Florida Keys Shakedown Cruise

John Simons


Committed to the liveaboard life, Ken and Lynn Baehr sold everything—business, house, car—to pursue their cruising dream. They asked me and my wife, Priscilla, to join them on their Hylas 54 sailboat Bistari for a shakedown cruise to Key West and back.

Fort Lauderdale to Rodriguez Key

We woke at 5:30 a.m. to prepare for departure from Las Olas Marina in Fort Lauderdale, Florida,
where Ken and Lynn had spent the last 30 days getting Bistari ready to sail.

Transiting the Las Olas bridge

That day, we planned to transit 79 miles from Fort Lauderdale to Rodriguez Key, a small island east
of Key Largo where we’d anchor overnight. We’d start by transiting the Las Olas Bridge at the 6:45
a.m. opening, fueling up at the 15th Street Marina and catching the 7:30 a.m. 15th Street Bridge

Everything went according to plan until a tiny fishing boat pulled up to the fuel dock ahead of us.

Two of the three fuel pumps had gasoline only. The third had both gasoline and diesel. We needed diesel. The small fishing boat pulled up to the only diesel pump. How long did it take them to fuel up, you ask? Just long enough for us to miss the 7:30 bridge opening.


Ken and Lynn had named their sailboat Bistari, a Nepalese word used by sherpas meaning “slow down and enjoy the experience.” Bistari, bistari, bistari.

After a long day’s sail, we slept snug in our Rodriguez Key until slapping halyards woke us at 2 a.m. The fickle wind gods had sent us a bit of extra breeze overnight. Having shifted north, the winds blew hard the rest of the night. Thankfully, we felt minimal waves in our protected anchorage, and Bistari’s 125-pound anchor held us firmly all night.

Rodriguez to Boot Key

With the winds still blowing from the northwest at 15 to 20 mph, we put up the sails and made way over crystal clear blue water to Boot Key at Marathon, our next port of call. The 50-mile cruise felt more reasonable than yesterday’s 80-mile slog.

Despite experiencing many firsts on this trip—the first overnight cruise and the first night at anchor—Bistari’s systems worked well. With the generator, solar panels, and watermaker, Ken and Lynn could live off the grid for a long time if they wanted.

After an epic battle requiring Ken’s help, John lands a 15-pound mutton snapper.

A pod of dolphins greeted us as we sailed along the Florida Keys. With good protection from west to north winds, Boot Key would provide another quiet night at anchor.

A comfortable boat, Bistari has a nice-size galley with ample refrigerator and freezer storage, a three-burner stove, and a propane oven, so we didn’t have to run the generator to cook. After a delightful dinner of shrimp, pasta, and broccoli in the salon, Ken and I went up top to enjoy a nightcap and the stars.

Boot Key to Key West

The next day, we dragged a lure for the first time on the trip. After an hour, I reeled in the line to check the lure, a dorado that looks like a squid. After clearing off a bunch of seaweed, I dropped the lure back in, let out about 75 feet of line, and headed back to the cockpit.

Later, when the line started singing out, I grabbed the rod and tightened the drag before the fish took all my line. Capt. Ken headed toward the wind, started the engine, and rolled up the jib to slow the boat. After fighting the beast for what seemed like an eternity, I brought the fish to the transom. Ken came back to help pull in what we estimated to be a 15-pounder.

The day’s sail was one of the best I’ve ever experienced. The wind blew briskly on our starboard quarter. The boat felt well balanced with a full mainsail and half genoa jib. With minimal waves and speeds of 9 to 10 mph, the 48-mile trip took only six-and-a-half hours.

Entering Key West Harbor always brings a sense of exhilaration, and this time was no different. On our way to our anchorage off Fleming Key, we entered the harbor from the east and passed the cruise ship docks and the customs house with its bright red roof.

Anchoring is never without drama. It’s tough finding that perfect spot where the water isn’t too deep (preferably 20 feet or less) and you’re far enough away from other boats that you don’t invade their social space or risk bumping them if the wind and current shift. On this trip, we were three for three on anchoring; we didn’t drag anchor or get the stink eye from other boaters.

Ken uses an anchor alarm app on his cellphone. He sets the anchor radius, and the alarm sounds when the boat moves outside that radius. If Ken takes his phone off the boat, the alarm thinks the anchor is dragging. Fortunately, he can forward the alarm to another phone so that he can monitor the boat’s position from any bar in Key West.

Squeezing into the Key West dinghy dock is like playing a game of bumper boats.

Going ashore in Key West means finding a spot on the lone transient dinghy dock, which is always filled to overflowing. You must purchase a dinghy day pass at the Key West Bight Municipal Marina gas dock for $8. Thankfully, we arrived in the late afternoon as a dinghy departed.

On Thursday, we dinghied ashore and ate lunch at BO’s Fish Wagon. We ordered the “square grouper” sandwich. As the story goes, a “square grouper” was a bale of marijuana tossed into the ocean by drug smugglers trying to elude law enforcement. Fishermen would rescue the bales and bring them ashore. At BO’s, ordering the “square grouper” sandwich nets you a free side of fries.

Returning to your boat after dark can be challenging. You hope your outboard motor won’t fail, leaving you to be swept out to sea with the current. You hope you aren’t run down by a speeding power boat with an over-served helmsman. And you hope you can find your “mothership” in a dark anchorage with only a sea of mast headlights to go on. Having learned my lesson previously, I left a trail of breadcrumbs to Bistari using my cellphone. On the way to shore, I plotted our journey using my Under Armour walking app. Later, we just followed the track back to the boat. Brilliant.

Key West Harbor to Stock Island

On Friday, we learned that the Perry Hotel and Marina on Stock Island had a slip available, which meant we wouldn’t have to wait another day, allowing us to avoid traveling during a big blow and docking in high winds.

We removed the dinghy’s outboard and hoisted it onto the foredeck cradle, battened down everything, closed hatches and portholes, and hauled anchor.

Lynn and Ken did all maneuvers on the boat, which was great practice for when Priscilla and I departed.

We cruised a quick 9 miles to the Perry Hotel and Marina. Ken called on the VHF and got our slip assignment. Slip D2 was all the way at end of the fairway against the main dock. Not an ideal location due to tight quarters next to the wall. What’s more, the powerboat in the next slip stuck out an extra 6 feet into the fairway, which made our turn even tighter. Ken docked the boat like a champ, and with the help of the dockhand Angel, we got tied up and plugged in.

The Perry Marina as seen from the upper deck of the boater’s lounge

A boat at anchor has much more privacy than one at the dock. Our slip had the laundry building on one side and acres of powerboat fiberglass on the other. Having said that, we’d be safe and secure until the high winds abated. Plus, we would enjoy the hotel amenities: three restaurants, two swimming pools, and an hourly shuttle bus with stops at downtown Key West, the beach, and Publix supermarket.

On our first night at the marina, we got a visit from Craig and Day Olney, longtime friends and cruisers who inspired us to make our first trip to Lake Huron’s North Channel. They’ll be a good resource for Ken and Lynn.

Docking next to the laundry has its advantages. I sat on deck watching people come and go with their clothes, so I knew when the facility was empty. The machines use a chip card instead of quarters. You buy a laundry chip card for $5 from a machine and load money onto it with your credit card. Each load cost $2.25 to wash and $2.25 to dry, which is well worth it for a week’s supply of clean clothes. We discovered a shower and restroom attached to the laundry, making our slip look even better.

We’ve been going to the Blue Heaven restaurant in Key West for over 20 years.

Priscilla and I took the noon shuttle bus to downtown Key West. You need to be early if you want a seat. After the 25-minute trip to the A&B Lobster House on Front Street, we walked to a dive shop and bought some attachment rings for our grandson’s snorkel. As we shopped, the wind blew over the displays whenever someone opened the door. One shopkeeper closed early because of it. Next, we walked to Duval Street for lunch at the Blue Heaven several blocks away. We’ve been going to Blue Heaven
for over 20 years. Priscilla even named our blue Pearson 39 sailboat Blue Heaven.

After a wonderful lunch, we returned to the lobster house to catch the hotel shuttle bus, which arrived 10 minutes early and filled up immediately.

That night, we spent a quiet evening onboard despite the howling wind, which sent a nice breeze throughout the boat.

On Sunday, Craig and Day stopped by to show Ken and Lynn how to operate their single sideband radio. Craig was confused as none of the frequencies matched and the clock time was off. It turned out that Bistari had spent the previous 10 years in the Mediterranean, and the SSB had been set up for European frequencies. After lots of noise and pushing of buttons, Ken learned how to turn on the SSB.

That night, Craig took Priscilla and me to his marina at Boca Chica Naval Station for cocktails and dinner at the harbor restaurant.

Key West to Boot Key

On Tuesday morning, we filled the water tanks, stowed everything, and lowered the dinghy into its cradle in preparation for departure. Although we had fun in Key West, it was time to sail again.

At 8:30 a.m., dockhands Angel and TJ as well as boat neighbors from all directions came by to help us cast off. TJ said, “Just take it slow,” which was a good omen for Lynn because Bistari’s name means just that. Ken backed the boat out of the slip like a boss and backed up the fairway. He spun it around, and we were on our way to Marathon and our anchorage at Boot Key.

Conditions were rolly until we unfurled the mainsail and jib. With southeast winds at 15 to 20 mph, we only put the sails out at 50%. Even with shortened sails, we were cruising at 8 to 10 mph. The sails also helped steady the boat in the 4- to 5-foot waves, so we didn’t bounce as much. We were at anchor by 3:15 p.m. With winds coming in from the side, the island provided no protection. But the forecast called for the winds to change and drop, so we hoped for the best.

Boot Key to Rodriguez Key

After a somewhat rolly night, we sat in the cockpit sipping coffee while a pod of dolphins swam nearby. I thought I saw someone swimming beside the boat until I saw the shell. The loggerhead turtle’s head was as big as a human’s.

On our way back to Rodriguez Key, we had southeast winds at 15 to 20 knots. Our track took us more to the north, giving us a more favorable wind angle for a flatter, faster sail.

At Rodriguez Key, we enjoyed a delightful night on the hook with only two other boats in the anchorage and a nice breeze to keep us cool.

Rodriguez Key to No Name Harbor

Lynn in her happy place

We woke to a slightly overcast sky and got underway by 8 a.m. Having a little shade and a cool breeze felt good, but we knew the Florida sun would soon be blazing.

As we cruised north, the wind clocked south to the point that Bistari could go wing-on-wing. With the jib on the opposite side as the mainsail, the wind pushed from behind both sails.

That night, we dropped anchor outside No Name Harbor with 20 other boats. The chart datum shows the harbor depth at 10 feet, but the controlling depth on the entrance is 6 feet. Since we draw 7 feet, we didn’t challenge the chart. We enjoyed a calm night with light winds.

No Name Harbor to Fort Lauderdale

Departing No Name Harbor, we headed to Fort Lauderdale sailing 12-plus mph dead downwind. I love long waterlines.

Since it was Friday, the ICW was a madhouse. (It’s even worse on weekends.) After transiting three bascule bridges (draw bridges), we made our anchorage in Sunrise Bay. The forecast called for a blowy few days, so Bistari needed a safe and secure spot to anchor after our good adventure.

John Simons


John Simons is a member of the Waukegan Sail & Power Squadron/20. He has his USCG Masters license 100 ton. In 2015 and 2016, John and his wife, Priscilla, cruised 6,500 miles while completing America’s Great Loop. You can read the blog of their Great Loop Adventure at captainfatherjohn.com. John is a yacht broker for Weber Yachts. Email him at John@Weberyachts.com.

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