So, we had an amazing time in Key West. We were up in Pennsylvania and there were no loads, I mean no loads available heading South. Normally we would just follow the money and head somewhere else but this was vacation on the line. So we just ran empty to Chattanooga and found a load from there to South Florida. Rates out of Florida looked amazing and that almost never happens. Usually if we book a load to Florida we demand a round trip rate because there is no freight out of South Florida. What we have been seeing, however, is a huge shortage of trucks throughout the South and the West Coast. After delivering we drove to the Flying J in Fort Pierce FL and parked the truck and Bandit (Jim) drove the 60 miles North to pick us up. We went out for a nice dinner with Sandi and Bandit and headed out for Key West in the morning. It is about a 4 1/2 hour drive from their house to Mile Marker Zero on Hwy A1A. Anne had never been to the Key’s so she was in for a treat.
We stopped at The Island Grill, one of my favorite little restaurants in Islamorada on Windley Key to start our vacation.
Then we headed out for Key West. The drive, if you have never done it, is stunning but long. We got into Key West and headed straight to our hotel, The Paradise Inn. Although we were a couple of hours early they had our room ready so we checked in and hit the town. I picked this little boutique hotel as it looked awesome and was in walking distance to all of the main spots off Duval Street. It was a VERY touristy kind of day. We stopped first at Irish Kevin’s, then on to Sloppy Joe’s and Capt Tony’s with a stop at The Hogs Breath, we then hit happy hour at Kelly’s (which was awesome).
We also stopped by the Curry Mansion Inn where Bandit and Sandi got married 15 years ago. Pretty cool.
From there, things got a little fuzzy and what really happened is a bit in dispute. I do know we ran into Scottty, who is the son of Bandit and Sandi’s old neighbor in St Louis. Great kid who is doing VERY well as a bartender at Bourbon Street Pub, a very crazy place. Ended up back at the hotel and a soak in the hot tub before bed.
The next day was more sightseeing with the highlight being we went sailing on a 85′ schooner. A perfect day for sailing and a ton of fun. We then got great advice from the crew to stop at Alonzo’s right on the water for their happy hour. Awesome food and great drinks. We ran into Scotty again here as it is a big hit with the locals.
We stopped by Sloppy Joe’s to refill our Rum Punch coozies and went back to the hotel for a swim and some relaxation. Bandit and Sandi decided the party was not over and headed back out late while Anne and I had a relaxing evening by the pool. Let’s just say that Sandi had a very good time and is not very quiet at 3 AM. lol.
The next morning we walked to a great restaurant (thanks Yelp) for an amazing breakfast. I highly recommend Blue Heaven for breakfast or brunch. Huge sandy courtyard under the trees with lots of shade and a great experience. We then jumped on the trolley to go to the South side of the island for the obligatory picture at the Southernmost Point. It was then time to pack up and head North.
It was a crazy, fun three days that felt like a week of fun. We will definitely be back. We are thinking this needs to be a yearly trip.























