Limited Spaces Available! For reservations call (866) 945-7917. Spaces are extremely limited this time of year so book early to ensure the date you want.
Captain's Choice Sunset Sail


  • All New Dolphin Watch!
  • Sailing on a 41-Foot Luxury Sailing Yacht, the Pelican 
  • Unlimted Open Bar, Champagne, Sangria, Wine, Beer & Sodas
  • Appetizers

Tour Summary

When it comes to sunset sailing with style and luxury, the Captain’s Choice Sunset Sail seems to be everyone’s main choice. This two-hour sunset sailing experience takes you out to the calm waters of the Gulf of Mexico to view the sunset on board a sturdy, comfortable, and luxurious 41-foot sailing catamaran. This is not the type of sunset cruise that piles a hundred guests onto a massive catamaran. This is the type of sunset cruise that prioritizes comfort, style and luxury to provide a truly magical and unforgettable Key West sunset watching experience to a select number of guests.


If you are looking for an intimate and memorable sunset watching tour out of Key West, let us recommend the Captain’s Choice! This sunset cruise is consistently rated one of the top sunset watching experiences anywhere in the Florida Keys! The main reason is the sailing yacht that we use for the Captain’s Choice. This boat is state of the art, sleek, and modern, and offers a perfect setting for sunset watching. But there is much more that makes this tour a top choice for sunset viewing. Our professional and serviceable crew is on hand for the entirety of the trip to offer you unlimited, complimentary drinks and snacks. Whether your drink of choice is sangria, wine, champagne, or draft beer, we have just what you want! Our snacks consist of an assortment of freshly prepared treats and snacks, including a delicious peel & eat shrimp platter.


There is nothing quite like the Key West sunset. And there are many ways to see our famous sunset. But if you want to really showcase the beauty and delight of sunset viewing, check out our Captain’s Choice Sunset Sail!


What is the weather cancellation policy?
If the activity must is cancelled due to bad weather, and you cannot reschedule, you will be issued a full refund.

Where is the departure point for this tour?
Check-in instructions will be included in your activity confirmation email.

Where can I park?
There is metered parking available near the check-in facility.

It is your responsibility to make sure you are aware of and understand all restrictions pertaining to this tour before booking online or over the phone. It is your responsibility to ensure that you are medically qualified and within any limits listed below in order to participate in this activity. No refunds will be given to those who reserve a spot and can not participate due to the restrictions listed below. For more information please read our cancellation policy and terms and conditions page or call our staff with any questions regarding your ability to participate.

  • You Must Bring a Valid, Government Issued Photo ID to Consume Alcohol.
  • All Passengers on This Tour Must be 18 & Up.
  • NOTICE: The discounted prices may not be available during Peak or Holiday periods. Peak/Holiday pricing is $79.95 per adult. 

Key West Vacation is always interested in your tour experience with us. We hope you enjoyed your tour and love to hear comments.

Bob Smith

I have been to the Bahamas many times, but Captain's Choice Sunset Sail is one of my favorite trips! It includes everything that everyone should do here. As a Bahamas veteran, I can say only the best about this experience!

Jim Peters

Thanks to the professional guides! I was a bit worried about kayaking because I had never done it before, but the instructions were great and I had such a good time!

Richard Dixon

The best way to discover nature! ( ͡° ͜ʖ ͡°)