where you manage to overcome one hill only to find a mountain range ahead that lunges out of the earth with each successive peak growing infinitely taller into the distance. This is how our most recent adventure in the Florida Keys began.

While the rest of the country hibernated under the frozen blanket of winter, we headed south in search of warm weather and sunshine. Our GPS led us in a new direction: to the Florida Keys, known for it's turquoise water and great fishing. Instead of spending lackadaisical days at the beach, like a typical family trying to escape the arctic grip of winter, we set our sights on something a bit more ambitious: kayaking the entire length of the Keys, all 120 miles, from Key Largo to Key West. Our motivation was simple: if we were going to explore a new place, we might as well really experience it, off the beaten path and explore every nook and cranny along the way. As we started planning out our adventure, I envisioned long days traversing transparent, azure water, punctuated periodically by deserted islands covered in white sand and palm trees: kayaking from one tropical oasis to the next, fishing in the afternoons and then feasting on our bounty as we camped on our own private island: the perfect family vacation for an adventurous threesome such as ourselves.

As with most things in life, our time in the Keys did not go exactly as planned. The first challenge was finding a deserted island every ten or so miles. In fact, with very few exceptions, every square inch of the keys is inhabited. So we modified our vision and instead started looking at State Parks and private campgrounds. Apparently, we were not the only people intent on a hiatus from winter in the Keys, and we quickly learned that campgrounds and dog kennels book up almost a year in advance, and there is literally no place to park an RV long-term without a monthly rental at an RV storage facility. After weeks of exhaustive research, we managed to secure a tenuous and incredibly expensive sequence of accommodations for each night and within reasonable paddling distance of each other by combining public and private campgrounds, interspersed with a few motels.

Our first day on Key Largo was blustery and with a forecast for winds of 15-20 knots over the next ten days, we were concerned how our 10 year old daughter, Abby, would fare with the less than optimal paddling conditions. We decided to test the waters (and wind) with a shorter kayak trip of only five miles. After several hours of kayaking on what felt like a treadmill, where if you stopped paddling for even a moment the wind reversed any forward progress, we decided on the prudent course of postponing our trip for a more favorable forecast. Fortunately, that night we had reservations at the Bayside Inn on Key Largo, a fabulous retreat, where we were able to regroup and come up with a Plan B.

It's never easy to call it quits on a project you have been working so hard on, especially before it even begins, but the huge relief we felt after deciding to postpone our trip confirmed it was the right decision. We will be back to paddle the full length of the keys, just not during the windy season and will make reservations to camp well in advance of our trip so that our next attempt will be a success.

Silhouette of palm trees, people at the beach and boat out on the water against the setting sun. An evening cruise on the Appledore II off of Key West

With the freedom afforded by two weeks with nothing on the schedule, we set out to explore the islands, and completely fell in love with Key West. We visited Ernest Hemingway's home and marveled at his six-toed cats, went sailing at sunset on the 86 foot schooner the Appledore II, and topped it all off with a day of jet skis, snorkeling and parasailing with Fury Water Adventures.

After a great day of snorkeling, it was so much fun to spend time at the Key West Aquarium and identify all the fish we saw on the reef. The festivities at the Sunset Celebration at Mallory Square were the perfect finishing touch to a great day.

Holcombe family parasailing.A family parasail in Key West

As much as we loved playing tourists in Key West, we were still hungry for adventure, and where better to start our quest than 70 miles out at sea. Dry Tortugas National Park is the westernmost group of seven islands in the Keys and is accessible by private boat, sea plane or by the Yankee Freedom III ferry that shuttles around 170 tourists daily to and from Garden Key, the epicenter of the park. With some quick research, we learned of a campground on Garden Key which rekindled my hope of an island oasis in the Keys.

Before we launched into a celebratory dance however, we still had the same Himalayan range scale of logistical mountains to overcome that previously thwarted our plans before we could pull off another multi-day paddling trip.

The first was booking our tickets on the ferry. Fortunately, the folks at Yankee Freedom III could not have been more accommodating and even arranged for us to bring our kayaks with us. Mountain #1 - check. Next was finding a place for the dog at the last minute for the three days we would be in the National Park. Unbelievably, Marathon Veterinary Hospital had a cancellation for the five nights surrounding our trip and Tucker Dog didn't even look back as we dropped him off with the kind folks at the kennel. Mountain #2 - check.

Lastly, we had to find a place to park Winnie the View in Key West for three days. The city has a very strict no RV parking anywhere on city streets regulation that is rigorously enforced, which left us completely at a loss as to where to leave our rig. There must have been something favorable in the alignment of the stars for us, because our friend, an officer in the Coast Guard, arranged for us to park at the base within walking distance to the ferry dock for the duration of our adventure: Mount Everest - check!

Yankee Freedom III boat at the dock.All's calm at anchor, but only after a stomach churning, high seas trip.

With the mountain of logistics at our back, all we had left to do was assemble our gear for three days of backpack style camping in a tropical paradise. We awoke at 5 AM the next morning to load our gear onto the ferry and park and secure our rig and were ready to board by 7:30 AM. The trip on the ferry was an adventure in it's own right with 20 knot winds and 6-8 foot seas. The highlight was standing on the bow of the ferry, and having your feet lift off the deck as the behemoth waves crested under the 110 foot, fast-moving vessel.

Although numerous passengers battled with seasickness, we thoroughly enjoyed the high-seas roller coaster ride on the two and a half hour trek to Fort Jefferson.

Fort Jefferson from with water surrounding.Brick magnificence. Fort Jefferson in Dry Tortugas National Park.

Initially just a dark spec on the horizon, Fort Jefferson rose from the depths of the sea, as imposing as the giant krakens of old as we approached and circled Garden Key. The hexagonal fortress composed of over 16 million bricks and complete with medieval moat, was an impressive display of 19th century engineering and resolve to defend America's perimeter. As we disembarked the ferry, and portaged the gear to our campsite, we were startled to discover Carlos: the nine foot American crocodile that inhabits the moat around Fort Jefferson. Perhaps spending three days on a remote island would be more exciting than what we had anticipated!

Two people on walking path next to moat with alligator in it.Carlos the alligator keeps a watchful eye from the moat at Fort Jefferson.

We quickly set up our tent, donned our snorkeling gear and set out to explore the perimeter of the island. With 15 knot winds, four foot seas, and the ever present concern of encountering Carlos outside of the moat, our tour of the pristine water was spotty, but a few minutes immersed in the warm waters of the Atlantic, all worry dissipated and we become lost within the pulsing rhythm, beauty and abundance of the sea life surrounding us. We discovered queen conch longer than our forearms, a barracuda that rivaled Abby in height and seemed ever present in our periphery throughout the afternoon, and an incredible abundance of colorful reef fish, coral and sponges. We were surprised when we emerged from the sea to find the sun low on the horizon stretching it's golden tentacles across the sea and sky signifying it's daily retreat.

Tent set up next to a a picnic table at Fort Jefferson.Our camp at Fort Jefferson.

As the ferry disappeared into the horizon on it's return voyage to Key West, we finally found the deserted island experience we originally envisioned. With only six other campers and a handful of park staff, we essentially had the entire island to ourselves. We launched our kayaks to fish the calm waters of the harbor in search of dinner. Exactly thirty seconds later, Abby landed a beautiful snapper. With dinner carefully secured on a stringer dangling below my kayak, we spent the next hour catching and releasing fish, cast after cast.

Just as I was starting to contemplate heading in to prepare our fresh fish feast, I looked into the crystalline waters below and was startled to discover a suspicious shadow, almost the length of my fourteen foot kayak mimicking my every move.

Kathy catching a fish from her kayak.Mom shops for dinner.

After a brief moment of fear induced paralysis, I flipped the stringer of scrumptious morsels onto the deck of my kayak and the shadow slowly turned and disappeared into the darkness. Lesson learned: there are many things much larger than myself in the ocean that are always looking for an easy meal. Don't tempt them!

After regaining a normal heart rate from my close encounter, Abby and I headed back to our camp to clean and cook the snapper. All along the path we heard an unsettling and persistent clicking and scratching sound coming from the shadows. It wasn't until we turned on the lantern and illuminated our campsite that we realized that we were completely hermit crabs.

Abby standing next to a boat that has hermit crabs sitting atop it.Abby catalogs hermit crabs.

Three small hermit crabs.Hermit crabs are efficient camp cleaners.

Unfortunately for me, the allure of the crustacean stole my sous chef leaving me to prepare dinner alone as I watched Abby collect dozens of inhabited shells of different shapes and sizes, and inspect, catalogue and name each one.

These unexpected companions provided endless entertainment for the duration of our trip, and proved to be persistent housekeepers relentlessly scrambling to remove any renegade crumbs from our campsite.

With full bellies and tired bodies, the rhythmic crashing of the nearby waves carried us easily off to dreamland. The next morning we awoke with the intention of kayaking the three miles to Loggerhead Key, known as one of America's top dive sites, for a day of snorkeling and exploration.

Unfortunately, the winds had increased overnight and were predicted at a prohibitive 30 knots by noon, so instead of a three mile open water paddle we decided to stay inland and circumnavigate Garden Key instead. Our kayak tour of the perimeter of the island provided a great perspective to fully comprehend the magnitude of the Fort, and to contemplate the lifestyle of the 2,000 inhabitants that occupied the island in the mid 1800s.

Abby showing a thumbs up while holding up a nice sized fish.Abby shows off her night fishing trophy.

After our kayak tour and the daily departure of the ferry, we again headed into the harbor in search of dinner and discovered a few more residents of the island: four goliath grouper that called the ferry dock home. These fellows were aptly named and weighed in at 300+ pounds and measured over six feet in length. They kept a careful watch on our fishing exploits and regularly pruned the bait from our hooks. Peter inadvertently hooked one of the colossal creatures while kayak fishing and it took him on a lively twenty minute tour before breaking his line. Not twenty minutes later, another five foot grouper launched out from under the dock and snapped at a jack fighting at the end of Abby's line, creating quite a ruckus, but her lightening fast and youthful reflexes snatched her catch right out of the groupers mouth and up onto the dock.

We fished well into the night, periodically shining our headlamps into the depths and were occasionally rewarded with fleeting glimpses of monstrous shadows lurking just below the surface as sharks and grouper patrolled the area below the ferry dock. Long after the moon was high we slipped groggily back to our tent and fell asleep almost before our heads hit the pillow.

Just an hour or so later we were awakened by a gentle rumble in the distance and a spectacular display of lightning creating intricate shadow art across our tent walls. We laid in our sleeping bags, mesmerized with the power of the rapidly approaching storm. The flapping of the tent intensified as the beats between lightning and thunder decreased, warning us of the rising crescendo of the storms fury. In time, the torrents of rain and wind eventually abated and we drifted off again, lulled into slumber by the steady patter of rain on our tent fly.

Abby fishing from the doc in the rain.A final morning of fishing. . .in the rain.

The rain continued on throughout the morning setting a dreary tone as we prepared for departure later that afternoon. As Peter and I schlepped loads of gear to the ferry dock, we noticed a small figure, covered in colorful Goretex, huddled at the end of the dock. It was Abby, sitting in the pouring rain, fishing rod in hand, reeling in fish after fish on almost every cast. Watching her bait her hook and release a toothy, floundering fish back into the water, completely lost in the art of fishing was a one of those precious and unforgettable moments where I am startled by her independence and tenacity, and intensely aware of the incredible young woman she is becoming: a powerful reminder of the fleeting nature of parenthood. These quiet moments that only happen when you are unplugged and focused on the moment are the inspiration for our journey and the motivation to continue onward in this incredible life on the road.

Kathy and Abby walking through brick archway at Fort Jefferson.A quiet walk through history at Fort Jefferson.

We spent the rest of our time in the Dry Tortugas exploring Fort Jefferson in the rain. Teasing each other in deserted ancient corridors, splashing across puddle filled courtyards, and simply enjoying each other's company. The ferry ride home was calm and quiet and we spent most of the trip on the bow, the salty air cool in our faces. As Key West appeared in the distance, we spotted a sea turtle just off our starboard bow - the perfect ending to our adventure.

Had we not completely failed in our original plan, we never would have discovered our deserted island paradise, complete with medieval fortress and crocodile patrolled moat: yet another reminder to keep moving forward, even when way off course.


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