When we visited Bob’s cousin Joyce and her beau Jim in January, he asked if we’d be interested in sailing to Key West with them the first week of February. Sailing in the aqua-blue waters off southern Florida? That’s an offer we couldn’t refuse!

We found an excellent boarding facility for Tessa, a place called Dog Dude Ranch in Miami where they adapted a stable into a homey boarding facility. Stalls have been converted so there are 3 “bedrooms” in each. The center aisle of the former stable has plants and chairs. There’s a grooming room and kitchen. Outside there are four very large dog runs. Dogs are evaluated and put into playgroups with dogs based on personality, size, age and activity level so that they play well together, and every dog gets three one-hour outside play sessions every day. They also get a daily head-to-toe examination to make sure they remain in good health. Once we felt comfortable that Tessa would be well cared for, we were ready to set sail!

On February 1, we headed to Miami, where Jim’s catamaran is docked. We were joined by Joyce’s brother, John (who is also Bob’s godson), his 7-year-old son Lyon, and friends of theirs, Elaine and Brian. The plan was to set out for the Keys on Monday, February 3. What would the eight of us do to pass the time on February 2 in Miami? Enjoy a Super Bowl party, of course!

Miami hosted the Super Bowl this year, so there were lots of things going on. We considered driving over to the stadium parking lot to tailgate with the crowd, but parking would have cost way too much, and we would have had to leave when the game started. Half of our group stayed near the boat and just hung out while the other half took public transportation to the stadium to visit the vendors. Brian and Elaine stayed at the stadium until game time, and they came back with the greatest story ever!

Scalping tickets is illegal in Florida, but Brian was approached by a guy who said he had two tickets to sell. They talked a bit, and the guy wanted to know how much money Brian was willing to pay. Of course, Brian wasn’t going to answer that, because saying that you’d be willing to pay, say, $1,000 for tickets is like saying, “I have $1,000 in my pocket.” Brian and Elaine parted ways with that guy and walked on. They walked around and visited vendors, sat in their folding chairs enjoying the party atmosphere, picked up their chairs and walked some more. Suddenly, they heard a guy screaming, saw a man running, and realized that the running man was the same man who had tried to sell them tickets. He had “sold” his tickets to the man who was screaming, took the guy’s money and ran … the tickets were fake! Feeling personally involved, since he had also encountered the guy, Brian wanted to stop him. Elaine agreed: “Go get him, Brian!” As Brian took off after the guy, Elaine yelled, “DROP THE CHAIRS, BRIAN!! DROP THE CHAIRS!” (This was the repeated refrain of the weekend … “Drop the chairs!”) Brian got the guy! Tackled him and, with the help of others, held him until the cops caught up to them! Brian was a hero!! What a story to take back home! We were so proud of him, we couldn’t believe the situation wasn’t caught on film and reported on the nightly news!!!

We attended a Super Bowl viewing party in an outdoor shopping area just a short walk from the dock called Brickell City Center where a large-screen TV had been set up, a DJ played in advance, and two bars served beverages and food. It was a lot of fun and great people watching.

On Monday morning, we set off for Key West on the Anatolya, a 38’ catamaran with 4 cabins, two bathrooms, kitchen and indoor and outdoor sitting areas. It was a gorgeous, sunny day and as we watched the Miami skyline recede, I was reminded of the opening of The Jackie Gleason Show in the 1960’s — “From Miami Beach!” It seemed like such an exotic and faraway place 50-some years ago.

When I finally turned from snapping pictures of the skyline, I saw the strangest thing … houses on stilts sticking up in the middle of this vast amount of water. Jim took us by the buildings, known as “Stiltsville.” Here is what I learned from the National Park Service website:

“Seeming to float above Biscayne Bay’s shallow seagrass beds, Stiltsville has a colorful history that dates back to the 1930s, when “Crawfish Eddie Walker” built the first shack on stilts above the water. Over the years more buildings were constructed, and the area took on an aura of mystery. Accessible only by water, the area was the place to see and be seen when visiting the winter resorts on nearby Miami Beach. Stories of illegal alcohol and gambling led to several police raids on the Bikini Club and Quarterdeck Club. At its peak in 1960, there were 27 structures on the flats, but hurricanes, fires and the ravages of being in such an exposed place made every building relatively short-lived. In 1985, the bottom land on which the stilt structures sit was deeded by the State of Florida to the Federal Government as part of Biscayne National Park. Hurricane Andrew in 1992 left only seven buildings standing.”

Only about 30 minutes away from the dock, and we were already seeing something fascinating!

We traveled 26 hours straight to arrive at Key West the next day … yes, we traveled through the night! The guys took turns at the helm in 2-4 hour shifts to keep watch and make sure we stayed on course (the route was run by GPS but needed adjusting every so often). During the night, the wind intensity picked up and so did the sea. Only a couple of us got seasick, thought … yes, I was one. I am certain it was because of the darkness combined with the rocking of the boat, because during the day I had no issues. Thankfully, the next afternoon, we arrived in Key West.

A brief history of the Keys taken from a Florida tourism website:

“Not long after Christopher Columbus reached the New World in 1492, adventurer Ponce de Leon and set sail toward Florida in search of the elusive Fountain of Youth. They never found the Fountain but they did find the Florida Keys. The day was Sunday, May 15, 1513.

“There is no record that anyone from their ship came ashore and for hundreds of years, the island chain was left mostly to the pirates. Eventually, the pirates were chased away by a fledgling U.S. Navy pirate fleet established here in 1822. Settlers followed while the native Indian population died out. The early settlers set up groves of Key limes, tamarind, breadfruit and pineapple. Other settlers in Key West and in Islamorada became wreckers who salvaged goods from ships that foundered on the nearby reefs. Key West became the wealthiest city in the United States.

“All this, in turn, died out, and in the Great Depression the Keys seemed to face a bleak future. The city of Key West went bankrupt. It was then, with federal aid, that Keys officials decided their islands still had something to offer: sea, sun and a good year-round climate. Today, more than three million visitors arrive each year. For most, the Florida Keys are the closest thing they will ever find to the fountain of youth.”

Key West is now an eccentric, Bohemian place with chickens running around, roosters crowing, plenty of open-air bars and lots of weathered-looking seafaring people. It’s like being on a Caribbean island … well, heck, it is a tropical island only 85 nautical miles from Havana, Cuba. We visited Ernest Hemingway’s home (and met descendants of his famous cats), his favorite bar (now called Captain Tony’s, formerly called Sloppy Joe’s) where bar stools are painted with the names of famous patrons, enjoyed good local music and just walked and took in the quirkiness that is Key West.

After a couple of days, we set sail again, this time on the bay side instead of the ocean side; calmer water meant less seasickness. We docked at Marathon Key, which is much quieter than Key West, and enjoyed a nice dinner. The following morning, we sailed on to Key Largo and Gilbert’s marina and tiki bar. There was a good dance band playing there and a special performance by magician Michael Trixx, which was quite a surprise because I remembered seeing him on America’s Got Talent. He made birds appear and disappear out of nowhere, swallowed fire and pulled yards and yards of scarves from his mouth. Our table was situated sort of behind him, so we were really impressed after his performance because none of us had been able to see any indication of how he did any of it! It was pretty amazing.

It was a totally unexpected adventure, thanks to Jim and Joyce, something we never even thought to put on any “bucket list.” Bob learned a lot about sailing, I learned a lot about seasickness (LOL) and we all learned about the Keys and Miami. We cannot thank Jim enough for inviting us!