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LGBT Friendly Tours LGBT Friendly Tours Kid-Friendly Kid-Friendly Excellent Quality Excellent Quality Wayfortravel Plus Wayfortravel Plus Sporting Event Tickets & Passes Sporting Event Tickets & Passes Best Conversion Best Conversion Involves Animals Involves Animals Good for avoiding crowds Good for avoiding crowds Seasonal & Special Occasions Seasonal & Special Occasions Classes & Workshops Classes & Workshops Travel & Transportation Services Travel & Transportation Services Tours, Sightseeing & Cruises Tours, Sightseeing & Cruises Tickets & Passes Tickets & Passes Food & Drink Food & Drink Art & Culture Art & Culture Outdoor Activities Outdoor Activities Small Group Small Group Likely to Sell Out Likely to Sell Out Audio Guides Audio Guides Sustainable Tours Sustainable Tours Limousine Transfers Limousine Transfers Donut Walking Tour Donut Walking Tour Virtual Experiences Virtual Experiences Additional fees Additional fees DSA non-compliant DSA non-compliant Low Last Minute Supplier Cancellation Rate Low Last Minute Supplier Cancellation Rate
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LGBT Friendly Tours LGBT Friendly Tours Kid-Friendly Kid-Friendly Excellent Quality Excellent Quality Wayfortravel Plus Wayfortravel Plus Sporting Event Tickets & Passes Sporting Event Tickets & Passes Best Conversion Best Conversion Involves Animals Involves Animals Good for avoiding crowds Good for avoiding crowds Seasonal & Special Occasions Seasonal & Special Occasions Classes & Workshops Classes & Workshops Travel & Transportation Services Travel & Transportation Services Tours, Sightseeing & Cruises Tours, Sightseeing & Cruises Tickets & Passes Tickets & Passes Food & Drink Food & Drink Art & Culture Art & Culture Outdoor Activities Outdoor Activities Small Group Small Group Likely to Sell Out Likely to Sell Out Audio Guides Audio Guides Sustainable Tours Sustainable Tours Limousine Transfers Limousine Transfers Donut Walking Tour Donut Walking Tour Virtual Experiences Virtual Experiences Additional fees Additional fees DSA non-compliant DSA non-compliant Low Last Minute Supplier Cancellation Rate Low Last Minute Supplier Cancellation Rate

Seasonal & Special Occasions in Key West

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Adult Only Sandbar Escape
Adult Only Sandbar Escape
Starting at
$139.00
5/5
Overview
One of the only Adult Only experiences offered in Key West, our excursions are top-notch, with the vessel, all equipment, food and beverage service being set to premium standards! We offer a more inti...
1 reviews
Dates and times: select dates and times during purchase
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Bimini Charters - Private 3hr Catamaran Charters, Sail & Snorkel
Bimini Charters - Private 3hr Catamaran Charters, Sail & Snorkel
Starting at
$750.00
5/5
Overview
Do it all on a luxury catamaran reserved just for you! Snorkel, dolphin watch, savor a sunset, bask in the sun, enjoy cocktails with friends on your own private yacht! If the big, crowded boats are no...
1 reviews
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Key West Christmas Cruise with Live Band and Drinks
Key West Christmas Cruise with Live Band and Drinks
Starting at
$88.15
5/5
Overview
Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our live band and celebrate the holiday...
1 reviews
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37' Private Luxury Sunset Charter w. Music & Drinks, up to 13 ppl
37' Private Luxury Sunset Charter w. Music & Drinks, up to 13 ppl
Starting at
$899.00
5/5
Overview
Ready to explore Sunset Charter with drinks and Music? aboard a luxurious private boat charter, accommodating up to 13 guests. Sailing aboard a 37’ private charter a smoother ride with plenty of dec...
1 reviews
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Dolphin Watching & Snorkeling in Key West with Sunset Dinner Cruise and Open Bar
Dolphin Watching & Snorkeling in Key West with Sunset Dinner Cruise and Open Bar
Starting at
$189.99
3/5
Overview
What a fun day in the sun with a 10am checkin and 11am departure to a 3 hours snorkeling and Dolphin watching adventure. At 4:45pm get ready for the Keywest sunset, dinner, live music and open bar. ...
1 reviews
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Dolphin Morning Watching & Snorkeling + open bar + 1 day Hop-On Hop-Off Fun
Dolphin Morning Watching & Snorkeling + open bar + 1 day Hop-On Hop-Off Fun
Starting at
$149.99
5/5
Overview
This is the best 1 day combo where you will enjoy the water and land in Key West. Get to Hop On Hop off the conch train, one of Florida's most popular attractions, going to Truval Village: Steps away ...
1 reviews
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Private 2-Hour Tiki Boat Party in Key West & Mini Sandbar
Private 2-Hour Tiki Boat Party in Key West & Mini Sandbar
Starting at
$403.13
4/5
Overview
Set Sail for Tiki Revelry in Key West's Historic Seaplane Basin! Journey back in time as we cruise to Key West's unique Seaplane Basin. In the early 1900s, this spot buzzed with activity as seaplanes ...
1 reviews
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Key West: Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling
Key West: Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling
Starting at
$159.99
5/5
Overview
Key West Water Fun with Snorkeling, Sunset Cruise, Dinner, Live Music and open Bar. Enjoy a bright and early morning snorkel Catamaran cruise departing 9 am for a full morning of Snorkeling fun. Retu...
1 reviews
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Key West Sunset Buffet Dinner Cruise with Open Bar and Live Music
Key West Sunset Buffet Dinner Cruise with Open Bar and Live Music
Starting at
$99.99
5/5
Overview
Key West is famous for stunning sunsets, and this dinner cruise offers the perfect way to enjoy them. Savor breathtaking views as the sky transforms, while indulging in a tropical buffet, live music, ...
1 reviews
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Schooner Bloody Mary Day Sail with Full Open Bar in Key West
Schooner Bloody Mary Day Sail with Full Open Bar in Key West
Starting at
$49.00
5/5
Overview
Sip cocktails and soak in your tropical surroundings. There is no better way to start your day in paradise! While enjoying your sail remember there is plenty to see on the water’s surface or circlin...
1 reviews
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Key West Photographer Private Historic Photoshoots
Key West Photographer Private Historic Photoshoots
Starting at
$499.00
5/5
Overview
If you want a professional photoshoot, with top photographers, in the most romantic city and beach at sunset?  this is the right place!. Golden Hour, ocean views, old town views, palm trees and more;...
1 reviews
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Key West: Smathers Beach & activities with a Sunset Catamaran & Open Bar
Key West: Smathers Beach & activities with a Sunset Catamaran & Open Bar
Starting at
$229.99
5/5
Overview
Fun in the sun when you make it over to Smathers Beachand have the best day with unlimited use of water activities. Go kayaking, paddle boarding, sailing or just seat in your beach chair and umbrella ...
1 reviews
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Private Tiki Bar Crawl by Water
Private Tiki Bar Crawl by Water
Starting at
$1295.00
5/5
Overview
Embark on a tantalizing journey through Key West's culinary and cocktail scene with our Bar & Food Crawl by Boat Charter. About Cruise along the picturesque coastline to a selection of outdoor Tiki e...
1 reviews
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