Top Key West Sunset Cruises

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Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Key West Wind & Wine Sunset Sail
69
The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running....
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2 Hours (approx.) Instant Confirmation
~~$95~~
$90
Details
~~$95~~
$90
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location
24
Looking for the perfect way to end your day? Join us aboard a 45ft Corinthian powercat, and ride in comfort with this relaxing, catered cruise...
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2 Hours (approx.) Hotel pickup offered Instant Confirmation
~~$75~~
$69
Details
~~$75~~
$69
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar
437
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran...
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2 hours Hotel pickup offered Instant Confirmation
Best Rate
$74.95
Details
Best Rate
$74.95
Details
Key West Sunset Cruise with Live Island Music
437
Come sail along on an ocean breeze and enjoy some of Key West’s best musicians performing live to the backdrop of the setting sun. You’ll...
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2 hours Instant Confirmation
from
$73.75
Details
from
$73.75
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Key West Sunset Champagne Catamaran Cruise
96
Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy...
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90 minutes (approx.) Hotel pickup offered Instant Confirmation
Best Rate
$49.95
Details
Best Rate
$49.95
Details
Key West Sunset Dinner Cruise with Tropical Buffet
148
Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar....
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2 hours Instant Confirmation
from
$88.88
Details
from
$88.88
Details
Key West Schooner Sunset Sail with Hors D'oeuvres and Full Bar
96
Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and...
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2 hours Hotel pickup offered Instant Confirmation
Best Rate
$99.95
Details
Best Rate
$99.95
Details
Key West Glass-Bottom Boat Tour with Sunset Option
105
See the only living coral barrier reef in the continental United States on this two-hour glass-bottom boat tour from Key West! As you relax on...
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2 hours Instant Confirmation
from
$53.70
Details
from
$53.70
Details
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
59
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 Instant Confirmation
from
$69
Details
from
$69
Details
Key West Sunset and Cocktail Cruise with Open Bar
13
“The Key West Cocktail Cruise is the best thing to happen to Sunsets since cameras and sunglasses!”This is not your average Key West pleasure cruise....
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2 hours Instant Confirmation
from
$75
Details
from
$75
Details
2-Hour Private Sunset Cruise around Key West
4
This is the only 2 hour sunset cruise in Key West that provides a private guided tour around the island.Sit back and relax while your...
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2 hours Instant Confirmation
from
$200
Details
from
$200
Details
Private Sunset Cruise Featuring Duck Key
Duck Key is known for having some of the bluest water in the Keys and we operate the only Sunset Cruise from the beautiful tropical...
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1 hour 30 minutes Instant Confirmation
from
$345
Details
from
$345
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Key West Sunset Sail Aboard Schooner
96
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 Instant Confirmation
from
$103.20
Details
from
$103.20
Details
Key West Sunset Booze Cruise with Unlimited Draft Beer and Wine
3
Key West Sunset Cruise with Live Music, Unlimited Beer & Wine. Join Cool Destinations out on the water on our custom 65 foot catamaran for...
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2 hours Instant Confirmation
Details
Details
Key West Wind & Wine Private Charter
42
The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running. See the sunset on...
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2.5 Hours (approx.)
Best Rate
$2,500
Details
Best Rate
$2,500
Details

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 Sunset Cruises?

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

Q: What Key West Sunset Cruises are taking additional safety precautions?

A: The following activities in Key West experiences are providing additional COVID-19 safety measures (to read the specific policies please click the activity name and read the "Keeping you safe during COVID-19" section located underneath the booking calendar):

Top Key West Sunset Cruises

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Nearby

Key West Wind & Wine Sunset Sail

Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location

Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar

Key West Sunset Cruise with Live Island Music

Key West Sunset Champagne Catamaran Cruise

Key West Sunset Dinner Cruise with Tropical Buffet

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

Key West Glass-Bottom Boat Tour with Sunset Option

Sunset Sail in Key West with Beverages Included

Key West Sunset and Cocktail Cruise with Open Bar

2-Hour Private Sunset Cruise around Key West

Private Sunset Cruise Featuring Duck Key

Key West Sunset Sail Aboard Schooner

Key West Sunset Booze Cruise with Unlimited Draft Beer and Wine

Key West Wind & Wine Private Charter

Frequently Asked Questions

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

Q: What Key West Sunset Cruises are taking additional safety precautions?