J+G Sailing; The Upper Keys

 A review of the upper keys and the Gigantic Nautical Flea Market. 

It was a rough day leaving Miami. The wind was whipping across the Biscayne Bay and gray rainy clouds were marching across the sky. Navigating the day before had been slightly stressful and I wasn’t looking forward to another day of chaos. Wanting neither to stay nor leave, I sat at the helm with a slight pout face as Joel pulled up the anchor. Though the conditions looked rough, the wind was in our favor. In the sailing world, as long as the winds in your favor and there's no hurricane, you otta go for it. 

the upper keys
sailing in bad weather
helms sailboat

Indeed, the wind was in our favor and our little boat speed across the bay headed for the first of the Florida Keys. As we crossed the first gap between where the peninsula ends and the Islands begin, the wind freely swept off the ocean and pushed our boat along with even more vigor. Our boat was heeled over more then she’d ever been. And we were having a ball. I guess with all the excitement, I decided I needed a front row seat. So I crawled over to the windward side of the boat (the side now high in the air as we are heeled over).  Hanging on to the life lines, I dangled my legs over the edge of the boat. As our hull interrupted the waves in their steady march across the ocean, the warm water would crash over the edge and soak me. Smiling ear to ear, I remember telling Joel this was the best day we’ve had sailing. That day, I think I really fell in love with sailing. Too think I didn’t even want to leave our anchorage. 

sailing couple
foul weather gear

The Florida Keys are sectioned off into the “Upper” keys, “Middle” keys and the “Lower” keys. Most people identify the keys as Key West, Marathon, and maybe Islamorada. But, actually there is a ridiculous amount of separate islands down here each with their own name. My favorite of them all is “little duck key” (only for the name).
Our first night anchored in the upper keys, we dropped the hook with only one other lonely boat floating near by. Other then our neighboring sailor, there was little in sight but salt water and mangroves. The morning time brought a few scattered thunderstorms. With no hurry, we threw some buckets out to catch the falling fresh water and sat in the cabin to wait out the storms.

ICW cruisers

Our days of long sun up to sun down traveling were behind us. We had finally arrived in the Keys and each day we only had to travel as far or as little as we wanted. So after the storms passed, we sailed a few miles down to the next key. I looked on google earth and found the closes spot with the clearest water and marked it as our destination of the day. 


ICW sailing
sailing blog

After adventuring around our google earth destination, we pulled the anchor and scooted on closer to shore for the night. The morning storm had given us just enough fresh water for a little “boat” shower. Which felt extra refreshing as the wind died out with the setting sun and we were left with a very humid little home. 

showering on deck
sunset sailing

The next morning, we woke to some wet floors. On a boat, it seems your daily challenge will either wake you or meet you by your bedside. We leaned over the bed and opened the bilge. Indeed, it was full of water with no sign of the bilge pump kicking in anytime soon. What a lousy crewmember. It had one job, too keep us from sinking, and it just up and quit on us.  With no manual bilge pump on board (oops), Joel got creative and used our wash-down station pump and some extra water lines to empty out the bilge. After a little trouble shooting, we discovered the bilge pump had not failed us but the float switch was down for the count. A relatively easy fix. 

living aboard a boat

With our daily challenge down and our fingers crossed there wouldn’t be another, we went our to see what the day had in store. The water was crystal clear so we jumped in for a little swim and then motored over to an anchorage where we could go ashore.

dive on anchor
cruising in florida keys
sailing blog

After exploring the town (and Joel somehow talking me into us buying a new pair of nicer dive goggles) we headed back out to our little home floating on the far end of the harbor. Joel climbed the mast for a little excitement, and then we called it a day.

climbing mast

ur next stop would be an island hop to Islamorada. We had a beautiful blue sky, clear water day of sailing. Our colorful rainbow spinnaker was itching for some air, so we got it out and hoisted it up. It was quite an enjoyable little sail. We even saw batman go by in his boatmobile. 

life on board
spinnaker sail
miami speedboat

slamorada was a fun little stop. I was surprised to find that many of the keys have no public beach access. But, we did pretend to be guests at a few resorts so we could walk along the ocean’s edge.

florida resort

ucked away from all the tourist traps on the main road, we found a couple cute local eats. One of which was Badboy Burritto , a restaurant after my own heart. Delicious burritos and fish tacos filled with locally sourced grub. They even grow their own herbs. We were highly impressed by this little foodtruck style food joint. Joel and I split a burrito and I scarfed down a kale and pineapple smoothie which satisfied the much needed veggie nourishment my body was craving. 

good eats florida
organic garden

We stayed in Islamorada for a few days. One day, we were enjoying warm weather and clear water swimming. I reckon we hadn’t encountered any daily challenge so it seemed we had to create one for ourselves. We decided to raise our rainbow spinnaker as a swing. Something I’d heard of through one of my sailing tale books and we had been egger to try for ourselves. Already out in the water and not wanting to sit down and do our research, we wrongly decided to do things the hard way. We figured we’d make it up as we went and if it didn’t work we’d just pull it in and try again. WRONG. We spun the boat around so that the anchor would be holding us stern into the wind. And, Joel tied a rope a few times back and forth between the two clews of the sail as a swing seat. With another rope hanging down for (what we thought would be) easy retrieval. 

spinnaker swing

Joel was the first to try it. We let the spinnaker swing loose and Joel grabbed the swing. He flew into the air. But, we had tied the corners too close together and the wind was gusting above 15knts (which we later read was a no no for spinnaker swing weather). So, as he flew up, the sail caught so much wind that it whipped up, ripping out of Joel’s grasp. Thus began our challenge for the day. Getting the large rainbow colored sail down as it flapped like a flag 30 feet in the sky. A few boats stopped to watch us as the sail played monkey in the middle. Us being the monkey. A coast guard boat even motored slowly by. Joel tried desperately to pull it in as I let out the halyard. But the spinnaker just took the extra line and Joels weight and heeled our boat over sideways, throwing our belongings all over the cabin and dragging our anchor a good 100 yards. Chaos. Soon I was in the dinghy driving with Joel standing ready to grab the spinnaker. After many failed attempts (and Joel getting thrown out of the dinghy twice) the sail finally dipped down at the right timing and we both grabbed it. Having it finally in my hands I pulled it in to the dinghy as fast as my arms would move while Joel twisted it trying to lower the surface area. We had it, but I still had to get the dinghy to the boat or the sail would fill again. The only problem was I had pulled the sail in so fast and hard that I had wrapped myself in it and couldn’t see to navigate. And of course, I was headed in the wrong direction. Joel yelled, “Towards the boat!” I gassed the engine and turned hard. As the dinghy did a 360 at full throttle, I simultaneously ripped at the sail that I was now engulfed in trying to free myself incase the wind caught it and ripped it out of the boat. Somehow in the midst of this, I caught a glimpse of my surroundings and pointed us toward the boat. We got it. We pulled it in and sat breathing heavily, not wanting to move, both feeling like we just wrestled a monster. With such an exhausting task completed, we said to heck with dinner, made brownies and watched a few episodes of 30 rock. 

spinnaker swing
spinnaker swing gone wrong

I guess you could say we learned the hard way of how not to fly a spinnaker swing. Luckily, we ended our time in Islamarada on a good note. We happened to be there during the famous “Gigantic Nautical Flea Market”. So, we rented bikes for a day and checked out the flea market. 

gigantic nautical flea market
nautical flea market

Our time in Islamarado came to an end with a morning bike ride to the sunrise, a delicious chia latte and returning our bikes

Until Next Time, 
Much Love