Florida Keys
Seasonal & Holiday Activities

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Our most recommended Florida Keys Seasonal & Holiday Activities

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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Ghosts & Gravestones Tour of Key West

2. 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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Key West: 2-Hour Sunset Sail with Live Music

3. Key West: 2-Hour Sunset Sail with Live Music

Set sail on a breathtaking sunset cruise aboard a spacious catamaran. Admire views of the Historic Seaport, pass jugglers and entertainers at the Mallory Square Sunset Celebration, and gaze at Fort Zachary Taylor. Enjoy unlimited drinks and appetizers on board, as well as live musical entertainment. Sail past the landmarks of Key West, as your captain positions the ship to maximize your view of the sunset. Savor a fantastic evening on the water.

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Key West: Sunset Sailing Trip with Open Bar, Food and Music

4. Key West: Sunset Sailing Trip with Open Bar, Food and Music

Join a sailing experience to get you closer to the sunset than ever before. Set sail from the historic sea port of Key West and head straight out to sea for a cruise with unobstructed views of the sunset on the horizon. During the cruise, enjoy an unlimited open bar, with a wide variety of drinks on offer including rum runners, Champagne, margaritas, and draft beer. Taste a selection of finger foods, ranging from Swedish meatballs, veggie treats, cheese and crackers, pita and hummus, and meat and veggie platters. You will be sailing on one of Key West's newest sailing catamarans, the Sandie Cat. This vessel has capacity for up to 149 passengers across 3 decks, so there will always be plenty of room onboard. Grab a drink, head to the upper deck, and dance to live music as you watch the sun go down. The captain and crew will even let you help raise the sails and you can ask to have a picture taken driving the boat.

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Key West: Bone Island Haunted Pub Crawl

5. Key West: Bone Island Haunted Pub Crawl

"Cayo Hueso" in Key West, as it was originally named, translates to "Bone Key" or "Bone Island". On this haunted pub crawl you will experience why Key West is consistently ranked as one of the top five most-haunted cities in America. Crawl along as you delve into some of the more spirited pubs of Old Town. You'll discover Key West's history of cursed treasure, voodoo, murder, suicide, haunted mansions, unexplained deaths, and more. Your professional "ghost host" will introduce you to the darkest side of Bone Island, and after 3 haunted pubs you will be issued a souvenir t-shirt before being released into the night.

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Key West Champagne Cruise at Sunset

6. Key West Champagne Cruise at Sunset

Leave your worries behind and set sail into a Key West sunset on a champagne cruise aboard a spacious, state-of-the-art catamaran. Cruise the tropical waters with a warm ocean breeze and magnificent sunset as your backdrop. Toast the end of another perfect day in paradise as you watch the sun slowly disappear beyond the horizon. Take advantage of the complimentary beer, wine, champagne and sodas and snuggle up with that special someone as the sun paints the sky brilliant hues of blue, yellow, orange, pink and red. Get a better understanding of why a sunset on the water is what this island paradise is all about. The sunset cruise is extremely popular, so book early!

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Key West: Haunted Walking Tour with Psychic Guide

7. 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: Ghosts of Key West Walking Tour

8. Key West: Ghosts of Key West Walking Tour

Explore the spooky side of Key West on this ghost-themed walking tour. See the city’s most popular haunted spots and hear fascinating stories about the ghosts of its past. Hear about Robert the Doll, the haunted doll with supernatural powers who sits in the city's East Martello Museum. Stop by the La Concha Hotel and learn about the ghostly legends contained within. See fascinating locations like the Hemingway House and the Artist House. Stroll the city's streets with a guide who is an expert on its dark, haunted history. Become a history buff after learning about the historic events and figures that helped shape the unique culture of Key West

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Other Sightseeing Options in Florida Keys

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What people are saying about Florida Keys

Awesome for new & experienced riders! Jake & crew were very friendly, fun, patient & professional. Thank you for an excellent ride! I would highly recommend!!! A few things: -Directions to jet ski office is confusing with address given & on Google maps. As you turn right off main rd., "lot 1" with valet parking will be immediately to left. Around the left side of that lot is where office & jet skiing are. Park at closest store. - Only 16+ can drive their own jet ski (but my 15 yo very active son had a blast being on the back!) - Bring towel & wear fitted sunglasses to keep wind out of eyes when riding (it's windy!)

Great trip on a calm lake with a very large and generous selection of drinks and various snacks. The sunset at Key West is an experience.

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

Top ! I can only recommend. Nice crew, great boat, delicious snacks and drinks as well as live music

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