Top Key West Sunset Cruises

Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Key West Wind & Wine Sunset Sail
52
The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running....
Read More
2 Hours (approx.)
Best Rate
$85
Details
Best Rate
$85
Details
Key West Sunset Harbor Cruise
11
...
Read More
2 Hours (approx.)
Best Rate
$75
Details
Best Rate
$75
Details
Key West Sunset Cruise with Live Island Music
80
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...
Read More
2 hours Instant Confirmation
from
$63
Details
from
$63
Details
Key West Sunset Dinner Cruise with Tropical Buffet
92
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....
Read More
2 hours Instant Confirmation
from
$67.65
Details
from
$67.65
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Key West Sunset Sail Aboard Schooner
19
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...
Read More
2 hours Instant Confirmation
from
$103.20
Details
from
$103.20
Details
Key West Glass-Bottom Boat Tour with Sunset Option
85
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...
Read More
2 hours Instant Confirmation
from
$49.77
Details
from
$49.77
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Small-Group Key West Sunset Sail with Wine
22
Cruise into the sunset with wines from all around the world, imported and domestic beers as well as hors d'oeuvres. This cruise is great for...
Read More
2 hours Instant Confirmation
from
$91.38
Details
from
$91.38
Details
Key West Sunset and Cocktail Cruise
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....
Read More
2 hours Instant Confirmation
from
$60
Details
from
$60
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
38
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...
Read More
1 hour 30 minutes Instant Confirmation
from
$61.46
Details
from
$61.46
Details
2-Hour Private Sunset Cruise around Key West
1
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...
Read More
2 hours Instant Confirmation
from
$200
Details
from
$200
Details
Private Sunset Boat Charter Key West
1
Enjoy a private 2 hour sunset cruise in Key West with your family and friends. Sit back and relax while your Captain points out all...
Read More
2 hours Instant Confirmation
from
$200
Details
from
$200
Details
2-Hour Private Sunset Cruise on Tiki Bar Boat in Key West
1
Key West is famous for it's sunsets and it doesn't get any better then on a private sunset cruise aboard our custom tiki bar boats....
Read More
2 hours Instant Confirmation
from
$456.88
Details
from
$456.88
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...
Read More
1 hour 30 minutes Instant Confirmation
from
$345
Details
from
$345
Details
Key West Sunset Booze Cruise with Unlimited Draft Beer and Wine
3
Key West Sunset Cruise with Live Music, Unlimited Beer & Wine. Join Sunset Watersports out on the water on our custom 65 foot catamaran for...
Read More
2 hours Instant Confirmation
Details
Details
Key West Wind & Wine Private Charter
1
The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running. See the sunset on...
Read More
2.5 Hours (approx.)
Best Rate
$2,500
Details
Best Rate
$2,500
Details