Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
Overview
Available languages
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.
Additional Info
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
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What To Expect
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.
What‘s Included
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
Options
Peak Holiday 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
Sunset Sail Champagne Upgrade
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
Holiday Premium 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
Key West Sunset Sail
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
Reviews
861 reviews
Total reviews and rating from Viator & Tripadvisor
Magnificent sunset, fun and relaxing sail in Key West
kimdR7173DA,Mar 31, 2026
- Review from Tripadvisor
5.00Wow! What a fabulous sunset sail on the America 2.0 schooner. Our group of 6 had such a relaxing and fun time. We were so fortunate to have such beautiful weather too. Captain Rae, along with Chelsea, Brian and Brad, were THE BEST! We look forward to returning to Key West and sailing again. This vessel and crew will be in New York Harbor in July 2026-I would highly recommend booking an excursion with them!
Awesome time - look no further set sail soon!
daveoT2073FU,Mar 30, 2026
- Review from Tripadvisor
5.00Ray, Jade & Brad were awesome! We had such a great time on our sailboat cruise. The crew was incredible and attentive and had so much wonderful energy to share! Highly recommend!
Green Flash Amazing
Adventurer466223,Mar 29, 2026
- Review from Tripadvisor
5.00Green Flash, amazing. We had such a delightful pleasant sunset cruise on America 2.0 with Capt Heather and crew Dan and Ray. The weather was perfect and the boat is beautiful. The crew was very attentive and the snacks were great. Huge selection of beverages. Highly recommend and will go with Classic Harbor lines on our next KW trip
America 2.0 Sunset
DON D,Mar 27, 2026
- Review from Viator
5.00A thoroughly enjoyable cruise! Captain and crew were awesome, weather great and the sunset was magnificent.
Beautiful Sunset Cruise aboard America 2.0 with Capt. Jan
M7894HTbobm,Mar 27, 2026
- Review from Tripadvisor
5.00We took a sunset cruise on the America 2.0. It was a beautiful evening with a nice wind made the sale so enjoyable. The rustling of the wind with no motor was a quiet invigorating experience. The crew of Jan, Mary, Dan and Milo were terrific attending to their sailing duties while waiting on patrons. They delivered to your assigned seat your choice of beer, wine or champagne. Veggie platters, cheese crackers, shrimp cocktails and a brownie to top it off were also provided. We saw a beautiful sunset as well. A great, relaxing experience, rounding off our week in Key West. Look forward to a return trip.
Worth every penny, highly recommend
KAREN H,Mar 26, 2026
- Review from Viator
5.00We loved it, felt safe but it was an exhilarating way to sèe the sunset. Definitely the best we have done and we have done a few sunset cruises
Beautiful sailing experience
KDelaneyPrice,Mar 24, 2026
- Review from Tripadvisor
5.00This sunset sail was the perfect way to watch the sunset. The crew took excellent care of us. Our drinks were never empty and the apps were perfectly light and filling. We sailed the whole trip except for in and out of the marina which was awesome. Saw dolphins who were jumping in our wake which was a highlight. The sunsets in key west are killer and this is a great relaxing and sweet way to watch it. It was between this sunset sail and a party boat for my husband and I on an anniversary trip and this was definitely the right move.
A spectacular evening sailing adventure with the best of friends.
I600IWricharda,Mar 23, 2026
- Review from Tripadvisor
5.00My wife and I and three other couples enjoyed and spectacularly beautiful evening on a Key West Schooner Sunset Sail (by Classic Harbor Line). The very capable young adult crew did an outstanding job of handling the ship and cheerfully provided 4 different simple but delicious Hors d'oeuvres plus a selection of liquid refreshments including adult beverages. The crew members were friendly, informative and sociable. The ship was well maintained and in excellent condition. The view of the sunset was amazing. In all respects this was a very memorable experience. I highly recommend this experience for your next trip to Key West.
Great sail
Robin M,Mar 21, 2026
- Review from Viator
5.00This was a fantastic sail. Staff was great. Capt Janet was great too. Food was nice too. We had ranch and veggies, cheese and crackers, boiled shrimp and a brownie for dessert. The drinks were free flowing also. I would do this again on the next visit. The only problem is finding the ticket booth. We went to three different ones before we found the correct one. It could be market for easier access.
Great trip on the schooner!
DavidJohn G,Mar 21, 2026
- Review from Viator
5.00Our outing was wonderful - smaller group of people, attentive and knowledgeable crew - Rae, Chelsea, and Brad - great night overall.
From US$122.59
Want a private experience? Upgrade to a private tour
Related Experiences
Operated by Classic Harbor Line