Tuesday, 18 March
The Journey from Miami to Sugar Loaf Key
Today, we journeyed from Larry and Penny Thompson Memorial Park and Campground, just outside Miami, to Sun Outdoors on Sugarloaf Key, a scenic drive that took us deep into the Florida Keys. To bypass the congestion of the Florida Turnpike, we opted for a more relaxed route, taking FL-997 South through agricultural lands and nurseries until it merged with US-1 just south of Florida City—the official gateway to the Keys.
Once on the Overseas Highway, we were treated to breathtaking views as we hopped from key to key, surrounded by shimmering turquoise waters and lush mangroves. Traffic moved smoothly for the most part, though we encountered a few stretches of bumper-to-bumper congestion. Rather than letting it frustrate us, we used the time to take in the surroundings.
Throughout the drive, we noticed several remnants of the historic 1912 Overseas Railroad, the ambitious project originally built by Henry Flagler to connect the Keys to the mainland. Some of its bridges had been repurposed into parts of US-1, while others now served as pedestrian walkways and fishing piers. A few remaining structures, abandoned to the elements, stood as haunting reminders of the railroad’s past, their skeletal frames jutting out into the water.
In addition to the stunning natural scenery, we delighted in the quirky roadside attractions that give the Keys their unique character. Oversized statues of everything from giant spiny lobsters to whimsical sea creatures dotted the landscape, while colorful stilt houses and lavish waterfront estates showcased the area’s blend of rustic charm and luxury. The variety of boats, from humble fishing skiffs to gleaming yachts, hinted at the region’s deep connection to the water.
As the miles slipped away and the sun began its slow descent, we found ourselves eager to settle in at Sun Outdoors and fully embrace the laid-back island vibe of Sugarloaf Key.
Sun Outdoors Sugar Loaf Key
Though we travelled only 123 miles, it took us about 3-1/2 hours to reach our campground. Sun Outdoors Sugarloaf Key offered a tropical atmosphere with 70 RV sites set along the coastline. It was a beautiful campground and we were given a site with a tiki hut with a table and chairs and a swinging bench. The site was not angled or wide, and it took us some struggle to get backed in, but we finally got settled in.
A walk around the park took us past the small heated pull, beautiful firepit area with plenty of tables, and a rack of free bicycles to use. A small pier went out into some man-made lakes with several floating “aquabanas”, or floating cabanas with round tables and benches that extended into the water. Unfortunately, there was a lot of sea moss around the tables, which discouraged me from wanting to use them. The campground also had several kayaks for rent.
After our walk, we enjoyed our tiki hut and had a margarita. We then joined most of the Caravan that walked to a nearby bar and grill called Mangrove Mama’s. We enjoyed some local beers: Crazy Lady Blonde/Golden Ale for Lisa and an Ismoralda IPA for Sam. We then split a Turkey Panini and had some Conch Fritters for an appetizer. The Conch Fritters were hush puppies with hard pieces of Conch inside, which neither of us enjoyed. The beer and panini were good, though.
Afterwards, we walked back to the camper and settled in for the night.
Wednesday, 19 March
Today, the Caravan took a motorcoach into Key West, where we were to meet a trolley for a tour. We left around noon, and the 20-mile trip took about 40 minutes. We entered Key West from the New Town side and met our trolley near the Historic Seaport in Old Town. Our driver began by taking us through Old Town, showcasing its charming streets, colorful architecture, and the laid-back atmosphere that makes this area so beloved. The district features a blend of Caribbean, Victorian, and Bahamian architectural styles, with pastel-colored buildings, royal palms, and lush gardens lining the streets. Duval Street, the main thoroughfare, was filled with Spring Break tourists, adding to the lively scene as people strolled between bars, restaurants, shops, and nightlife.
Truman Little White House
Our first stop was outside the Truman Annex, a former military housing area that has since been converted into a private, upscale residential neighborhood. This part of Key West was once an active naval base, playing an important role in U.S. military operations throughout history. Today, it is one of the most exclusive and picturesque areas of the island, with its gated streets, historic buildings, and beautiful waterfront views. The annex is home to luxury residences, including the current U.S. Coast Guard headquarters, making it a quiet, well-preserved part of the island.
We walked through the annex to the Truman Little White House, originally built in 1890 as naval officers’ quarters. President Harry S. Truman visited the house 11 times between 1946 and 1952, using it as a retreat from the pressures of Washington, D.C. During his stays in Key West, Truman conducted official business, signed important legislation, and spent time with his advisors in a relaxed setting. The home provided Truman with a peaceful environment, and he often took morning walks, played poker with staff, and enjoyed the tropical island atmosphere, which he credited with improving his health and decision-making.
Our guided tour of the house gave us the opportunity to see original furnishings and personal items from Truman’s visits, preserving the home as it was in the 1940s. Notable items included Truman’s desk, poker table, and tropical-themed living spaces. The guide was incredibly knowledgeable, giving us insight into Truman’s presidency, his time in Key West, and the importance of the house in American history. The house was also used as a retreat for other presidents, including Dwight D. Eisenhower, John F. Kennedy, Jimmy Carter, and Bill Clinton. It became a site for significant Cold War-era meetings, including discussions on the Marshall Plan and key international affairs.
Hemingway Home and Museum
We then reboarded the trolley and made our way to the Hemingway Home and Museum, one of the most famous historical sites in Key West. This Spanish Colonial-style mansion, built in 1851 from native limestone, was purchased by Ernest Hemingway and his second wife, Pauline Pfeiffer, in 1931. The house remains one of the most iconic properties in Key West. With its wide wraparound balconies, arched windows and doors, and thick masonry walls designed to keep the interior cool, the home perfectly captures the charm of old Key West. The interiors are filled with many of the original furnishings from Hemingway’s time, including European antiques curated by Pauline, and the home’s original decor has been carefully preserved.
One of the standout features of the house is the in-ground swimming pool, which was built in 1938 at a staggering cost of $20,000—an enormous sum at the time. It was the first pool in Key West and represented a luxurious addition to the property. However, the pool’s history is tinged with drama. Our guide told us that the pool was built to spite Hemingway, who was allegedly having an affair. After the pool was completed, Hemingway threw a penny on the ground and told Pauline, “Here, take my last cent!” The penny was retrieved by Pauline and embedded into the concrete near the pool, a quirky reminder of the home’s colorful past. Another oddity we saw was a urinal from Sloppy Joe’s Bar, which Hemingway allegedly took when the bar was being relocated. He humorously claimed to have flushed a lot of money down it.
Behind the house is Hemingway’s writing studio, where he worked diligently every morning. The studio has been largely preserved, with his desk, typewriter, bookshelves, and hunting trophies still in place. Hemingway wrote many of his most famous works in this space, including To Have and Have Not and The Snows of Kilimanjaro, making it a must-see for literary enthusiasts.
Adding to the home’s charm are the famous six-toed cats. These cats are descendants of Hemingway’s polydactyl cat, Snow White. Around 60 cats now roam the property, many of which still carry the unique genetic trait of extra toes. These feline residents can be found everywhere, including on the beds inside the house, adding a fun, quirky touch to the visit.
The surrounding lush tropical gardens add to the home’s serene atmosphere, providing a peaceful retreat from the busy streets of Key West. The gardens, filled with exotic plants and towering palm trees, once served as a personal oasis for Hemingway, where he could unwind and enjoy the beauty of the island.
Mattheessen’s Ice Cream
After visiting the Hemingway House, we walked over to Mattheessen’s Ice Cream, located on the vibrant Duval Street. Known for its rich, homemade ice cream and giant cookies, the shop is a local favorite. We both decided to try their ice cream: I had a scoop of Cuban coffee-flavored ice cream, and Lisa enjoyed Key Lime. The oversized cookies caught our attention, though we didn’t purchase any.
We found a bench outside St. Paul Episcopal Church on Duval Street in Key West, a historic stone church known for its beautiful stained-glass windows and deep roots in the island’s history. As we sat down to enjoy our ice cream and watched the world go by, a mischievous hen, followed by several fluffy chicks, wandered over, eagerly begging for food.
Convent of Mary Immaculate
The trolley picked us up again after we finished our ice cream and we continued our exploration of Old Town. We passed the Convent of Mary Immaculate, also known as the St. Mary Star of the Sea Convent, which dates back to the 19th century. The convent is part of the St. Mary Star of the Sea Catholic Church, one of the oldest Catholic parishes in Florida. On the grounds of the church sits Our Lady of Lourdes Grotto, a replica of the famous Lourdes grotto in France. Built in 1922 by Sister Louis Gabriel, the grotto was designed to protect Key West from hurricanes. Locals believe the grotto has shielded Key West from direct hits, and it remains a place of prayer and pilgrimage.
New Town Key West
As the trolley continued its loop, we entered New Town Key West, an area that developed in the 20th century as the island expanded. The area grew rapidly as Key West’s population increased and dredging projects were undertaken to fill in the shallow waters surrounding the island, creating new land for development. New Town is now home to modern buildings, the Key West International Airport, shopping centers, and other commercial spaces. It contrasts with the historic charm of Old Town, offering a more contemporary atmosphere.
Party Cat
The trolley dropped us off near the Historic Seaport in Old Town, where we boarded the Party Cat, a multi-level, open-air catamaran. This 90-minute cruise around Key West’s scenic coastline was a fun and relaxing way to end our day. We stayed near the shoreline, just south of Sunset Key, and enjoyed unlimited drinks from the bar while listening to live music from a talented guitarist. Lisa and I were the first to start dancing, setting the festive mood.
Halfway through the cruise, we descended to the first level to enjoy a Caribbean buffet. Although the seating area was tight, we enjoyed the meal before quickly returning to the deck to keep dancing and enjoying the music. As the boat cruised back toward the dock, we watched the stunning Key West sunset from the water, a perfect end to a fantastic day.
The Party Cat Tour was an exciting, fun-filled way to experience Key West’s stunning waters, socialize, and soak in the island’s vibrant, laid-back vibe. It was the perfect conclusion to a day spent exploring the history and beauty of Key West.
Thursday, 20 March
Visiting Quarters, NAS Key West
We left the trailer park in the morning and headed over to the Visiting Quarters on NAS Key West where we had reservations for that night. Though we arrived early, they allowed us to check-in mid-morning. Our room was excellent and we even had a beautiful view of the ocean.
Old Town Key West
We unloaded our bicycles and set off to explore the charming neighborhoods of Old Town Key West, pedaling past streets lined with colorful conch-style homes, lush tropical gardens, and swaying palms. Many of the houses, with their pastel facades, gingerbread trim, and wide front porches, dated back to the 19th century, reflecting Key West’s rich maritime and cultural heritage. We rode through residential streets where roosters strutted freely, a reminder of the island’s quirky character, and passed historic guesthouses, boutique inns, and quaint corner cafés that exuded an old-world Caribbean charm.
From Old Town, we decided to make our way toward the Southernmost Point Buoy. We biked past the Truman Annex with its white-framed homes and manicured lawns and the Bahama Village with its colorful Bahamian-inspired architecture.
Upon reaching the Southernmost Point, we found the massive anchored concrete buoy standing boldly at the edge of the island, painted in bright red, yellow, and black stripes. Established in 1983, it famously claims to mark the southernmost point of the continental United States, though this is not entirely accurate. In reality, parts of Fort Zachary Taylor Historic State Park and the Truman Annex extend slightly farther south, and the true southernmost landmass of the contiguous U.S. is Ballast Key, a privately owned island about 10 miles southwest of Key West.
As expected, the lines to snap a selfie at the buoy already stretched several blocks long, with tourists patiently waiting for their turn to capture the iconic moment. Rather than join the crowd, we opted to skip the photo op and continued our ride toward the Key West Cemetery, where we planned to visit the USS Maine Memorial. Along the way, we wove through more of Old Town’s scenic lanes, appreciating the island’s relaxed atmosphere and the fusion of history, culture, and tropical beauty that makes Key West such a unique and captivating place.
USS Maine Memorial
During our trolley tour the previous day, our guide recounted how Key West was the last U.S. port of call before the USS Maine set sail for Havana, Cuba. At the time, Key West was a vital strategic outpost for the U.S. Navy, serving as a refueling and supply station for American ships navigating the Caribbean. With tensions rising between the United States and Spain over Cuba’s fight for independence, the Maine was sent to Havana to safeguard American interests and citizens in the region. The battleship arrived in Havana Harbor on January 25, 1898, where it remained anchored for three weeks as a show of strength and diplomatic presence.
Then, on the night of February 15, 1898, a devastating explosion ripped through the Maine, sinking the vessel and killing 266 American sailors. While the exact cause of the explosion remains a subject of debate—ranging from an internal coal bunker fire to an external mine—it was widely blamed at the time on Spanish sabotage. The incident ignited public outrage in the United States, amplified by sensationalized newspaper reports that rallied the American public toward war. The rallying cry “Remember the Maine! To hell with Spain!” became a powerful slogan that helped propel the nation into the Spanish-American War just months later.
In the immediate aftermath of the disaster, Key West played a critical role in the response efforts. The city became a medical and logistical hub, receiving survivors from the wreckage and providing treatment to the injured. Naval operations in Key West intensified, and as war preparations escalated, the island remained a crucial staging ground for U.S. forces deploying to Cuba.
Today, the legacy of the Maine lives on in Key West. One of the most poignant reminders of the tragedy is the USS Maine Memorial, located in Key West Cemetery on the highest natural elevation of the island. The memorial consists of a large granite obelisk, enclosed by an iron fence, with a plaque honoring the sailors who perished in Havana Harbor. Surrounding the monument, we found the graves of three sailors who died in the explosion, their headstones bearing solemn inscriptions. Nearby, additional graves mark the final resting places of other service members who lost their lives in military conflicts, creating a somber but powerful tribute to those who served.
Historic Seaport
We rode our bikes back to the Historic Seaport, a lively and picturesque area that blends Key West’s maritime history with its signature quirky charm. We parked our bikes and stopped to check out some of the seaport’s more offbeat attractions, starting with the infamous “sticker car.” This one-of-a-kind vehicle, parked near the waterfront, was completely covered in layer upon layer of colorful stickers—some weathered and peeling, others freshly applied—each representing a traveler, a business, or a bold personal statement left behind by past visitors. It was a living piece of Key West’s eccentric character, and we couldn’t resist snapping a few photos of the ever-growing collage.
Nearby, we came across the signpost displaying the distances to far-off locations around the world. With arrows pointing in every direction, it reminded us just how far Key West is from other famous spots—New York City, Havana, and even the equator. The mix of whimsical and practical signs perfectly captured the island’s adventurous spirit.
Another fun stop was the life-sized Key West postcard painted on the side of the Cuban Queen Coffee Stand. Designed like a retro travel advertisement, the mural featured vibrant, vintage-style lettering and iconic island imagery, making it the perfect backdrop for a classic tourist photo. The coffee stand itself, housed in a charming little shack, added to the area’s old-Florida feel, and the aroma of freshly brewed Cuban coffee drifted through the air.
After soaking in the waterfront views for a few more moments, we made our way toward our next adventure. It was nearly noon, and we were eager to meet up with the food tour we had scheduled—ready to taste our way through the flavors of Key West.
Southernmost Food Tasting & Cultural Walking Tour
From the cemetery we rode our bicycles through more of Old Town until we reached our meeting point for a Food Tasting Tour that I had booked for noon. We locked our bikes up outside the El Siboney Restaurant and joined our guide, Kyle.
The Southernmost Food Tasting & Cultural Walking Tour began outside El Siboney Restaurant, known for its authentic Cuban cuisine. After everyone gathered, we were escorted inside to enjoy a plate of Mojo Pork with Onions, Cuban Bread, White Rice, Black Beans, and Fried Plantains. Our guide gave us an informative overview of Cuban food, noting that White Rice was traditionally favored by older settlers, while Saffron or Yellow Rice was reserved for fancier meals. The food was delicious and provided a great introduction to the island’s Cuban influence.
We then walked down Catherine Street, where Kyle shared insights about Key West’s history. He pointed out the Eduardo Gato Cigar Factory and stopped outside several shotgun houses, which were provided to factory workers. He also explained how the city is working to preserve these historic homes from demolition.
Next, we arrived at the Speakeasy Inn and Rum Bar, where Kyle talked about Prohibition and Key West’s rum running industry. We enjoyed a Rum Runner cocktail while hearing about the building’s history, including the fact that it had the only basement in Old Town and was used to hide from police raids. He also highlighted the lattice work on the balconies, which indicated that both alcohol and prostitutes were available at the establishment during Prohibition.
After our drinks, we continued our walk and stopped at the Key West Lighthouse, where Kyle explained the role of wreckers, or shipwreck scavengers, in the island’s history.
Our next stop was the Bahamian neighborhood, where we admired the Cornish House, a late 19th-century conch-style home with distinctive brass trumpet-shaped lattice work. This unique feature is a tribute to former owner William H. Cornish, a musician and bandleader. Nearby, we saw an unpainted house showcasing Dade County Pine, known for its strength and termite resistance. The house’s unpainted exterior is historically significant, as it was never painted, reflecting a common practice in Key West to avoid the maintenance required by the harsh sun, salt air, and humidity.
We then visited the mural outside the “In One Era” Antique Store, where Kyle shared stories about the figures depicted, all of whom helped shape the culture of Key West.
Our next tasting stop was Mangoes, where we sampled Conch Chowder (a tomato-based soup) and Conch Fritters (similar to hush puppies). While the small amount of chewy conch didn’t add much flavor, the dishes provided a taste of local seafood culture.
We then headed to Kaya Island Eats, where we enjoyed Mahi-Mahi with saffron rice accented by their signature island-inspired seasonings. We also saw a patron eating a fish they had caught, which had been cooked by the restaurant.
Finally, we walked down Moe’s Way to Cuban Coffee Queen, where we enjoyed a sample of Cuban Coffee and a slice of Key Lime Pie. Lisa walked over to the shed where they were grinding the coffee which smelled so good. This was a perfect end to the tour.
Old Town Key West
We were about a mile away from where our tour would begin and where we had left our bicycles. Rather than rushing back, we decided to take our time, strolling through the area and soaking in more of Key West’s vibrant atmosphere.
We decided to get an iced café con leche from the Cuban Queen Coffee to bring with us. The drinks came thoughtfully covered at the top, with just a small slit for the straw, keeping them cool and spill-proof. Even better, instead of regular ice, they used frozen coffee cubes—ensuring that every sip stayed rich and bold without getting watered down.
With our coffees in hand, we meandered up and down Duval Street, exploring its eclectic mix of art galleries, jewelry stores, and boutique shops. Each art gallery featured unique and striking pieces, and the curators in every shop were eager to share the stories behind the artwork. We lingered over displays of beautiful and sometimes quirky paintings and sculptures, and handcrafted pieces that reflected the island’s creative spirit.
In one of the jewelry stores, we admired beautiful pieces made from silver coins and artifacts salvaged from shipwrecks, each one a tangible piece of history from Key West’s maritime past. The souvenir shops, with their quirky knick-knacks and funny T-shirts, provided a few laughs as we browsed through their endless selections of island-themed memorabilia.
As we made our way back toward our bikes, we passed by Gato Village Pocket Park, a charming little spot featuring a replica façade of a Gato Cigar Cottage and the world’s largest cigar sculpture. The display paid homage to Key West’s rich cigar-making heritage, once a thriving industry that attracted Cuban immigrants in the late 19th and early 20th centuries.
When we finally reached our bicycles, we decided to take an indirect route back to the Historic Seaport, once again enjoying the sight of colorful conch-style homes, lush tropical landscaping, and streets lined with palm trees and fragrant flowering vines. The slower pace allowed us to appreciate the island’s beauty in a way we might have missed if we had simply hurried back.
Once at the Historic Seaport, we locked up our bikes near a rack and took a short stroll along the waterfront again, where the late afternoon sun shimmered off the boats in the marina. Wanting to relax before our next adventure, we grabbed a table at The Boat House, a laid-back dockside restaurant. As we settled in, we ordered a couple of Crazy Lady beers from Waterfront Brewery, a local Key West craft brewery. With the sea breeze drifting in and the marina bustling around us, it was the perfect spot to unwind and take in the lively energy of the seaport.
Glass Bottom Boat Tour
We eventually made our way to the ticket office for the 6 p.m. Fury Glass Bottom Boat Tour in Key West, eager for a chance to experience the stunning underwater world of the Florida Keys National Marine Sanctuary. While waiting to board, I wandered over to Sunset Pier, a lively spot with a fantastic view of the water. The pier was already filling up with people claiming the best seats for the famous Key West sunset.
Once aboard the Fury catamaran, we chose seats on the sun deck, wanting to take full advantage of the beautiful afternoon. As the boat glided away from the dock, we felt a quiet excitement knowing we were heading toward North America’s only living coral barrier reef, about seven miles offshore.
The ride itself was smooth and peaceful. A crew member provided occasional commentary, but for the most part, it was a quiet, relaxing journey. We watched as sailboats passed in the distance, their white sails catching the last rays of the sun, and seabirds skimmed across the surface of the water.
After about 40 minutes, we arrived at the reef, and Lisa and I made our way downstairs to the climate-controlled viewing area, where large glass panels at the bottom of the boat allowed us to peer into the underwater world below. We had been expecting a vibrant, colorful display of coral and marine life, but the view was not as clear as we had hoped. The water was slightly murky, and while we could make out some coral formations, they appeared mostly brown-green and lacked the vibrant hues we had imagined.
A crew member pointed out different fish and coral structures, doing their best to describe what we were seeing, but the lack of clarity made it difficult to fully appreciate the marine life. We spotted a few fish darting between the coral, but without bright sunlight penetrating the water, the colors remained muted. It was a bit disappointing, though we still appreciated the chance to glimpse the reef in person.
After about 20 minutes, the boat began its return journey to shore. As we got closer to Key West, the sun had dipped lower in the sky. The captain slowed the boat for a few extra minutes, allowing everyone to soak in the breathtaking view. The sea mirrored the sky’s changing colors, and the sight of sailboats silhouetted against the glowing sun created a picture-perfect moment.
To make the experience even more special, a crew member passed out champagne, giving us a chance to toast to the beauty of the evening. We sipped our drinks and watched as the sun slowly disappeared beyond the horizon, casting its final golden glow over the water.
Although the reef had not been as vibrant as we had hoped, the peaceful boat ride, ocean breeze, and stunning sunset made the experience worthwhile. As we docked back at the harbor, we stepped off the boat feeling grateful for another beautiful Key West sunset.
Key West Evening
After we left the boat, we took a short walk around Duval Street. The bars were loud and crowded as expected. Captain Tony’s Saloon was amusing with all the bras hanging from the ceiling. We bought a quarter pound hot dog from a street vendor called Chubbs outside Sloppy Joe’s that was very good. She had 11 different sauces available which was fun.
We walked back to the Historic Seaport Boardwalk and along the water back to where we had left our bikes. We then biked back to our hotel room at the Air Station to relax for the evening.
Friday, 21 March
Dry Tortugas
We packed up and left our hotel room at 6:30 that morning to catch the Ferry to the Dry Tortugas National Park. We arrived at the ticket office before they were open, so I left Lisa to stand in line while I walked over to the Cuban Quenn for some Cafe con Leche. I also bought us a Key Wester to split which consisted of two eggs, American cheese, turkey, on Cuban bread. Several roosters and a hen with chicks walked around me as I waited for our food and coffee.
The ticket office opened just as I returned and we were given our wristbands and a boarding pass. We sat down in the waiting room and enjoyed our coffee and breakfast while waiting to board. A staff member came out and told the crowd that it was windy with up to 10 foot swells, and the journey was not going to be pleasant. Because of that, they would allow us to get a refund. Lisa and I decided to stay. We had put on some dramamine patches that morning and were ready to accept the challenge. The staff member came out two more times to announce that we could get refunds, and emphasized that we would be surrounded by puking people for 2-1/2 hours there and 2-1/2 hours back. That clinched the deal for us, and we went and got refunds.
Southernmost Point Bouy
Since it was early, we decided to bicycle to the Southernmost Point buoy and take the obligatory tourist photo. Along the way, we passed a mural that looked like Washington Crossing the Delaware, but a closer examination shows the artist’s real intent was to portray the parallel of America’s fight for freedom with those of the Cubans,
When we reached the bouy, there were only two other couples there, so we got a quick picture. We also examined the Bishop Albert Kee statue and an old concrete bunker that once protected a telegraph cable that ran to Cuba.
Mile 0
We then rode down to the Mile 0 marker that designated the end/beginning of US-1. US-1 is the only road that connects the Florida Keys to the Mainland, and it stretches all the way to Maine.
The development of this road over the open ocean, swamps, and small islands of the Florida Keys was fascinating to learn. It began when the Overseas Railroad was built along the same path as US-1 in 1912 by Henry Flagler. Key West was chosen as the terminus because of its proximity to trade routes with Cuba and the recently open Panama Canal. In 1935, major sections of the railroad became unrepairable after is was destroyed by a Cat 5 hurricane. The State of Florida then took control of the infrastructure and converted it into a highway in 1938. Because US-1 already ran down the east coast of Florida and ended in Miami, it made sense to extend it over the new highway.
Across the street, the church had a colorful sign designated the end of the highway near an old mangrove tree. The roots extended out of the ground were taller than I was.
Fort Zachary Taylor
We then rode our bicycles to Fort Zachary Taylor, where the entrance fee was $2.50 each. Upon arrival, we headed straight for the fort. Construction of the fort began in 1845 to strengthen U.S. coastal defenses and was named after President Zachary Taylor. During the Civil War, it was used by Union forces occupying Key West, serving as a key defensive base, though it saw no direct combat. The fort remained in use during the Spanish-American War, World War I, and World War II, primarily as a strategic post.
The fort itself is an imposing structure made of brick and stone, with a distinctive design featuring bastions and curved walls built to withstand artillery fire. Inside, we explored several preserved rooms, including armament storage, barracks, and officer’s quarters, giving us a glimpse into military life during the fort’s active years. The grounds are dotted with large cannon emplacements and artillery, emphasizing the fort’s role in defending the area. In the 1960s, it was decommissioned and transferred to the State of Florida in 1971, becoming a state park.
The park also boasts one of Key West’s most popular beaches, so we rode over to the beach and took a walk along its rocky shores. Though it was still early, people were already enjoying the water, collecting seashells, and even participating in a beach yoga class. After strolling along the beach, we explored some of the farther reaches of the park before moving on to our next destination.
Florida Keys National Marine Sanctuary – Eco Discovery Center
Just outside the entrance of the park was the Eco Discovery Center, a free museum that offered a wealth of information about the Florida Keys National Marine Sanctuary. The center featured a wide range of displays highlighting the diverse marine life found in the area, along with the conservation efforts aimed at preserving the delicate ecosystem. We explored exhibits showcasing the sanctuary’s coral reefs, fish species, and the importance of protecting these natural resources.
The highlight of our visit was a 15-minute presentation by the facility manager, who stood over a map board and explained what makes the Florida Keys reefs so unique. We learned about the sanctuary’s role in safeguarding the underwater environment and how scientists and conservationists are working to maintain the health of the reefs despite the challenges posed by climate change and human activity. The presentation helped us better understand the importance of preserving this vibrant marine ecosystem, adding a deeper layer of appreciation to our visit.
Mallory Square
We then road back to Mallory Square and locked up our bikes so we could walk around Duval Street. There was not much activity around the square yet but we enjoyed walking around the square before it got too crowded with tourists.
Key West First Legal Rum Distillery
We then walked up Duval Street to Key West’s First Legal Rum Distillery which offered tours every 30 minutes. The distillery, located in a charming, historic building, is notable for being the first legal rum distillery in Key West, established after the end of Prohibition.
We were the only ones in our tour group so we got a very personal and informative tour. The tour began with an introduction to the distillery’s history. Our guide explained the significance of rum in Key West’s past, from the days of piracy and early trade to its role in the region’s economy during Prohibition. We learned how rum was often made in small batches using traditional techniques passed down over generations.
The next part of the tour took us through the distillation process. We got an up-close look at the copper pot stills, fermentation tanks, and the various ingredients that go into making rum, like molasses and sugarcane. The guide explained each step in the process, from mashing to fermentation, distillation, and aging, highlighting how each stage affects the flavor and quality of the final product.
Afterward, we participated in a rum-tasting session, sampling several of the distillery’s range of rums. Our guide shared fun facts and stories about the distillery’s history and the rum-making process while we enjoyed the tasting. We were even given a smminature of rum to take with us at the end.
We also visited the retail shop where we were able to sample more rum including a daiquiri slushie.
Celtic Conch
Probably the most fun we had all day was when we stopped into the Celtic Conch. The live music drew us into this small Irish Bar where we got two seats at the bar. Two lads from Ireland were behind the bar on a raised platform engaging the audience with interactive songs which made the environment lively. One played the guitar and one played the accordian, and they kept our hands clapping. We both enjoyed some Smithwick’s Red Ale and had a great time there. After our second beer, we relunctantly left to continue exploring Key West.
Southernmost Pint Brewpub
We then walked over to the Southernmost Pint Brewpub just off Duval Street and ordered a flight of beers that we enjoyed out on its patio. This micro-brewery had a selection of 18 beers brewed in-house. Despite its name, it is not the southernmost brewery as that honor goes to First Flight Island Restaurant & Brewery, though it might claim the title of southernmost micro-brewery.
Angelinas Pizza and Tree Bar
We walked back to Duval Street, the lively heart of Key West, and found a charming table in a little courtyard nestled between Angelina’s Pizzeria and Tree Bar. The setting was perfect—shaded, breezy, and just far enough from the street to offer a bit of respite while still allowing us to soak in the energy of the area.
The Tree Bar, true to its name, is built around a large, sturdy tree that provides natural shade for patrons enjoying a drink in the open air. It sits adjacent to Rick’s Bar, part of the larger Rick’s & Durty Harry’s Entertainment Complex, a well-known hub of nightlife in Key West. The rustic wooden bar, combined with the tree’s sprawling branches, created a relaxed and inviting atmosphere that felt quintessentially Key West—casual, fun, and full of character.
With a cold Yuengling Beer in hand and a hot, cheesy slice of Angelina’s Pizzeria in front of us, we settled in to watch the never-ending stream of tourists strolling past. The people-watching was just as entertaining as the surroundings—groups of sunburned visitors in tropical shirts, couples pausing to snap selfies, groups of people enjoying spring break, and the mix of music from nearby bars added to the festive vibe.
Irish Mikes
We did a quick walk-through of the bar. We thought the music was good, it was too loud and crowded.
Kermit’s Key West Key Lime Shoppe
Next, we made our way to Kermit’s Key West Key Lime Shoppe, a beloved local institution with a history spanning over 30 years. Famous for its dedication to authenticity, Kermit’s uses 100% Key lime juice in its products, setting them apart from those made with the more common Persian limes. This commitment ensures that every bite bursts with the true, tangy essence of Key lime.
Eager to indulge in the shop’s signature treat, we bought a slice of Key lime pie to share and found a cozy spot in the small courtyard. The first bite was pure perfection—tart, refreshing, and silky smooth, with a velvety texture that melted on the tongue. The light, flaky graham cracker crust added just the right amount of crunch, balancing the bright citrus flavors beautifully.
Beyond their famous pie, Kermit’s offers an impressive selection of Key lime-infused products, ranging from candies and sauces to seasonings, jams, and even body care items like shampoo and lip balm. We couldn’t resist sampling a variety of free treats, including cookies, nuts, jelly beans, lollipops, and hard candies, each delivering a delightful burst of that unmistakable Key lime zing.
It was a delicious stop that perfectly captured the flavors of Key West!
The Wreckers Monument
As we headed back to our bikes on Mallory Square, we stopped at the “Wreckers” monument. This impressive sculpture, measures 18 feet long and 25 feet high, was created by master sculptor James Mastin of Miami, Florida. It depicts the early wreckers who saved lives and salvaged cargo from ships that had met peril on the treacherous reefs surrounding Key West. The sculpture captures the spirit of Key West as a bold, boisterous, and bustling sea town during the frontier days of young America. Wreckers played a vital role in the island’s economy, as the dangerous reefs led to frequent shipwrecks, and salvaging operations became a significant industry.
The Key West Historic Memorial Sculpture Garden, established in 1997, features 39 bronze busts honoring individuals who have had a significant impact on Key West’s history. Notable figures include Ernest Hemingway, Harry S. Truman, and Henry M. Flagler. The garden serves as a place to reflect on and celebrate the rich cultural heritage of Key West.
As we continued toward our bikes, we explored a couple more gift shops. Though we saw several groups of people setting up for the evening performances on Mallory Square, it was still several hours till sunset and we were too exhaused to stay.
Saturday, 22 March
This morning we packed up and headed to Fort Lauderdale.