Last Train to Islamorada

Our latest, and likely last, trip to Islamorada was a lot of fun, with perfect weather the entire time. Changes to the property by the new owners though made it easier to decide not to come back. Still a great place to be, especially when compared to NJ in February, but all the unique Keys personality has been removed. Fear not, this won’t be a rant about those changes.

      The trip started a little rocky with a 1 ½ hour ground stop after we boarded the plane and pulled back from the gate (so the airline could get credit for on-time departure) but we made-up  time in flight and landed in Key West less than an hour late. I got upgraded on my rental vehicle to a VW Tiguan Wolfsburg Edition. A fun vehicle to drive up to Islamorada and tool around in during the week. As a bonus, traffic was light, so the drive was quicker than usual, and the BBQ place near the resort provided a delicious first-night dinner.  

      As usual, I dropped my stuff in the room and headed for the tiki bar. Having just missed happy hour I was in for a shock when I saw that they did not yet have the good local beer on tap and all bottled beer was $9. Our friends checked the wine list and experienced similar sticker shock. We headed back to their patio to enjoy some of the spirits we had brought along. Needless to say, we didn’t spend much money at that bar. Too bad, as the new owners did a nice job upgrading the pool area and bar, and added bathrooms. We weren’t the only ones to keep our money as the bar was never crowded the entire week, even when there was a musician playing. On that evening, as soon as happy hour ended, we adjourned to my patio where we could see and hear him playing – and he could see and hear us - while enjoying our own drinks.

      Next morning we all headed a few miles north to hike in one of the quarries where rock was extracted to build the overseas railroad and highway – and to create some of the Keys. Being thirsty after, we stopped at Florida Keys Brewing for a few pints and some tacos from the food truck on-site. With their 10th anniversary celebration scheduled for that Sunday we had to scout out the tap list, pick up some merchandise, and make our plan for Sunday’s festivities.

Confirming they had a few stronger brews in the original brewery tasting room down the street, we decided to head there first on Sunday before others caught on. That proved to be the right move as we got there for a few tastings before it got crowded and then found a table in the shade in the beer garden where we could enjoy the beer, music and food for the afternoon. A great time celebrating 10 years of beers at one of the best breweries in Fl.

In between visits to the brewery, I got in a bike ride back through the neighborhoods of Islamorada. Always a highlight of the trip for me, just pedaling around the island is relaxing and it’s fun to ride to several spots that cars can’t get to. A much different perspective from a bike than from a car. There would be 2 more rides during our stay as I explored some new places and got enough exercise to justify having “another” pint.

The highlight of the trip was a sunset cruise with our friend Chris on his boat. He picked us up at our dock and we headed off for what turned out to be quite an adventure. In all the years we have been going to the Keys we had never been to Indian Key, a small island just off what is now Islamorada so that is where we went. As the tide was going out and the dock had been destroyed in the last hurricane, we had to drop anchor and wade onto the island. And so the adventure begins. Once on the Island, which is a park preserving the artifacts of the original white settlement – one of the first in the Keys – Chris gave us a guided tour complete with the history of the settlement. Quite a story, but in the interest of time, I’ll let those of you interested Google it on your own. Though we were on the island only a short time, the tide had stranded our boat. It was all hands off-deck as we had to disembark and push the boat out to deeper water. No small feat for a bunch of NJ landlubbers, though just another day for Captain Chris.

Now thoroughly soaked, it was time for the sunset part of the cruise. We headed to the Bay side toward a channel in the mangroves, spotting a crocodile in open water near the boat. A rarity to see one outside of the mangrove shelter according to our captain. Out of the channel we were in open water again to see the most magnificent sunset we had ever seen in the Keys. A great reward for the work we had put in earlier. Speeding back through the channel and to our dock, the colors were still vibrant even as they faded.

Over the 15 years of our “get the hell out of NJ in Feb.” trips we have created memories that will last a lifetime. Most recently, that cruise, but so many others over the years: Riding on and steering the African Queen (yes, the actual boat from the movie), driving the Old Road into Key Largo from Homestead, other cruises with our friends and captains Jacob and Chris, kayaking among the mangroves, bike rides, hikes, sunsets at Lorelei with Dana Collins playing guitar, absorbing the history, great meals – and beer at FKB, seeing friends year after year and making new friends. It was a great run. I’m thankful we found Pines and Palms so many years ago and I’m a little sad to say goodbye.

Happy St. Patrick’s Day!

www.RetiredandInspiredat55.com  03-17-2025