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(256)Key West1 hour
VIATOR4.8(42)TRIPADVISOR4.9(214)

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.

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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
256 reviews
5
245
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(256)

G
garybH2399FR
August 8, 2026
Peaceful Sunset Cruise

My wife and I loved our sunset cruise on the Appledore Star. The trip does cost a little more than many of the others, but it is well worth it. The group is much smaller than other cruises (limited to 16, I think), and it is so peaceful. There’s no loud music, and once we were clear of the harbor, the motor was shut off and we sailed. The quiet trip allows you to talk to the other guests and crew and just enjoy the sounds of the ocean. The trip lasted about two hours. Our crew was Captain Luana and First Mate Vitali. They were hardworking, friendly, and interesting to talk with. We will definitely plan to sail with Appledore the next time we’re in Key West.

B
Bruce_M
August 6, 2026
Perfect relaxing sun set cruise!

Wife and I enjoyed! 2 young people did a great job sailing us. So glad we weren't on the party boat that could be heard across the bay!

G
G1416LNkarenb
August 2, 2026
Beautiful Key West Evening ❤️

I highly recommend this historical schooner sunset cruise. It is a must do while in Key West. Drinks and hors d'oeuvres, which were fantastic, are included in the admission fee. You will sail for about two hours and every seat on the boat has views of the sun set. Our crew turned the boat around, giving everyone great views! Our crew was excellent, experienced, and friendly. My husband and I chose this for the smaller group experience and historic schooner vs. the catamaran sailings that hold far more people.

Operator response

Thank you so much for your wonderful review! ⛵🌅 We’re honored that you chose our historic schooner for your Key West sunset sail and are thrilled to hear it was a highlight of your visit. We’re so glad you enjoyed the delicious drinks and hors d’oeuvres, the intimate atmosphere, and the chance to experience a true sailing vessel rather than a larger tour boat. Our crew takes great pride in making sure every guest has the best possible view of the sunset, and they’ll be delighted to hear their friendliness and expertise made your evening even more memorable. Thank you for your thoughtful recommendation. We truly appreciate you sailing with us and hope to welcome you both back aboard for another relaxing and unforgettable sunset adventure! 🌊☀️

S
SUSU25
July 29, 2026
A true sailing experience

Joe and Christina were not only excellent host but extremely knowledgeable sailors. The Appledore is powered by her sails, eliminating engine noise, blaring music and fuel odors. Drinks and snacks are served to you. This is sunset sailing not the cattle car experience offered on the big boats. Book this trip, you won’t regret it.

Operator response

Thank you so much for your incredible review! ⛵🌅 We’re thrilled to hear you enjoyed the authentic sailing experience aboard the Appledore. There’s something truly special about gliding under sail with the sounds of the wind and water instead of engines, creating a peaceful and relaxing atmosphere. Joe and Cristina will be delighted to hear your kind words about their hospitality and sailing expertise. We’re also glad you enjoyed the onboard drinks and snacks and appreciated the intimate experience our schooner offers. Thank you for your wonderful recommendation. We truly appreciate you sailing with us and hope to welcome you back aboard for another unforgettable sunset sail! 🌊😊

L
Lisa_K
July 23, 2026
Sailing with style

We booked the Appledore Star champagne sunset sail with three generations aboard and it worked beautifully for all of us. If you’re comparing Key West sunset cruises and worried about ending up on a loud party boat, this is the other kind: a real two-masted schooner, a calm deck, and space to actually watch the sun go down. The captain and first mate made the evening. Both were funny, warm, and genuinely knowledgeable, with great stories about the boat and the water, and they handled the sails with an ease that was fun to watch. The hors d’oeuvres were fresh and thoughtfully done, the drinks were generous, and the sunset was as romantic and beautiful as ever.

Operator response

Thank you so much for your incredible review! ⛵🌅 We’re thrilled to hear that the Appledore Star Champagne Sunset Sail was the perfect experience for three generations of your family. Creating a relaxing, memorable evening where guests can truly enjoy the beauty of the water is exactly what we strive for. We’re especially grateful for your kind words about our captain and first mate. They’ll be delighted to know that their stories, humor, and knowledge helped make your evening so special. Watching the sails go up and experiencing the tradition of a schooner is such a unique part of the adventure, and we’re glad you enjoyed every moment. Thank you for highlighting the hors d’oeuvres, drinks, and peaceful atmosphere aboard the Appledore Star. We truly appreciate your recommendation and hope to welcome your family back aboard again soon for another beautiful sunset sail! 🌊😊

M
Mike_M
July 21, 2026
Excellent Sunset Sail Cruise

We had wonderful time on a sailboat with drinks and hors-d'œuvres watching the sunset. The captain was very informative and the scenery was amazing.

Operator response

Thank you so much for your wonderful review! ⛵😊 We’re thrilled to hear you had a great sail and enjoyed the beautiful views of the harbor, lighthouses, and islands. Our crew will be delighted to know their knowledge and hospitality helped make your experience memorable. We’re glad you were able to relax, take in the scenery, and enjoy a drink while out on the water. Thank you for your high recommendation, and we hope to welcome you aboard again soon for another unforgettable sail! 🌊☀️

K
kelly_e
July 20, 2026
Crew was top notch. Very...

Crew was top notch. Very relaxed but on task and went out of their way to make everyone feel comfortable.

Operator response

Thank you for your wonderful review! ⛵😊 We’re so glad to hear that our crew helped make your experience comfortable, enjoyable, and memorable. Their goal is to create a relaxed atmosphere while ensuring everyone feels safe, welcome, and well cared for throughout the sail. We truly appreciate your kind words and are grateful you chose to join us on the water. We hope to welcome you aboard again soon for another fantastic adventure! 🌊☀️

J
John_T
July 16, 2026
Sunset Cruise

Great cruise! The crew were super friendly and knowledgeable. The food was very nice and drinks were refreshing.

Operator response

Thank you so much for your great review! ⛵😊 We’re delighted to hear you had a wonderful cruise and enjoyed our friendly, knowledgeable crew. It’s great to know the food and refreshing drinks added to your experience as well. We appreciate you sailing with us and hope to welcome you aboard again soon for another fantastic adventure on the water! 🌊☀️

J
Justin_O
July 15, 2026
Sunset cruise on the Appledore Star

It was so peaceful and relaxing. The view was beautiful. Luanna was an excellent captain and her first mare was excellent to

Operator response

Thank you for your lovely review! ⛵😊 We’re so happy to hear that you enjoyed such a peaceful and relaxing sail while taking in the beautiful views. Captain Luanna and her first mate will be delighted to know their care and expertise helped make your experience special. We truly appreciate you joining us on the water and hope to welcome you aboard again soon for another memorable cruise! 🌊☀️

G
Gemma_B
July 15, 2026
Amazing cruise!

The best boat trip ever!! Luanna and vitali (sorry if I’ve spelt the names wrong) were incredible. Luanna was the best captain, engaging, entertaining and just lovely.. the host trip was smooth, with the best sunset. Vitali kept us fed and watered, honestly cannot recommend this relaxed sunset cruise enough.we went as a family with teenagers, and they absolutely loved it.

Operator response

Thank you so much for your incredible review! ⛵🌅 We’re absolutely thrilled to hear your family had the best time aboard our sunset cruise. Captain Luanna and Vitali will be so happy to know their warmth, knowledge, and attention to detail helped make your experience unforgettable. We’re especially glad to hear that everyone—including your teenagers—enjoyed the relaxed atmosphere, beautiful sunset, and time on the water. Creating memorable experiences for families is exactly what we love to do! Thank you for your enthusiastic recommendation, and we hope to welcome you all back aboard again soon for another amazing sail. 🌊😊

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