The compact island of Key West packs remarkable value into its guided experiences. Walking tours and bike excursions efficiently cover major sites like Mallory Square and the Southernmost Point in just two hours. I particularly love the kayak eco-tours through the mangroves – they’re intimate and authentically local. The Southernmost Food & Cultural Walking Tour stands out for connecting Hemingway’s legacy with today’s vibrant food scene. For maximum enjoyment, travelers should consider these carefully selected top tours:
Key Points
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The Guided Bicycle Tour of Old Town Key West offers a comprehensive introduction to the city’s landmarks and attractions at a leisurely pace.
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The Key West Historic District Small-Group Walking Tour provides an engaging exploration of the area’s diverse architecture and historical significance.
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The Key West Mangrove Kayak Eco Tour offers an immersive experience in the local ecosystem, with opportunities to encounter various wildlife.
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The Southernmost Food & Cultural Walking Tour by Key West Food Tours showcases the city’s diverse culinary scene and cultural heritage.
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The Key West Afternoon Sail, Snorkel, Kayak & Sunset Excursion combines multiple water-based activities for a diverse and adventurous experience.
Guided Bicycle Tour of Old Town Key West
Although Key West offers a variety of tour options, the Guided Bicycle Tour of Old Town Key West stands out as a popular choice among travelers.
With an impressive 2,321 reviews and a 99% recommendation rate, this tour provides an engaging and informative way to explore the historic district. Guests can expect to visit iconic landmarks like Mallory Square, Mile Marker Zero, and the Southernmost Point Buoy, all while enjoying panoramic ocean views.
The tour includes a helmet, bottled water, and a delightful Key Lime Pie snack. While not recommended for those with back problems or serious medical conditions, the tour is accessible to infants and stroller users.
With morning and afternoon options available, this leisurely-paced bicycle tour is an excellent choice for first-time visitors looking to enjoy the rich history and culture of Key West.
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From Miami: Small Group Key West 1-Day Tour
For travelers seeking a comprehensive Key West experience from Miami, the Small Group Key West 1-Day Tour provides an excellent option. Priced from Kč 4,193 per person, this full-day tour includes professional transportation, a knowledgeable driver-guide, and admission to the Key West Narrated Tour.
Highlights along the way include the iconic Seven-Mile Bridge, the Southernmost Point Buoy, and a visit to the Hemingway Home & Museum.
Visitors will enjoy 2 hours of free time in Key West, where they can explore attractions like the Truman Little White House, the harbor area, the Old Customs House, and Seaside Plaza.
The tour departs at 8:00 AM from the SpringHill Suites by Marriott Miami Airport South, and good health is required to fully participate.
With a flexible itinerary that may adjust to weather or traffic conditions, this small-group tour offers a convenient and immersive way to experience the best of Key West from Miami.
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Key West Mangrove Kayak Eco Tour
The Key West Mangrove Kayak Eco Tour provides travelers with a unique opportunity to explore the captivating mangrove ecosystem of the Florida Keys.
This 2-hour tour, which has earned a 98% recommendation rate from over 1,840 travelers, immerses participants in the diverse wildlife and natural wonders of the region. Guided by knowledgeable experts, guests can expect to encounter a variety of marine life, including tropical fish, crabs, sea stars, jellyfish, and sea birds.
The tour also includes an educational component, where visitors learn about the local geology, ecology, and the significance of the Florida Keys’ unique environment.
Accessible to all ages and skill levels, the tour offers morning and afternoon departures, making it suitable for a range of schedules.
With a maximum group size of 10 participants, the experience ensures a personalized and intimate encounter with the mangroves. While not wheelchair accessible, the tour is stroller-friendly and welcomes service animals, providing an inclusive and memorable adventure for all.
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Key West Afternoon Sail, Snorkel, Kayak & Sunset Excursion
This 4.5-hour Key West Afternoon Sail, Snorkel, Kayak & Sunset Excursion offers travelers a captivating blend of activities to explore the island’s picturesque waters. Departing from the Opal Key Resort & Marina, guests can enjoy sailing, snorkeling, and kayaking for a personalized experience limited to 20 people.
The tour includes all necessary gear, from masks and fins to kayaks and wetsuits. Participants can discover the vibrant coral reefs and mangrove channels, with instruction provided for beginners. Along the way, knowledgeable eco-guides share insights about the Key West National Wildlife Refuge.
After the activities, guests can refuel with healthy snacks, soft drinks, and even wine and beer.
With a 4.7/5 rating based on customer reviews, this excursion promises memorable encounters with marine life, from dolphins and sea turtles to stingrays and small sharks.
Offering a flexible booking and cancellation policy, this afternoon adventure is a must-try for those seeking to enjoy Key West’s natural wonders.
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Southernmost Food & Cultural Walking Tour by Key West Food Tours
Designed to immerse travelers in Key West’s vibrant culinary scene, the Southernmost Food & Cultural Walking Tour by Key West Food Tours invites guests to embark on a 1.2-mile exploration of the island’s lesser-known mom-and-pop eateries.
With an impressive 98% recommendation rate and over 1,370 reviews, this guided tour offers a taste of local seafood, Cuban cuisine, and iconic key lime pie, providing a hearty lunch’s worth of samples.
Led by knowledgeable local guides, the small-group experience (limited to 12 participants) delves into the history, architecture, and culture of Old Town Key West, showcasing the city’s unique character.
Accessible for wheelchair users and those with strollers, the tour accommodates dietary restrictions and operates in all weather conditions, with ponchos provided if needed.
Priced from £77.31 per person, the Southernmost Food & Cultural Walking Tour promises an immersive and memorable experience for travelers seeking to savor the authentic flavors and sights of Key West.
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Kooky Key West Amazing Race & Tour
Seeking a more adventure-filled way to explore Key West? Consider the Kooky Key West Amazing Race & Tour. This 2-hour activity allows you to discover the island’s hidden gems while solving clues and tackling quirky challenges.
Work collaboratively with your group to score points and climb the leaderboard. The experience is family and dog-friendly, featuring a mix of indoor and outdoor activities. Interact with locals to find clues and complete tasks. A live host provides hints and assistance throughout the game.
The activity begins at a scenic local favorite and takes you to various checkpoints around the city. Suitable for corporate groups, travelers, locals, bachelorette parties, birthdays, families, and friends, the Kooky Key West Amazing Race & Tour is a unique way to experience the island.
Custom-designed experiences and virtual team-building options are available. With free cancellation up to 24 hours in advance and the option to reserve now and pay later, this tour offers flexibility and value starting from $24 per person.
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Historic Seaport Food & Walking Tour by Key West Food Tours
Although the Kooky Key West Amazing Race & Tour offers an adventure-filled way to explore the island, the Historic Seaport Food & Walking Tour by Key West Food Tours provides a more immersive experience for those seeking to discover the local cuisine and culture.
With a solid 4.9 rating from over 570 reviews, this tour offers a badge of excellence and a 98% traveler recommendation. Participants can expect to sample a variety of local seafood, as well as non-seafood options, at five different locations.
The tour also includes a guided walking exploration of downtown Key West, providing insight into the city’s history and culture. While hotel pickup and gratuities aren’t included, the tour does accommodate most dietary restrictions.
Ultimately, the Historic Seaport Food & Walking Tour presents an excellent opportunity for both first-time visitors and locals to explore the culinary and cultural richness of Key West.
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Key West: All Day Eco Tour – Kayak, Snorkel and Sail!
The Key West: All Day Eco Tour – Kayak, Snorkel and Sail! offers adventurous travelers a chance to experience the natural beauty of the Florida Keys in a single excursion.
This 6.5-hour tour includes kayaking through the mangrove forests, snorkeling along the coral reef, and sailing on a catamaran. Participants can expect to see a variety of marine life, such as colorful tropical fish and possibly even dolphins.
The tour is highly rated, with a 4.9 out of 5-star review from 9 customers. At $48.56 per person, it provides excellent value for the diverse activities and stunning scenery.
The tour is suitable for all skill levels, making it an ideal choice for both experienced adventurers and those new to water sports.
With pickup and drop-off from select hotels in Key West, the All Day Eco Tour offers a seamless and convenient way to take in the natural wonders of this Florida destination.
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The Original Key West Island Jet Ski Tour From the Casa Marina
Offering a thrilling way to explore the scenic island of Key West, the Original Key West Island Jet Ski Tour from the Casa Marina provides adventurous travelers with the opportunity to experience the destination from a unique vantage point.
With 305 reviews and a 98% traveler recommendation, this tour has earned a reputation for delivering an exhilarating experience guided by knowledgeable staff.
Suitable for all experience levels, including novices, the tour allows for free play time on the water, catering to those seeking a fun and customized adventure.
Outfitted with life jackets and towels, participants can enjoy the tour’s moderate physical demands, though it’s not recommended for those with serious medical conditions or pregnant travelers.
Located at 720 Seminole St, the tour starts and ends at the meeting point, offering convenient parking options nearby.
Priced from $150 per group with a free cancellation policy, this jet ski tour is an excellent choice for couples, families, and groups looking to add a thrilling water-based activity to their Key West itinerary.
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Key West Historic Homes and Island History – Small Group Walking Tour
For travelers seeking a deeper exploration of Key West’s rich history and captivating architecture, the Key West Historic Homes and Island History – Small Group Walking Tour offers an immersive experience.
With 375 reviews and a 99% traveler recommendation, this 2-hour guided tour takes visitors on a journey through the island’s unique landmarks and historic homes.
The tour visits sites like the Casa Antigua, Curry Mansion Inn, and Truman Annex Park, providing participants with fascinating insights into Key West’s past.
Led by knowledgeable local guides, the small groups of up to 10 people ensure a personalized experience. Rain ponchos and umbrellas are provided, and bottled water is suggested, with alcoholic beverages available for purchase.
While the tour is accessible for wheelchair users and those with strollers, a moderate fitness level is required. Travelers with back problems or serious medical conditions may want to consider alternatives.
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The Dark Side of Key West Adults Only Walking Tour
Though Key West is renowned for its vibrant culture and laidback island charm, the Dark Side of Key West Adults Only Walking Tour takes visitors on a captivating journey through the city’s darker history.
Priced at $34.99 per person and lasting 1.5 hours, this adult-only tour explores the haunted sites and grisly tales that have shaped Key West’s unique identity.
Led by knowledgeable guides, you will visit the Hemingway House, Artist House, and other notable locations, learning about historic events and figures that have contributed to the town’s shadowy past.
From stories of paranormal activities to accounts of grisly murders, the tour provides a glimpse into Key West’s more sinister side.
With an overall rating of 4.3/5 based on 26 reviews, the Dark Side of Key West Adults Only Walking Tour offers a thrilling and informative experience for those intrigued by the city’s macabre legacy.
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Key West Island 90-Minute Jet Ski Tour From the Marriott Beachside
The Key West Island 90-Minute Jet Ski Tour from the Marriott Beachside allows adventurous travelers to experience the island’s stunning coastline at thrilling speeds. Rated 4.8 out of 5 stars with 171 reviews, this guided tour takes participants around Key West at speeds up to 45 mph.
Travelers will visit popular landmarks and learn about the island’s history from a local licensed guide. The tour includes stops at a deserted sandbar for water activities, and life jackets and boaters safety certification are provided.
The meeting point is Barefoot Billy’s Watersports, where free parking is available. Not recommended for those with medical conditions or mobility issues, the tour requires a moderate fitness level.
With a maximum of 12 travelers per tour, participants can expect an intimate and personalized experience. Overall, reviewers highlight the informative and friendly guides, the enjoyment of high speeds and maneuvering, and the tour’s ability to provide both sightseeing and thrills.
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Key West: History and Culture Southernmost Walking Tour
Offering a comprehensive introduction to Key West’s rich history and vibrant culture, the Key West: History and Culture Southernmost Walking Tour provides an engaging 1.5-hour experience for visitors.
Priced at $39.99 per person, this guided walking tour takes participants through the island’s southernmost area, highlighting its captivating past, including shipwrecking, sponge harvesting, and cigar manufacturing.
Led by knowledgeable local guides, the tour concludes at the iconic Southernmost Point buoy, where guests can explore further using free maps provided.
Suitable for couples, groups, solo travelers, and families, the tour isn’t recommended for individuals with limited mobility, as it covers approximately 1.4 to 1.8 miles in warm weather.
With a 4.9/5 rating based on 13 reviews, the tour is praised for its engaging guides and informative content, offering an immersive way to discover Key West’s enduring heritage.
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Guided Clear Kayak Eco-Tour Near Key West
Travelers seeking an immersive eco-adventure near Key West can embark on the Guided Clear Kayak Eco-Tour. This small-group tour, limited to a maximum of six participants, provides a personalized experience as guests explore the underwater world in 100% clear kayaks.
With a 95% recommendation rate and 439 positive reviews, the tour offers the chance to spot diverse marine life, including starfish, tropical fish, nurse sharks, turtles, and jellyfish.
The tour includes all necessary equipment, such as life jackets, whistles, and dry bags for personal items. Knowledgeable guides lead the way, sharing their expertise on the local ecology. Guests also receive bottled water, hats, sunscreen, and sunglasses.
While the tour isn’t wheelchair accessible, it’s suitable for those with moderate physical fitness, with a weight limit of 425 lbs per tandem kayak. Priced at $79 per person, the Guided Clear Kayak Eco-Tour provides a unique and memorable way to take in the natural beauty of the Florida Keys.
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Key West: Ghosts & Gravestones Guided Trolley Tour
For those seeking a chilling adventure in Key West, the Key West: Ghosts & Gravestones Guided Trolley Tour offers a unique opportunity to explore the city’s supernatural history.
This 1-hour tour takes guests on a spooky journey through Key West’s haunted sites, including the Marrero House, Porter Mansion, and the infamous Hanging Tree. Led by a gravedigger guide, the tour delves into tales of lynching, clandestine burials, and local superstitions, providing a thrilling and informative experience.
Priced at $39.85 per person, the tour departs from the Old Town Trolley ticket booth and is wheelchair accessible with 24-hour advance notice.
Guests will also have the chance to step inside the Shipwreck Treasures Museum and learn about the eerie legends surrounding Count Karl Von Cosel and Robert the Doll.
With an overall rating of 4.2/5 from 119 reviews, the Key West: Ghosts & Gravestones Guided Trolley Tour is a must-do activity for those eager to uncover the darker side of this vibrant island city.
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The Dark Side of Key West Ghost Tour
As the sun dips below the horizon, the streets of Key West come alive with tales of the supernatural on the The Dark Side of Key West Ghost Tour.
Rated 4.6 stars with 91% of travelers recommending it, this 90-minute walking tour explores the city’s darker past. Guests visit landmarks like St. Paul’s Episcopal Church and Captain Tony’s Saloon, learning about the spooky and grisly aspects of Key West’s history from knowledgeable guides.
The tour, which costs $34.99 per person, is an entertaining way to discover the city. While most reviews praise the guides’ engaging storytelling, some mention issues like misleading descriptions and no-shows.
Wheelchair-accessible with a maximum group size of 30, the tour isn’t recommended for those with back problems or who are pregnant.
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Key West: Reef Snorkel Morning Tour With Breakfast & Mimosas
This 3-hour Key West: Reef Snorkel Morning Tour with Breakfast & Mimosas offers a chance to explore the third longest coral reef in the world. Priced at $49.95 per person with free cancellation 24 hours in advance, this tour provides a comprehensive snorkeling experience.
Guests will see over 110 species of coral and 500 species of tropical fish while enjoying a light breakfast and mimosas. The tour also includes free draft beer on the return journey and stunning views of Key West’s coastline.
Departing from the Sunset Watersports kiosk, the tour includes snorkel equipment, safety gear, and hotel pickup and drop-off. A safety briefing is provided before snorkeling, and guests are advised to bring swimwear and a towel.
With an overall rating of 4.4/5 based on 182 reviews, the tour receives high praise for its knowledgeable guide, efficient transportation, and excellent value for money.
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Key West Historic District Small-Group Walking Tour
Explore the rich history and unique charm of Key West’s Historic District on this 2-hour small-group walking tour.
Led by knowledgeable local guides, you’ll stroll 1.4 to 1.8 miles at a moderate pace, taking in the area’s diverse architecture, cultural influences, and historical landmarks.
The tour departs from the Flamingo Boutique & Mimosa Bar and ends at Mary Ellens Bar & Restaurant, with a maximum group size of 12 travelers.
Along the way, your guide will share engaging stories and provide valuable insights, using visual aids like photos, maps, and historical documents to enhance your understanding.
While the tour is stroller-accessible, it’s not wheelchair-friendly.
Amenities include a bike rack and ponchos if it rains, but no restrooms are available.
Paid parking is offered at 616 Simonton St.
With an impressive 99% recommendation rate and 5.0 overall rating, this tour is a must-do for anyone exploring the rich history and charm of Key West.
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Key West: Dolphin & Snorkel Boat Tour With Sunset Option
Embark on an unforgettable 3-hour journey to discover the marine wonders of Key West. The “Key West: Dolphin & Snorkel Boat Tour with Sunset Option” takes you to watch dolphins in their natural habitat and explore the Key West National Wildlife Refuge.
Snorkel in a beautiful reef with the chance to spot fish, turtles, and even sharks. With options for day or sunset cruises, you can choose the experience that suits you best. The tour includes safety equipment, snorkeling gear, and hotel transportation.
While some customers report a lack of marine life during the snorkeling portion, the overall experience earns a 4.3/5 rating. Enjoy an ice-cold beer on the return journey as you reflect on the day’s adventures.
With a price from Kč 1,830 per person and a flexible cancellation policy, this tour provides great value for your money. Don’t miss the opportunity to learn about the natural beauty of Key West.
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Ultimate Jet Ski Tour of Key West
Adventurous travelers can’t miss the “Ultimate Jet Ski Tour of Key West,” a 28-mile scenic adventure around the island’s stunning coastline.
This top-rated jet ski tour provides a thrilling way to experience Key West’s tropical blue waterways, including the Atlantic Ocean and Gulf of Mexico. Guests have the opportunity to spot dolphins, stingrays, sea turtles, and manatees during the guided tour led by professional instructors.
Equipped with top-of-the-line Sea-Doo jet skis, accommodating up to two adults or one adult and two children, participants can look forward to an adrenaline-pumping experience.
With a convenient meeting location near the Hyatt Centric hotel and a 45-60 minute check-in, the tour is easy to fit into any Key West itinerary.
Rated 4.6 out of 5 based on 589 reviews, the “Ultimate Jet Ski Tour of Key West” is a must-do for anyone seeking an adventurous and scenic way to explore the Florida Keys.
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Key West: Snorkeling Tour With Mimosas or Margaritas
For those seeking a refreshing way to experience the vibrant marine life of Key West, the “Key West Reef Snorkeling with Drinks and Sunset Option” tour provides an ideal opportunity. Priced from £28.28 per person, this 3-hour adventure aboard a 65-foot catamaran takes visitors to North America’s only living coral reef.
Guests can snorkel in crystal-clear waters and discover an array of marine life, all while enjoying complimentary drinks like mimosas, margaritas, rum punch, beer, and wine. The tour offers morning, afternoon, and sunset options, each with its own unique appeal.
Participants must know how to swim, and those under 18 require a parent or guardian. With an overall rating of 4.2/5 from 217 reviews, the tour is praised for its professional crew, clean boat, and exceptional service.
While the snorkeling spots may have mixed feedback due to jellyfish presence, the experience remains a top choice for those seeking to explore Key West’s underwater wonders.
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Highlights and Stories of Key West – Small Group Walking Tour
Exploring the captivating history and vibrant culture of Key West comes alive through the “Highlights and Stories of Key West – Small Group Walking Tour.”
This immersive 2-hour excursion takes visitors on a journey through the island’s Old Town, showcasing its renowned landmarks and hidden gems. Led by knowledgeable local guides, the tour focuses on Key West’s rich history, legends, biodiversity, and unique cultural heritage.
Guests will stop at iconic sites like the Audubon House, the US 1 Mile Marker 0, and the Southernmost Point, while learning fascinating stories and insights.
With a maximum of 10 travelers, the tour provides personalized attention and opportunities to engage with the guide. Rated 5.0 stars with 100% traveler recommendation, the tour is praised for its informative and engaging nature, as well as the guide’s exceptional storytelling abilities.
Whether you’re a first-time visitor or a seasoned Key West enthusiast, this walking tour offers an unparalleled introduction to the island’s captivating essence.
It’s the perfect way to kickstart your exploration of this unique Florida destination.
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Key West: Guided Bicycle Tour With Key Lime Pie
Immersing oneself in the captivating charm of Key West is effortless with the “Key West: Guided Bicycle Tour With Key Lime Pie.” This 2.5-hour excursion provides participants the opportunity to explore the island’s historic Old Town while learning about its rich heritage, including tales of smuggling and shipwrecks.
The tour includes visits to iconic sites such as Mallory Square, Mile Marker Zero, Ernest Hemingway’s home, and the Southernmost Point. Participants will also discover Higgs Beach, White Street Pier, and the Key West Cemetery.
The tour concludes with a slice of traditional key lime pie, the perfect ending to a delightful experience.
Priced from £44.51 per person, the tour is led by knowledgeable, English-speaking guides and includes a helmet, basket for belongings, water, and the key lime pie.
Participants must reach the meeting point independently, as no hotel pickup or drop-off is available. The tour isn’t suitable for individuals unable to ride a bike or for wheelchair users.
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Hemingway Food and Walking Tour
What better way to discover the captivating life and culinary tastes of Ernest Hemingway than the Hemingway Food and Walking Tour in Key West? This 2-hour excursion takes visitors on an immersive journey through the renowned author’s stomping grounds, exploring the food, culture, and history that defined his time in the island city.
With a maximum of 15 travelers, the small-group tour provides a personalized experience led by knowledgeable guides like Caleb and Liz, who earn high praise for their engaging storytelling. The tour covers approximately 2 miles of walking, offering an intimate glimpse into Key West’s historic district.
Highlights include savoring Hemingway-inspired dishes such as chicken street tacos and conch fritters, as well as sipping on included alcoholic beverages.
The tour concludes at the iconic Capt Tony’s Saloon, a favorite haunt of the literary legend. Despite some feedback about pricing and occasional cancellations, the Hemingway Food and Walking Tour remains a highly recommended way to experience the writer’s legacy in Key West.
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Key West: Afternoon Reef Snorkel Tour With Open Bar
Visitors to Key West can embark on a thrilling 3-hour Afternoon Reef Snorkel Tour with an open bar. Priced from $59.95 per person, the tour allows participants to snorkel in the warm tropical waters around the only living coral barrier reef in North America.
Experienced instructors guide snorkelers as they marvel at the vibrant sea life. During the return sail, there’s a chance to spot dolphins. The tour includes a round-trip catamaran ride and an open bar featuring cocktails, beer, wine, and soda.
Guests can relax on the catamaran’s sun deck and enjoy the drinks. With a 4.2/5 overall rating based on 253 reviews, the tour is praised for its great crew, good experience for families, and friendly and entertaining guides.
Travelers can take advantage of the free cancellation policy and reserve now and pay later option. All that’s required is to arrive 30 minutes early, bring a passport or ID, hat, swimwear, towel, and sunscreen.
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Recap
Key West offers a diverse array of tours that cater to various interests. From guided bicycle rides and kayak eco-tours to sunset sails and food-themed walks, visitors can enjoy the island’s rich history, culture, and natural beauty. These tours provide an engaging and memorable way to explore the unique charm of this iconic Florida destination.