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Key West Special Occasion Activities, Tours & Attractions

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Key West Sunset Dinner Cruise

Key West Sunset Dinner Cruise

259 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,...
Cruise was fun. Staff was awesome. Seeing the sunset was amazing. The buffet dinner part was not the best. Food was not good and there was not enough seating inside for everyone at the same time so you had to wait for seats. You had the option of fixing your plate and bringing it to the upstairs deck. But there were no tables there, so you had to sit and eat with your plate on your lap if you did that.
My wife and I had a great time. The DJ was awesome, good music and a great personality. The food tasted great and the portions were good. The drinks were good, and you can take them to go! All in all we had a great time!
We love the cruise and staff were very friendly DJ was rocking It’s a great memory on our anniversary we will cherish this memory
from $70
$59
Dolphin Watch Sunset Sail with Premium Wine and Tapas Pairings

Dolphin Watch Sunset Sail with Premium Wine and Tapas Pairings

88 ratings
Duration2.5 Hrs.
Embark on an unforgettable sailing adventure through the crystal-clear waters of Key West with the Dolphin Watch Sunset...
The crew was so friendly and knowledgeable! Food and beverages were great! We did get to see a few dolphins too! Highly recommend - would definitely go again. Thank you!
My granddaughter and I really enjoyed our dolphin Sunset trip on your catamaran
This was very nice. We saw several pods of dolphins in the harbor. Key West has some of the prettiest sunsets and it did not disappoint. Crew were friendly and helpful.
from $80
$74
Southernmost Sunset Sail with Bar and Hors d’Oeuvres

Southernmost Sunset Sail with Bar and Hors d’Oeuvres

177 ratings
Duration2 Hrs.
Entice yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See local...
Very nice experience sailing sunset
Captain Johnny & crew plus singer were fantastic hosts. looking forward to our next Sebago cruise
it was amazing...crew was very friendly and professional. The appetizers were amazing and the local talent was great!! Will definitely recommend this sunset cruise to our friends!!
from $70
$69
Key West Kayak Eco-Tour

Key West Kayak Eco-Tour

9 ratings
Duration2 Hrs.
Join in on this guided Key West Kayak Eco-Tour and paddle at a relaxed pace through the crystal clear water of Key...
We had a great time with our first experience in a kayak. Heather with the dreads was patient, knowledgeable and experienced on the water and helped us through our first time using a kayak. We had a wonderful time paddling our way through the mangroves and we learned a lot about the ecosystem in the process. We would definitely take this tour again!
Great paddle and wonderful guide
from
$50
Key West Sunset Sail on America 2.0

Key West Sunset Sail on America 2.0

33 ratings
Duration2 Hrs.
Embark on a spectacular sunset sailing adventure off the coast of Key West, Florida in search of the famed "Green...
Fabulous energetic hard working and friendly crew on a beautiful schooner. Great snacks, too! We highly recommend it!
The staff was friendly but professional and we loved everything about this trip! If you love the water and romantic sunsets, this is a must when you visit Key West!
Very friendly and attentive crew. Great captain. Really enjoyed this sail.
from
$96
per ticket
Downtown Parasailing Adventure

Downtown Parasailing Adventure

389 ratings
Duration1 Hr.
If you are looking for something exciting to do over downtown Key West, then this is the adventure for you. Parasail the...
Great place to rent jet skis. We rented the 9am slot since reservations were limited. The guide was Jake who was very friendly. I would recommend them again.
Had a great time with the crew. They were very nice and talked with us like we were old friends. I just wish the time in the air was longer but I understand the constraints of money and all that.
We had a fantastic time. The staff was great and took good care of us.
from
$70
Paddleboard Rentals at Casa Marina

Paddleboard Rentals at Casa Marina

342 ratings
Duration1 Hr.
Feel like your walking on water as you take in the beauty of Key West on your personal paddleboard. Glide over sparkling...
Hands Down a must do!! The crew at Barefoot Billy's is top notch! We rented Jet Ski's and had an awesome time! We will be going back again!
It was a great experience. All the guys are super friendly and knowledgeable. Made us feel safe whilst showing us the beautiful Florida Keys coastline....
Barret was fantastic. He was very patient and explained everything.We had a small group, which was great, and he made it pleasurable!!!!
from
$30
Champagne Sunset Catamaran Cruise

Champagne Sunset Catamaran Cruise

85 ratings
Duration1.5 Hrs.
Enjoy a night you’ll never forget on a Champagne Sunset Catamaran Cruise in Key West. Watch the masterfully painted...
Great cruise, great crew.
Not really meant for a young couple, more for a bit of an older crowd. However, we still had fun!
This cruise was awesome! Nice crew on board. They were very professional and friendly. The drinks were also very good and they weren’t stingy about handing them out. I would definitely recommend it.
from $50
$48
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