Classic Key West Schooner Sunset Sail with Full Open Bar - The Experience on Board: Sails, Drinks, and Atmosphere

Classic Key West Schooner Sunset Sail with Full Open Bar

Enjoy a 2-hour sunset sail on a classic schooner in Key West for $109, with a full open bar, stunning views, and friendly crew. Book 32 days in advance.

Savor the beauty of a Key West sunset aboard a classic schooner with this two-hour sailing experience that features a full open bar. Priced at $109 per person, this tour is designed for those who want to combine the timeless charm of traditional sailing with the lively spirit of Key West’s waterfront. With a rating of 5.0 based on 91 reviews and recommended by 100% of participants, this cruise has earned a reputation for delivering a memorable evening on the water.

The tour departs from 200 William St, at the Key West Historic Seaport, a vibrant area buzzing with shops, restaurants, and colorful boats. It’s a small-group experience, accommodating up to 22 travelers, making for an intimate and relaxed atmosphere. Bookings are generally made about 32 days in advance, highlighting its popularity. While the two-hour duration offers enough time to enjoy the sunset and drinks, it’s a concise escape that suits those seeking a relaxed, scenic outing with no stops along the route.

Key Points

Classic Key West Schooner Sunset Sail with Full Open Bar - Key Points

  • Price and Duration: The tour costs $109 per person and lasts about 2 hours, offering a quick yet immersive sunset experience.
  • Departure Location: Starts at 200 William St in the Key West Historic Seaport area.
  • Inclusions: Features an all-you-can-drink full open bar, including cocktails, wine, premium beer, and champagne, plus soda and bottled water.
  • Stops and Sights: The cruise includes stops at Mallory Square, Sunset Key, Fort Zachary Taylor, and the Key West Historic Seaport, showcasing the area’s best sunset viewpoints and historic sites.
  • Expert Crew: Captain Joe and First Mate Michael are praised for their attentiveness and professionalism.
  • Crowd Size: Limited to 22 guests, ensuring a comfortable, non-crowded environment.
  • Weather Policy: Cancellable free if weather cancels; can be rescheduled or refunded.
  • Reviews: Consistently high ratings, with comments highlighting beautiful sunset views, friendly staff, and a cool sailing experience.

Classic Key West Schooner Sunset Sail Overview

Classic Key West Schooner Sunset Sail with Full Open Bar - Classic Key West Schooner Sunset Sail Overview

This schooner sunset cruise combines the charm of sailing with some of the most stunning views in Florida. As the sails are hoisted and lowered under the guidance of experienced crew, guests are treated to panoramic vistas of the Gulf of Mexico. The full open bar keeps spirits high, with signature cocktails like the Schooner Bloody Mary and Dark & Stormy flowing freely.

The cruise’s timing aligns with the sunset, allowing guests to witness the sky light up in shades of orange, pink, and purple. The two-hour journey starts at the Key West Historic Seaport, a lively waterfront hub with old buildings and colorful boats that add to the nautical atmosphere.

The Stops: Exploring Key West’s Best Sunset Views

Mallory Square is a highlight of the cruise, where the vibrant sunset celebration takes place. Known for street performers and lively music, this spot offers a lively backdrop for the sky’s changing colors. The Sunset Key stop gives a glimpse of the luxurious private island just off the coast, famous for its pristine beaches and spectacular sunsets.

Fort Zachary Taylor provides a historic perspective, as this mid-19th-century military fort played roles during the Civil War and the Spanish-American War. Now part of the state park, it offers scenic views and the chance to appreciate the area’s rich history while enjoying the sunset.

While there are no formal stops along the route, the combination of these locations ensures a variety of scenic and historic sights as the schooner gently sails through calm waters.

The Experience on Board: Sails, Drinks, and Atmosphere

Classic Key West Schooner Sunset Sail with Full Open Bar - The Experience on Board: Sails, Drinks, and Atmosphere

The crew, led by Captain Joe and First Mate Michael, is known for their professionalism and attentiveness. They not only assist with sailing the schooner but also ensure guests are comfortable and well-served. Watching the sails open and the crew’s expertise adds a layer of authenticity and skill that enhances the experience.

The full open bar is a standout feature, with bartenders crafting signature cocktails and pouring premium beer, wine, and champagne. Reviewers highlight that the drinks flow freely, and the limited guest count means no crowded feeling, allowing guests to relax and socialize comfortably.

Meeting Point and Practical Details

Classic Key West Schooner Sunset Sail with Full Open Bar - Meeting Point and Practical Details

The meeting point for the cruise is located at 200 William St in Key West, a location that is accessible via public transportation and central to the waterfront. The tour begins on time, and guests are advised to arrive promptly to ensure a smooth boarding process.

Guests should note that most travelers can participate, and the tour is suitable for those comfortable on a boat for two hours. It’s a mobile ticket experience, and the weather can impact the tour — if poor weather cancels, a full refund or alternative date is offered.

The Value of the Sunset Schooner Cruise

Classic Key West Schooner Sunset Sail with Full Open Bar - The Value of the Sunset Schooner Cruise

Priced at $109, this tour offers excellent value, considering the full open bar, scenic stops, and the personalized experience of sailing aboard a historic schooner. The limited group size enhances the feeling of an exclusive outing, while the professional crew ensures a smooth ride.

Review highlights emphasize that guests find the experience worth every penny, especially for the stunning sunset views and the friendly service. While some note that the crew could share more historical facts, the overall atmosphere remains warm, relaxing, and enjoyable.

Who Will Love This Experience?

Classic Key West Schooner Sunset Sail with Full Open Bar - Who Will Love This Experience?

This cruise is perfect for sunset lovers, sailing enthusiasts, and anyone seeking a relaxing evening on the water in Key West. The full open bar makes it suitable for those who enjoy drinks with a scenic backdrop. Its small-group setting appeals to travelers who prefer a more intimate, less crowded experience.

It’s an excellent choice for romantic evenings, special celebrations, or simply unwinding after a day exploring Key West. The timed sunset viewing and historic stops add layers of interest, making this more than just a bar crawl on the water.

✨ Book This Experience

Classic Key West Schooner Sunset Sail with Full Open Bar



5.0

(91 reviews)

98% 5-star

“The sunset views on the Appledore Star were beautiful! However, we expected a crew who would proactively share relevant historical or current day f…”

— Lesley W, Apr 2025

Frequently Asked Questions

Classic Key West Schooner Sunset Sail with Full Open Bar - Frequently Asked Questions

Is the tour suitable for children?
The tour is primarily designed for guests over 21 due to the full open bar. Children are not typically permitted to participate.

What should I bring on the cruise?
Guests should bring sunscreen, sunglasses, and a hat for daytime sun protection. Comfortable clothing is recommended, though the cruise itself is shaded.

Can I request specific drinks?
Bartenders craft a variety of cocktails, including signature options like the Schooner Bloody Mary and Dark & Stormy. Guests can ask for their favorites, and drinks are included for those over 21.

What if the weather is bad?
The tour is weather dependent. If canceled due to bad weather, guests are offered a reschedule or full refund.

How far in advance should I book?
Most bookings are made around 32 days in advance, reflecting its popularity. Early reservations are recommended to secure a spot.

Are there any hidden costs?
All drinks and amenities mentioned are included; gratuities are not included and are at guests’ discretion.

The Classic Key West Schooner Sunset Sail with Full Open Bar offers a beautiful, relaxing, and well-organized way to enjoy Key West’s famous sunset. With professional crew, delicious drinks, and stunning views, it’s a memorable experience for anyone wanting to combine sailing with a scenic evening.