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22 results | All Key West Tours

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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
539
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

Key West Craft Cocktail Crawl

Key West Craft Cocktail Crawl

star-5
137
Explore Key West through the eyes of a local on a craft cocktail tour that stops at five off–the–beaten–path establishments, from a historic mansion to a boutique hotel that was once a hospital. In addition to navigating for you, your guide uses the city’s bar scene to give you an overview of its history and culture. The tour includes five craft cocktails and two gourmet food tastings.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$88.68
From
$88.68
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
254
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

Key West Pub Crawl

Key West Pub Crawl

star-4.5
161
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

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
1131
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 Sunset Champagne Catamaran Cruise

Key West Sunset Champagne Catamaran Cruise

star-4.5
334
Experience a sunset you’ll never forget on this 2-hour catamaran cruise in Key West. Sip on your choice of wine, champagne, beer or sangria as you watch the sun go down over the water. As you sail you’ll catch glimpses of the island and marvel at the views from the turquoise water. Cocktails are also available at a cash bar on board.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$51.95
From
$51.95
Taking safety measures

Key West Sunset Cruise with Live Island Music

Key West Sunset Cruise with Live Island Music

star-4.5
496
Jam to island beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Unlimited drinks and appetizers included; multiple departure times available to suit your schedule.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$73.75
From
$73.75
Taking safety measures

Key West Haunted Pub Crawl and Ghost Tour

Key West Haunted Pub Crawl and Ghost Tour

star-4
184
Experience Key West’s dark side on this fun yet frightening haunted bar crawl. Hear tales of known paranormal activity from your local guide and visit the most eerie bars in Old Town Key West – located in two haunted mansions and repurposed morgue. By the end of the 2‐hour tour, you’ll see ‘Bone Island’ in a different (and profoundly spookier) light.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$26.82
From
$26.82
Taking safety measures

Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

star-5
289
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

Hard Rock Cafe Key West Dining Experience

Hard Rock Cafe Key West Dining Experience

star-4
27
At the Hard Rock Café Key West, every meal is an experience, whether on the road or on a lunch break. Dine in style and feel like a star at this popular restaurant, located on world-famous Duval Street in downtown Key West. Savor a 2- or 3-course, fixed-price meal with choice of theme. Enjoy the Legendary Burger, ribs, salmon, steak or a vegetarian option for the main course along with a side and desert. Coffee, tea or soft drink included.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$34.49
From
$34.49
Taking safety measures

Key West Historic Homes and Island History - Small Group Walking Tour

Key West Historic Homes and Island History - Small Group Walking Tour

star-5
51
Key West is home to many unique architectural landmarks and historic homes. Rather than wandering around alone, you can learn the fascinating stories of each by taking a guided tour. This small-group walking tour provides in-depth insights into the people and places of historic Key West.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
Taking safety measures

Yes, Queen! Drag Queen Pub Crawl of Key West

Special Offer

Yes, Queen! Drag Queen Pub Crawl of Key West

star-4.5
9
Meet your guide for the night, a world-class drag queen, at the award-winning Aqua Nightclub. Grab a cocktail and mingle with your fellow crawlers as you await the ring of the ‘b*tch bell’ to announce the kick-off of the tour. 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. Spend the night at a number of Key West 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 live! *Ticket includes tour only. The Cabaret show at Aqua/ 801 Bourbon will not be included, but will have tickets available for purchase*
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  • 2 hours
  • Taking safety measures
From
$36.80
$46.00
$9.20 savings
From
$36.80
$46.00
$9.20 savings
Taking safety measures

Key West Sunset Dinner Cruise with Tropical Buffet

Key West Sunset Dinner Cruise with Tropical Buffet

star-4
431
Watch Key West's sunset — a main island attraction — on an evening dinner cruise. Feast on a tropical-themed buffet dinner and sip provided cocktails, beer, wine, and soft drinks as you take in views of the sea, the waterfront, and the sky's warm glow. Live music provides a festive atmosphere, and a cash bar is also available for premium drinks.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$88.95
From
$88.95
Taking safety measures

Highlights and Stories of Key West - Small Group Walking Tour

Highlights and Stories of Key West - Small Group Walking Tour

star-5
42
Key West Highlights and Stories- “2020 WINNER Best Key West Walking Tour" Join our award-winning guides for a wonderful, fun, and informative 2.5 hour stroll through the historic streets of Old Town Key West. Our goal is for you to have a fantastic time as your local guide brings to life the rich and colorful history, legends, points of interest, flora/fauna, and culture that make Old Town Key West unique and famous across the globe. There's something for everyone to enjoy on this fascinating and story-filled look behind the scenes of historic Key West. *Consistently ranked as the top “Highlights Tour” by Keys Tourism Association *Voted Top Tour Guides of North America *Over 20 years experience *Our guides have been featured in many leading publications including Gentry, Conde Nast, Frommer’s Travel Guide, Jetset, Hamptons, Travel Weekly, Private Islands, and USA Today. We look forward to sharing Old Town Key West with you.
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  • 2 hours 15 minutes
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
Taking safety measures

ConchTales and Dreams: Food, Drink and Fun Tour of Key West
Likely to Sell OutLikely to Sell Out

ConchTales and Dreams: Food, Drink and Fun Tour of Key West

star-4.5
45
Get to know the sights, sounds and tastes of Key West on this guided, 3-hour, small-group tour. Enjoy three drinks and three food tastings at some of the best pubs, dives and diners in Old Town and the Historic Seaport at Key West Bight Marina. Also, visit the Key West Legal Rum Distillery for a tour and tasting. Along the way, learn about the rich history and traditions of this island city, whose visitors have included fortune hunters, wreckers, spongers, pirates, tobacconists, artists, poets and writers.
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  • 3 hours
  • Free Cancellation
From
$93.75
From
$93.75

Hemingway Food and Walking Tour

Hemingway Food and Walking Tour

star-5
19
This guided walking tour will take you to the real places that Hemingway lived, worked and played, including where he watched and refereed boxing matches, where he kept his boat the Pilar, the bookstore where his books were sold, his first apartment in Key West where he finished writing “A Farewell to Arms”. Along the way you will have three food samplings, before visiting where he took the train, fished and charted boats in the Key West Harbor, and finally where he spent a lot of time drinking- Sloppy Joe's. An alcoholic drink is also included for you to experience Hemingway's favorite bar. Numerous other historical sites that Hemingway frequented while he lived in Key West will also be visited on this incredibly authentic tour.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$88.00
From
$88.00
Taking safety measures

Private 2-Hour Wind and Wine Sunset Sail in Key West
Likely to Sell OutLikely to Sell Out

Private 2-Hour Wind and Wine Sunset Sail in Key West

star-4.5
16
This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from around the world and a variety of beers. You will be sailing on a 65-foot schooner while watching the sunset into the ocean. There will be hors d'oeuvres passed around throughout the trip. A great way to have a private sail with your friends, family, or co-workers.
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  • 2 hours
  • Taking safety measures
From
$2,299.00
per group
From
$2,299.00
per group
Taking safety measures

Key West Waterfront Cocktail Walk to Mallory Square’s Sunset Celebration!
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Key West Waterfront Cocktail Walk to Mallory Square’s Sunset Celebration!

star-5
6
There's so many great places to eat and drink in Key West that it can be difficult to choose. Let this guided tour make the decisions for you. You'll stop into several locals' favorite restaurants to sample cocktails and food before heading to Mallory Square in time for the sunset celebration.
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  • 2 to 3 hours
  • Free Cancellation
  • Taking safety measures
From
$79.00
From
$79.00
Taking safety measures

Parrot Head Tour

Parrot Head Tour

star-5
5
Jimmy Buffett has left his mark on Key West since he arrived 50 years ago. If you have a passion for all things Buffett and Margaritaville, this walking tour is the best way to find the locations around Old Key West that inspired his songs. Your guide will also take you to the location of his first gig, some of his favorite watering holes, bars he played in and his recording studio.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$69.00
From
$69.00
Taking safety measures

Private Highlights and Stories of Key West Walking Tour

Private Highlights and Stories of Key West Walking Tour

star-5
5
Swap the standard sightseeing tours of Key West for a more personalized experience. This private tour is exclusively for your group and led by a Key West local and unofficial "mayor." As you stroll through the Old Town streets, you'll learn all about the colorful histories and personalities that have shaped Key West.
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  • 2 hours 15 minutes
  • Free Cancellation
  • Taking safety measures
From
$79.00
Price varies by group size
From
$79.00
Price varies by group size
Taking safety measures

Private Key West Historic Homes and Island History Walking Tour

Private Key West Historic Homes and Island History Walking Tour

star-5
5
Historic Homes & Stories of Key West- "2020 WINNER- Best Key West History Tour" Join our award-winning guides for a wonderful, fun, and informative 2 hour stroll through the celebrated Old Town neighborhoods where you'll discover many of the most beautiful, historic homes and unique architectural landmarks that have contributed so significantly to the history, culture, and legends of our remarkable island community. We’ll see the exteriors of a variety of beautiful homes and public buildings, each with its own legendary story, notable history, and rich style. There's something for everyone to enjoy on this fascinating look behind the scenes of historic Key West. *Voted Top Tour Guides of North America *Over 20 years experience *Our guides have been featured in many leading publications including Gentry, Conde Nast, Frommer’s Travel Guide, Jetset, Hamptons, Travel Weekly, Private Islands, and USA Today. We look forward to welcoming you and sharing Old Town Key West with you.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$79.00
Price varies by group size
From
$79.00
Price varies by group size
Taking safety measures

Key West Sunset Sip & Stroll Audio Tour

Key West Sunset Sip & Stroll Audio Tour

star-5
1
Turn your phone or tablet into a local tour guide! This location-aware audio/multimedia tour lets you enjoy historic photos, recordings and videos plus links to happy hour menus and websites at your fingertips. In just 35 minutes of walking, you can cool off at a tiki bar with a gorgeous waterfall, then stroll along a hidden boardwalk with stunning ocean views. Find the best best happy hours with the tastiest seafood snacks. Stroll past Jimmy Buffett’s secret recording studio. Enjoy Key West’s most popular brewery, best mojito, or the world’s yummiest coffee. Learn where locals watch the sun set into the Gulf of Mexico. Sight-see at your own pace, avoid being herded in a crowd, and linger only in the places that truly interest you. Soon after booking, you'll receive an email with login instructions and a coupon code giving you access to your tour.
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  • 35 minutes to 2 hours
From
$9.99
From
$9.99

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