Key West Historic District

Key West Historic District

Architecture • Key West, Florida United States

The Key West Historic District in Florida is a captivating neighborhood that showcases a rich tapestry of political history through its architecture. This district serves as a living museum, offering visitors a glimpse into the past of this vibrant community. The architectural styles found here reflect the various influences that have shaped Key West over the years, from Spanish Colonial to Victorian and Bahamian conch houses.

Strolling through the streets of the Historic District, visitors can admire the beautifully preserved buildings and homes that date back to the 19th century. Many structures feature intricate details, colorful facades, and charming verandas that evoke a sense of nostalgia. The district is also home to significant political sites, such as the Harry S. Truman Little White House, where the former president spent time during his administration.

Exploring the Key West Historic District is like taking a step back in time, with every building and street corner telling a story of the city's past. Whether wandering through Duval Street or meandering along the quieter lanes, visitors can appreciate the architectural heritage that makes this neighborhood a true gem in the heart of Key West.

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$45 Tour Provided by Viator
5.00 (16 reviews)

iWitness Key West True Crime Walking Tour

True crime in Key West? Bold, bizarre, and unforgettable, this new innovative tour walks you into the island’s real-life scandals — smuggling, gambling, murder, and shocking history exposed where it happened. More thrilling than a ghost tour and more revealing than a history tour, Key West’s underworld comes alive, Key West-style. Be the next eyewitness. We're bringing crime to the streets!

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$44 Tour Provided by Viator
5.00

Hula Hank's Key West Tipsy Tiki Sunset Cruise

Imagine gliding over gentle waves aboard the Lazy Lady, a 53-foot, one of a kind tiki boat. Soak in the vibrant colors of an iconic Key West sunset - hues of orange, pink and purple. Sip on ice-cold beverages prepared by your friendly crew while the warm sea breeze carries the sounds of island music and laughter. The atmosphere is relaxed and festive, perfect for making new friends or sharing moments with loved ones. Expect a laid-back and enjoyable trip while unwinding with a refreshing beverage from the bar. As the last sliver of sun disappears below the water, watch for the green flash, an enchanting touch of magic. Sail back to Key West Harbor under the star-filled sky, creating a Key West memory to last a lifetime.

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$229 Tour Provided by Viator
4.99 (71 reviews)

Key West Conch Republic Tiki Pedicab Experience by Kokomo Cabs

You will sit and relax on our spacious and comfortable tiki bike as your private guide/driver takes you on a pleasant ride around the enchanting streets of Old Town and Historic District. Experience its amazing architecture and historic sites as you learn the rich history, culture, and folklore of our beautiful island of Key West. First-row, Historic, Cultural and Fun, the only VIP experience tour in Key West.

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$89 Tour Provided by Viator
4.97 (364 reviews)

Key West Sunset Sail Aboard Legendary Schooner Appledore

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comfortable. We limit passengers to just 36, guaranteeing you'll have room to move about and have an intimate evening experience. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship. With the painted sky as an exquisite backdrop, your sunset sail takes you past Key West’s Historic Seaport, Mallory Square’s Sunset Celebration, the Navy Mole where the big ships dock and the civil war era Fort Zachary Taylor. Soak in these sights while enjoying a glass of premium wine, an icy cold premium beer, full cocktail bar or soft drinks.

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$137 Tour Provided by Viator
4.96 (28 reviews)

Marathon to Key West Private Tour of Florida Keys

Visit the one-and-only island city of KEY WEST! Enjoy a narrated tour on the way down, and island music on the way back. HIGHLIGHTS • See the sights in Key West • Stay for the Key West sunset • Plenty of Free Time • Designated Driver • Narrated Tour Do what you want in Key West! We're doing the driving! Sightsee, enjoy a happy hour, eat a nice dinner, check out Mallory Square at sunset, take a sunset sail, and more! Sit back & enjoy the scenery as we drive down to Key West. Learn the history, culture, and ecology of the Florida Keys & Key West from your friendly local guide. See the Southernmost Point, Hemingway's House, Mile Marker Zero, Sloppy Joe's, and Mallory Square It's more like a road trip than a tour - ask questions, point out wildlife, make new friends.

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$70 Tour Provided by Viator
4.94 (62 reviews)

Key Lime Pie Walking Tour of Key West Historic Seaport

Taste the sweetest adventure in Key West—sunshine, stories, and the island’s most iconic dessert. Led by a Key West expert who’s part historian, part foodie, and fully obsessed with the island’s iconic slice, this small-group tour is a feast for all your senses. Wander the Historic Seaport while savoring three decadent Key Lime Pie tastings, each with its own tropical twist, and sip a refreshing Key Lime cocktail. Along the way, your guide shares insider tales, quirky legends, and secret local spots you won’t find in any guidebook. Fun, flavorful, and unforgettable—this is the Key West experience you’ll be raving about long after the crumbs are gone.

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$49 Tour Provided by Viator
4.91 (113 reviews)

Schooner Appledore Day Sail with Full Bar in Key West

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comfortable. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship.

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$138 Tour Provided by Viator
4.91 (22 reviews)

PRIVATE Welcome to Key West Walking Tour

Welcome to Key West! Stroll through Old Town Key West with a long-time local, see & learn about the unique places you can visit during your vacation. This is private tour is customizable, meaning you can request to adjust the meeting point to better suit your day, and even request what kind of stories you'd like to hear. Perfect for wedding party, couples, family & friends, bachelor/bachelorette, birthdays, reunion, corporate groups, and more! **If it's too far or too hot to walk, you can hop on the Duval Loop bus with your guide** It's air-conditioned with several convenient stops throughout Old Town. The best part about your own private tour is you can ask questions and customize the tour to your interests! Feel free to include notes in your booking about: - what you want to know about Key West - points of interest you'd like to include - if you're celebrating an event - mobility challenges or other needs we can accommodate Total distance about 1 1/2 miles.

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$143 Tour Provided by Viator
4.90 (591 reviews)

Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling

Introducing Squid! The quietest experience you will have on a boat while watching dolphins. We worked with David Walworth, an MIT educated Naval Architect and Principal Engineer known for his high-efficiency catamaran designs, to build the perfect boat for our trips from scratch. Our amazing crew are closely trained by our Honest Eco Biologists. Crew training starts on land with research and mission alignment before moving onto the water where we hone our seamanship skills and work to become as effective as possible at delivering on our Purpose. We Work to Spread the Value of Wildlife Conservation “People Protect What They Love.” Jacques Costeau said it, and it inspires us at Honest Eco as we work to help people discover and fall in love with the environment we are all part of. We are continuously learning and pushing ourselves to be as environmentally responsible as possible.

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$109 Tour Provided by Viator
4.89 (271 reviews)

Classic Key West Schooner Sunset Sail with Full Open Bar

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Key West, promising an unforgettable experience for all. As you sail further into the sunset, the full open bar comes to life, offering an enticing array of cocktails, wines, and spirits to complement the evening's splendor. Sip on our signature Schooner Bloody Mary or Dark & Stormy as you watch the sky ignite with color. The skilled bartenders are on hand to craft your favorite drinks, ensuring that your glass is never empty as you drink in the sights and sounds of the sea. As the schooner begins its journey back to Key West, you find yourself lost in the timeless rhythm of the sea, grateful for the opportunity to witness the beauty of a Key West sunset from the deck of a historic schooner.

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