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21 results | All Key West Tours

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Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

star-5
273
Leave behind the crowds of Key West and catch a quintessential Florida sunset while enjoying drinks on a sailboat. There is no better vantage point for watching the sunset over the water than from the water itself. And, while larger sunset cruises can get overcrowded, this small group experience ensures you have a spot at the rail when it comes time to capture photos of the setting sun.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$61.46
From
$61.46
Taking safety measures

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
Likely to Sell OutLikely to Sell Out

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres

star-4.5
1105
Watch the sun set and the moon rise off the coast of Key West on this sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset as the sun glistens and gently settles into the water. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer and soft drinks are included.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$89.95
From
$89.95
Taking safety measures

Key West Historic Seaport Food Tasting and Cultural Walking Tour
Likely to Sell OutLikely to Sell Out

Key West Historic Seaport Food Tasting and Cultural Walking Tour

star-5
243
Taste your way through Key West's Historic Seaport on a gourmet walking tour with a local guide. You'll stroll from the beach and docks into some of the most colorful neighborhoods in Key West, pausing to sample locally-caught fish tacos, Key West pink shrimp, spiny lobster, or other just-as-delicious non-seafood options, learning about Key West history along the way. Don't forget to save room for a refreshing glass of white wine and our famous key lime pie! Exploring Key West on foot is an ideal way to soak up the vibrant atmosphere, and group size is limited to 10 people to ensure personal service from your guide.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$88.68
From
$88.68
Taking safety measures

Shark and Wildlife Viewing Adventure in Key West
Likely to Sell OutLikely to Sell Out

Shark and Wildlife Viewing Adventure in Key West

star-5
729
Get up close with sharks and other marine wildlife on this boat tour from Key West. Travel on board an eco-friendly, 34-foot catamaran just a few miles off the coast of Key West. See dolphins, stingrays, turtles and birds and learn about Key West’s waters, and then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat. Bring a camera to capture the excitement as these super predators swarm. Cold drinks, snacks and polarized sunglasses are included on this Key West shark cruise.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$84.27
From
$84.27
Taking safety measures

Key West Pub Crawl

Key West Pub Crawl

star-4.5
153
Get ready to party in paradise on this guided, 2.5-hour Key West pub crawl. The beautiful island city of Key West is famous for its raucous bar scene. Visit some of its most popular and entertaining establishments, beginning downtown and then traveling to the historic seaport and back to busy Duval Street. Enjoy a domestic beer or mixed drink at each of the five locations and receive a free souvenir t-shirt to commemorate the event. Guests must be at least 21 years old to participate.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$34.99
From
$34.99
Taking safety measures

Parasailing in Key West with Professional Guide

Parasailing in Key West with Professional Guide

star-4.5
143
Get a bird’s-eye view of Key West from high above the crystal blue waters of the Atlantic Ocean on this parasailing tour. Experience the thrill of flying while watching the bustling activity along the coastline and the abundance of marine life below. See dolphins, turtles, fish, and more from 300 feet in the air. Enjoy gentle, dry takeoffs and landings.
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  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
$89.95
From
$89.95
Taking safety measures

Key West Southernmost Food and Cultural Walking Tour
Likely to Sell OutLikely to Sell Out

Key West Southernmost Food and Cultural Walking Tour

star-5
532
Eat your way around Key West on this food tour with a guide who introduces you to 'mom and pop' eateries in the Old Town historic district. Taste seafood, Cuban cuisine, and, of course, key lime pie. The walking tour route takes you off typical touristy streets so you can see Key West like a local, listening to insights about the city's food, architecture, and history along the way. Tastings are enough for a hearty lunch.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$88.68
From
$88.68
Taking safety measures

Guided Bicycle Tour of Old Town Key West

Guided Bicycle Tour of Old Town Key West

star-5
1223
Ride through the streets of Old Town Key West during a leisurely bicycle tour—a perfect introduction for first-time visitors. Learn about the island's history and see highlights such as Mallory Square, Mile Marker Zero, and White Street Pier. Pedal out to the Southernmost Point Buoy and enjoy panoramic ocean views. Plus, choose from morning or afternoon times to easily fit this tour into your schedule.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$49.81
From
$49.81
Taking safety measures

Key West Mangrove Kayak Eco Tour

Key West Mangrove Kayak Eco Tour

star-5
660
Paddle a kayak through mangrove creeks and shallow water on a Key West kayaking tour that offers an up-close look that this unique coastal environment. This guided tour is the perfect way to spot Florida wildlife in a natural habitat.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$50.00
From
$50.00
Taking safety measures

Key West Full-Day Power Adventure: Sailing & Watersports Package

Key West Full-Day Power Adventure: Sailing & Watersports Package

star-4.5
585
Enjoy the Key West sunshine on a full-day catamaran excursion, and take part in a range of watersports, too. As you cruise around the alluring Gulf of Mexico, gaze out at the scenery and spot local marine life. Choose from a range of activities from snorkeling and kayaking to adrenaline-fuelled parasailing or Jet Skiing. Breakfast and lunch are served on board.
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  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$209.95
From
$209.95
Taking safety measures

Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar
Likely to Sell OutLikely to Sell Out

Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar

star-5
228
Enjoy the sunset from the water on this Key West cruise aboard a classic schooner. As you stand on the deck of the tall ship, pass by sights such as Mallory Square with its Sunset Celebration and the Navy Mole, where big ships dock. Hors d'oeuvres and unlimited drinks are included onboard. Take your pick of beer, wine, sparkling wine, cocktails, soda, and homemade tropical sangria.
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  • 2 hours
  • Free Cancellation
From
$99.95
From
$99.95

Parasailing in Key West Seaport

Parasailing in Key West Seaport

star-4.5
96
Try something new in Key West: parasailing. Adventure seekers who've booked this trip will love soaring over the Key West Seaport. The experience is available for singles, doubles, and even triples so it's a fantastic activity for a group of friends or a family. You'll board a state-of-the-art boat, get briefed by the crew, and then fly over the city—free as a bird.
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  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
$89.95
From
$89.95
Taking safety measures

Key West Sunset Sail Aboard Schooner

Key West Sunset Sail Aboard Schooner

star-5
239
Set sail on a replica of the 1851 Schooner America on a cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$103.20
From
$103.20
Taking safety measures

Paradise Taxi & Tours USVI - St. Thomas, Virgin Islands- Island Scenic Tour

Paradise Taxi & Tours USVI - St. Thomas, Virgin Islands- Island Scenic Tour

star-5
93
Paradise Taxi & Tours USVI with Big Moe is your personal guide to tours and transportation. A trip to St. Thomas is exactly the Caribbean vacation you dream of. Spectacular views, paradise beaches, calypso music, culture and history-straight out of a magazine. During our Island Scenic Tour enjoy the peace and quiet of driving around and exploring the idyllic views, beautiful bays and lush tropical ridges. Magnificent Island views from Mountain Top (2,100 ft above sea level) while sipping banana daiquiris, along with duty-free shopping of jewelry, T-shirts, spirits, and souvenirs. Witness the natural beauty from Skyline Drive Lookout and Drake’s Seat of fringe rolling hills, Magen’s Bay Beach and other Caribbean islands. Historical landmark, Fort Christian, for historical highlights of the oldest standing structure in the USVI. Visit our breathtaking beaches? Check out our Island Beach Tour. Private tours available. Less than 6 persons? Contact us “Your Destination is Our Goal!”
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$32.25
From
$32.25
Taking safety measures

Key West Day Sail Aboard Schooner

Key West Day Sail Aboard Schooner

star-5
71
Experience a slice of sailing history while soaking up fantastic Key West views on a cruise aboard the America 2.0, a replica of the schooner that won the very first America’s Cup. Relax on padded benches and teak decks as your captain navigates the island coastline past landmarks like Fort Zachary Taylor and Sand Key Light Tower, and sip unlimited drinks from the full onboard bar.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$60.20
From
$60.20
Taking safety measures

Old Town Key West Literary Walking Tour
Likely to Sell OutLikely to Sell Out

Old Town Key West Literary Walking Tour

star-5
55
Explore the literary highlights of Key West during this walking tour, inspired by David A. Kaufelt’s original literary walking tour. An in-the-know guide whisks you around the Old Town to the former homes and favorite haunts of writers that have called the island home, including Shel Silverstein, Tennessee Williams, and Robert Frost. Since this is a small-group tour, you’ll have plenty of time to ask questions, too.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$30.00
From
$30.00

Southernmost Key West History and Culture Small-Group Walking Tour

Southernmost Key West History and Culture Small-Group Walking Tour

star-5
49
Join us for a 1.5-hour adventure! Our tour is led by knowledgeable local guides. As we walk through the streets of Key West’s old town, you will discover the history and culture of our island. Shipwrecking, sponging, cigar manufacturing, treasure hunting - it’s all about Key West! What to bring: Hat, sunglasses, and sunblock is a must. Bring at least one bottle of water for yourself. Wear comfortable clothing and shoes. Sneakers are the best option. Camera or your phone to take pictures. Your adventurous spirit :)
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  • 1 hour 45 minutes
  • Free Cancellation
From
$39.99
From
$39.99

Key West Historic District Small-Group Walking Tour

Key West Historic District Small-Group Walking Tour

star-5
28
You will be amazed by how much history and culture our small island has! Local Guide will take you on a time travel adventure. As you stroll through the scenic streets of the Old Town, you will learn how the island was discovered and became one of the richest cities in the USA! Hear the stories of the first industries on the island, such as shipwrecking, sponge harvesting and cigarmaking. Also, learn what key role Key West played in the Cuban fight for its independence and find out why Key West declared the war against the United States. What to bring and to wear: Comfortable clothing and shoes, sunscreen, hat, sunglasses, water.
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  • 2 hours
  • Free Cancellation
From
$46.99
From
$46.99

Miami: Key West Open Bar Snorkel Boat or other options

Miami: Key West Open Bar Snorkel Boat or other options

star-3.5
11
Enjoy the scenic and breathtaking drive on the Overseas Highway One passing Key Largo and the famous Seven Mile bridge to America’s southernmost city Key West. If you selected the snorkel tour option in Key West we will board a boat for 3 hours and go out to the reef where we will snorkel and experience Florida's underwater world. Beer, wine, margaritas and sodas are provided as well as basic snorkel gear. This is a tour ideal for snorkel beginners. After the snorkel tour you will have some time to experience the highlights of Key West on your own including the white Victorian conch villas and lush tropical gardens. Stroll along Duval Street with its cute shops, bars, galleries and cafes to the famous southernmost point monument located just 90 miles north of Cuba. Key West’s Caribbean flair and charm will seduce you and is a favorite day tour from Miami. Round trip transportation from select Miami meeting points is included.  
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  • 15 hours
  • Free Cancellation
From
$129.00
From
$129.00

Florida Keys Private tour from 7-Mile Bridge to Key Deer and Overseas Highway
Likely to Sell OutLikely to Sell Out

Florida Keys Private tour from 7-Mile Bridge to Key Deer and Overseas Highway

star-5
8
Private, exclusive tour of the islands near Key West. The only land-based tour in the Florida Keys, operating from Key West. Small groups of up to 12 travel in a comfortable customized air-conditioned vehicle along the Overseas Highway. Drivers are professional tour guides who share fun and interesting information about the Florida Keys and the islands we traverse. Experience the iconic 7-Mile Bridge, relax on the world-famous Bahia Honda Beach, and photograph endangered Key Deer on Big Pine Key. Children are welcome. This tour is customizable. You'll love this tour so much, you'll book it again next year!
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$294.00
Price varies by group size
From
$294.00
Price varies by group size
Taking safety measures

Private Tour of Florida Keys from Marathon to Key West
Likely to Sell OutLikely to Sell Out

Private Tour of Florida Keys from Marathon to Key West

star-5
4
Visit the one-and-only island city of KEY WEST! Enjoy a narrated tour on the way down, and island music on the way back. HIGHLIGHTS • See the sights in Key West • Stay for the Key West sunset • Plenty of Free Time • Designated Driver • Narrated Tour Do what you want in Key West! We're doing the driving! Choose to sightsee, enjoy a happy hour, eat a nice dinner, check out Mallory Square at sunset, take a sunset sail, and more! Sit back & enjoy the scenery as we drive down to Key West. We're licensed like a limousine, so you can enjoy your favorite beverages en route. Learn the history, culture, and ecology of the Florida Keys & Key West from your friendly local guide. See the Southernmost Point, Hemingway's House, Mile Marker Zero, Sloppy Joe's, and Mallory Square It's more like a road trip than a tour - ask questions, point out wildlife, make new friends.
More
  • 8 hours
  • Free Cancellation
  • Taking safety measures
From
$200.00
Price varies by group size
From
$200.00
Price varies by group size
Taking safety measures

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What people are saying about Private and Luxury in Key West

star-5
Sunset Sail in Key West with Beverages Included
"Beautiful scenery and the best captain and mate. Very friendly and excellent service with a smile.👍👍👍"..."
star-5
Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
"Had the best time. Great staff, good food, music and food. And the view was absolutely beautiful!! I would totally recommend this trip!! Well worth the money."..."
star-5
Key West Historic Seaport Food Tasting and Cultural Walking Tour
"our tour guide Rose was very friendly and knowledgeable about the area. The food was really good! Best part of my trip!"..."
star-5
Shark and Wildlife Viewing Adventure in Key West
"This was such an awesome experience! Knowledgeable, friendly and enjoyable tour guides. Made sure everyone was able to get a good view. Clean boat with plenty of seating, shade, and open sides. Saw sharks, sea turtles and jellyfish! Definitely worth the price. Would go again!"..."
star-5
Key West Pub Crawl
"Had a ball the Guide was awesome he made all of us laugh had a lot of hilarious jokes brought the group together as one everyone became friends it was a blast I would definitely do this again"..."
star-5
Parasailing in Key West with Professional Guide
"Great guide and captain. It was my kids’ first time. They had a blast and I felt it was very safe. I appreciated the guide joking and connecting with the passengers. Kids want to go back and I am going up next time!"..."
star-5
Key West Southernmost Food and Cultural Walking Tour
"Had a great tour experience with Dana. Learned some fun facts and history of Key West while meeting other people and enjoying some great food. Favorites: Cuban food at El Siboney and Jerk Fish at Kaya Island Eats."..."
star-5
Guided Bicycle Tour of Old Town Key West
"Awesome bike ride thru the town. Tour guide James was very funny and interactive, full of information. Highly recommend if you're into biking and seeing highlights of the town. The pie at the end was awesome too"..."
star-5
Key West Mangrove Kayak Eco Tour
"We went on the Key West Eco Tour with Peyton as our guide. It was a great experience: out guide made the trip interactive, fun and brought it to life. The water was very calm and the mangrove tunnels were exceptionally peaceful. I would highly recommend this tour to anyone visiting the Keys!!"..."
star-5
Key West Full-Day Power Adventure: Sailing & Watersports Package
"We had a great time! Best part of our trip. Highly recommend! Staff was super nice. Alcohol served was very limited, only drawback. A margarita would have been nice. They only had Landshark beer and red and white wine. Wine is just kind of unfitting for a day playing in the sun."..."
star-5
Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar
"The sunset was spectacular. The crew did and excellent job keeping everyone safe and beverages plenty."..."
star-5
Parasailing in Key West Seaport
"What a wonderful time, crew very professional yet a fun time, sights of key west we’re beautiful, pristine water"..."
star-5
Key West Sunset Sail Aboard Schooner
"From start to finish this was an amazing sunset cruise. The staff was top notch! Loved every second!"..."
star-5
Paradise Taxi & Tours USVI - St. Thomas, Virgin Islands- Island Scenic Tour
"Wow! If you want to not only see the points of interest on St. Thomas but hear the history, this is the way to go. Big Mike picked us up at our hotel and escorted us to all the places that are a must to see. He was so informative and personable. Well worth the time"..."
star-5
Key West Day Sail Aboard Schooner
"Beautiful day, great crew And great weather Made for a fantastic day of sailing. Highly recommend it."..."
star-5
Old Town Key West Literary Walking Tour
"Sarah was terrific! This is the third time I have done this tour and she managed to keep it fresh and entertaining."..."
star-5
Southernmost Key West History and Culture Small-Group Walking Tour
"Alejandro was very knowledgeable and friendly. Both my son and I appreciated seeing scanned old photos and documents describing the unique history of Key West."..."
star-5
Key West Historic District Small-Group Walking Tour
"We had a wonderful time. Our guide was very knowledgeable and professional. The in-depth history of the island and architectural descriptions were excellent."..."
star-5
Miami: Key West Open Bar Snorkel Boat or other options
"Tour guide was super cool. Key west is awesome and snorkeling is a must. 6 hours in key west is not long enough! But very very enjoyable!"..."

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