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Dorchester Center, MA 02124

Experience a private sunset sail in Key West on a 60 ft Schooner Serenity, with dolphin sightings, sail training, and drinks, all in a 2-hour group or family cruise.

A private sunset cruise in Key West offers an intimate way to enjoy the island’s famous evening views. Priced at $395 for about 2 hours, this experience takes place aboard the classic 60 ft Schooner Serenity. It’s perfect for families, friends, or small groups seeking a relaxed, personalized adventure on the water. The tour begins at 6810 Front St, Naval Air Station Key West, with departure scheduled for 5:30 pm.
What makes this tour stand out is its private nature, meaning only your group participates, and a knowledgeable captain guides you through the art of sailing. You can choose to sit back and relax or take the helm, learning how to raise and trim the sails. Snacks and beverages are included, and you’re welcome to bring your own alcoholic drinks to toast the sunset. This tour is an engaging, flexible option for anyone eager to combine sailing, marine life viewing, and scenic beauty in one experience.

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The tour begins at 6810 Front St, Naval Air Station Key West, a convenient starting point near public transportation. After arriving, you’ll board the classic 60 ft Schooner Serenity, which sets the perfect scene for a memorable sunset. The private transportation included ensures a smooth start, and the whole experience is designed for comfort and intimacy.
The departure at 5:30 pm aligns with the sunset, offering optimal views of the colorful horizon. The tour ends back at the starting point, completing a relaxed and scenic cruise that fits comfortably into an early evening schedule. With confirmation received at booking, you can plan your evening knowing this activity is specially reserved for your group.

The Schooner Serenity is the star of this tour, providing an authentic sailing experience. Its classic design evokes the golden age of schooner cruising, and its size allows for an intimate group setting. You’ll have opportunities to sit back and enjoy the scenery or try your hand at sailing, with the captain explaining the process along the way.
The vessel’s spacious deck offers excellent viewing points of Key West’s coast and marine life. Its sturdy build and seaworthiness ensure a comfortable ride during the 2-hour cruise. The captains are knowledgeable, ready to share insights about sailing and marine ecosystems, making the experience both fun and educational.
One of the highlights of this cruise is the chance to see dolphins and turtles in their natural habitat. The waters off Key West are home to various marine creatures, and the captain actively points out these animals during the sail. These sightings add an exciting element for nature lovers, reinforcing the tour’s appeal beyond just scenic views.
The marine activity is natural and dependent on the day’s conditions, but the knowledgeable guides do their best to maximize your chances of encountering marine life. Watching dolphins leap beside the schooner or turtles bobbing in the water produces unforgettable moments on the water.
This tour offers a flexible pace: you can sit back and soak in the sunset or try raising and trimming the sails under the captain’s guidance. For those interested in the art of sailing, this is a rare opportunity to get hands-on with the vessel’s operations.
If you prefer a more laid-back experience, the comfortable deck is perfect for relaxing, enjoying snacks and drinks, and taking in the beautiful scenery. The captain explains the sailing process clearly, so even novices feel engaged and informed. The private guide ensures the experience is tailored to your group’s interests and energy levels.
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Included in the tour are snacks and beverages, making it easy to enjoy a casual drink while watching the sunset. You are also welcome to bring your own alcoholic beverages, adding a personalized touch to your cruise. Whether you prefer wine, champagne, or cocktails, this flexibility creates a more festive and relaxed atmosphere on deck.
The vessel is equipped to handle your drinks and snacks, ensuring you remain comfortable throughout the 2-hour sail. This aspect makes the cruise ideal for celebrating special occasions or simply unwinding after a day in Key West.
The success of this tour depends on good weather conditions. If canceled due to poor weather, you will be offered a full refund or a different date. Cancellation is free if made at least 24 hours in advance; cancellations within this period are not refunded, so timely planning is advised.
The tour is suitable for individuals with moderate physical fitness, as boarding and moving about the vessel may require some mobility. The service animals are allowed onboard, accommodating guests with disabilities.
This cruise is ideal for those seeking a personalized, intimate experience with the option to learn sailing or relax while watching the sunset. Its private setting and flexible activities make it perfect for families, friends, or small groups celebrating a special moment. The marine life sightings and scenic views add to its appeal for nature and photography enthusiasts.
Since the tour is 2 hours long with a late afternoon start, it fits neatly into an evening plan in Key West. The informative captain and comfortable schooner ensure an enjoyable, memorable experience without feeling rushed or crowded.
This private sunset sail on the Schooner Serenity offers a relaxed, intimate, and engaging way to enjoy Key West’s iconic sunset. Its flexibility—whether you want to learn sailing, spot marine life, or simply unwind—makes it a versatile choice. With snacks and drinks provided, plus the option to bring your own alcohol, the tour encourages a festive yet laid-back atmosphere.
While weather-dependent, this cruise provides a beautiful scenic experience with personalized guidance from friendly, knowledgeable captains. It’s best suited for those who value privacy and customization in their water adventures, especially families or small groups celebrating a special occasion.
How long is the sunset sail?
The cruise lasts approximately 2 hours.
Where does the tour start?
The meeting point is at 6810 Front St, Naval Air Station Key West.
Can I bring my own drinks?
Yes, you are welcome to bring your own alcoholic beverages to enjoy during the cruise.
Is this tour suitable for children?
While specific age restrictions are not mentioned, it is suitable for groups with moderate physical fitness and can be enjoyed by families.
Are marine animals usually seen?
There are opportunities to view dolphins and turtles during the sail, depending on the day’s marine activity.
Do I need sailing experience?
No prior sailing experience is required; you can sit back or try sailing under the captain’s guidance.
What if the weather is bad?
If canceled due to poor weather, you receive a full refund or can reschedule for a different date.
How many people can fit on the schooner?
The vessel’s size supports a private group, making it perfect for small parties or families.
Can service animals join the tour?
Yes, service animals are allowed onboard.
What is the cost of this tour?
The price is $395 for the 2-hour private sunset sail.