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A guide to history, events, tours, and attractions in Boston, Key West, San Diego, St Augustine, Savannah, and Washington DC...
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Key West Attractions, Tour & Ticket Center. Conch Train, Dry Tortugas, Key West Aquarium, Old Town Trolley, & more.
See the Best of Key West
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  100% Satisfaction Guarantee*
 
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  Old Town Trolley Tours  
 

The original Old Town Trolley Tours was conceived right here in Key West. It was more than 25 years ago when the three founders of Historic Tours got together to work towards preserving the historic sites of the city and along the way, created an exciting and entertaining sightseeing tour.

trolley tour signEach year, thousands of visitors come to Key West to see the attractions, enjoy the magnificent weather and get their own taste of paradise, after all, there’s no place quite like it on earth. Old Town Trolley Tours of Key West offers a comfortable seat, a humorous and interesting narrative and a way to see the best of the city at your own pace.
trolley driving by shipwreck museum
 
tourists at conch fritter stand

The orange and green trolleys transport guests around the city of Key West, showing off the city’s most intriguing points of interest and sharing the fascinating stories that helped shape one of the country’s most visited destinations. From the colorful cast of transplanted Conchs, like Harry Truman, James Audubon and Ernest Hemingway, to the resident legends, artists, poets, and musicians that make Key West so alluring, Old Town Trolley Tours gives every visitor a look at the people and places that the city is so famous for.

On board the Old Town Trolley, guests of all ages are given a 90-minute tour through Key West with numerous stops at the most popular sights. You may hop on and off at our convenient stops throughout the day. From Mallory Square and Duval Street to Henry Flagler’s historic Railroad Museum - and everything in between, the trolley tour is a showcase of all the best of Key West.

Throughout the tour, knowledgeable trolley conductors offer an amusing, historic account of many of the most well-known Key West events and sights; it’s our own unique brand of Transportainment! So next time you’re in town, climb aboard and get set to be thoroughly entertained!


Here are just a few reasons why Old Town Trolley is the best sightseeing tour in town:

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  From 1828 to 1850 Key West was the richest city per capita in the United States.  
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• 100% Satisfaction Guarantee*

• Ride Second Consecutive Day For Only $15

• Top rated on Trip Advisor

• Full color map and discount coupons for attractions, restaurants and shopping with every ticket

• Hop on and off at your leisure

• Key West's most comprehensive tour fully narrated by our expert tour conductors

• On and off FREE reboarding at 13 stops

• Complimentary admission to Papa’s Hemingway Pilar Rum Distillery included with your ticket

• Colorful anecdotes and well-research historical facts

• Exclusive stops and attraction discounts

• More than 100 Points of Interest

 
   
 

Learn more information about Key West Tours.

   
     
       
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  conch train driving by neighborhood    
 
 
Conch Tour Train

For a historic adventure through Key West, take a ride on board Key West’s original sightseeing tour, the Conch Tour Train.

 
     
 

conch shellAs a legacy to Henry Flagler’s “railway over the sea” the Conch Tour Train has treated visitors to an in-depth view of the city’s most charming, historic and interesting attractions for 50 years...and counting. The Conch Tour Train took its inaugural ride in 1958 and has been offering tours throughout Key West ever since.

conch tour train with water in backgroundThe Conch Tour Train departs daily from the Front Street Depot and ends at Mallory Square—one of Key West’s most famous spots. Throughout the tour, you’ll not only see the area’s well-known sights, you’ll also learn about the many residents, both past and present, that make the Conch Republic one of the world’s most unique places. See some of the spots Hemingway frequented and find out why Harry Truman spent so much time on the island. Listen to accounts of how pirates, indians and wreckers lived, fought and worked, giving Key West its extraordinary reputation.

Our experienced engineers are “Conchs” themselves, a term used to describe Key West locals who either grew up here or came for a visit and never turned back! They’ll delight and enlighten you with amusing tales of days gone by and interesting facts about one of America’s most talked about cities. You’ll also get an up-close view of some of the southernmost city’s lovely Victorian architecture and famous tin roofs.

The historic Conch Tour Train tour is 90 minutes long making one full loop through Old Town Key West, includes three stops, and highlights marvelous sights, stories and entertainment. It is a true icon in Key West with more than 15 million satisfied guests over the years. Take your seat on the Conch Tour Train and discover the many reasons why it’s a favorite among visitors and locals alike.

conch train driving by southernmost point   ernest hemingway home
 
     
 

With your train ticket, you will receive our full color free map along with our coupon sheet; valued at over $50, the coupons include discounts for attractions, restaurants and shopping.

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  If you’re born in Key West you are a conch. If you’re born elsewhere but live here 7 years you become a fresh water conch.  
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• 100% Satisfaction Guarantee*

• Ride Second Consecutive Day For Only $15

• Ranked Top 20 on Trip Advisor

• Full color map and discount coupons for attractions, restaurants and shopping with every ticket

• Complimentary admission to Papa’s Hemingway Pilar Rum Distillery included with your ticket

• Stops at Truval Village: Steps away from the Ernest Hemingway Home and Museum, the Key West Lighthouse, the Southernmost Point and Key West Butterfly and Nature Conservatory

 
   
 

Learn more information about Key West Tours.

   
       
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Key West Aquarium

With all its natural beauty, Key West has a multitude of exciting activities—the Key West Aquarium tops the list with magnificent displays of the numerous marine animals that make the waters around the island their home.

 
 

yellow fishHold a live starfish or pet a shark! At the Key West Aquarium you’ll get closer than you’ve ever been (without getting wet) to some of the world’s most intriguing marine species. Opened in 1934, the Key West Aquarium was the very first attraction in the city; it was also the largest aquarium of its kind at the time.

guests and exterior of key west aquarium Today, it’s twice the size and showcases many of the sea animals that live in the waters surrounding the Florida Keys. See moray eels, stingrays, barracuda, parrotfish, tarpon, sharks, sea turtles and an array of tropical fish. Learn about their habitats and habits from the Key West Aquarium’s knowledgeable guides.

guests petting stingraysHave a hands-on experience like never before as you see, feel and pick-up the amazing animals that live in the Touch Tank. They are all harmless, gentle creatures just waiting to get a closer look at you! Listen carefully as Aquarium staff reveal facts and information about these mysterious species.


stingraysBe sure to be on hand as hungry sharks and sea turtles devour their breakfast, lunch or late afternoon snack; feedings occur daily at 11am, 1pm and 4:30pm. The Atlantic Shores exhibit offers visitors a chance to learn about a mangrove environment. And the 50,000-gallon tank is home to many colorful and lively tropical and game fish.

 

family looking petting fish and ladies viewing tanks  
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  In 1934 Key West was the poorest city in Florida. President Roosevelt, under the WPA program, had the Key West Aquarium built which is still in use today.  
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Learn more information about Key West Aquarium.

 
   
       
     
       
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  Casa Cayo Hueso y Habana Historeum

It was a time when pirates and indians roamed the shores looking for fortune and battling for territory. It was a place when human bones lay scattered in the sand - a vivid symbol of the passion and determination of those who came first.

 
 

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  paintings of buildings and balconies  

Cayo Hueso or Bone Key, was Key West’s first name, deemed so by the first Spanish settlers who discovered the remains on the beach when they arrived. Cayo Hueso, soon became Key West, when English-speaking residents at that time erroneously translated the name.

Throughout its vibrant and colorful past, Key West has undergone many changes and been home to people from all walks of life. But perhaps none with such a rich influence as that of the Cuban people. In the 1860’s, Cuban Cigar makers flocked to the island to work and sell their sought-after product. Their presence on the island made such an impact that Key West was soon referred to as “Cigar City USA”.


  family entering historic warehouse   man hand rolling cigars inside store  


Today, Key West’s rich Cuban heritage is still apparent throughout the island. Casa Cayo Hueso y Habana Historeum offers a unique journey to that era for all who visit. Located in the heart of historic Mallory Square, the Historeum is housed inside an antiquated brick warehouse that dates back to 1879.

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Sample the tastes, sights, sounds and culture of Cuba as you stroll through this marvelous collection of shops, displays and the well-known Pepe’s Casa Cayo Restaurant. Witness the skill and mastery of the craftsmen who meticulously hand-roll authentic Cuban cigars—see for yourself what makes a Cuban Cigar so extraordinary. View beautiful and intriguing art and memorabilia and learn more interesting facts about the original Cayo Hueso. Delight in the delicacies of Cuba and savor the true flavors that became a lasting part of Key West. A visit to the Casa Cayo Hueso y Habana Historeum is fun and entertaining for people of all ages.

 
 

For more information visit Casa Cayo Hueso y Habanna Historeum.

 
   
       
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Truman Little White House

Visited by Presidents, dignitaries, royalty, Prime Ministers and an array of prestigious people, the Harry S. Truman Little White House in Key West holds a special place in the history of the United States.

 
     
 

painting of President TrumanIt was here that President Truman came in search of a place to rest and relax. When our 33rd President arrived he discovered much more than a peaceful island hideaway, he found a place he’d like to call home.

  President Truman fishing in Key West
   
  Harry S Truman sitting on chair in front of Little White House

Built in 1890 as quarters for the Naval Base Commander and Paymaster, the Little White House took its place in history early on. 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.

In 1946, the Little White House became Truman’s winter home and he proceeded to stay for 175 days. Always at work, the President held various meetings in the home, 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. A setting so magnificent, in fact, that Truman was known to spend an afternoon in town or out on the water fishing with friends. It's said that he was friendly with the locals and fit right into the island lifestyle.

Although several other United States Presidents visited the Little White House in the years that followed, it ultimately was named for Harry Truman because of his deep affection and adoration for the home and Key West.

desk sign that reads the buck stop here

Today, visitors from all over the world are able to get a glimpse into Truman’s life and times, 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.

key west citizen newspaper with picture of Harry Truman  
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  In 1987, The state of Florida recognized the Little White House as a state historic site, guaranteeing permanent protection for Florida’s only Presidential Museum.  
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For more information go to trumanlittlewhitehouse.com.

 
   
 
   
       
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  picture showing exterior building of sails to rails museum with train and ticket booth to the left    
 
  Sails to Rails Museum at Flagler Station

Highlights of the museum include displays and video presentations on the history of sponging, turtling, fishing, wrecking, and cigar making. Visitors can view an interpretative model on Fort Jefferson National Park.

 
 

Guests to the Sails to Rails Museum will journey through the Age of Sail, a time when tall ships plied the treacherous waters of the Caribbean, Gulf of Mexico and Florida Keys from the 1500s to early 1900s. These waters were once filled with treasure-laden Spanish galleons, dreaded pirates, merchant ships and more as the New World made its riches known to all who sailed her waters. As a young nation began to grow and her influence grew, the Age of Sail gave way to The Age of Rail. Railroads opened up frontiers of this emerging nation whose commerce, wealth and independence reached out to many. The United States of America was built on the foundation of its railroads and Florida was certainly no exception. The Age of Rail, particularly for Florida, was an opportunity for expansion.

picture showing sails to rails museum exhibit of two figures sitting on chairs with a barrel between them as well as artifacts on the walls Sail power was used the day the treasure fleets returned from Mexico and South America, initially to rid the Caribbean of piracy, and in the industries that made Key West the richest city per capital in the United States: sponging, turtling, fishing, wrecking, and cigar making.

The end of the Age of Sail came with the beginning of steam power in the 1820s and during the Civil War years of the 1860s, when the vicissitudes of industry gave way to the speed and reliability of steam. Despite its rapid decline, sail remained part of the industrial fabric of Key West until its last ship was built in 1939: The Western Union, the cable tender serving its namesake company.

There was a time in America when railroads opened up the frontiers of an emerging nation. Railroads meant connection to commerce, wealth, and politics of a young country. In a sense, the United States of America was built on the foundation of its railroads, and Florida was certainly no exception.

picture of sails to rails museum showing model shipsIn 1900, the life expectancy of males in the United States of America was a mere 47 years. Henry Flagler was 70-years-old and one of the wealthiest men in the world from his partnership with John D. Rockefeller in the founding of the world’s largest company, Standard Oil of New Jersey. For the health of his wife, Henry Flagler first came to Florida in 1885 and became entranced with the dream of seeing it become the country’s Riviera. His aspirations for luxury hotels along the East Coast of Florida developed it into the state it is today.

Realizing that the Panama Canal was going to be completed in 1913, Henry Flagler in 1897, first conceived of establishing a rail head in the southernmost deep-water port of the state: Key West. Thought to be impossible and even labeled “Flagler’s Folly,” the Key West extension was begun in 1905 and was, indeed, an engineering marvel.

 
     
   
       
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  shopping mallory square    
 
  Mallory Square

A name synonymous with good times, fun crowds and carefree celebrations, Mallory Square is one of those places you must experience to understand its majesty.

 
 

performers with soccer balls and knives Known for centuries as a waterfront bustling with activity, Mallory Square has been a focal point of Key West since the very beginning. When pirates dwelled in the city seeking their fortunes on the ocean floor, it was here that they docked and frequented the local watering holes and hotels. Throughout the years, Mallory Square became known for its collection of unique shops, artists, performers and locals who sought an audience for their chosen talents.

sunsetToday, Mallory Square is perhaps most well known for its world-famous view of the magnificent sunset - and for the celebration that takes place every evening in its honor. There’s truly nothing more spectacular than a Key West sunset and Mallory Square offers the most stunning vistas of the sun’s dramatic departure into the horizon. Celebrity “Conchs” like Tennessee Williams and James Audubon were known to be entranced with the view from the square and the nightly sunset celebration.

family strolling through mallory squareWhether it’s Winter, Spring, Summer or Fall, the historic waterfront comes alive with festivities late afternoon and into the night, every day. Tightrope walkers, fire-eaters, jugglers, musicians and artists take the stage, showcasing their skills and thrilling crowds of people. Local food vendors bring on the eats with scrumptious Key West specialties like conch fritters, key lime pie and fresh-squeezed key lime-aid. It’s a wonder to watch and an experience not to be missed.

Day or night, there’s always something happening in Mallory Square. Stroll through some of the shops and galleries or stop in at one of the many restaurants or bars. Strike up a conversation with a local and gain an understanding of why Key West really is heaven on earth.

 
     
 
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  Key West is the southernmost city in the Continental United States; 160 miles south of Miami but only 90 miles north of Cuba.  
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  wooden signs pointing to sponge market and shell warehouse
 
   
 

For more information, go to mallorysquare.com.

   
       
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  aerial view of fort jefferson    
 
 
Yankee Freedom III

If you love history and the great outdoors, embark on an adventure like none other on board the Yankee Freedom III.

 
 
yankee freedom boat with fort jefferson in the background  
   
group of guests on boat looking at Fort Jefferson and lighthouse  

A luxurious, state-of-the-art catamaran, docked in Key West, the Yankee Freedom III will transport you to the famous Dry Tortugas and Fort Jefferson National Park.

Just 70 miles west of Key West, the Dry Tortugas is a collection of secluded islands that boast a military fort, a national park, camping grounds, sandy beaches, crystal waters, coral reefs, fishing, snorkeling and so much more. See the historic Fort Jefferson and the place where Dr. Samuel Mudd was held prisoner due to his involvement in the assassination of President Lincoln. Come face to face with colorful fish and marine species that live on the coral reef. Spend the afternoon exploring the island, bird watching, having a picnic on the beach or soaking in the sun, gather the family and spend the weekend camping. The Dry Tortugas offers extraordinary experiences for people of all ages.

There’s no better way to get to The Dry Tortugas than on board the Yankee Freedom III which has been ferrying guests for more than 30 years. The spacious catamaran is the fastest way to get there and features an air-conditioned cabin, outdoor deck with comfortable seats, restrooms, showers and a snack bar that serves sodas, beer, wine and mixed drinks.

view from top of fort jefferson   guests touring inside of fort


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  During the Civil War Key West, although the southernmost city in the country, was Yankee territory. Key West was the only place where you had to go north to fight for the South.  
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As you travel in comfort and style on the Yankee Freedom III, our experienced captain and crew will share with you fascinating facts and information about the Dry Tortugas, the wildlife and the natural surroundings of the area. Keep an eye out for playful dolphins swimming alongside of the boat and other friendly sea animals; the journey to the islands is half the adventure!

RESERVATIONS ARE REQUIRED!

 
 

For more information, go to drytortugas.com.

 
   
     
       
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  guests at lookout tower looking at ocean    
 
 
Key West Shipwreck Treasure Museum

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.

 
 

starburst - lift genuine silver bar

family standing in front of shipwreck museum
 
aerial view of guests viewing treasures inside shipwreck museum

Wrecking and salvage – the recovery of wrecked ships and their cargos (as well as the rescue of their crews & passengers) - was the foundation of Key West’s economy throughout the 1800’s. By the mid 1850’s, Key West had become the richest city per capita in the entire United States – all due to the wrecking industry.

The Key West Shipwreck Treasure Museum celebrates the rich history of the Key West wreckers with two floors of shipwreck artifacts that include treasures from the Spanish fleets of the 16 & 1700’s, as well as a vast collection of pieces from the 1856 wreck of the Isaac Allerton. Guests can even lift a silver bar salvaged from the Spanish treasure galleon, Nuestra Senora de las Maravillas.

The museum itself is a recreation of 19th Century wrecker tycoon Asa Tift’s warehouse that includes a 65-foot lookout tower. A variety of audio-visual displays (including a below-sea-level theater) create windows into Key West’s past and allow our guests to experience life as it was for the brave souls who risked their lives to retrieve shipwreck treasures.

Storytellers in period costume bring history to life with tales of the wreckers and their daring rescues, ensuring a fun and fascinating experience for the entire family.

old candles and candle holders• Two floors of artifacts from shipwrecks spanning 400 years
• 65-foot lookout tower offers a spectacular view of the island
• Numerous audio/visual presentations including a below-sea-level theater
• Storytellers in period costume bring Key West’s rich history to life
• Lift a silver bar from the wreck of a Spanish treasure galleon!

 
     
 
exterior of shipwreck museum old looking glass
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  The Issac Allerton became the largest individual award in the history of wrecking, with the cargo valued at $150,000. The salvaging was done bareback, diving without the aid of masks and tanks or diving suits.  
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For more information, go to keywestshipwreck.com.

   
 
   
       
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  two young girls reading plaque    
 
 
Key West Walking Tour

Discover the beauty of Key West hidden on its shady side streets and lanes, beginning at the Key West Memorial Sculpture Garden, dedicated to many influential people in Key West’s history.

 
 

cigar makers in factoryDuring your stroll through old town, our guide will point out the blend of architecture, tropical foliage and culture that makes Key West unique. You’ll hear about the island’s fascinating history, from the U.S. Navy presence in 1823 to combat piracy through the heydays of the wrecking, sponging and cigar industries. You’ll learn how Key West developed into one of the wealthiest cities in the country, and how it declined into one of the poorest. Join us for a fact-filled historical tour full of heartfelt stories, experiences and anecdotes about our island life!  

One Whitehead Street • Key West, FL 33040 • (305) 292-8990   
November - May: 9:30am

 
   
       
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  ghost trolley    
 
 
Ghosts & Gravestones Tour

Do you dare board the TROLLEY OF THE DOOMED? Many find Key West strange during the day; but after the sun goes down, the restless souls of the island’s frightful past begin to stir.

 
 

lantern and glow

You will hear their tales that have been all but forgotten as you travel the narrow, dark streets of Old Town - filled with 19th century wooden houses that hold on to the secrets of their former inhabitants. Stories so tragic, so chilling, you’ll see why Key West is one of the top ten most haunted cities in America.

robert the doll sitting on chairEXCLUSIVE nighttime entry into one of the island’s haunted Civil War forts - once quarantine barracks for suffering soldiers left to die from yellow fever; now home to an eerie doll that can play tricks on you if you don’t play nicely. Our Ghost Host will add a pinch of humor to Key West's dark side with tales of deathly love, tragic endings, scores to settle, wrongs to right and ghastly folk – some so strange it will be hard to believe they’re true.

Exclusive! Visit with Robert the Doll.

Reservations are required. Space is limited for this very popular excursion, so DON’T DELAY!

Where: 501 Front St. • 305-29-GHOST (305-294-4678)
When: Nightly.
Tour Length: 1 hour and 30 minutes.

 
   
       
 

Learn more, go to our Key West Ghost Tour.

   
       
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*Special exemptions apply to the following reservation based attractions: Yankee Freedom III, Boston Tea Party Ships & Museum and Ghosts & Gravestones charters.
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Historic Tours of America is a member of Trusted Tours & Attractions and our E-tickets are sold exclusively through them. Trusted Tours offers industry-leading value, guarantees, security and pricing for hundreds of the top tours and attractions throughout the United States.

To learn about more Key West packages, attractions and tours provided by other Trusted Tours & Attraction Members, go to TrustedTours.com.

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  Old Town Trolley Tours
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Historeum
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White House
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Historic Tours of America ® 201 Front Street, Key West, Florida 33040 • Phone: 855-629-8777 • Copyright © Historic Tours of America ®
Old Town Trolley Tours, Transportainment and Boston Tea Party Ships & Museum are registered trademarks of Historic Tours of America® .
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