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Enjoy a 2-hour small-group sunset sail off Key West with wine, beer, and gourmet snacks, led by experienced crew in an intimate schooner experience.

This $120.50 per person tour offers a relaxing way to enjoy Key West’s sunset on a 65-foot schooner. Lasting around 2 hours, this cruise provides a small-group setting with up to 26 guests, ensuring a personalized experience on the calm waters off the coast of Key West. The departure point is 255 Front St, where you check in half an hour before the cruise begins.
What sets this experience apart is its focus on fine wines, with the chance to sample up to eight different wines from around the world, including red, white, and champagne varieties. The tour also features five beers for those who prefer brewed beverages. Alongside the drinks, a gourmet cheese buffet and other appetizers like summer sausages, green apples with honey drizzle, and water crackers with brie are included, making the cruise as much about delicious snacks as it is about the scenery.
The sunset views are a key highlight, with the boat cruising on calm waters as the sky transforms into a canvas of oranges and pinks. Many reviews note the beautiful sunset, often accompanied by sightings of dolphins or even the rare Green Flash at sunset, thanks to the skillful maneuvering of the crew.

This intimate sailing experience is perfect for those who prefer a peaceful cruise without the noise of larger boats. The schooner, operated by Danger Charters, features a friendly, attentive crew led by experienced guides who focus on making each passenger comfortable. The small-group size ensures plenty of space to relax, chat, and enjoy the scenery.
The boat’s calm waters and smooth sailing contribute to a relaxed atmosphere. Several reviews praise the crew’s professionalism and warm hospitality, noting that Captain Tony and others provide informative and friendly service. The boat is near public transportation, making it a convenient start point for many visitors.
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This cruise’s standout feature is its carefully curated wine list, which includes eight different wines sourced from all over the world. The selection typically features four reds, three whites, and a Champagne, providing a variety suited for most wine lovers. Many reviews mention the top-tier quality of the wines, with some guests noting that it’s not just house wine, but a carefully chosen collection.
Along With wine, the cruise offers unlimited beer, wine, and soft drinks, allowing guests to drink as much as they like. The beverages are served with the gourmet snacks and hors d’oeuvres, including summer sausages, green apples with honey drizzle, and brie with water crackers. These complement the wines beautifully, creating a delightful tasting experience.

The food offerings are designed to enhance the wine tasting and sailing experience. The cheese buffet features brie, summer sausages, and water crackers, along with green apples with honey. Many reviews highlight the quality and variety of the snacks, often describing them as delicious and well-presented.
Guests appreciate the attention to detail, noting that the snacks are on point and pair well with the wines and beers. The gourmet buffet elevates the cruise from a simple sunset sail to a luxurious social event, making it especially popular for celebrating special occasions or just treating oneself.

The tour starts at 255 Front St in Key West, with check-in scheduled 30 minutes before departure. The activity is near public transportation, making it easy for most guests to access. The meeting point is conveniently located in the heart of Key West, and the activity ends back at the same location.
Booking is highly recommended, with an average of 26 days in advance, and the tour is suitable for most adults 21 and over. The minimum age to participate is 13 years, so families with older teenagers can also enjoy the experience.

The tour is dependent on good weather. In case of poor weather conditions, the tour may be canceled, with guests offered a full refund or the option to reschedule. Several reviews mention variable weather, including cool or cloudy days, which may shorten the sail or affect visibility. However, safety always takes priority, and the crew is attentive to weather changes.
Guests are advised to dress appropriately, especially if wind conditions are strong. Some reviews suggest bringing a light jacket, particularly for cooler evenings, but the crew’s friendly, attentive service helps ensure a comfortable experience regardless of conditions.
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One of the most memorable moments on this cruise is witnessing the Green Flash at sunset, a rare optical illusion that many find breathtaking. The crew, led by Captain Logan, expertly maneuvers the boat to maximize the chance of viewing this phenomenon, which is often considered a bucket list sight for sailing enthusiasts.
The sunset itself is described as spectacular, with many reviews emphasizing the beautiful colors and the peaceful calm of the surrounding waters. Some guests report seeing dolphins joining the sail, adding to the magical atmosphere.

Throughout many reviews, the crew’s friendliness and attentiveness are consistently praised. Captain Mary, Connor, Josh, and Captain Logan are highlighted for their professionalism, knowledge, and warm hospitality. Their tips on local beaches and key sights enhance the experience, making the cruise not just about wine and scenery but also about local insights.
Guests frequently mention the seamless service and personalized attention, which elevate the cruise from a typical sailing trip to a luxury experience. Many reviewers comment on the crew’s efforts to ensure everyone has a great time, whether by sharing interesting stories or making sure everyone’s drinks are topped off.
“Spectacular experience all around! Capt Mary, Connor and Josh were excellent crew and hosts for the evening. Classy evening on calm waters and a be…”

This small-group sunset sail receives nearly perfect ratings, with a 5.0/5 based on over 1,200 reviews. The consistent praise for quality wines, delicious snacks, friendly crew, and beautiful scenery makes it a top choice for those seeking a relaxing, wine-focused cruise.
It’s especially recommended for adults 21+ who enjoy sailing, fine wines, and scenic sunsets. The limited group size ensures a personalized and intimate atmosphere, ideal for romantic evenings or small gatherings.
While weather can influence the experience, the crew’s attention to safety and the potential to see rare sights like the Green Flash make this tour a worthwhile option for many visitors to Key West.
What is the price of the sunset sail?
The tour costs $120.50 per person.
How long does the cruise last?
The experience lasts approximately 2 hours.
What beverages are included?
Guests enjoy unlimited beer, wine, and soft drinks, with up to eight wines and five beers available.
Is food provided?
Yes, a gourmet cheese buffet and other appetizers like summer sausages, green apples with honey, and brie with water crackers are included.
Where does the tour start?
The departure is from 255 Front St, Key West.
What is the group size?
The maximum is 26 travelers, ensuring a small, personalized experience.
What is the minimum age to participate?
Participants must be 13 years or older, with a minimum drinking age of 21.
Can the tour be canceled?
Yes, full refunds are available if canceled more than 24 hours in advance. Cancellations less than 24 hours prior are not refunded.
What should I wear?
Guests should dress appropriately for weather conditions, especially if it’s windy or cooler in the evening.
Is the trip suitable if I don’t drink alcohol?
Yes, soft drinks and non-alcoholic beverages are available, making it accessible for everyone.
Will I see the Green Flash?
Many guests report witnessing the Green Flash at sunset, a rare and memorable optical phenomenon.