Fred and Karin Rosenthal’s Americana Road Trip to the Florida Keys…

Karen and Fred Rosenthal. Photo courtesy of the Rosenthals.

Karin and Fred Rosenthal. Photo courtesy of the Rosenthals.


We vacationed in the Keys (FL) a couple years ago but my sister and her husband, who live in Nashville, TN, had never been further south than Orlando, FL. They were planning to attend a wedding in Fort Myers over the Fourth of July weekend and decided to extend their plans and venture through the Everglades and drive Highway•1 to Key West.

When I mentioned they could spend a couple hundred dollars a night at a Key West hotel, their thought of a side trip to the Keys vanished! Knowing there might be a possibility of spending a few days in Key West if rooms were available at the Key West Naval Air Station, I made a call and booked two rooms at the Truman Annex facility for $60 per night (per room). I wasn’t sure of the Navy Gateway Inns & Suites’ policy regarding booking additional rooms for other family members, but fortunately it wasn’t an issue!

Our itinerary was to depart Clermont early Monday morning and meet my sister and brother-in-law in Homestead around 1100. They would leave their car at the hotel, and I would drive to Key West. After giving some thought to the early morning, five-hour drive to Homestead, I decided if I could get a room at Homestead Air Reserve Base, we would leave Sunday.

With reservation made at $56 for a room, we left Clermont mid-morning on Sunday and headed south. However, before we could drive too far, I needed to fuel up our 2012 Hyundai Santa Fe. Gas prices are pushing $4 per gallon, so it’s important for us to find the cheapest prices in the area. One resource we use is through Publix Supermarket that promotes purchasing discounted gas cards. Frequently they offer a $50 gas card for $40, for every $50 spent on groceries. There are other large supermarket chains across the country that offers similar promotions, but for this trip I filled the tank to the brim with 14.290 gallons at $3.499 per gallon and used the entire $50 card. But, instead of paying $3.499 per gallon my actual cost was $2.799 per gallon.

We arrived at Homestead ARB Sunday afternoon, and though I did not expect much activity, the base seemed desolate. I spoke briefly to the MP as we entered the main gate, and he informed me his security unit and an Army attachment were the only active duty personnel stationed at Homestead. I’m sure many remember the devastation in 1992 when Hurricane Andrew virtually destroyed the base.

Homestead was taken off active status with the Air Force and reopened as an Air Force Reserve facility in 1994. And though it has been 22 years since Hurricane Andrew, I was quite fascinated to be on a base where all the buildings were relatively new. I understand the military has spent millions to modernize their facilities, but Homestead was unique and worth the visit! We checked in at the Homestead Inn and were pleasantly pleased with the clean and comfortable billeting accommodations.

Alabama Jack's near Homestead. Photo courtesy of Fred Rosenthal.

Alabama Jack’s near Homestead. Photo courtesy of Fred Rosenthal.


After a long day on the road and settling in at Homestead, it was time for us to go to one of our favorite eating establishments—Alabama Jack’s! Alabama Jack’s is located about halfway between Homestead and Key Largo on Card Sound Road. There isn’t another business within 10 miles in either direction, but Alabama Jack’s is a “hole-in-the-wall” restaurant that serves fantastic seafood! We enjoyed a couple of Kalik Gold Key West beers, cold smoked fish pieces for an appetizer, a cup of Conch chowder and a grilled, blacked dolphin sandwich. We have to admit “life is good” when it comes to eating at Alabama Jack’s.

I contacted my sister and advised her we were already in Homestead and would pick them up at their hotel Monday morning around 0900. If I have any complaints about Air Force billeting, it’s they do not offer a complimentary continental breakfast like the Army offers at the facilities we’ve stayed. So we opted for a burrito and coffee breakfast at McDonald’s, which was located directly across the street for the Hampton Inn where my sister and her husband were.

We left McDonald’s and drove to the hotel when my wife realized she had left her purse hanging over a chair in the restaurant. The pit in my stomach and the pounding of my heart gave me the feeling I was about to have an anxiety attack! And though it was just a purse with cash, credit cards and keys, and I knew everything could be replaced, it was that immediate instant when you think the worst!

We drove back to McDonald’s but caught a stoplight at the intersection, and it seemed like an eternity while I waited a couple minutes for the light to turn green! When my wife frantically went through the front door, a gentleman who apparently just sat down right after we left said a customer gave the manager the purse. She offered a cash reward but no one would take it! What a relief and a feeling of thanksgiving to know what could have happened, didn’t!

So back to the Hampton Inn: we loaded up the car and headed south on Highway 1 (aka: Florida Keys Overseas Heritage Trail). Certainly the drive offered beautiful scenery and of course there were the typical tourist shops (traps) that lined the highway, but we all agreed our primary focus was to drive straight through to Key West. Surprisingly the traffic was light, so the 127-mile drive was under three hours.

We headed straight to the Naval Air Station Key West billeting office at Trumbo Point where check-in was a breeze. We left Trumbo Point and drove to the Truman Annex where our rooms were located. As we went through the security gate at Truman Annex, I realized even though my sister and her husband were allowed to stay on a military base, getting on the base without either my wife or me could create a logistical problem. The security guard suggested we drive to Navy’s Boca Chica Field and get them temporary passes so they could come and go as they pleased.

So after we unpacked our gear, we got back into the car and headed north on Highway 1 for about five miles to Boca Chica Field. I expected the process to take the remainder of the afternoon, but we were in-and-out of the registration office within 10 minutes and were ready for three days in Key West. We drove back to the Truman Annex and parked the car for the duration of our stay.

My sister is a college professor and my brother-in-law is a curator at a museum in Nashville, but they met each other while they were both involved in the food industry near Boston. They are always looking for unique dining experiences.

From our previous trip to Key West, my wife and I had a couple restaurants in mind, but for this trip we pretty much left it up to my sister and her husband to pick the places to eat. Thirsty and hungry, we put on our walking shoes and headed towards downtown on Whitehead Street. First stop, the Green Parrot Bar, a Key West saloon where the locals come to kick back and enjoy a drinkor two. It’s off the beaten path from the tourist area and offers a very laid-back atmosphere. We each had a beer, munched on pop corn and found ourselves making conversation with a few of the interesting patrons.

Green Parrot Bar Key West. Photo courtesy of Fred Rosenthal.

Green Parrot Bar Key West. Photo courtesy of Fred Rosenthal.


We left the Green Parrot Bar and continued our search for an eating establishment. My sister read a review about DJ’s Clam Shack on Duval Street and suggested we try it. Their menu was limited as was their establishment, but the Mahi Mahi tacos were excellent. The restaurant is more of a food stand between two permanent buildings with picnic tables in the back of their stand with plenty of flies to swat for our entertainment. Not exactly a five-star restaurant I expected my sister to select, but the reasonably priced tasty tacos and the casual ambience made it worthwhile.

Our journey continued down Duval Street, which is the main street for tourists in Key West. Artist from around the globe sell their creative works in unique galleries and shops on Duval. Most of the artwork was a little pricey for us, but we enjoyed window shopping and occasionally a walk through a shop. Sandwiched between these galleries were the typical souvenir shops, bars, restaurants and the occasional XXX-rated store. There were a few empty buildings but many of businesses on this particular Monday afternoon seemed to have traffic.

I don’t mind walking but after a long time of window shopping, I had to sit and relax for a while. The best place I could find was at the corner of Sloppy Joe’s Bar. They originally opened on Greene Street in 1933 but moved to the corner of Duvall and Greene in 1937. It was a nice place to kick back, unwind and enjoy a craft beer and live music. Part of the history of this bar are the stories told about Ernest Hemingway and his frequent visits to this establishment. Unfortunately, it wasn’t this location that Hemingway patronized, but the first Sloppy Joe’s on Greene Street.

Ship off Mallory Square Key West. Photo courtesy of Fred Rosenthal.