The Trip – Part 1 of 2: Floridays

“Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bow lines. Sail away from the safe harbor.” – Mark Twain

One beautiful Miami morning in the summer of 2003, I awoke in the forward berth of our newly purchased Cheoy Lee ketch, my body wedged in between the hull side and my husband as the boat leaned to starboard. The previous day, we’d departed our mooring, bound for the Gulf of Mexico. We navigated the channel from marker to marker and ran aground very near a marker labeled “danger.” Clearly, we were in need of better binoculars. Undaunted, we waited for high tide, floated off the sandbar, and turned around. We made it back to our mooring, but in the dark and the rain I was unable to grab it. So I grabbed the tiller instead and navigated us to our overnight resting place on the sandbar in the lee of a little mangrove island that protected Dinner Key marina. I had been heading for the fuel dock.

The mooring field at Dinner Key marina, Miami, FL, 2022.

In the morning, Lee, my husband and captain, went above deck to survey the situation. From the shore of the island, a voice called out “It looks like you’re aground.” That would explain the odd lean to the berth. “Get off and push.” Pushing didn’t do much for our full keel boat, so once again we waited for the tide to rise then limped back to our mooring to regroup and revise our float plan. Within a few days, our friend who’d signed on for the trip had parted our company, and “Go-John,” for whom we’d provided the entertainment that morning on the island, had helped us find a captain to take us around Florida to our destination, Anna Maria Island.

What I remember of the rest of that trip is exceedingly pleasant: gliding through Biscayne Bay thanks to Captain Winston’s local knowledge, pausing for a snorkel at Hens & Chickens, pushing on through the keys to the Seven Mile Bridge at Marathon, where we were rewarded with a green chili cheeseburger at Burdines. Even the passage up the west coast was magical. I’d never been out of sight of land on a boat of any size, and admittedly I was afraid to sail at night, but the Gulf breezes and our Cheoy Lee carried us peacefully north. We put in at Venice and enjoyed dinner at the Crow’s Nest. The next day, we docked on Anna Maria Island, our new home.

S/V Westward, minus a mast, Beaufort, NC, circa 2006

Years later, we awoke as Island Packet owners for the first time on a balmy Sunday in June, 2021. The day before, we’d met Nick from Island Packet for a whirlwind tour of our new boat. That pleasant morning, our old percolator, retained from the days aboard the Cheoy Lee, was still in service, and Lee made coffee while I proceeded to unpack. We made plans for the next day. In fact, we had hatched many plans. Arrive in St. Pete on Saturday, and depart on Wednesday. Pick up a friend in Key West on Friday. Splash a couple of days in the clear blue water then run the outside up to Beaufort, NC.

Our dinghy on her launch day.

Monday, at least, went as planned. We delivered donuts and coffee to the Island Packet Factory up in Largo and met up with Darrell, owner and President of the company who’d built our dream boat. We picked up our dinghy, a 10’3” rigid hull inflatable sourced at the 11th hour by AI Boats of St Pete. She launched complete with a 20 horsepower outboard, apparently the last one available in all of Florida.

The rest of the day’s agenda: sailing with Darrell, followed by docking practice. I learned to work the roller furlings (new to me). Darrell had to remind me twice that I didn’t need to hold the line coming off of the self-tailing winch (also new to me). Returning to the marina, Lee expertly parallel parked the boat on the first try, and Darrell departed. I guess he didn’t think we needed any more “docking practice.” All in all, it was a great first sail. At the end of the day, our short punch list stood at five items.

Sailing with Darrell Allen of Island Packet Yachts.

Then, on Tuesday morning, Harv arrived.

Neil Harvey is without a doubt the most accomplished sailor I have met in my life. In the online archives of various sailing rags, he’s described as a “world famous Australian ocean racer” (1) and the “grand old man of bareboat racing.” (2) He may favor you with an anecdote about his time on the Australian America’s Cup Team, or a tale of a yacht delivery spanning continents. He’s known to many from his years at Harken Yacht Equipment, which is why, when I noticed that my Gill sailing gloves had developed a hole in the palm, he turned my hand over and remarked, “that’s because you bought the wrong brand.” Apparently, it didn’t take Darrell at Island Packet long to talk him out of complete retirement, and he now teaches new Island Packet owners how to sail their boat. Fitting, as he worked with the Island Packet team to design the rig.

Harv watches Lee at the helm.

Sailing with Harv was a good bit more spirited than Monday’s outing, and not just because we had a bit more wind. The world famous ocean racer set us up on a point of sail and at a heel angle that frankly, I was not prepared to endure. Flashing back to our days on the Cheoy Lee (also a full keel boat): the first time she started to to heel over, I instinctively jumped to the windward (high) side. At the time, my very new husband couldn’t help but laugh. Eighteen years later, I haven’t shaken that instinct. I’ve turtled far too many a tech dinghy in the relative calm on the river to ever want to do it on a “big” boat at sea, or even in the bay.

Harv eventually assented to my fears and let us sail the boat a little more flat, which lost us about a knot and a half of speed. Ultimately, he had our best interests at heart. In the very short time we’d allotted ourselves for “learning,” he taught us as much as he could about how to get the best performance out of our boat and her sails. He gave us tips for maintaining the boat’s rigging and our own safety underway. He took us to the riggers to commission a jack line for the cockpit. He secured me an extra winch handle, because as Nick had been quick to point out, we ordered our boat with “no electric winches.” We enjoyed anchoring practice and Harv’s favorite local sandwich shop. We even enjoyed a bit of our finest John Watling’s rum from the Bahamas, because when you have a legend aboard, you break out the best.

A beautiful sail under main and reacher.
Harv instructs us on how to set the reacher.

As we settled into life aboard our new sailboat, a few other issues arose. The air conditioner made a funny noise at night. The butter in the fridge went soft. Wednesday saw the first major “sailboat surgery” aboard Siar, as Nick and his team removed and replaced the fridge / freezer unit. Thursday we got in another sail with Harv, albeit with no wind. We did get to stretch out the reacher, our big, light air headsail. Practice tacking? No. Post pretty pictures on Instagram? Yes.

Friday was the final frenzied punch list day. Having changed our plans to delay the boat’s departure from St. Pete, our friend was able to change his flight arrival from Key West to Tampa. In Thursday evening’s rain storms, we had discovered a couple of leaks in the aft cabin. Their repair on Friday involved disassembling and reassembling of one of our cockpit winches. The day before our rescheduled departure, Nick took a spray to the face in order to find our leak, tweaked and repaired everything possible and necessary, and did it all with a vacuum in his left hand. I’m not sure the boat has ever been so clean since.

Goodbye, old fridge.
The guts of a Harken winch.

Our friend arrived in time to venture out into downtown St. Pete for dinner. It was the second time we’d been off the boat in a week. Back aboard Siar, tired but exhilarated for our upcoming adventure, we decided to do the champagne dedication. We’d asked Harv about the tradition of breaking a bottle over the bow. In his wisdom, he’d told us we’d be better off pouring a bit on her and enjoying the rest, which is exactly what we did. “May all who sail aboard her…”

Siar dockside, Safe Harbor marina, St. Petersburg, FL, 2021

The last Saturday in June, we awoke, had our coffee, and made the boat ready to get underway. We mounted the GoPro on the stern rail to film our departure, and untied Siar’s docklines. I received an encouraging text from Harv – the quote above from Mr. Twain. We’d chosen to make day one of the trip an “in-and-out” to build up our confidence. On day two, we’d head for the keys. By our calculations, after five and a half hours of sailing, we’d be docked in Venice well before the standard afternoon thunderstorms. Everyone thought we were heading into a good weather window. Everyone, that is, except the National Weather Service.

Read Part 2 of 2: Red Sky



(1) Neil Harvey in Cruising World Magazine, 2018

(2) Neil Harvey in Sail Magazine, 2017

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