Florida Keys
History & Heritage

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Our most recommended Florida Keys History & Heritage

Key West: Old Town Trolley 12-Stop Hop-On Hop-Off Tour

1. Key West: Old Town Trolley 12-Stop Hop-On Hop-Off Tour

Enjoy the sun, charming setting, and clear waters of Key West on this Old Town Trolley Hop-On Hop-Off Tour. This tour covers the entire city. You can avoid the trouble of driving and parking in a new place. The trolley tour is also designed so that you can hop-on and off and explore on your own, on any of the 12 stops. Your ticket is valid for all day, so you can tour at your own speed. There are frequent pick-ups at all of the 12 stops so you’ll never have far to walk. And our Old Town Trolley conductors will be there to guide you through this tropical paradise on one of the distinctive orange and green trolleys. Don’t miss this great day out!

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Key West Conch Train Tour

2. Key West Conch Train Tour

Climb aboard Key West’s conch train for a 90-minute sightseeing tour of the tropical paradise. The train departs from Front Street Depot and loops through the Old Town to end back behind the Depot at Mallory Square. Stock up on ice cream and homemade fudge at the Depot to eat on board during your tour. You can jump off at Truval Village to visit the Ernest Hemingway Home and Museum, Key West Lighthouse, Southernmost Point, and Key West Butterfly and Nature Conservatory. Climb to the top of the observation tower at Key West Shipwreck and Treasures Museum. Travel back in time to the days of hand-rolled cigars at Mallory Square. And stroll through the Cayo Hueso y Habana Historeum. Back on the conch train, learn about Key West characters, such as Mel Fisher, whose lifelong search for 2 sunken Spanish galleons finally turned up treasure worth USD 450 million. Jump off to enjoy great shopping on Duval Street, and fine dining at restaurants such as Hog's Breath Saloon, Jimmy Buffet's Margaritaville or the Hard Rock Café.

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Key West Shipwreck Treasure Museum Tickets

3. Key West Shipwreck Treasure Museum Tickets

Since the first Spanish galleons began to traverse the Florida Straits in the 16th century, ships have wrecked along the treacherous reefs of Key West and the Florida Keys. Now, you can learn all about the area’s maritime past with a trip to the Key West Shipwreck Treasures Museum. Wrecking and salvaging – the recovery of wrecked ships and their cargo – was the foundation of Key West’s economy during the 1800s. The economic boom it created meant that by the mid-1850s, Key West had become the richest city per capita in all of the United States of America. Learn the history of the region’s shipwrecking past at the Key West Shipwreck Treasures Museum, with two floors of genuine recovered artifacts. See pieces of wrecked Spanish fleets dating back to the 1600s and 1700s, as well as pieces from the Isaac Allerton, wrecked way back in 1856. Guests can even lift a silver bar, which was salvaged from the Spanish treasure galleon Nuestra Senora de las Maravillas. The museum itself is a recreation of the 19th century wrecker tycoon Asa Tift’s warehouse, and includes a 65-foot look-out tower. At the Historeum, you can also expect storytellers in period costumes and an array of audio visual displays that brings the history of Key West to life.

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Key West: Day Trip from Fort Lauderdale w/ Activity Options

4. Key West: Day Trip from Fort Lauderdale w/ Activity Options

Experience the southernmost city in the US, Key West. On this day-long adventure, you will explore the many sights, shops and restaurants in Key West, all the while soaking in the Caribbean feel of the city. Beginning bright and early, you will be picked up at "Four Points by Sheraton Fort Lauderdale Airport" by your professional bilingual driver. En route to Key West, you will cross 42 bridges and hop 32 islands. Upon arrival in Key West, you will be enchanted by the colourful atmosphere, street artists and outdoor cafes. This day trip is perfect for travellers who like to do their own thing. You will have approximately 6 hours, from 12:00h to 18:00h to explore all that Key West has to offer. There are plenty of interesting and entertaining things to do in Key West, including visiting the Hemingway House, taking a trolley or train tour, going on a kayaking eco-adventure or enjoying a dolphin-watching cruise. These are only a few of the many possibilities. No pre-arranged activities are set during this time, so you can have the freedom to create the day on your own. If you do only one thing in Key West, a visit to Mallroy Square is a must. It is a place where many gather for a never-planned, always unique, daily celebration. Mallory Square is located by the historic waterfront. Key West is a beautiful, historic and culturally unique place with so much to see and do that you might just have trouble making up your mind!

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Key West: 3-Hour Guided Bicycle Tour with Key Lime Pie

5. Key West: 3-Hour Guided Bicycle Tour with Key Lime Pie

Meet your friendly guide at the local partner’s office and get kitted out with your bike gear. After a short safety briefing it's time to head out on your island paradise adventure to see the very best that Key West has to offer. The first stop of the tour is the iconic Mallory Square, home to a popular nightly sunset celebration. Here, learn about the island’s history of smuggling and the shipwrecks that have crashed on the nearby reef. Next, pass by the presidential gates that lead to Harry Truman’s Little White House, which is known to have been his favorite vacation spot. Continue the tour onto Mile Marker Zero, which is quite literally the end of the road in the USA, then stop outside Ernest Hemingway’s former home where the famous writer penned many of his treasured novels. Head to the Southernmost Point in the Continental USA for a photo opportunity, then complete your circuit of the island as you ride past Higgs Beach, the White Street Pier, the Key West Cemetery, and the historic Seaport. At the end of an unforgettable 3-hour tour, enjoy a well-deserved rest and a slice of traditional key lime pie, an absolute must for any visitor to the island.

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Key West 2.5-Hour Urban Adventure Quest Scavenger Hunt

6. Key West 2.5-Hour Urban Adventure Quest Scavenger Hunt

If you’re looking for a way to turn Key West into a giant game board, Urban Adventure Quest has created an interactive scavenger hunt that combines the fun of the Amazing Race with a 2.5-hour sightseeing tour of Key West. Guided from any smart phone, teams make their way around the well-known and the overlooked gems of the city, solving clues and completing challenges while discovering Key West’s art, culture, and architecture. Race to be the first to finish the game, or take as much time as you need, solving clues, completing challenges, and learning about local history along the way. The adventure begins at the Historic Seaport and takes you on a well-designed course down Duval Street, in and around Mallory Square, and through a famous cemetery and other unique sites. The tour involves a bit more than 2 miles of walking. Using a smart phone as your guide means that you can start when you want and determine your own pace of play. Stop for a burger in paradise or a slice of key lime pie – you’re on your own schedule! Offered at a fixed price for a group as opposed to per person pricing, this city tour/game is a great value for those on a budget.

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Truman Little White House: Key West

7. Truman Little White House: Key West

Presidents, Prime Ministers and royalty have visited the Harry S. Truman Little White House in Key West. You can be next by taking a tour of this stunning historic building. No trip to Key West is complete without seeing the Harry S. Truman Little White House. Built in 1890 as quarters for the Naval Base Commander and Paymaster, the Little White House has now taken its place in history. In 1912, President William Taft visited the house, and in 1918, Thomas Edison lived there for several months as he worked on inventing new weapons for the war effort. Always at work, the President met with the Joint Chiefs of Staff, worked on the Marshall Plan and the Truman Doctrine, and continually attended to his duties while enjoying the magnificent setting in Key West. It's said that he was friendly with the locals and fit right into the island lifestyle. Today, visitors from all over the world are able to get a glimpse into Truman’s world, see where he and Bess entertained guests, where critical meetings were held, and how the business of our government was conducted in this lovely historic building.

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Key West: Food Tasting and Cultural Walking Tour

8. Key West: Food Tasting and Cultural Walking Tour

Celebrate Key West's diverse and abundant local fruits of the sea. This 3-hour guided small-group experience stops at 6 tasting locations, each carefully chosen to give you an eclectic view of Key West's best restaurants along the historic seaport. Enough for a hearty lunch, tastings are served from adored local eateries, tucked-away hidden gems, and a fisherman-owned seafood market. This tour will allow you to bypass the Duval Street tourist traps and go straight to the spots that the locals frequent to eat, drink, and discover the island. As you stroll the charming side streets and docks, you will experience the island’s seaport, as well as the rich industrial history which has transformed through the generations. Your friendly and knowledgable local guides will share stories of local industry, including the colorful past and historical landmarks. Following the tour, you can explore Old Town with confidence and take advantage of recommendations on restaurants, attractions, entertainment, and cultural offerings. You'll also receive a collection of exclusive recipes, ensuring that you can enjoy memories from this tour for many years to come.

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Key West: Haunted Walking Tour with Psychic Guide

9. Key West: Haunted Walking Tour with Psychic Guide

Begin your Key West spooky walking tour by meeting at the Aquar Bar and Nightclub. Tap into your sixth sense and connect with ghosts that linger in the most haunted places.  Converse with the spirits and access your sixth sense with the tools your guide will provide for you. Hear the tales of the Key West Water Witch and the Corpse Bride. Rub elbows with a famous spirit at the Hemingway House and keep a lookout for the ghost that resides at the Lighthouse. See Key West differently with the help of your gifted guide.

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Key West: History and Culture Southernmost Walking Tour

10. Key West: History and Culture Southernmost Walking Tour

Start your journey at the famous Kino Sandals Plaza, where you will meet with your local guide. On your walk listen to stories about how Key West became one of the wealthiest cities in the mid-1800s. Learn about the island’s shipwrecking industry, sponge harvesting, and cigar manufacturing.  The end of the tour will end at a buoy showing the Southernmost Point of the continental U.S. Here, your guide will give you free maps so that you can continue to explore the various shops,  museums, and other points of interest along this section of the island.

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Other Sightseeing Options in Florida Keys

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What people are saying about Florida Keys

Our tour guide, Bill, was great! We had fun and the bike ride was awesome! Thank you Silvia&Adriano

Very nice walk, very good driver guide… but only in English for 90 minutes…

We had a lot of fun and the tour covered all of the important sites.

GREAT staff on the bus ride dwn and back. So much to do in key west

Bruce was the best tour guide. Very informative and entertaining.