Our one-way charter with 360 Yachting (360yachting.com) allowed us to begin here, in Key Largo, and sail seven days southwest to Key West, where the company picked up our boat, Keremeos, and sailed her back for us. Navigating this narrow channel was perhaps the most challenging bit of navigation all week
Molasses Key was the first of many snorkel and swim stops for us. The Florida Keys is an archipelago that stretches east to west. Three to four miles offshore lies a vibrant great barrier reef – the only in the U.S. – which makes for multiple perfect lunchtime stops
Holiday Isle Marina had more than enough to offer in terms of dockage, facilities, provisions and shoreside entertainment. Here, our Fountaine Pajot Orana rests peacefully at the dock
Holiday Isle on Whale Channel is also home to a large fleet of charter fishing vessels, an activity we often try to incorporate into our charters. We discovered caption Robert and his first mate, Casper, and they took us deep-sea fishing about four miles offshore. Casper’s bait methods ranged from nets to chum to to trolling to kite fishing. Both Casper and Robert were extremely entertaining and knowledgeable about the area
At the end of the day, Capt. Robert and Casper sent us home with enough yellowtail and mackerel to keep us happily fed for days. We’d also caught parrotfish and grouper, but with grouper out of season and parrotfish notorious for causing ciguatera, we opted to leave them where we found them
Sombrero Key topped our list of favorite snorkel spots. The bright red lighthouse sets a picture-perfect backdrop to this underwater aquarium
The water in the Keys is warm and mostly clear and parrotfish and barracuda are bountiful
Entering Boot Harbor Marina on Marathon Key, you’ll find this old bascule bridge, which is no longer operational, allowing sailboats to enter and exit with ease
Boot Harbor is a quiet marina with a handful of transient mooring balls. We were put on one near the entrance, which afforded us this great view of the sunset
Another gorgeous sunset on Keremeos
The Fountaine Pajot Orana was laid out in such a way that double-handing it was simple. All lines are led to two winches near the helm and extra line is collected in a massive rope bag that hangs off the side. The raised helm and wide side decks combine to make this helm station a safe and easy place from which to drive
Keremeos was a joy to sail. With her square-top main, she bit into the wind nicely. The owner also pulled out all of the stops on her accommodations, opting for such luxuries as bow speakers, pillows on the trampoline, a luxurious owners’ suite in the starboard hull and electric heads
This is a common sight as you sail along the Keys. The little islands are connected by a plethora of bridges, the longest of which stretches for seven miles
At anchor near Bahia Honda State Park, we enjoyed a particularly nice sunset. This anchorage lies between the old and new Route 1s, which gives is a sort of urban feel mixed with a sense of remote quiet. Ashore, there’s a nice beach, a butterfly pavilion, a campground and a three-mile running trail
Sailing into Key West, we had a classic “would you rather” moment with this cruise ship. We all decided our sailboat was the way to go
Around sunset, Key West’s Mallory Square is the place to be for street performers. In addition to watching this guy swallow a sword, we watched six-toed cats tightrope walk, a man juggle fire on a ten-foot unicycle and juggler throw around pins on a tightrope. All of this takes place before a beautiful nautical background
All of our sunsets were spectacular, but Key West’s was also entertaining. A few hundred others joined us in applauding this gorgeous view
If you’re looking for an entertaining food stop, make time for Peppers of Key West, where you can sample dozens of different hot sauces ranging from tangy to set-your-mouth-on-fire
At the end of the week, we got to relive our trip in reverse. Our crew rented cars in Key West and drove the length of Route 1 back to Miami to catch our flights home. This lends an interesting perspective to the area, as you can see the route you’ve taken from an entirely different point of view
