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Book Your Private 2-Hour Day Sailing Experience in Downtown Orlando

Join the first and only sailing tour in Central Florida and discover how Sailing Orlando brings the joy of sailing to guests and visitors in Downtown Orlando and greater Orlando; on our private tours you’ll sail a 25-foot sloop-rigged sailboat for day sails, relaxing sunset cruises, or hands-on “learn the ropes” sessions that are both entertaining and educational, teaching you fundamental sailing principles while you soak up the Florida sun.

About this activity in Downtown Orlando

Cancellation policy
For a full refund, cancel at least 24 hours before the scheduled departure time.

Highlights

  • Private sailing tours aboard a 25-foot sloop-rig in Downtown Orlando - choose day sails, sunset cruises, or hands-on lessons
  • Guided, small-group experiences that blend entertaining storytelling with practical sailing instruction
  • Comfortable cockpit seating for up to four adults plus a below-deck cabin for extra seating and dry storage
  • Enjoy Florida sunshine and waterfront views while learning fundamental sailing skills from an experienced instructor

Important Information

  • Bottled water and life jackets for most sizes are provided; towels and dinner are not included - plan accordingly
  • Service animals are permitted and public transportation options are available nearby for easy access to the dock
  • Not recommended for travelers with spinal injuries or serious cardiovascular conditions; generally suitable for varied fitness levels
  • Tours operate from a Downtown Orlando marina; expect an informative, safe experience whether you book a family outing, romantic cruise, or educational workshop

Meeting Point

Meet at the designated marina dock in Downtown Orlando listed on your Varoom reservation. Look for the Sailing Orlando signage at the boarding slip; your instructor will greet you there a few minutes before the scheduled departure time.

Includes

  • You’ll receive bottled water on board for refreshment during your Downtown Orlando sailing experience, so you can stay hydrated while you explore the area.
  • Life jackets are provided in most sizes to help ensure safety for a range of passengers while you’re out on the water near the city.
  • Comfortable cockpit seating for up to 4 adults gives you a relaxed place to sit and socialize during your outing in the region.
  • An experienced guide and sailing instructor leads your activity, offering expert direction and local knowledge throughout the experience.
  • A cabin down below includes additional seating and dry storage so you can stow belongings and take breaks out of the elements while in the area.

Excludes

  • Towels are not included, so plan to bring your own if you’ll need one during your time here.
  • Dinner is not provided as part of this offering; food is not included in the booking.

Other

  • Service animals are allowed, making the activity accessible to travelers who require them during their visit to Downtown Orlando.
  • Public transportation options are available nearby, helping you reach the meeting point and return to the area with ease.
  • This activity is not recommended for travelers with spinal injuries; please consider your medical needs before booking.
  • This experience is not recommended for travelers with poor cardiovascular health due to activity demands.
  • The outing is suitable for all physical fitness levels otherwise, accommodating a broad range of participants who want to enjoy the region.

Customer Reviews

10/10
Based on 10 Reviews
Jaida_K
Aug 9, 2025 10:39:26 AM
Summary: Dan was a wonderful host and tour guide! You can tell that he really loves what he does. I would highly recommend this excursion if you are in orlando!
394mims
Jun 24, 2025 07:32:18 AM
Summary: It was a nice experience. Even though there was not much wind Dan educated us all about how to sail and was very interesting.
Diane_F
Jun 13, 2025 05:49:36 PM
Summary: Thanks, Captain Dan. We had a great sail with you, and thanks again for the impromptu lesson. We’re really looking forward to continuing to learn to tack and jibe.

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Know more about Downtown Orlando

You can book private day sailing, sunset cruises, or hands-on learning sessions aboard a 25-foot sloop-rigged sailboat. Each experience blends sightseeing, relaxation, and instruction so you can enjoy the Florida sun while taking in local waterfront views.
Absolutely. The tours teach guests some of the fundamental principles of sailing, so you can learn the ropes during a private lesson-style cruise aboard the 25-foot sloop while benefiting from hands-on guidance.
Yes. Day sailing and sunset cruises provide an active Water-Based adventure that introduces you to sailing techniques while letting you enjoy the outdoors and scenic views from a private sailboat.
Yes. The private tours are both entertaining and educational, offering family-friendly opportunities to learn sailing fundamentals and enjoy a safe, shared experience on the water with an experienced guide and sailing instructor.
Sunset cruises offer an intimate, private setting on a small sloop where you can relax and watch the sky change colors. The combination of gentle sailing, expert guidance, and waterfront ambiance creates a memorable romantic experience.
You’ll experience comfortable cockpit seating for up to four adults, hands-on instruction from an experienced guide, and a combination of entertainment and education as you learn fundamental sailing principles while enjoying the Florida sun.