Small Boat Cruising in the Florida Keys

A couple enjoy the Keys on their Nor Sea' 27 as part of their path around the Great Loop.

Bahia Honda anchorage
Inside the Bahia Honda anchorage, between the bridges. Having a small boat makes it easier to anchor out at night. Bianca Dumas

We were tied to the fuel dock in Marathon, the midpoint of the Florida Keys, in the early part of 2022, when I realized our mistake. 

Other cruisers traveling the Great Loop were on the loop’s southern stretch of the route, while some bluewater cruisers were starting to stage for passage to the Bahamas and beyond. I asked the dockmaster if any slips were available, and learned that it’s perpetually high season in the Keys, including at that moment. Along with cruisers and sailors, fish migrations change throughout the year, calm summer conditions attract divers, and festivals bring in the party crowds.

“We’re always booked out,” he said, shaking his head. Then he paused, perhaps realizing that he’d just sold us a total of 6 gallons of diesel. “Wait, what size is your sailboat?”

We were on Jackalope, a Nor’Sea 27. He shifted into a smile. “Oh yeah, we can probably squeeze you in down there,” he said, pointing to the inner harbor. 

Florida Keys
A storm approaches in the Florida Keys. Our sails can go up and down quickly, in order to take advantage of the wind. Bianca Dumas

We were grateful for the offer, but in the end, we stuck with our plan to anchor out. We had stayed on a dock—at Bahia Honda State Park—only once during our monthlong Keys cruise. While a lot of people on bigger boats doing the loop preferred marinas, anchoring out seemed to fit with our small-boat cruising style. We were basically camping, which required few amenities and created a lot of options. We took bucket baths when we couldn’t go ashore for showers. We cooked from simple ingredients that didn’t have to be refrigerated: lentils, rice and pasta. We paddled our inflatable kayak to shore for an occasional restaurant meal. 

We laughed when we were once mistaken for homeless people on a resupply walk, but how could we argue? We don’t have the same look as those who can blow-dry their hair and pull clothes off a hanger. 

But our small boat makes for a big adventure. We crossed the Gulf of Mexico from Fort Myers Beach directly to Key West, and because the 90-mile crossing took us three days and two nights, we had the experience of a much bigger, more challenging passage than other boats would. Our sails go up quickly and easily, so we take advantage of every quarter-hour of good wind that we can find.

Checking out Key West, Florida, through the porthole of our small boat while sailing the Great Loop. Bianca Dumas

Moving slow and low, we don’t fear crab pots; they’re easy to see and steer around, even in the dark. And since a keel-hung rudder protects our small propeller, hitting a crab-pot float head-on doesn’t cause trouble. At our top motoring speed of 4 knots, we can see dolphins, turtles and manatees before they dive for cover. 

We can’t avoid getting tan because we steer from an open center cockpit. Nor can we avoid getting exercise because we have to paddle ashore rather than motor. (Jackalope’s canoe stern means we don’t have a motorized dinghy on davits.) 

Like the mythical Western creature that shares its name, Jackalope has a small stature. Just right for us.

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