There have been several “full-circle moments” along the Loop, like when we cruised through downtown Chicago or when our boat touched the Mississippi River for the first time. This week, however, may have been the “fullest circle” yet.
After celebrating the new year with good friends in Naples, we had tunnel vision for the Florida Keys. Beyond the obvious draws like crystal-clear water, great fishing and a slower pace of life, we’ve been dreaming of returning to Marathon, Florida, on our own boat ever since our first visit years ago.
Before we could reach Marathon, though, we had three jumps to make: Naples to Marco Island, Marco Island to Little Shark River, and finally Little Shark River to Marathon.
Naples to Marco Island was a quick 1.5-hour jump, although the ocean was a tad rolly. With two weeks of land life prior, it’s safe to say we were still getting our sea legs back. We could have bypassed this stop altogether and gone straight to Little Shark River in the Everglades, but neither of us had been there before, so we figured why not check the island out! It was a quick stopover, so we anchored in front of Rose Marina, where we were able to use its dinghy dock. We walked around the town and had a nice meal at The SpeakEasy before heading to sleep early for a 55-nautical-mile run the next day.
Friday morning, we were up before sunrise, heading south toward the Everglades. The Gulf continues to amaze us with how shallow it is. I don’t think we ever saw anything deeper than 20 feet, even while being miles offshore — and that might be generous! The cruise was uneventful besides the occasional dolphin playing in our bow (which never, ever gets old), and we pulled into Little Shark River mid-afternoon. This was possibly our only stop along the Loop in 4,500 nautical miles that didn’t have great shore access for Ripley. We always make it a point to confirm a sandy shore, boat ramp or some sort of land access for her to go to the bathroom, but this anchorage did not offer any of those. Instead, there was a small sliver of muddy land tucked between two sets of mangroves that was less than ideal but did get the job done.
Saturday, we were up before sunrise yet again, making our final jump south. Not only was this our final jump south of the week, but it brought us to the southernmost point we will reach in Northern Attitude. Because we’ve visited just about every key by car, we don’t have plans to take the boat further south to Key West.
Now that we’ve brought you up to speed, let me share the special full-circle moment I mentioned at the beginning. Evan and I spent our second wedding anniversary road tripping through all the Florida Keys. It was around this time that we declared we would complete America’s Great Loop before starting a family, so we spent the entire trip dreaming of what that would look like. One day, we found ourselves at Dockside in Boot Key Harbor, a waterfront bar and restaurant in Marathon. We were taunted by dinghy after dinghy pulling up with full-time cruisers hopping out to listen to the live music. We knew deep in our souls that we would be back there one day on our own boat, and this past weekend we made it happen.
Shortly after dropping our anchor, we didn’t waste any time. We lowered the dinghy and headed straight to Dockside, where we both ordered the same drinks we had our first time there. I’d argue that the drinks tasted a whole lot sweeter this time around!
We’re continuously pinching ourselves along this journey and feel blessed beyond measure that we get to live out a dream many never will. Cheers to continuing this grand adventure!
Leaving the dock in Naples

