Top Key West Day Cruises

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  • Key West Sunset Sail Aboard Schooner
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Sunset Sail Aboard Schooner

    1119

    Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $122.58
    Details
    from
    $122.58
    Details
  • Sunset Sail in Key West with Beverages Included
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Sunset Sail in Key West with Beverages Included

    561

    Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $69
    Details
    from
    $69
    Details
  • Key West Day Sail Aboard Schooner
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Day Sail Aboard Schooner

    116

    Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $75.29
    Details
    from
    $75.29
    Details
  • Snorkel, Sandbar & Dolphin Excursion
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Snorkel, Sandbar & Dolphin Excursion

    23

    Max 6 people. Explore the waters around Key West in the Looking Glass, our 28' glass bottom boat. This versatile boat let's you plan your...
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     3 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $800
    Details
    from
    $800
    Details
  • Key West Private Morning Sail on Schooner America 2.0
    Likely to Sell Out

    Key West Private Morning Sail on Schooner America 2.0

    9

    Enjoy a morning sailing experience and have Schooner America 2.0 all to yourself! Let us whisk you and yours away on a glorious morning sail...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $1,032
    Details
    from
    $1,032
    Details
  • Private Key West Sunset Sail
    Likely to Sell Out

    Private Key West Sunset Sail

    40

    2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for...
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     2 hours  Instant Confirmation
    from
    $595
    Details
    from
    $595
    Details
  • Key West Sunset Buffet Dinner Cruise with open bar and Live Music
    Likely to Sell Out

    Key West Sunset Buffet Dinner Cruise with open bar and Live Music

    2

    Key West is know for one of the worlds most incredible sunsets. On this Sunset buffet dinner cruise you will enjoy not only the incredible...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $109.99
    Details
    from
    $109.99
    Details
  • Key West Sandbar Charter

    Key West Sandbar Charter

    New To The Site!

    Come experience the Crystal clear waters and sandbar island surrounding the Florida Keys. This tour can be completely tailored to whatever you have in mind....
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     4 hours  Free Cancellation
    from
    $800
    Details
    from
    $800
    Details
  • Key West: Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling

    Key West: Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling

    New To The Site!

    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...
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     5 hours  Free Cancellation
    from
    $159.99
    Details
    from
    $159.99
    Details
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Frequently Asked Questions

The answers provided below are based on answers previously given to customers' questions.

Q: What are the best options for Key West Day Cruises?

A: According to verified reviews on Cool Destinations and TripAdvisor, the best Key West Day Cruises are:

Q: What are the best kid-friendly options for Key West Day Cruises Tours?

A: According to verified reviews on Cool Destinations and TripAdvisor, the best kid-friendly Key West Day Cruises are:

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Q: Which Key West Day Cruises have Instant Confirmation?

A: Key West Day Cruises with Instant Confirmation include:

View all Tours with Instant Confirmation →

Q: Which Key West Day Cruises have Free Cancellation?

A: Key West Day Cruises with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

Q: Got any more Key West trip ideas?

A: We sure do. Check out our curated lists of hand-picked Key West Tours.

View all Key West Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Key West?

A: Based on our sales data over the past year, the most popular styles of tours and activities in Key West are:

View all tour styles in Key West →