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2 hours
Mobile ticket
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 West, as you sail by Mallory Square, Sunset Pier, Sand Key Light Tower and more. Enjoy complimentary beverages throughout your sail along with individually plated hors d'oeuvres. Sit back and relax as your captain sails you effortlessly through the emerald green Key West waters and off toward the horizon for a quintessential Florida sunset experience.
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Suitable for all physical fitness levels
We recommend bringing a light jacket as it's often cooler on the water.
Must be 21 years or older to consume alcohol.
Meet at Key West Bight Marina 30-45 minutes prior to your selected departure time to check in at ticket booth and board the sailboat for your sunset cruise
For a full refund, cancel at least 24 hours before the scheduled departure time.
Mallory Square
Enjoy views of some famous Key West landmarks from the water as the boat sails along the coast and onward into the sunset!
Fort Zachary Taylor Historic State Park
See the famous Fort Zachary from the water as you sail by.
Your 2-hour sailing experience aboard America 2.0
Individually plated hors d'oeuvres
Complimentary beer, wine, Champagne and soda
Gratuities
Hotel pickup and drop-off
Duration: 2 hours: This experience is 2-hours. Please check in at the ticket booth 30-45 minutes prior to the departure time for boarding passes Champagne upgrade: This option includes a bottle of champagne & souvenir glassware. Beer, wine, soda, water, & light snacks are also included. Requirement: There is a 2 ticket purchase minimum for this upgrade option
Duration: 2 hours: This experience is 2-hours. Please check in at the ticket booth 30-45 minutes prior to the departure time for boarding passes Bar & Food included Premium rates apply
Duration: 2 hours: Please check in at the ticket booth 30-45 minutes prior to the departure time for boarding passes White Wine Upgrade: This option includes a bottle of white wine & souvenir glassware. Beer, wine, soda, water, & light snacks are also included. Requirement: There is a 2 ticket purchase minimum for this upgrade option
Duration: 2 hours: This experience is 2-hours. Please check in at the ticket booth 30-45 minutes prior to the departure time for boarding passes Bar & Food included Peak Holiday Rates Apply
Duration: 2 hours: This experience is 2-hours. Please check in at the ticket booth 30-45 minutes prior to the departure time for boarding passes Bar & food included: This option includes our house beer, wine, sparkling wine, and hors d'oeuvres
889 reviews
Total reviews and rating from Viator & Tripadvisor
Jane C,May 19, 2026
- Review from Viator
Worth it! Pay the extra money for this over the catamaran boats. Food and wine was great but the sailing and crew were even better.
Barb T,May 19, 2026
- Review from Viator
It was an awesome experience. The crew, Ray, Chelsea, and Brad were wonderful. Best experience so far in Key West.
Stuart G,May 18, 2026
- Review from Viator
The crew is fantastic. Not just sailors, but great hosts. Our wine glasses were never empty, and the snacks just kept coming.
Ajay K,May 17, 2026
- Review from Viator
Best experience ever. The crew was awesome and the vibe was abwesome. It’s pure dialling boat so we loved it

Harvey S,May 16, 2026
- Review from Viator
snacks are minimal. boat is lovely. crew friendly and considerate. lovely to be on real sailing ship
James P,May 16, 2026
- Review from Viator
It's not a rock concert, it's not a dance club- it's a cruise, quiet and peaceful and serene: the way God intended sailing to be..

Sandee B,May 15, 2026
- Review from Viator
It was so beautiful! We had the perfect evening weather wise! But what made it even more amazing was the crew! Captain Janet, Mary & Chelsea were so sweet and so knowledgeable! It was so fun watching them put the sails up and take them down! They were also wonderful hostesses! They made sure we always had a fresh drink in our hand. The hor d’oeuvres were fresh and tasty! I highly recommend doing this sail! We will definitely do it again if we come back! One of the highlights of our trip!
mandy h,May 13, 2026
- Review from Viator
Amazing amazing experience. What a well put together crew and vessel.!! drinks and snacks were on point worth every penny and more!! Book this!!!👏
Mark L,May 8, 2026
- Review from Viator
Amazing fun crew that started the cruise off with making everyone feel comfortable and well informed!
whitecla,May 8, 2026
- Review from Tripadvisor
Our experience with the Sunset Sail was amazing. The Captain and Crew were knowledgeable, welcoming and very friendly. We would definitely recommend this experience.
Operated by Classic Harbor Line