Florida Keys
Theme Tours

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Our most recommended Florida Keys Theme Tours

Key West: 2-Hour Sunset Sail on Schooner America 2.0

1. Key West: 2-Hour Sunset Sail on Schooner America 2.0

Take in the vibrant colors of Key West's fabulous sunset as you glide through the waters on one of the finest boats in the Key West Schooner Fleet. Watch the sun fade into the horizon and the stars emerge into the deep blue sky. America 2.0 features teak decks, mahogany-trimmings, and 3,600 square feet of canvas! Sit back and relax while she plies effortlessly through the crystal-clear waters off Key West, heading towards the horizon for the quintessential Florida sunset experience! Some of the sights on this sailing adventure include a view of Fort Zachary Taylor from the water, and views of the famed Sand Key Reef, Mallory Square, and Sunset Pier. Keep your eyes peeled for wildlife such as dolphins, sea turtles, and water birds – and for the famous Key West "Green Flash" at sunset. Bring your family or friends and join the courteous and professional crew for this sunset sail that completes the Key West experience in comfort and elegance.

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Key West: Sunset Cruise with Buffet Dinner and Open Bar

2. Key West: Sunset Cruise with Buffet Dinner and Open Bar

Climb aboard "The Party Cat" for a wonderful 2-hour cruise around the harbor.   Enjoy a freshly prepared tropical food buffet in an enclosed air-conditioned dining room. Choose from dinner options such as roast pulled pork in mojo sauce, deep fried sweet plantains, black beans and rice, marinated grilled chicken, fried fish, mixed vegetables, mashed potatoes, pasta with mini shrimp and Cuban bread and butter. Sip on your choice of tipple — margaritas, rum runners, champagne, beer, wine or spirits. After dinner, stroll upstairs to the upper deck for live music. Dance the night away or simply listen to the beat as you watch the sun set over the horizon into the Gulf of Mexico. Witness the beautiful display of colors across the night sky.

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Key West: Jet Ski Island Tour with Free Second Rider

3. Key West: Jet Ski Island Tour with Free Second Rider

Climb on a brand new jet ski and set off on a thrilling island jet ski adventure. With your experienced guides, navigate through mangrove islands, stop at a local sandbar for a dip in the crystal clear waters, get a picture of the southernmost point from the water, and more. Each tour has 2 guides to ensure the complete safety of riders. The first guide sets the pace at the front, allowing all riders who want to go fast the opportunity to floor it. The second guide brings up the back, allowing the riders who want a more leisurely tour to go at their own pace. This tour has been voted the best jet ski tour in Key West. Get a great deal with a free second rider on each jet ski.

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Ghosts & Gravestones Tour of Key West

4. Ghosts & Gravestones Tour of Key West

Many find Key West a strange place during the day; but after the sun sets, the restless souls of the island’s frightful past begin to stir. On this 1-hour ghost tour, you will hear all-but-forgotten tales as you travel the dark and narrow streets of the Old Town. Pass 19th-century wooden houses that hold secret stories of former inhabitants; stories so tragic and chilling, you’ll soon see why Key West was named one of the top 10 most haunted cities in America. Your 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…

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Miami: Day Trip to Key West with Optional Snorkeling

5. Miami: Day Trip to Key West with Optional Snorkeling

Start your day on an air-conditioned bus from Miami Beach to Key West with a 4-hour drive. Watch as your tour guide points out the famous 31 Caribbean Islands along the drive known as the Florida Keys. Cross 43 bridges as you travel through the Keys to Key West. See the Atlantic Ocean and the Gulf of Mexico while driving by the coastline. Key West is the most southern point of the USA and only 90 miles from Cuba. Once you arrive in Key West, get 6 hours to explore the island at a leisurely pace. You can enjoy water activities, go on a hop-on trolly, stroll the artistic streets, or sit at outdoor cafes. Key West is the home of Ernest Hemingway, and you can visit his former residence. Nearby the cruise port, you can visit Mallory square for shopping. You may also choose to add one of the most popular adventure activities such as hop on hop off tour or the Conch Tour Train, Key West Aquarium, Key West Shipwreck Museum, Sails to Rails Museum, or the Truman Little White House. Make your way back from Key West to Miami Beach at 5:00 PM.

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Key West: Rum and Reggae Afternoon Snorkel and Sunset

6. Key West: Rum and Reggae Afternoon Snorkel and Sunset

Enjoy 2 exciting activities in 1 trip as you snorkel North America’s only living reef system from a spacious catamaran, enjoying the rhythmic sounds of reggae music in tropical waters. Then, watch the sunset over the horizon! Climb aboard the state-of-the-art catamaran from the most luxurious fleet in the Florida Keys. Upon arrival at the reef, get assistance and instructions from the friendly crew before you descend “the stairway to the sea.” Discover the wonders of the aquatic environment and its pristine coral reefs, and snorkel among an abundance of marine life, including tropical species found nowhere else on earth. Upon completion of your snorkeling adventure, enjoy some complimentary rum punch, a signature tropical beverage, beer, wine and champagne. Then, leave your worries behind as you sail off into Key West’s famous sunset. Feel the warm ocean breeze as you watch a magnificent sunset. Toast the end of another perfect day in paradise as you see the sun slowly disappear beyond the horizon.

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Key West: Drag Queen Guided Pub Crawl with Sing-a-Longs

7. Key West: Drag Queen Guided Pub Crawl with Sing-a-Longs

Meet your guide for the night, a world-class drag queen, at the award-winning lounge, Aqua Bar and Nightclub at 711 Duval St. in Key West. Grab a cocktail and mingle with your fellow crawlers as you await the ring of the ‘bitch bell’ to announce the kick-off of the tour. First, follow your guide through the vibrant streets of Key West and prepare to sing and dance your way through the city as you learn how to party like a true queen. Now you know how to behave like a queen it's time to be treated like one too — skip to the front of the line at every bar and pub along the crawl. Then, spend the night at a number of Key West's best bars and clubs, drink delicious and reasonably priced cocktails, laugh with your fellow crawlers, dance like a queen, and experience how the other half lives. Enjoy a fun-filled tour that's perfect for bachelorette parties, birthdays, and other memorable events.

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Key West Beachside Parasailing

8. Key West Beachside Parasailing

Board the parasailing boat from Smather's Beach. Get strapped into the harness on the aft of the parasailing boat then slowly rise into the air under a beautiful red, white, and blue parasail. Get an unobstructed panoramic view of Key West from over 300 feet in the air. Slowly sink down for a cooling dip in the waters before you rise high above Key West again. Get reeled back onto the aft deck of the boat following your memorable high flying adventure.

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

9. 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: Southernmost Food and Cultural Walking Tour

10. Key West: Southernmost Food and Cultural Walking Tour

Celebrating the Cuban and Caribbean influences on both food and culture, enjoy a 3-hour guided small group experience. Visit 5 different locations, carefully chosen to help you check off those "must try" dishes that Key West is known for. Enough for a hearty lunch, tastings are served from locally adored eateries, unique "hole in the walls", and family-owned ethnic restaurants. Discover the spots that the locals frequent to eat, drink and discover the island. Between tastings, explore the island’s different cultural neighborhoods and rich history through the generations. Your knowledgable local guide will share stories of the local industry, Key West's colorful past, and historical landmarks. After the tour, 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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Other Sightseeing Options in Florida Keys

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What people are saying about Florida Keys

Super fun. Food was excellent and plenty enough time to get all you want to drink. We stayed up top and Was able to hang out near the DJ. Music wasn’t too loud and the sunset was awesome. Crew were very nice as well.

The boat is stunning, the crew are warm and welcoming and the service is impeccable - a great addition to any trip to Key West!

I was very impressed with the quality of the food. The DJ/Performer was excellent. Good time. Thank you.

As advertised!. Great hard working crew on the Sunset Cruise on 12-29-21. Highly recommended.

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