Key West, FL > Sunset Cruises
04/16/2021 ~ 04/22/2021
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Dolphin Watch Sunset Sail with Premium Wine and Tapas Pairings
$80
$74
Duration2.5 Hrs.

Key West Sunset Cruises

Key West Sunset Dinner Cruise

Key West Sunset Dinner Cruise

192 ratings
Duration2 Hrs.
If you are looking to make memories on a glorious Key West sunset as you dine and enjoy drinks with your loved ones,...
Entertainment and food was great. Loved every minute would definitely do again.
Had a lot of fun
A highlight of our vacation. The captain and crew took great care of us, so welcoming and polite. We were very fortunate with the weather and calm seas. The food was amazing and just the general vibe was outstanding. Watched the sunset with no blocked views on the top deck. Even tho a cloud blocked the last 5 mins of the sunset, it was worth every penny. Cruised back in past Mallory Square all light up
from $70
$69
Southernmost Sunset Sail with Full Bar and Hors d’Oeuvres

Southernmost Sunset Sail with Full Bar and Hors d’Oeuvres

91 ratings
Duration2 Hrs.
Entice yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See local...
Everything from check in to the wonderful crew and the view of the sunset was excellent!!! I would highly recommend!
Great value for all they do for you. Lot’s of food and all the drinks you can handle!
Absolutely a blast! Wonderful service!
from $70
$69
2 Hour Private Sunset Cruise on a Tiki Bar Boat

2 Hour Private Sunset Cruise on a Tiki Bar Boat

1 rating
Duration2 Hrs.
If you are looking for a way to float away the day, then this 2 Hour Private Sunset Cruise on a Tiki Bar Boat is the...

New to TripShock

from
$425
Glass Bottom Boat Reef & Eco Tour

Glass Bottom Boat Reef & Eco Tour

12 ratings
Duration2 Hrs.
Climb aboard for an adventure through the most diverse underwater ecosystem in the United States with the Glass Bottom...
The crew was great - boat was in excellent condition. Was a pretty cool trip - even though water was a bit rough, we were still able to have some great sights
We had a great time on the ride! Marta was very knowledgeable and we very much enjoyed our trip to the barrier reef.
from
$50
Dolphin Watch Sunset Sail with Premium Wine and Tapas Pairings

Dolphin Watch Sunset Sail with Premium Wine and Tapas Pairings

43 ratings
Duration2.5 Hrs.
Embark on an unforgettable sailing adventure through the crystal-clear waters of Key West with the Dolphin Watch Sunset...
Great cruise, great service. So kind to my children who were a bit bored, but they staff engaged them and they had a wonderful time.
Loved everything about it. Light on food, but wine was excellent, and a couple of beer options were available. The music, atmosphere, staff, and fellow guests were excellent. Lots of dolphins up close, and the sunset was beautiful. Highly recommended.
Easy to book, great experience
from $80
$74
Triple Combo Snorkeling, Dolphin, and Sunset Cruise

Triple Combo Snorkeling, Dolphin, and Sunset Cruise

42 ratings
Duration3 Hrs.
This triple combo tour gives you three amazing experiences in one package. Watch pods of local dolphins playing in their...
Loved it. It was beautiful. Very friendly snorkeling guide. Good folks. I wouldn’t hesitate in recommending it to someone.
Crew was great. Highly recommend.
Dolphin viewing and sun set were great. The snorkeling was disappointing really wavy and water was cool and jelly fish every where. The crew did an out standing job to make our trip the best it could be.
from $74
$64
Sunset Cycleboat Cruise Key West

Sunset Cycleboat Cruise Key West

New to TripShock
Duration2.5 Hrs.
Pedal, pedal then bottoms up! Now is the time to book this Sunset Cycleboat Cruise in Key West for your chance at an...

New to TripShock

from
$45
Champagne Sunset Catamaran Cruise

Champagne Sunset Catamaran Cruise

53 ratings
Duration1.5 Hrs.
Enjoy a night you’ll never forget on a Champagne Sunset Catamaran Cruise in Key West. Watch the masterfully painted...
The staff was nice,the one even took pictures of us. The sunset was beautiful. Of course free alcohol is nice. The only thing was that the ad said margaritas, but there wasn't any.
Nice sunset tour. We had a lot of fun. Music was great. Con . Better organization at the boarding process. It's was a cluster F***
Nice time with a nice crew and good music.
from $50
$42
Sunset Sip and Sail with Open Bar and Live Music

Sunset Sip and Sail with Open Bar and Live Music

28 ratings
Duration2 Hrs.
Have you ever seen Key West at dusk on the open ocean? Just sit back and immerse yourself in the ambiance of this...
Our sailing trip was great we had a great time enjoyed Pete with the music and rest of staff were awesome. When we come back we will definitely do this again Thank You
Was a great sun set cruise with great entertainment and drinks
This was the highlight of our visit to Key West. Crew was great and very fun to be around. Unbelievable view and very comfortable trip. Highly recommend it and will be back in the future for another voyage.
from
$49
Wind and Wine Sunset Sail

Wind and Wine Sunset Sail

41 ratings
Duration2 Hrs.
Sail into an unforgettable Key West sunset while sampling beer, delicious hors d'oeuvres, and 8 fine wines from around...
Loved this excursion!
I booked this for myself and 5 friends. It was most of the group's favorite activity. We have such a great time and the staff was wonderful.
We had a wonderful time in the wind and wine sunset sail! The crew was AWSOME and the weather was perfect. Will definitely do it again next trip to the Keys!
from
$85
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"....
Live Music Sunset Cruise with Cocktails Included
Sail away with an ocean breeze for a night of music, drinks, and dancing on this Live Music Sunset Cruise. Experience...
Sunset Snorkel Sail with Open Bar & Live Music
Treat yourself to an evening of incredible snorkeling, delicious drinks, and groovy melodies on the Sandie Cat...
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 Snorkel & Sail with Rum & Reggae Included
Leave the land behind for an evening of snorkeling and Reggae music on this Sunset Snorkel & Sail with Rum & Reggae...
Private Tritoon Charter on the Barefoot One
Hang out like the locals! The shallow, clear backcountry waters of the Florida Keys sets it apart from anywhere else in...
Rum Runner Bar Boat Sunset Cruise
Enjoy a sunset cruise on the water on the best value bar boat in Key West. Cruise the gorgeous water on this Rum Runner...
Private Sunset Cycleboat Cruise Key West
Pedal, pedal then bottoms up! Now is the time to book this Private Sunset Cycleboat Cruise Key West for your chance at...
Mallory Square Hydrobike Sunset Tour
Witness a sunset from one of the most sought out vantage points on the island, Mallory Square, but do it from the water...
Private Snorkel and Sunset Sail Excursion
Climb aboard and set out on a private snorkel and sunset sail. You'll get the best of both worlds as you glide across...
Key West Sail, Snorkel, & Kayak Adventure
Get out on the water for an incredible day of sailing, kayaking, and snorkeling in one awesome package on this Key West...
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 aboard for a leisurely adventure through the Florida Keys with this Private Luxury Yacht Charter. Experience the...
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...
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...