Tours/Key West/Classic Key West Schooner Sunset Sail with Full Open Bar
Viator · group up to 22 pax

Classic Key West Schooner Sunset Sail with Full Open Bar

4.9(245)Key West1 hour
VIATOR4.8(34)TRIPADVISOR4.9(211)

Description

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Key West, promising an unforgettable experience for all. As you sail further into the sunset, the full open bar comes to life, offering an enticing array of cocktails, wines, and spirits to complement the evening's splendor. Sip on our signature Schooner Bloody Mary or Dark & Stormy as you watch the sky ignite with color. The skilled bartenders are on hand to craft your favorite drinks, ensuring that your glass is never empty as you drink in the sights and sounds of the sea. As the schooner begins its journey back to Key West, you find yourself lost in the timeless rhythm of the sea, grateful for the opportunity to witness the beauty of a Key West sunset from the deck of a historic schooner.

Tour Options

Classic Key West Schooner Sunset Sail with Full Open Bar

Itinerary

Pass by

The Key West Historic Seaport is a picturesque area located along the waterfront of Key West, Florida. It serves as both a working marina and a vibrant hub for visitors. The seaport features charming old buildings, colorful shops, restaurants, and bars, all set against the backdrop of the sparkling waters of the Gulf of Mexico.

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Mallory Square is a popular waterfront area located in Key West, Florida. It's famous for its vibrant sunset celebration, where locals and visitors gather every evening to enjoy street performances, live music, and food vendors while watching the sunset over the Gulf of Mexico.

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Sunset Key is a small, private island located just off the coast of Key West, Florida. It is known for its luxurious accommodations, beautiful beaches, and stunning sunsets.

Pass by

Fort Zachary Taylor is a historic military fort located at the southernmost point of Key West, Florida. Constructed in the mid-19th century, it played a significant role during the Civil War and later in the Spanish-American War. The fort is named after President Zachary Taylor and is now part of the Fort Zachary Taylor Historic State Park.

Highlights

Soda/Pop
Bottled water
In-person Guide: English
Full open bar with cocktails, premium beer, wine and champagne for guests >21 years of age

What's included

Included
Soda/Pop
Bottled water
In-person Guide: English
Full open bar with cocktails, premium beer, wine and champagne for guests >21 years of age
Not included
Gratuity

Traveller Ratings

4.9
245 reviews
5
234
4
6
3
3
2
0
1
2

Important Information

  • Public transportation options are available nearby
  • Infants are required to sit on an adult’s lap
  • Suitable for all physical fitness levels
  • Total sailing time is 2 hours. There are no stops.

Reviews(245)

J
jimbV9066PC
July 1, 2026
Great Relaxing Adventure

Great atmosphere. Only about 20 people on board. Drinks and hors d'oeuvres were really good (especially the shrimp). Nothing over the top, just sailing and beautiful views. If you want an easy, restful, quiet sunset cruise, this is it. Crew were great, friendly, and competent. Highly recommend this compared to many of the party boats you see.

K
Karen_D
June 23, 2026
Sails up, tranquil waves and great fun!

The evening sunset tour was absolutely the perfect end to our trip. The captain answered all of our questions about Key West and his Stew was friendly and hospitable. We loved that the group is limited 30 people since we did not want to be on a “party cruise” with music and large crowds. Our evening included sails up, the sound of the waves and great conversations. Absolutely will do this again when we return to the Keys!

Operator response

The evening sunset tour was absolutely the perfect end to our trip. The captain answered all of our questions about Key West and his Stew was friendly and hospitable. We loved that the group is limited 30 people since we did not want to be on a “party cruise” with music and large crowds. Our evening included sails up, the sound of the waves and great conversations. Absolutely will do this again when we return to the Keys!

A
Amy_F
June 20, 2026
Family friendly

This was perfect for our family. A nice relaxing experience. Not a party boat. Good conversation, food and drinks. The crew was Amazing!

Operator response

Thank you so much for the kind review! ⛵😊 We’re really glad to hear the experience was a great fit for your family and that you enjoyed the relaxed, laid-back atmosphere out on the water. It’s wonderful that the conversation, food, drinks, and especially the crew all helped make it such a positive outing for you. We appreciate you sailing with us and hope to welcome your family back aboard again for another peaceful and memorable trip soon! 🌊🌅

G
Greg_B
June 17, 2026
Sunset at sea

Calming magic, relaxing, safe cruise. Captain and crew were awesome. Great drinks and snacks. Friendliness abounded!

Operator response

Thank you so much for the lovely review! ⛵😊 We’re really glad to hear your cruise felt calming, relaxing, and safe—that’s exactly the kind of atmosphere we aim to create out on the water. It’s great that you enjoyed the drinks, snacks, and the friendly energy from the captain and crew as well. We appreciate you sailing with us and hope to welcome you back again soon for another peaceful day (or sunset) on the bay! 🌊🌅

H
Holli_H
June 1, 2026
Great Tour!

Wonderful experience with a very kind tour guide, took us to great spots with plenty of fish and upside down Jellies.

Operator response

Thank you so much for the kind review! We’re thrilled to hear you had such a wonderful experience and enjoyed exploring some of the area’s unique marine life. 🌊🐟 Seeing plenty of fish and the fascinating upside-down jellyfish is always a special treat, and we’re glad your guide helped make the adventure both enjoyable and memorable. We truly appreciate you joining us and hope to welcome you back for another great day on the water soon! ⛵😊

P
P6136PItonir
May 20, 2026
Once in a lifetime

Amazing experience. I highly recommend!!! Joe and his female colleague did an amazing job entertaining us and sharing information.

Operator response

Thank you so much for the wonderful review and recommendation! We’re thrilled to hear you had such an amazing experience aboard. 🌅⛵ Joe and his crew mate will be so happy to hear your kind words. We love creating a fun, welcoming atmosphere while also sharing stories and information that make the sail even more memorable. We truly appreciate you joining us and hope to welcome you back aboard again soon for another fantastic sunset cruise!

S
S2548OYbarryc
May 16, 2026
Sunset cruise

Great cruise on the Appledore Star

Operator response

Thank you for sailing with us aboard the Appledore Star! ⛵ We’re so glad you had a great cruise and truly appreciate you taking the time to share your experience. We hope to welcome you back aboard again soon for another beautiful day on the water! 🌅

S
shelleeo2025
May 14, 2026
Wonderful sunset sail

John , Andy , Ryan and Yann made a very enjoyable and entertaining experience! It was a lovely long sail and delicious appetizers . Also enjoyed the history lessons given by the crew as we sailed ! Overall great experience!! 10/10 !!

Operator response

Thank you so much for the amazing review! We’re thrilled to hear that John, Andy, Ryan, and Yann helped make your sail such an enjoyable and entertaining experience. 🌅⛵ It’s great to know you loved the long sail, the appetizers, and especially the little history lessons along the way—our crew really enjoys sharing those stories while out on the water. A 10/10 from you means a lot to us! We truly appreciate you sailing with us and hope to welcome you back aboard for another great adventure soon.

1
119caroly
May 13, 2026
Fantastic

It was the best experience for my husband and I. Captain Joe, and the first mate. Christine were wonderful. Very friendly, kept our glasses filled, and the food was great. I would recommend it to anybody and do it again. The cruising experience itself was hands-down the best we’ve done.

Operator response

Captain Joe and First Mate Cristina will be so happy to hear your kind words. They truly love making guests feel welcome, relaxed, and well taken care of—from keeping the drinks flowing to creating a fun and memorable atmosphere onboard. We’re also glad you enjoyed the food and overall sailing experience. Your recommendation means so much to us, and we’d love to welcome you both back aboard anytime for another unforgettable sunset sail!

J
jimmya273
May 11, 2026
Marvelous Sunset Cruise

The boat and crew, outstanding! Food and beverages added to the experience. What started as a possible cloudy sunset turned into a beautiful photo opportunity! Our fellow passengers were fun to be with and we met new friends! The cruise on Appledore Star was a highlight of our Key West trip!

Operator response

Thank you so much for this wonderful review! 🌅⛵ We’re thrilled to hear that the Appledore Star and her crew helped make your Key West trip so memorable. It’s great that the food, drinks, and even the changing skies all came together for such a beautiful sunset and photo-worthy moment. We also love hearing that you enjoyed the company onboard—those unexpected connections with fellow passengers can really make the experience extra special. We truly appreciate you sailing with us and are so glad it ended up being a highlight of your trip. Hope to welcome you back aboard again someday for another unforgettable evening!

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