Sailboat silhouetted at sunset on calm lake, evening sail

Private Sailing Trips & ASA Sailing Courses in Orlando

Small-group and private cruises on Lake Fairview — sunset sails, day sails, and ASA 101 certification.

Featured Trips

Private 2-hour day and sunset sails, plus a 3-day ASA 101 certification course.

Sunset Sailing Cruise with Sailing Orlando in Florida

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.

Sunset Sailing Cruise with Sailing Orlando in Florida

boat charters

water activities

Orlando, Florida

About Sailing Orlando

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.

Sailboat cockpit and full sails under blue sky, daytime sail

Two sailors raising sail on small cruiser in calm inland waters

Sailing Orlando Private Sails ASA 101 in Orlando

Sailing Orlando operates from Lake Fairview Marina in Orlando, FL, offering private two hour day sails, two hour sunset sailing cruises, and a 3 day ASA 101 sailing class. Private cruises run on a 25-foot Com-Pac sailboat with an experienced captain, and guests are invited to bring snacks and drinks for a relaxed, personalized outing on the water. The ASA 101 course delivers 15 hours of hands on instruction over two or three days in a small class setting to earn official ASA certification.

Why Choose Sailing Orlando

Experienced captains prioritize safety with pre departure briefings, proper safety equipment, and local navigation expertise on Central Florida waterways. Small party sizes and private charters ensure personalized instruction and attentive service whether booking a day sail, sunset cruise, or an ASA certification course.

Featured Trips

Two Hour Sunset Sailing Cruise — private 2 hour sail to watch Central Florida sunsets aboard a 25 foot sailboat with an experienced captain.
Two Hour Day Sail — private 2 hour daytime cruise on Lake Fairview for relaxation, beginner friendly sailing experience, and scenic lake views.
3 Day ASA 101 Sailing Class — 15 hours of hands on instruction on a Com Pac sailboat, structured to meet ASA 101 standards and certify new sailors.

What to Expect

Each trip includes professional captain service, flexible snack and drink policies, and clear pre sail briefings covering safety, basic sailing roles, and weather considerations. ASA students receive focused coaching on maneuvers, points of sail, docking basics, sail trim, and teamwork to complete the ASA 101 syllabus.

Booking & Logistics

Reservations are recommended for private sails and required for the 3 day ASA 101 class to secure space in a small group. Most sails depart from Lake Fairview Marina in Orlando, making trips accessible for local residents and visitors. Booking information, schedules, and contact details are available online via the operator listing on The Adventure Collective and direct booking channels.

Frequently Searched Keywords

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Why Book Now

Limited availability on private sunset sails and small class ASA courses means early booking secures preferred dates. Booking early also helps tailor the experience to guest preferences, from pacing and instruction focus to onboard snacks and celebrations.

Contact & Next Steps

Prospective guests can view the Sailing Orlando listing on The Adventure Collective for trip details, schedules, and direct booking links. For ASA 101 students, review course prerequisites and required documentation before enrollment to ensure readiness for the certification process. Sailing Orlando delivers private sails and certified instruction focused on safety, clear coaching, and memorable lake experiences in Orlando.

Who Benefits

Sailing Orlando trips suit couples, small groups, beginner sailors, and students seeking ASA certification. Private cruises are ideal for celebrations, romantic outings, and relaxed sightseeing, while ASA classes target learners wanting official credentials and hands on practice.

What to Bring

Personal ID
Snacks & drinks
Sunscreen
Soft soled shoes
Light jacket

Safety & Instruction

All courses and charters include safety briefings and required flotation devices. Captains deliver hands on instruction while maintaining a calm, controlled environment to support learning and enjoyment on Lake Fairview.

Find the Sailing Orlando listing on The Adventure Collective to compare trip dates, view pricing, and read guest reviews. Early reservations are recommended for sunset cruises and ASA 101 sessions. Enjoy a safe, instructive, and scenic sailing experience on Orlando's Lake Fairview. Reserve a private sail or enroll in ASA 101 today to secure a spot. Book now.

Yacht deck at sunset over reflective water, peaceful sailing

Book a Private Sail or ASA Course in Orlando

Reserve a 2-hour cruise or enroll in the 3-day ASA 101 class — limited spots for a personalized sailing experience.