Small-group and private cruises on Lake Fairview — sunset sails, day sails, and ASA 101 certification.
Private 2-hour day and sunset sails, plus a 3-day ASA 101 certification course.
boat-charters · Orlando
Experience the breathtaking colors of a Florida sunset aboard a private sailboat with Sailing Orlando. Perfect for unwinding, this 2-hour cruise offers a tranquil escape just minutes from the city, with stunning water and sky views to cherish.
Sailing Orlando is a small charter and sailing school based in Orlando, FL, offering private sails and ASA instruction on Lake Fairview.
The company specializes in 2-hour private cruises — a Two Hour Sunset Sailing Cruise and a Two Hour Day Sail — and a 3-Day ASA 101 Sailing Class that provides 15 hours of hands-on training.
Private cruises run aboard a 25-foot Com-Pac sailboat with an experienced captain. Guests may bring their own snacks and drinks and enjoy relaxed, personalized time on the water. The Two Hour Sunset Sailing Cruise emphasizes scenic Central Florida sunsets and quiet lake passages, while the Two Hour Day Sail focuses on daytime relaxation and basic onboard experience for beginners and seasoned riders alike.
The 3-Day ASA 101 Sailing Class is held at Lake Fairview Marina and delivers structured, practical instruction across two or three days to meet the ASA 101 curriculum. Students receive hands-on sailing time, guided maneuvers, and skills assessments necessary to earn official ASA 101 certification.
Sailing Orlando emphasizes safety, small-class attention, and local knowledge of Central Florida waterways. Captains provide individual guidance, clear instruction, and a calm sailing experience suitable for first-time sailors and repeat guests. Booking options include private charters and scheduled certification classes, designed to offer memorable lake sailing, practical skill building, and confident, certificate-backed progress for new sailors. Experienced captains maintain safety equipment and local navigation knowledge, provide pre-departure briefings, and tailor each sail to passenger experience level for a secure, enjoyable, educational time on Lake Fairview and memories.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Sails from Lake Fairview Marina
Short cruises and multi-day courses
Official ASA entry-level certification
Private charters with experienced captain
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Sailing Orlando listing.
Sailing Orlando offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Reserve a 2-hour cruise or enroll in the 3-day ASA 101 class — limited spots for a personalized sailing experience.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.