To say I have a lot of catching up to do would be an understatement… I’m going back to early December for this post! I’ll try and get caught up and into 2025 soon!

In early December I was invited to join some members of ourr sales team on a trip to Key West for a team building exercise - a chance to get to know the team better and spend some quality time in the sun. It was coupled with a trip to meet with a customer and a partner, so it was an effect trip, and one that I will try and remember the details on almost 2 months after-the-fact.

A rough map of the drive from Orlando to Jacksonville

My trip started off with the very long flight from Vancouver to Orlando. It’s one of the longest trip you can do inside North America, at least from Vancouver. It makes for a beast of a day. I flew to Orlando on Wednesday, getting in fairly late in the evening. I was meeting Dan, the head of our Eastern Sales Team, and our host for Key West the next morning for our customer visits.

Thursday we met with Seminole County, one of our long standing customers, as well as one of our partners, Modern Networks. We had a good customer meeting, then met Robert from Modern Networks to check out their new offices. It’s a great looking facility, and we went for lunch afterwards, rounding out our day. Dan lives in Jacksonville, sp we had a fairly long drive back on Thursday afternoon.

Dan was kind enough to play tour guide on the way back up to Jacksonville, and so rather than taking the highway the full distance (which would have been about 2 hours), we took the more scencic route up the coast, stopping in a number of pplaces along the way. This turned out drive into more like four or five hours, but it was totally worth it.

We were meeting one of the other members of our crew for the trip on Jacksonville - Andrew, one of our partners from GetWireless was flying into Jacksonville later that evening to meet up with us for the drive to Key West on Saturday.

The highway part of the trip was pretty uneventful, but the scenery got spectacular once we made our way east, out to the coast.

One of the nicest stops was in St. Augustine. I did not take enough photos of this beautiful little town, so rich in hostory. It’s one of the oldest settlements in the US.

Castillo de San Marcos National Monument

Founded in 1565 by Spanish colonists, it is the oldest continuously inhabited European-established settlement in what is now the contiguous United States. Gotta love the huge trees and all the Spanish moss.

The highway crisscrosses the Intracoastal Waterway (ICW), a river that parallels the coast. The ICW is a 4,800 km inland waterway along the Atlantic and Gulf of Mexico coasts, running from Massachusetts southward along the Atlantic Seaboard and around the southern tip of Florida, then following the Gulf Coast to Brownsville, Texas. Some sections of the waterway consist of natural inlets, saltwater rivers, bays, and sounds, while others are artificial canals. It provides a navigable route along its length without many of the hazards of travel on the open sea.

Some typical views along the drive.

The PGA Tour Headquarters.

It was later afternoon as we arrived in the outskirts of Jacksonville. Dan took me to one of his favorite spots, a bar/restaurant along the Intracoastal Waterway. It was happy hour, so we had a drink and some oysters, and enjoyed the sun setting on our day.

The oysters were pretty good!

Thursday night, agfter Andrew arrived, we headed downtown into Jaksonville. Dan drove us around a bit and showed us the town. The older part was nicer than I imagined. The owner of the Jacksonville Jaguars (NFL team) owns a 440’ yacht, which was docked right down in the city center. We did a drive by - the thing was huge. We ended up at a steak house that was housed in a restored bank building, which was spectacular. None of us had huge appetites, so we shared some appies and drinks, and thn called it a night. I might need to go back.

Friday, I worked from the hotel in the morning getting some things done and catching up on a bunch of work tasks. For lunch, we drobe out to this cool little restaurant, on a very different stetch of the Intracoastal Waterway. You had to know the place was there to find it - it would have been a great place to bury the bodies if Dan was looking to kill us off! But instead we had a nice lunch, even if we had to sit inside as it was damn cold out! Not what I was expecting for Florida, even in December!

A couple of views out over the Intracoastal Waterway from the patio of the restaurant.

After lunch, Dan continued is tour guide duties. He took us out to Amelia Island and we parked in the old downtown and did a bit of a walk around. The goal was The Palace Saloon - the oldest bar in Florida! “Amelia Island's The Palace Saloon is the oldest bar in Florida and was the last American tavern to close during Prohibition. It survived that dry era as an ice cream parlor. Once a favorite haunt of the Carnegies, the Rockefellers and other socialites, The Palace Saloon is still operating today.”

After stopping for a drink or two, we headed back out and Dan took us back to the coast. We found a stretch of beach that we could drive on! I got out to have a look around, but the two of them though it was too cold (and Andrew’s from Minnesota…).

We continued on, Dan showing us some of the nice sites around Jacksonville. We even took a small ferry across the everpresent Intracoastal Waterway, just for something different. It was getting close to sunset, and as we were waiting in a ferry line, I was pleased to see a whole flock of pelicans on the ferry terminal.

We had an amazing sunset as we waited on the ferry.

The pelicans were squawking and fighting with each other. I think they were mostly juveniles, still being fed by their parents.

While I was enamored with the pelicans, Dan was clearly over them. I guess when you see them all the time - but they were cool to me!

Dan’s wife, Sam, is Thai, and is part of a fairly large Thai community in the area. One of her friends has a restuarant, and that’s where we went for dinner on Friday night. It was a fairly large group and I got to meet a lot of new people. The food was amazing - a mixture of Thai and Laos cuisine, and I was sweating like crazy right for the start. But it was really tasty, all of it, and we were treated like family. It was a really great night out.

We also stocked up on some supplies (read: burbon) for the rest of the trip, in preparation for our long drive on Saturday.

Saturday we were up early, as we had a huge drive ahead of us. We were basically driving the full length of Florida, from Jacksonville down to Key West. As it was a Saturday morning, we were hoping the traffic would not be too bad, and for the most part we had smooth sailing.

Dan does this drive frequently - he has a time share in Key West, where we were staying and it seemed that he was happy to drive the full distance. Dan is a retired police officer and former Police Chief, so I imagine long hours behind the wheel do not phase him.

The majority of the drive was uneventful - lots of long stretches of boring highway. But the company was good and we chatted and watched the miles roll by.

It was a beautiful day as we headed out and onto the Overseas Highway.

While most of the drive was fairly broing, I was excited for the final 100-odd mile stretch - the Overseas Highway. I’ve been wanting to do this drive for a long time, and it di live up to expectations. From our friends at Wikipedia:

“The Overseas Highway is a 113-mile (181.9 km) highway carrying U.S. Route 1 (US 1) through the Florida Keys to Key West. Large parts of it were built on the former right-of-way of the Overseas Railroad, the Key West Extension of the Florida East Coast Railway. Completed in 1912, the Overseas Railroad was heavily damaged and partially destroyed in the 1935 Labor Day hurricane. The Florida East Coast Railway was financially unable to rebuild the destroyed sections, so the roadbed and remaining bridges were sold to the state of Florida for $640,000.

Since the 1950s, the Overseas Highway has been refurbished into a main coastal highway between the cities of Miami and Key West, offering travelers an exotic roadway through a tropical savanna environment and access to the largest area of coral reefs on the U.S. mainland. Many exotic animals such as the American alligator, American crocodile and Key deer inhabit the tropical islands of the Florida Keys.”

I took some screen shots as we made our way along the highway.

One of the survivng sections of the old railway.

A ypical view from the passanger seat - spectacular!

Getting closer to Key West.

One of the typical views along thwe way, on one of the many small islands that the highway connects.

Some of the mangroves (I think)

We finally made it to Key West!

As mentioned Dan has access to a timeshare at a Hilton property, near the airport. Well actually right next to th airport, and it was close enough that you could walk! Which is what the final member of our party had done. Don had arrived by plane shortly before we arrived, and had walked over to the hotel.

Our chariott. One of Key West’s quirks (charms) is that everyone drive around in golf carts. On the main city streets. This gyu got us around the whole trip. So fun!

After getting settled, Dan took us on tour around downtown Key West. On our cool golf cart. Key West was pretty much what I imagined - I see it as a cross between what Lahania was, with New Orleans. Funky downtown with lots of bars and live music, but with it;s very own sense of style. I love the architecture, and there are lots of cool things to see!

A pretty typical view of downtown Key West.

The original Sloppy Joe’s was a hangout of Hemmingway. This is not the original - it was a few blocks over and was renamed.

One of the cool parts of the trip was that we were close enough to Christmas that the town was decked out. And boy do they like to decorate for Christmas!

Dan, Don and I

Golf carting around Key West.

The architecture is just so perfect. And in this case looking very tropical.

There are lots of very old buildings that have survived the hurricanes and other events.

The days in Key West followed an enjoyable pattern. Sleeping in a bit late, getting some work done in the mornings, then heading out for brunch or lunch. Afternoons involved catching up on work or enjoyng some sunshine on the deck. A late afternoon drink and then off inot town for dinner, followed by finding a cool bar to watch live music or chill with a drink. It was good times.

Hemmingway’s house. It’s a museum now, but I did not go in.

There is a cool, old lighthouse right in downtown.

One of our brunch spots. It was delicious.

Me, Dan, Andrew and Don.

An amazing old building, now sadly a Walgreens.

This was very typical of the amount of decorations that were up, all across town.

The Green Parrot, where we watched some live music one night.

As the sign says - you can’t get any further south.

The beach across and up the road from the hotel. Sadly enough, I did not get in the ocean once!

Our lunch spot one day.

I had to try a slice of their Key Lime Pie - it was delicious!

The view from our seats at lunch.

One of the fun things Dan booked for us was a sunset sushi cruise. Basically a sunset cruise, with sushi! How can you go wrong? Here’[s the map of the cruise.

We had a nice cruise out around Key West.

On Monday night, we went to this cool little hole-in-the-wall bar for cheap martinis!

They go all-out with the holiday decorations!

Even palm trees can be Christmasy

Our last morning, and arguably the best breakfast of the lot!

Leaving the write up so late, I probably have not done this trip justice. It was a welcome break from Vancouver winter, getting a touch of warmth and sunshine. Dan was an amazing, graciious host and tour guide and I feel like we got a bit of the locals view f the place. With the holiday season in full effect, it was fun to see this side of Key West. I hope I get invited back next year!