We dropped sails and head north into the current. Both Don and Melora had been to Key West many times, but always by car. To head into the port on your own sailboat for the first time…well, let’s just say that the feeling that “YOU MADE IT, YOU OWN IT” just slightly covers it. Lots of people go to Key West. Most drive. Way too many come on cruise-ships. But to sail into Key West on your own boat. And to do it after sailing a couple thousand miles. Nobody, nobody can ever take that away from you.
We hailed the marina and they gave us our docking instructions. We tied up in a small wharf that would have it’s own interesting vagrancies. It would be our home for the next month, but it wasn’t some funky Key West aged dock full of woody characters. We took a berth at the Key West Hilton. But, as we would find, it would give us all the old Key West charm many times over, as we would make friends with schooner captains and crew and hit the town like few other have. Don would comment as he threw the dock lines off a year later as “the best month of the best year of his life.”

Our first of two slips.
Key West
While we paid through the nose for our slip at the Hilton, by comparison it was one of the best deals in Key West. Slips are paid for the day or for the month. By the day, while we cruised, it was common to pay between $1 and $2 a foot per night for transients. For us, that meant something between $34 and $70 a night. For a monthly transient (non-year) rate we paid anywhere between $5 a foot (Salt Pond) and $18 a foot. When we hit Key West the rates…um…changed a bit. But we saw it coming. For our stay at the Hilton we paid $60 a foot. Gladly. It’s a nutty price, but to us, it meant that we’d be paying the cheapest rate for real-estate in Key West over the course of the month. And Don had some great projects and got out some serious billing while we were here, so it was worth every dime.

A view from our future slip to our exiting slip.
For other cruising sailors, you either locked into a cheaper $40 a foot marina before they were all booked, got a mooring WAY early in the season or you anchored out. We didn’t want to spend a month worrying about the weather and dinghying ashore to walk the dog several times a day. No, our time in Key West was about resting, working (for Don) and having fun. We did all three in right order.
Our first bulkhead sucked, and was great. It sucked because the PWC (personal watercraft) rental was directly to our starboard. Everyday, actually about four times a day, people who had never operated a water craft (usually from the cruise ships) would rent these things and bumble about a few feet from our boat. It drove Don crazy. When one slammed into our boat he went to the Dockmaster and demanded a new slip. And we got it.

A cruiser’s view of the new Key West
The thing that was great about the slip was that two tall ships shared our wharf and a couple times a day their crew would hang out and walk around the slip and we began to make some good friends. By the time we moved from our “pinball palace” we had gotten to know the captains and crew of the tall ships and they would pave the way for us to have a grand time and grander memories in this wonderful town.
It didn’t take long for us to get into the grove here. We had, more or less, a “room” at the Hilton. We had full access. That meant the heated pool. The hot tub, and for Don … the executive office suite with broadband WiFi (still new in these days). We also had showers, fresh hotel towels and of course, limited access to the docks. It was paradise at the cost that most of our mortgages cost. Cheaper if you factored in the pool, hot-tub, electric and WATERFRONT ACCESS. Again, very likely the best deal in town. On top of this, if you wanted to have some fun, Duval Street was one block away.
But for us, this isn’t what made Key West special. While we enjoyed these, there would be two other things we had much more fun with. The Schooner Liberty and her sister ship the Clipper Liberty. Before we jumped to the other side of our concrete harbor, the crew of these two ships would become our close friends, and for our entire time in Key West our time would be spent hanging out with, having dinners with and generally partying with these folks.
But, let’s start at the…um…beginning. Makes sense. When Don and Melora came to the keys (separately) decades before Mallory Square was a different animal. In the 70’s it was a hodge-podge collection of street performers. Now it was a “rent the space of paved brick” in front of hotels with ice cream and t-shirt ground level shops. Very Odd. But the same cast of interesting locals could still be found in these rationed squares. And at sunset they all opened shop and it became the Key West Circus.

Savannah and Bounce learning the basics.
Since we’d show up every day, it didn’t take long for our crew to involve themselves on a first-name basis. Savannah, and then Ginny, would have fun with our closest show, Bounce and Ulla.

Ginny and Savannah would become the ‘pigeons’ and have fun with it.
It wasn’t all fun and games, of course. We didn’t have a car, so we locked up our bikes near the boat, and would use them to ride to the stores for provisions and would quickly find where the locals bought their food. Almost every night we’d fire up the grill to cook some fresh fish.
And there was work. Every morning Don would load up his laptop and to the hotel’s business center (the docks didn’t have WiFi yet) to work. This month would turn out to be a profitable one, with a dozen deadlines from key clients. The girls would come by a few times each day to check their e-mail and visit. In an odd contrast to the party atmosphere around him, Don would have one of the best single months of his career here.

Savannah and Uncle Jim, our own sunset.
But, if anything would earmark our time in Key West, it would be sunsets. At five, Don would leave the office and head back to the boat. We’d pour a drink and walk over (as slip-holders we had access to the cruise-ship wharf) to a great spot to watch the sunset. Behind us on the other side of the marina would be hundreds of people lined up to watch the sunset on Mallory square. And there would be about a dozen of us in our own space (our crew and the Liberty crew). As the month grew, so would the size of the sunset crew.

Front row seats.
We didn’t miss one. Not a single sunset. Some were just a fun way to end the day, but in other cases there would be magical moments that we’d all remember.

Jacob plays the violin. The ship’s carpenter would become a good friend.
On one of our sunsets, Jacob the Carpenter on the Libery brought out a violin and played during sunset He didn’t play well, but that was OK. Savannah listened for a while and asked to try. She had never played a violin before (and it was obvious that Jacob was struggling, he had just bought the violin days before). She picked up the instrument and played through the rest of the sunset, with all of us in amazement. It was a special moment and we all knew it.
He handed her his violin. He said “this belongs to you.” She still has it to this day.

One of the great KW sunsets. Every night had one.
The sunset cruise schedule would rotate between the Liberty crews and we’d have a full attendance at sunset each night. Twice through the course of the month we’d all see the fabled ‘green flash’ at sunset. It wasn’t hard to claim, on both nights there was absolute silence for a few seconds followed by somebody saying “did you see that.” Only twice, and each time, yes…we all saw it.

Our home for the next few weeks.
Our dockmaster, Dennis, moved us to a better slip, away from the clue-less tourists. We had made friends with our tall ship friends and had a great spot to spend the month on a nice floating dock. We threw out our bumpters and tied up tight. One interesting angle about this dock was that our neighboring boat would account for how we slept through the night. The Hilton dock, at the very end of the wharf, was also the home of one of many visiting cruise ships. They would come in the middle of the night. If we had a southern swell, it would stop. Very nice. We liked having cruise ships acting as a breakwater. In the morning a couple thousand people would walk down the ‘public’ wharf and it was always a great show.

Rugg Dog, the Key West Comfort Dog
Rugg liked it too. He was the Key West companion dog. On our walks everyone that owned a Golden would see Rugg and pet him and tell us about their dog at home. Given that a single cruise ship had 2500 people, Rugg was never without attention. Ever. Really. If this dog had a tip cup (common in KW) he would have made more than Don.

Our fellow cruisers played for us, and made another perfect night.
Memorable nights piled up. You almost felt sorry for someone in Ithica who worked the night shift at the Pump and Go. One of our favorites was a small sailboat that pulled up for a few nights. They were here for some kind of music fest, but for us, at sunset, they pulled out their violin and guitar and played on one of our sunsets. Again, the tourists were at bay behind fences, and we sat on our wharf with the crews of the Liberty and while they played, we watched the sunset. Few people will ever have an experience like this, and we enjoyed it almost every night. The same stage, different players. As much as we’d like to yearn for the ‘Key West’ of the past, we found a little nook that offered something that wasn’t of the past, yet wasn’t commercialized. It was (and hopefully for others still is) a little snapshot of Key West as is and will continue to be. Small little undefined pockets of individuality that hope to be unique, but want to be discovered. Key West is the the original reality show without a camera.
Don’t tell anyone, or “KEY WEST” will be the next reality show.

Key West Jim. The best seat in the house.
Don’s brother-in-law Jim came down for a visit for a week, and we think he had a good time. It didn’t take long for him to get into the groove of the routine. During the day he’d do the tourist thing, and at night we’d cook dinner and watch the sunset.

Our new dock, we slept better and it was a shorter walk to the showers.
Directly off our dock is the “Truman Complex”, in ‘the day’, they called this the Key West Whitehouse. For a long time it belong to the Navy. Eventually it became public and the complex was sold. The area is still rich in history and the public is still allowed to walk the streets, even if the houses are now private. The couple we met in Savannah rented a loft in the Truman complex every year, and shortly after we arrived, we met with them again. Their grandchildren visited every winter, and were the same age as our kids. For a week the kids would hang out and explore the island.

The Key West Follies…the best of all of us.
While our goal of setting sail before the girls hit high-school age was noble, there was one little detail cruising sailor who should follow our suit should note.
Braces
In the middle school years we hit the same road bump that most parents face. Braces. Being good parents we signed our kids up for the best care. Our doc did the his duty, x-rays, fitting, pre-exams and all of that. While I did my best to explain our plans to our Ortho, he pretty much set out HIS plan for any kid.

Savannah shows her teeth.
For the first year we did just fine, but after that we head out. Ortho visits every six months would be hard for most cruising sailors, but we were cruising the south. Our arch allowed us to get back to the office on time. Sure, it was a long drive, but we still did it. When we hit the Keys, however, and knew we’d be living in Florida (more on that) we finally signed off of our doc and found one in central Florida. No free ride, with a couple years done…we were going to start again from (financially) from scratch. Again, such is life.

The gathering of the crews, a daily event.
Our days would be full of small adventures on the island. Shopping at the local stores (not the ones the ones the tourists would go to) and finding the best deals. Don would work in the office suite at the Hilton and the girls would continue to explore and cover the ship’s needs. We’d have fresh fish and produce every night. It didn’t take long to figure out where the pickup with the ‘good stuff’ or which store had a fresh shipment of produce was.

Jacob and Don, another sunset
The girls continued their school. Don went to work every day. The tall ships head out every day. But in the evening the Calypso’s grill would fire up. Dinner would be served (usually local fish) and when the sun began to set, we’d all meet again at the wharf. Every night.

Life on the island. Note the Liberty Schooner to the left and the cruise ship on the wharf.
Don and Melora celebrated their 17th anniversary in Key West, Don bought Melora a necklace made by a local craftswoman.

Our home in Key West. Not the hammock.

It’s a dog’s life in Key West
Of the many highlights of our visit was our sunset sail with the crew of the Liberty Schooner. The captain invited us aboard for a sail and we took him up on it. It wasn’t too crowded of a night and we had a great time. The crew, who by now knew our crew, let the girls help run the ship. They hauled the lines and took the helm. One by one we invited the crew of the Liberty over to our boat for dinner and got to know each one, and their story of how the ended up here. Great kids all. To this day we still stay in touch with some of the crew of the Liberty.

Ginny hauls a halyard on the Liberty

Savannah raises the sail.

Ginny runs the helm of a 32 ton schooner
Another great day on the water. We’d hang out with the crew, hit the bars with them (they knew all the good spots) and enjoy their company during our time on the island. They were young, but they were also hand-picked. They knew their jobs and weren’t just wanna-bees picked off the island. They were experienced sailors from around the country and, while incredibly nutty off the job, very focused on the job. The girls would crew on the boat during our stay.
One of Don’s favorite moments was the night we all decided to watch Captain Ron in the Schooner. Don brought over the DVD and we all kicked back to watch the flick.
To understand this, you have to understand that the movie “Captain Ron” is the cruiser’s “Caseblanca.” It’s a hugely quote-able movie and it takes a cruising sailor to really love the movie. As a tradition, Don watches it once a year. So to sit back with a few drinks (the only way to watch the movie) and shout out the lines in the crew deck of a schooner docked in Key West…well it just was about the best screening of Captain Ron that may have ever occured.

Ginny sounding the horn at sunset.
It’s a tradition for sailors in the southern waters to blow a conch horn at sunset. So we’d bring our own, or borrow one from the Liberty and sound off at sunset.
Food
We made the early mistake of buying a few provisions near Duval Street. The famous road was just a block away from us, and EVERYTHING was expensive. It didn’t take long for us to learn where the locals shopped. Our bikes were instrumental in our daily foraging. The local fish shop was great, and a source of many of our meals. But we also found the ‘guy with fresh fish on the back of his truck’ as well as the Wal-Mart a couple miles away. Within a short period of time we knew every street on the island and how best to hunt down what we needed. Since it was nearby, and kind of fun, we generally got on our bikes and went out to get food for the next dinner. The home-run was when the Key West firecracker shrimp were running. It’d be hard to find better food.

Another great sunset. The crew of the Liberty

The Calyspo Crew and Liberty Crew in Ginny’s berth.
One of the perks of making friends with the crew of the Liberty Clipper and Schooner was getting free access to some of the local tourist attractions. One of the skipper’s wives worked for one of the primary tourist companies, and he presented us with tickets to some of the local attractions. One of those was the Wrecker Tower. It’s actually pretty cool and worth the price of regular admission.

A view from the tower.

Mallory Square, near our boat.
The Green Flash
There’s this fabled moment about a sunset in the right conditions. Just as the sun hit the horizon, on rare occasions, there would be a subtle green flash. Up to this point in our life we had never seen it. Key west and specifically Mallory Square, was known for this event. As noted, we watched the sunset every night. Not for green flashes, but just because we loved the sunsets. One night while watching, just at the moment of sunset, the usual chatter stopped…and someone said “did you see that.” And we all quickly jumped in about the green flash we just saw. This happened twice during our stay.

Another in a series of sunsets.
The Party
We were planning to head out at the end of the month. The girls all had ortho and doctor appointments in Cocoa Beach, so they’d drive north and Don would take the boat up the coast. When the Liberty crew heard we’d be heading out soon, they planned a party aboard the Liberty Clipper, the flagship. Hearing that, we rode our bikes up to Wal-Mart and bought 20 good quality T-shirts and a box of ink-jet transfer paper. For a day we made “Calypso” T-shirts, borrowing an iron from the Hotel (Dennis had the hotel bring us an iron…what a great dockmaster).

Rugg Parties down
One of our crew members that was always welcome aboard either of the Liberty ships was Rugg. If there wasn’t a paying customer aboard, the Liberty crew loved having Rugg come aboard and hang out. I think some of them missed the simple things at home, like having a dog to play with. They’d never admit it. They were young and in the middle of one of the best times of their lives (even if they didn’t know it). Rugg was the ships dog for that month and they loved him. So it was only natural on the night of the party, he had free run of the ship.

What a great place for a party!
And then there was the great pig-foot debate. The writer will pause here for a moment to remember what the bet was, but one of the crew members said he’d eat a certain number to win. And, I think he did.

Ahh, the pig-foot challenge

Savannah and the crew, great ladies

Foley crew at the helm

Good food, great night.

And a great setting.

And not a single person was thrown overboard that night.
We absolutely knew we were experiencing a very unique time with this crew. We’d hear from a couple of the crew over time, and they would feel the same.
Wrapping up the month
There were things to do before heading out. We needed to provision the boat for at least a week, fuel up and pump out. We ran the boat over to the other side of the island that had fuel and waste facilities. On the way we cruised by the Liberty Schooner about to head out for the day. Savannah was crewing that day, so we took some photos and head to the dock.

Liberty preparing to head out for the day.

The Libetry Clipper and the Liberty Schooner (girls aboard, just docking from a cruise)

The last sunset.
We had retrieved the van from Don’s brothers and the girls head up A1A to Cocoa Beach. Don cast off the lines and picked up the radio and hailed “Sailing vessel Calypso heading out of the Hilton harbor, all concerned or conflicting traffic we’re standing by on 16.” The crew of the Liberty Clipper stood on rail and gave a salute and the Calypso head out through the harbor entrance and out into the sea. On our way the Calypso crossed paths with the Liberty Schooner and gave another hail.

Liberty Schooner on the last pass. Fairwinds.
With that, the Calypso rounded the island and head east. For this run Don spent most of the time in the ocean. He’d set the autopilot, keep watch, read a couple books and tuck in each evening just before sunset to the local port. Because he was sailing solo, he never left the cockpit unless he needed to. When he did, he wore auto-inflating safety gear.
Don’s waypoints.
Key West, day one.
Newfound Harbor (Big Pine Key)
Channel Key (anchored in the lee of a small island on the inside)
Tarpon Basin (Key Largo, dock now closed)
Barne’s Sound (anchored off a causeway)
No Name Harbor (two days, deadline delay) out to the Atlantic.
Lake Boca Raton (three days, broken draw bridge, bad weather) out to the Atlantic. Here he provisioned in a driving rain thanks to another cruiser from his favorite internet forum. The bridge was waiting on a part, and it could take a few days, and we had 20-30 knot squalls from the south. Once the winds dropped he left through the inlet (testing the waters for other cruisers tired of waiting for the bridge repair) and reported shoal depths every 30 seconds to the dozen sailors with deeper drafts.
Lake Worth one night, then out to the Atlantic.
Fort Pierce (anchored north of the inlet) the rest on the ICW.
Grant (anchored off the islands)
Merrit Island…home base.
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Settling Down
We rented a place in Ocean Woods until the property we bought (and leased) in Harbor Heights became available. Both were next to each other, so we often walked by to check things out. Finally, we moved into our house and within a few days the girls began the fall term at Cocoa Beach Jr/Sr High School. The timing was perfect, and we began the next phase of our life.
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We’d sail the Calypso in the local waters through 2007, but she was a cruising boat and not a day sailor. In 2007 we decided to sell her and to get a boat for the local waters. The good ship Calypso had been our home for a year and had given us a lifetime of memories. She is now somewhere in Canada with her new owner. We wish her, and her new crew, the best.
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With that, it’s time to edit the first draft of the last nine pages. Until this note is removed, this is all being edited. Please remember, until this note is gone, everything here is the first draft.