Key West, FL > Sunset Cruises
03/30/2020 ~ 04/05/2020

Key West Sunset Cruises

Getting the best experiences for you...
Private Snorkel and Sunset Sail Excursion

Private Snorkel and Sunset Sail Excursion

36 reviews
Duration4 Hrs.
Climb aboard and set out on a private snorkel and sunset sail. You'll get the best of both worlds as you glide across...
What an interesting ship! We brought our own beverages and chose from a high variety of nut, fruit, and cheese tray (way better than cheap included...
We can't recommend this Sunset sail enough! The captain and crew were fabulous, the service is on point. And what can I say about sailing on a classic...
Hands down one of the highlights of our trip to Key West!Shawn and the "When and If" crew are very knowledgeable and top shelf. I loved every minute‼
Champagne Sunset Sail

Champagne Sunset Sail

10 reviews
Duration2 Hrs.
Enjoy a night you’ll never forget on a Champagne Sunset Sail in Key West. Watch the masterfully painted sunset fade...
The Captain and crew were great and the evening was fun and beautiful.
We took my best friend on a sunset sail as part of her bachelorette trip and it was AMAZING. Eric and his crew were awesome and we had the best time celebrating! Highly recommend - can’t beat the price and experience!
Great evening, Wonderful boat, great crew, and the drinks weren't bad either.
from $50
Key West Sunset Cruise with Beer and Wine

Key West Sunset Cruise with Beer and Wine

17 reviews
Duration2 Hrs.
Be enchanted by the magic and awe of the world famous Key West sunset aboard a luxurious Party Cat catamaran. This...
We had a great time on this trip. The entertainment was great, the food was great, and the crew was great! Could not have asked for a better time!
Excellent bartender service. Complete gorgeous panoramic views including sunset. Smooth journey on the water with live music.
My son and me had a great time! I will definitely do this again.
Triple Combo Snorkeling, Dolphin, and Sunset Cruise

Triple Combo Snorkeling, Dolphin, and Sunset Cruise

16 reviews
Duration3 Hrs.
This triple combo tour gives you three amazing experiences in one package. Watch pods of local dolphins playing in their...
Amazing trip. We saw six dolphins, got stuck on low tide but unstuck thanks to the amazing female captain. We snorkelled at sunset and drank beer all the way back. Highly recommend!
My husband and I had a great experience. We were originally supposed to do the sunset cruise but the weather wasn’t looking in our favor so reschedule. We got to see dolphins up close, go snorkeling and enjoyed the captain and assistant.
Great Captain and Crew, lovely weather this day and fantastic and cooperative dolphins. I got so many pics of them. Afterwards we were snorkeling at a beatiful reef where we saw stingrays, baracudas and even sharks. It was worth each and every pence!
from $74
Southernmost Sunset Sail with Full Bar and Hors d’Oeuvres

Southernmost Sunset Sail with Full Bar and Hors d’Oeuvres

11 reviews
Duration2 Hrs.
Excite yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See the local...
Wonderful sunset cruise, great apps, plenty of "beverages", cheerful staff! Highly recommend!!
This was a fantastic sunset cruise. We enjoyed the open bar and light appetizers. The crew was attentive and the music added to the experience. Highly recommend!
It was cloudy and rainy, but a very pleasant evening overall. Fortunately, the cloud front moved to the east, so we were able to see a fantastic sunset.
from $70
Wind and Wine Sunset Sail
Sail into the Key West sunset while sampling 8 fine wines from around the world, beer, and delicious hors d'oeuvres....
Sunset Snorkel Sail with Open Bar and Live Music
Treat yourself to an evening of incredible snorkeling, delicious drinks, and groovy melodies on the the Sandie Cat...
Live Music Sunset Cruise with Adult Drinks Included
Sail away with an ocean breeze for a night of music, drinks, and dancing on this Live Music Sunset Cruise. Experience...
Seabreeze Sunset Harbor Cruise with Wine and Beer
Escape the hustle and bustle and experience a breathtaking Key West sunset with a Seabreeze Sunset Harbor Cruise. Your...
Sunset Sip and Sail with Open Bar and Live Music
Have you ever seen Key West at dusk on the open ocean? Just sit back and immerse yourself in the ambiance of this...
Key West Catamaran Snorkel Trip
Get an incredible day of sailing, kayaking, and snorkeling in one awesome package and finish of your day with a famous...
Private BYOB Sunset Sailing Excursions
Cruise the picturesque waters of Key West at sunset aboard the 33' yacht of Sunset Sail Key West. Among the most popular...
Private Luxury Yacht Charter
Climb onboard the After Hours for a one-of-a-kind adventure through the Florida Keys with this Private Luxury Yacht...
Schooner Champagne Sunset Sail
Come along on this Champagne Sunset Sail and step into the lap of luxury. Sip, relax, and unwind aboard a gorgeous...
Captain's Choice Sunset Sail with Wine and Tapas Pairings
Embark on an unforgettable sailing adventure through the crystal-clear waters of Key West with the Captain's Choice...
Sunset Sail Aboard the Historic When and If
Set sail on Key West’s most elegant historic schooner, the When And If. Built in 1939 for General George Patton’s...
Key West Sunset Sail on America 2.0
Embark on a spectacular sunset sailing adventure off the coast of Key West in search of the famed "Green Flash"....