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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.

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

Rested and ready to continue our walk, we headed towards Mallory Square on the west end of Duvall Street. And though I consider most of Key West a historical area, Mallory Square is a plaza facing the Gulf of Mexico in a location know as “Key West’s historic Old Town.” Street vendors and entertainers set-up on Mallory Square and cater to the hundreds of tourists there on this particular afternoon.

There was still a lot to see and do, but it was a long day, starting with a lost purse, so Karin and I decided we’d head back to Truman Annex and leave my sister and her husband to do their thing!

From Mallory Square we headed down Whitehead to Southhard Street to our quarters, which was just over a mile. It gave us a chance to walk through Truman Annex, which is both a neighborhood and military installation. We walked past the Harry S. Truman Little White House, which President Truman used as his winter home and the United States Coast Guard Cutter Ingham. The Ingham was built in 1934 and decommissioned in 1988. Through a series of acquisitions the Ingham was finally towed to Key West in November 2009 and is now a Key West Memorial Museum.

Mallory Square Entertainer Key West. Photo courtesy of Fred Rosenthal.

Mallory Square Entertainer Key West. Photo courtesy of Fred Rosenthal.

As we walked through the security entrance, I couldn’t help but feel relieved that I didn’t have to come back in a few hours to escort my sister and her husband on to the base.

Tuesday started with breakfast at the Blue Heaven on Thomas Street, another great choice by my sister (I learned later she was asking Siri on her iPhone for recommendations!). I had an excellent omelette and enjoyed their robust, fresh brewed coffee. And though I am not accustomed to live entertainment for breakfast, a local musical group added more fun to our dining experience.

After breakfast we strolled towards “the southernmost point in the continental United States” where the city has a large painted concrete buoy anchored at the corner of South and Whitehead. A popular tourist attraction, this buoy is actually an old sewer junction that was dug up in the area and found too heavy and large to move, so it was painted to look like a buoy. The truth is, Florida’s southernmost point is Ballast Key, a privately owned island southwest of Key West.

Southern most point bouy - Key West. Photo courtesy of Fred Rosenthal.

Southernmost point bouy – Key West. Photo courtesy of Fred Rosenthal.

We continued our walk on South Street and of course what a surprise to find: the Southernmost Hotel, theSouthernmost House and the Southernmost “On the Beach” all anchored within a few hundred yards of Key West’s southernmost concrete buoy. Of course, “tourist attractions” drive the economy, but Key West also offers an array of tropical horticultural beauty.

Our next stop was the Basilica of Saint Mary Star of Sea Catholic Church on Truman Avenue. The current Church building was built in 1905 but the parish has a history dating back to 1566. We walked a couple blocks from the church to the Key West Cemetery, where we found ourselves interested in reading headstones and trying to piece together a sense of the past. Unfortunately, many of the older graves dated back to the mid-1800s were weathered, broken or difficult to read.

After we left the cemetery we meandered through the back streets of Key West with no particular destination in mind until someone suggested we find a place to have a cold beer! Now my sister, the college professor, figures she’ll ask Siri where we could go! The saloon the iPhone Siri suggested had been demolished for new construction. So much for modern technology!

Basilica of St. Mary Star of Sea. Photo courtesy of Fred Rosenthal.

Basilica of St. Mary Star of Sea. Photo courtesy of Fred Rosenthal.

Our other option was more practical: just look around since there seemed to be a restaurant or bar on almost every corner in Key West! We stood on the corner of Duvall and Caroline. As luck would have it, across the street from us was a beautiful two-story, historic Victorian mansion that was converted into a cozy bar with an amazing selection of craft beers on tap. The Porch turned out to be a great place to relax and cool down from the mid-day heat.

Not ashamed to admit it: I love power naps, and I was getting tired of walking so my wife and I decided to head back to Truman Annex for a siesta and agreed to meet my sister and her husband at Kelly’s Caribbean Bar—Grill & Brewery on Whitehead Street for cocktails and dinner around 1700.

Now you can probably tell from the various stops we’ve made that I am a beer drinker! I do not consider myself a beer expert nor a connoisseur, but I really love beer and there are so many great craft, regional, micro, and nano breweries today that whenever I get a chance to try something different, I’ll order it! Unfortunately, what I tasted at Kelly’s was the worst micro-brew I ever experienced. Even the horrible Carlings Black Label we drank in Thailand during the Vietnam War was far better than Kelly’s microbrew. Maybe it was the $2 Happy Hour Special that got me interested in trying their beer, but it was so horrible I had to wash it down with a Key-Lime Margarita.

But aside from their tasteless beer, their 50 percent off appetizers were excellent, including the Black and Blue Ahi Tuna, seared rare with pickled ginger, wasabi aioli and key lime ponzu. We decided after a bite to eat to stroll down to Mallory Square and enjoy the ambiance of the evening. As mentioned before, it is a great place to watch the sunset but we were early so we found a comfortable seat on the pier and watched the people.

Key West sunset. Photo courtesy of Fred Rosenthal.

Key West sunset. Photo courtesy of Fred Rosenthal.

People watching was interesting—the sunset was spectacular. Third and final full day in Key West, Siri suggested Sarabeth’s for breakfast! Apparently Siri was not programmed to find an inexpensive restaurant because $40 for two omelettes with coffee was a little too much for my taste. It’s not that the food was bad, but I was born and raised in the food business. I learned at a young age you pay for ambience and that’s exactly what Sarabeth’s was all about. Certainly not knocking the quality of the food served nor the server, who was very pleasant, but Sarabeth’s is an upscale restaurant and quite honestly not worth what we paid.

Am I complaining? Probably, but I blame myself for not walking away because I knew better! You don’t eat ambience, you pay for it! Lesson learned, and the journey continued. We decided to return to Truman Annex to visit Fort Zachary Taylor. Located adjacent to Truman Annex, Fort Zachary Taylor is a National Historic Landmark the U.S. Department of Interior deeded to the State of Florida in 1976. In 1985, it was opened to the public for use as a recreational site as part of the Florida State Park system.

We spent a better portion of the morning in Fort Taylor but very disappointed at the deterioration of the facilities. The fort construction initially started in 1845 and was decommissioned in 1947 following the abolishment of the Coast Artillery Corps. However, Fort Taylor served as a military training site during the Cuban Missile Crisis in 1962 and again retired from service without ever having been attacked. Granted it was a fortress that remained useful for our military for almost 125 years, but today the facility is in so much need of restoration and quite honestly I am surprised the State of Florida has not returned the Fort back to the Federal Government because the State does not have the funds to adequately restore the fort!

Key West Banyan Trees. Photo courtesy of Fred Rosenthal.

Key West Banyan Trees. Photo courtesy of Fred Rosenthal.

After a long, hot and humid morning trekking thru Fort Taylor, it was time for a rejuvenating power nap! My sister and her husband decided to roam the streets of Key West and we agreed to meet mid-afternoon at a location of our choice for dinner—Hog’s Breath Saloon!

Like so many businesses in Key West, Hog’s Breath Saloon is difficult to describe! A couple hundred feet from Duvall, this establishment has obviously passed the building inspectors but not sure if it is a free standing building or sandwiched in between other buildings. (Apparently code enforcement approved whatever it is!) Anyway, they have great beer selection and I love their blackened dolphin sandwich served with homemade bread. I’m sure there are other fantastic restaurants in Key West with excellent food and certainly worth experimenting, but Hog’s Breath Saloon is worth a visit!

With our journey to Key West completed it was time to head back to Truman Annex for a good night’s sleep and a road trip back north on Highway 1.

The trip home on Hwy 1 North. Photo courtesy of Fred Rosenthal.

The trip home on Hwy 1 North. Photo courtesy of Fred Rosenthal.

At 0800 on Thursday, we packed our bags and headed towards Homestead. Three hours later we were the first customers for lunch at Alabama Jack’s, and I couldn’t resist a cold Kalik Gold Key West beer and their grilled, blacked dolphin sandwich.

We made a stop at RaceTrac for $2.79 per gallon of gas, courtesy of Publix Supermarket promotion and then dropped my sister and her husband off at the Hampton Inn in Homestead to pick up their car. Four hours later, Karin and I were home in Clermont!

For us, it was an enjoyable trip to a part of the United States many Americans will not ever see. Five days and four nights utilizing one of the few benefits remaining for military retirees made this Americana Road Trip very affordable.

MSgt. Fred J. Rosenthal, USAF, (Ret.) and Karin D. Rosenthal Clermont, FL therosenthalgroup@

Reprint from Jan–Feb 2015 • Volume 45, No. 1


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