(Photo) Key West Extreme Adventures Shark Tour.

Piece 1: Old Town Key West/Historic District. Nestled at the southernmost tip of the continental United States, Key West FL is the end of the Florida Keys island chain, connected to the mainland by a series of bridges.

The city of Key West is the seat of Monroe County, which includes a majority of the Florida Keys and part of the Everglades. Only 90 miles away from Cuba, it is the southernmost city in the continental United States.

The main part of Key West is divided into two areas known as Old Town South of Truman Avenue and Old Town North of Truman. We stayed in a charming rental home located in the southern Old Town area.

While the island is a small and somewhat pedestrian-friendly community, we enjoyed using a rented golf cart to explore on our first day. We also found the public transportation, notably the free of charge “Duval Loop” shuttle, to be a convenient way to move between the primary tourist destinations. Rentable bicycles and motor scooters are also readily available. That said, walking is probably the best way to enjoy Key West’s beautiful architecture, vibrantly colored buildings, public art, and extraordinary horticulture.

One of the highlights of the northern Old Town area is historic Mallory Square, a focal point of Key West’s industrial shipping and trade activity in the 19th century. The square has now evolved into a popular public space and artisan marketplace that offers visitors a perfect spot to watch the sunset.

We particularly enjoyed the Historic Memorial Sculpture Garden located at Mallory Square on the corner of Wall Street and Tifts Alley. The exhibit features 36 bronze busts and biographies of men and women relevant to Key West history. In the center of the garden is a 18′ x 25′ sculpture entitled “The Wreckers,” which shows two men salvaging the remains of a sailing ship wrecked on the notorious reef near Key West.

Just steps away from “The Wreckers” sculpture is The Key West Shipwreck Treasure Museum at 1 Whitehead Street. Located in a historic salvage warehouse, the museum uses original artifacts and immersive exhibits to recreate the exhilarating world of 19th-century wreckers. From the second level, visitors can climb a 65-foot observation tower and enjoy beautiful views.

Also in this area of the island, launching off Pier B within the OPAL Key Resort Complex at 245 Front Street, is the Key West Extreme Adventures Shark Tour. We rode on a special pontoon-style vessel out into shallow waters teeming with Lemon Sharks, and watched them aggressively feed on bait fish.

We enjoyed seeing numerous mangrove islands off the Key West shoreline during our adventure boat ride. Mangrove trees grow mainly in coastal saline or brackish water, and have root systems that slow water flow and allow sediment to settle. This process builds up soil around the trees, eventually creating new islets which serve as riparian buffers against erosion and destructive flooding.

For a quick snack during our time around Mallory Square, we stopped at the Hog’s Breath Saloon on the corner of Front and Duval Streets. We shared an order of house made shrimp ceviche (chopped shrimp tossed with onion, tomato, cilantro, and fresh lime juice) and freshly cooked tortilla chips while enjoying live music. The Hog’s Breath gift shop also had a great selection of t-shirts!

Speaking of Duval Street, this iconic Key West road stretches just over a mile from the Gulf of Mexico (Old Town North) to the Atlantic Ocean (Old Town South), and features examples of Bahamian, Victorian, and Mediterranean influenced architecture housing a variety of shops, boutiques, bars, and eateries. Over the years, the street’s bohemian charm has attracted many artists, writers, and musicians; most notably Ernest Hemingway.

We particularly enjoyed visiting the decorative Walgreens Pharmacy on Duval which occupies the city’s old Strand Theater, and retains historical elements such as the cinema’s facade and marquee signage.

Hemingway House-View of Back Veranda

Piece 2: Historic Homes/Points of Interest. Key West has been a destination point for many people of cultural and political influence. President Harry Truman converted a structure originally built as officers’ quarters for the Key West naval station into his winter residence, and actively used the retreat from 1946 to 1952.

Truman came to his Little White House on Key West eleven times during his presidency. It was here that he worked on the creation of the Marshall Plan, aimed at reviving European economies after World War II, and dealt with early Cold War tensions.

The interior of Truman’s Little White House features spacious rooms with high ceilings that encourage airflow, and large windows to maximize natural light and provide expansive views of the lush surroundings. There are also many interesting artifacts, such as a mahogany poker table.

During the early 1930s, influential writer and journalist Ernest Hemingway spent his winters in Key West, where the climate and culture provided him inspiration.

The circa 1851 Spanish Colonial-style house at 907 Whitehead Street in Key West would become Hemingway’s home in 1931. The property included a carriage house, the second floor of which was converted into a writing studio where the author composed some of his most celebrated works, including “To Have and Have Not,” his only novel set in the United States.

The two-story Hemingway House is distinguished by its wide verandas that stretch along the perimeter of both floors, serving as transitional spaces that blur the line between indoor and outdoor living. The interior of the home features high ceilings, hardwood floors, antique furnishings, and memorabilia.

An added touch of whimsy to the Hemingway House experience is that an estimated 60 cats freely roam the grounds, all descendants of the writer’s original polydactyl (six-toed) feline, Snow White.

Tennessee Williams was another influential author drawn to the tranquil atmosphere of Key West. The playwright first visited the island in the early 1940s, and (like Hemingway) found it to be a source of creative inspiration. Williams established a home on Duncan Street in Key West, and lived there until his death in 1983.

A museum at 513 Truman Avenue in Key West celebrates the life and legacy of Tennessee Williams. Visitors will find an extensive collection of photographs, first edition copies of plays and books, rare newspaper and magazine articles, videos, a typewriter used by the author, a scale model of his Duncan Street residence, and other remarkable artifacts.

There are a number of other attractions and points of interest in Key West to discover.

For military history buffs, Fort Zachary Taylor State Park is a National Historic Landmark housing the largest cache of Civil War armament in the world.

For nature enthusiasts, the Key West Butterfly and Nature Conservatory allows visitors to stroll among hundreds of delicate butterflies and exotic birds.

For souvenir photo seekers, the Southernmost Point Buoy and the U.S. Route 1 Mile 0 marker are two great opportunities.

After a busy day of sightseeing, a good spot to enjoy a tasty snack and an ocean view is the Southernmost Beach Café. We relaxed there with a cold beverage, an order of coconut shrimp, and some sweet chili glaze to dip them in.

Jim and Becky on Food and Culture Tour

Piece 3: Key West Food and Cultural Tour. The Southernmost Food Tasting & Cultural Walking Tour was a great way to conclude our trip to Key West, allowing us to more fully experience the island’s unique “Floribbean” culinary style.

We began at El Siboney, a Cuban restaurant located at 900 Catherine Street, just a short walk from our rental house. Here we got to sample a Cuban-style meal featuring roast pork, yellow rice, black beans, sweet plantains, and fresh bread. The plantains (a banana-like fruit) were prepared in a way that made them taste more like a tuber (potato), and they were a wonderful flavor complement to the pork.

Our next stop was The Rum Bar at 1117 Duval Street, where we sampled a “Rum Runner.” This delicious mixed drink included two types of rum, and variety of other fruit and berry flavorings.

The third stop was Mangoes, a family-owned (3rd generation) Caribbean-American restaurant located at 700 Duval Street. Here we tried fritters and chowder made with conch, a large sea snail that is a popular Caribbean food. The fritters were especially good with a lime aioli to dip them in.

Our fourth stop was Kaya Island Eats, another Caribbean-American restaurant, located at 628 Duval Street. Here we enjoyed a taste of Reggae Fish. This unique dish was composed of jerked mahi, yellow rice, pineapple mango salsa, goat cheese, and a drizzle of key lime aioli. We also got to sample Kaya’s signature Mai Tai. Before we left, our group was treated to an impromptu magic demonstration by a local performer. A really fun (and flavorful) experience!

Our tour ended at the Caribbean Coffee Queen Cafe, located at 5 Key Lime Square, where we enjoyed a tart but sweet slice of key lime pie and a small shot of Cuban expresso. While tasting local food and drink were the focus of this experience, the walk also included opportunities to stop and view architecture, public art, and horticultural features reflective of Key West culture.

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