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Top Key West Sunset Cruises

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Key West Tours

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Key West Wind & Wine Sunset Sail
Likely to Sell Out
Likely to Sell Out
5.0 (1,702)

Key West Wind & Wine Sunset Sail

Wind & Wine has been the #1 rated sunset sail on Cool Destinations for over a decade. In our opinion, this is the best wine...

2 hours (approx.) • Free Cancellation
5.0 (1,702)
$115
$99
Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar
4.8 (3,793)

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

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...

2 hours (approx.) • Free Cancellation
4.8 (3,793)
from
$80
Key West Sunset Cruise: Dinner, Live Music & Drinks Included
4.4 (1,905)

Key West Sunset Cruise: Dinner, Live Music & Drinks Included

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....

2 hours • Free Cancellation
4.4 (1,905)
from
$93
Key West Schooner Sunset Sail with Hors D'oeuvres and Full Bar
4.9 (1,701)

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

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...

2 hours (approx.) • Free Cancellation
4.9 (1,701)
from
$100
Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location
Special Offer
Special Offer
4.9 (128)

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

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...

2 hours (approx.) • Hotel pickup offered • Free Cancellation
4.9 (128)
$99
$89
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
Likely to Sell Out
Likely to Sell Out
4.9 (1,701)

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

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...

2 hours • Free Cancellation
4.9 (1,701)
from
$123
Key West "Commotion on the Ocean" Live Music Sunset Sail
Likely to Sell Out
Likely to Sell Out
4.8 (974)

Key West "Commotion on the Ocean" Live Music Sunset Sail

This is the Key West sunset cruise party everyone talks about — live music, open-bar beer, wine, & margaritas, delicious appetizers, dancing, and a great...

2 Hours (approx.) • Free Cancellation
4.8 (974)
from
$80
Sunset Sail in Key West with Beverages Included
4.9 (972)

Sunset Sail in Key West with Beverages Included

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...

1 hour 30 minutes • Free Cancellation
4.9 (972)
from
$79
Key West Glass Bottom Boat Reef Eco Tour with Sunset Option
4.6 (533)

Key West Glass Bottom Boat Reef Eco Tour with Sunset Option

The Key West Glass Bottom Boat Tour combines an entertaining, educational exploration of the reefs & marine life around Key West with a classic sunset...

2 hours (approx.) • Free Cancellation
4.6 (533)
from
$70
Sunset Sail Cruise in Key West
Likely to Sell Out
Likely to Sell Out
5.0 (290)

Sunset Sail Cruise in Key West

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's...

2 hours • Free Cancellation
5.0 (290)
from
$95
Key West Private Wind & Wine Charter
5.0 (1,702)

Key West Private Wind & Wine Charter

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Cool Destinations three years running. See the sunset on...

2 hours (approx.) • Free Cancellation
5.0 (1,702)
from
$3,499
Island Sunset Cruise 2 Hour Catamaran Tour in Marathon Florida
Likely to Sell Out
Likely to Sell Out
5.0 (20)

Island Sunset Cruise 2 Hour Catamaran Tour in Marathon Florida

Cruise into a stunning Florida Keys sunset aboard a comfortable 53’ catamaran. Your crew will guide you through the waters surrounding Marathon, passing local landmarks...

2 hours • Free Cancellation
5.0 (20)
from
$102
Key West Sunset Sail Aboard Legendary Schooner Appledore
5.0 (364)

Key West Sunset Sail Aboard Legendary Schooner Appledore

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern...

2 hours • Free Cancellation
5.0 (364)
from
$89
Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar
4.9 (179)

Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

“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...

2 hours
4.9 (179)
from
$65
Sandbar Adventure Cruise in the Florida Keys
Likely to Sell Out
Likely to Sell Out
4.9 (15)

Sandbar Adventure Cruise in the Florida Keys

Discover the enchanting beauty of the Florida Keys with Island Girls Excursions. This adventure combines relaxing sandbar experiences with stunning sunset cruises. Unwind on your...

4 hours • Free Cancellation
4.9 (15)
from
$87
Florida Keys Sunset Cruise with Champagne Toast and Seafood
Likely to Sell Out
Likely to Sell Out
5.0 (26)

Florida Keys Sunset Cruise with Champagne Toast and Seafood

Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Sparky’s Landing in Marathon, this relaxing cruise includes a complimentary champagne toast and...

2 hours • Free Cancellation
5.0 (26)
from
$72
Classic Key West Schooner Sunset Sail with Full Open Bar
Likely to Sell Out
Likely to Sell Out
4.9 (269)

Classic Key West Schooner Sunset Sail with Full Open Bar

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This...

2 hours • Free Cancellation
4.9 (269)
from
$109
Private Sunset Cruise around Key West
Likely to Sell Out
Likely to Sell Out
4.9 (65)

Private Sunset Cruise around Key West

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour around the island of Key West on our 20 foot pioneer center console. Your...

2 hours • Free Cancellation
4.9 (65)
from
$400
Private Key West Sunset Sail
Likely to Sell Out
Likely to Sell Out
4.9 (50)

Private Key West Sunset Sail

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...

2 hours
4.9 (50)
from
$695
The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise
Likely to Sell Out
Likely to Sell Out
5.0 (9)

The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise

Drift into tranquility on this private 2-Hour Sunset Tiki Cruise and witness the stunning sunset over the Florida Keys. Glide across crystal-blue waters as the...

2 hours • Free Cancellation
5.0 (9)
from
$599

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
A beautiful night!
New York City
Key West Sunset Sail Aboard Legendary Schooner Appledore
Lisa_M, Sep 2026
A beautiful night!
This tour was amazing! The boat was beautiful and the crew amazing!! My husband and I took this and very happy we did it made our key west trip so memorable!!!
Read more
Great wine, great views!
New York City
Classic Key West Schooner Sunset Sail with Full Open Bar
chadaD2073YZ, Sep 2026
Great wine, great views!
Cristina and Jordan were very professional, the Schooner was beautiful and everyone was very friendly. The sunset sail was something everyone should do when they visit Key West and we will probably do it again next time we visit.
Read more
Sail away
New York City
Classic Key West Schooner Sunset Sail with Full Open Bar
O9659XYbillyg, Sep 2026
Sail away
Exciting Experience, small admin fee, perfect tour length, amazing atmosphere, crazy perfect crowd size. Perfect staff, best for a good time’!!
Read more
30th Anniversary Cruise
New York City
Key West Sunset Cruise: Dinner, Live Music & Drinks Included
Kandy_P, Sep 2026
30th Anniversary Cruise
Great love music and good bartender. Was a great night with lots of laughs and plenty of pictures to remember the time.
Read more
10/10
New York City
Key West Sunset Cruise: Dinner, Live Music & Drinks Included
cherykac, Sep 2026
10/10
This was a really nice cruise for couples. The sunset was beautiful and the crew was very friendly and helpful
Read more
Sandbar cruise
New York City
Sandbar Adventure Cruise in the Florida Keys
lisawW6430ZW, Sep 2026
Sandbar cruise
The sandbar cruise was one of the best experiences on our trip to the keys!
Read more
Scott made this night amazing!
New York City
The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise
E373DFannaw, Sep 2026
Scott made this night amazing!
Scott was amazing!!! Fun and he knew so much about the area! Such a great sunset cruise. When we’re back in the area we will definitely request Scott again!
Read more
Amazing Key West Sunset Sail with h'ors durves, drinks and champagne.
New York City
Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar
Susan G, Aug 2026
Amazing Key West Sunset Sail with h'ors durves, drinks and champagne.
We had a great time. Our captain and crew were absolutely amazing. Our entertainer Tim was extremely talented - he played all kinds of music from rock and country, to hip hop and pop (even a little Taylor Swift). Who ever heard of a guy and his guitar doing show tunes from Hamilton?!? So much fun , along with a beautiful sunset. This was our second trip (first was in 2024). Will definitely do it again.
Read more
Sunset sail
New York City
Sunset Sail in Key West with Beverages Included
L566UTashleyh, Aug 2026
Sunset sail
This was our favorite thing we did in Key West. The sunset sail was so relaxing, we had a very small group of 5 total on the boat and it was perfect. I am so glad we booked this over a party cruise. The guides were so friendly and made it an all around great experience!
Read more
Beautiful evening on the water
New York City
Sunset Sail in Key West with Beverages Included
Donna_S, Aug 2026
Beautiful evening on the water
Excellent experience. Friendly staff. We had a beautiful evening on the water watching the sunset and enjoying Key West harbor.
Read more
Perfect late kayak trip!
New York City
Island Sunset Cruise 2 Hour Catamaran Tour in Marathon Florida
Regina_B, Aug 2026
Perfect late kayak trip!
Had one of the best experiences we’ve had in the Keys on this tour. Susanne is so knowledgeable and helpful. She took the time to find and point out a lot of wildlife. The water was clear and calm and the sunset was a show stopper. Couldn’t recommend this more!
Read more
Great sunset experience
New York City
Sunset Sail Cruise in Key West
sdcd24, Aug 2026
Great sunset experience
Had a beautiful sunset cruise with friendly staff
Read more
Awesome all the way around!
New York City
Sunset Sail Cruise in Key West
Weslie_P, Aug 2026
Awesome all the way around!
Great experience. Sunset was awesome and boat was great. Crew was absolutely top notch! Highly recommend this excursion.
Read more
Relaxing and informative
New York City
Florida Keys Sunset Cruise with Champagne Toast and Seafood
Y8114WUlindac, Aug 2026
Relaxing and informative
Doug and Sarah were very congenital explaining items of interest and history along the way from their Port to the Gulf where we watched the sun set. The ride was smooth and relaxing. Sarah was especially attentive to all of the passengers and I would recommend this excursion to young and old alike.
Read more
Amazing
New York City
The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise
Trek11715299746, Aug 2026
Amazing
Captain Ross was absolutely amazing, we had fun, good conversations and the best sunset view ,docked.
Read more
Sunset cruise
New York City
Key West Sunset Sail Aboard Legendary Schooner Appledore
T76NewOrleans, Aug 2026
Sunset cruise
The view was amazing . Captain Joe and his crew Vitali and Jordan were super nice and attentive . Boat ride was smooth and beautiful. Highly recommended
Read more
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