Orlando might be famous for its theme parks, but it’s also a surprisingly good place to enjoy sailing on beautiful lakes like Lake Fairview. Unlike the busy theme park crowds, these sailing tours offer a peaceful escape on the water, with options for private trips, romantic sunsets, and even sailing lessons. We particularly like the Private 2-Hour Day Sailing Experience for its relaxed vibe and personalized touch, letting you learn sailing basics or just soak up the scenery. Whether you’re an experienced sailor or a total newbie, Orlando’s lakes provide a calm, scenic backdrop perfect for any occasion.
While Orlando is known for its theme parks, its lakes are often overlooked for leisure sailing. These tours give visitors a chance to see a different side of the city—more laid-back, more natural. You’ll get out on the water in a comfortable sailboat, with some tours even including the chance to help with sailing tasks. If you’re here for romance, the Sunset Sailing Tours are a hit, offering sunset views most visitors miss and the opportunity to bring food and drinks along. They make for memorable evenings or special occasions.
Quick Overview
This list features four top sailing experiences in Orlando, each offering something unique: private daytime sails, sunset cruises, and even sailing lessons with certified instructors. All tours are about 2 hours long and rated highly for their friendly guides and beautiful lakes. Check out the options below to find the best fit for your trip.
1. Private 2-Hour Day Sailing Experience
At number 1, the Private 2-Hour Day Sailing Experience offers a peaceful escape from Orlando’s busy attractions. This tour is perfect for anyone wanting to experience sailing without the crowds. You meet at Lake Fairview Park and hop aboard a comfortable 25-foot MacGregor sailboat. The focus here is on relaxing and enjoying the scenery, but you also have the chance to learn the basics of sailing from your crew, especially if you’re curious about how boats work.
What makes this experience stand out is its private setting, meaning you get all the attention, and the flexibility to tailor the trip to your preferences. The reviews highlight how serene and enjoyable it is, with one saying, “Sailing on a private boat with Captain Dan was pure bliss,” and others mentioning how relaxing the trip felt under perfect weather. The tour is well-suited for couples, small groups, or anyone wanting a personalized, quiet adventure on the water.
The value here is excellent: for $85 per person, you get two hours of private sailing, with the option to participate in sailing basics or simply kick back and enjoy. This is ideal for those wanting a low-key, scenic experience without the fuss.
Bottom Line: A flexible, intimate sailing trip perfect for relaxing, learning, or celebrating a special day in Orlando.
2. Private 2-Hour Sunset Sailing Tour on Lake Fairview
Next on our list, the Private 2-Hour Sunset Sailing Tour offers a different kind of magic. Set out at the end of the day to enjoy the golden glow of sunset, with views that are often missed by visitors confined to land. This tour also starts at Lake Fairview, but its focus is on soaking up the scenery as the sky transforms.
It’s perfect for romantic dates or a special family outing, especially since you can bring your own drinks and snacks. The reviews rave about the cozy, friendly atmosphere and the stunning sunsets, with one traveler sharing, “Captain Dan was great! We felt very comfortable and safe.” The tour’s intimate setting makes it easier to connect with your loved ones or make new friends on board.
The tour costs $89 per person, making it a slightly more premium experience, but the focus on sunset views and personalized service justifies the price. During this cruise, you’ll enjoy a peaceful ride and beautiful scenery that’s hard to match from land.
Bottom Line: Perfect for a romantic evening or a memorable way to see Orlando’s lakes as the sun dips below the horizon.
3. Orlando: Private Sunset Sailing Trip on Lake Fairview
The Private Sunset Sailing Trip on Lake Fairview offers a more relaxed, scenic experience that’s ideal for couples or small groups wanting an intimate moment on the water. For around $89, this 2-hour tour provides a chance to reconnect and unwind as the Florida sun sets.
What makes this tour stand out is the chance to actively participate—learn from an experienced captain, get involved in sailing tasks, and really feel like part of the crew. The boat, a 25-ft sloop-rigged MacGregor, provides a stable platform for enjoying the calm waters of Lake Fairview, with breathtaking views of the sunset reflected in the lake.
Reviews mention how soothing and enjoyable the experience is, with one guest noting, “Relaxing, scenic, and educational — the perfect way to end a day.” This tour is best suited for those looking for a peaceful, personalized sailing experience with a touch of instruction.
Bottom Line: An ideal choice if you want to learn a bit about sailing while enjoying a scenic sunset cruise.
4. Sailing Tour with Certified Sailing Instructor
Finally, the Sailing Tour with Certified Instructor offers a more hands-on experience for those eager to learn how to sail. For $58, you spend 2 hours on a 25-foot MacGregor sailboat, guided by a certified instructor.
What’s special about this tour is its focus on teaching you sailing skills. The instructor shares their knowledge in a relaxed environment, making it suitable for complete beginners or those wanting to improve their sailing technique. Guests have described the experience as involving and involving, with some saying they “got involved and became part of the crew,” which makes the experience more memorable.
This trip is perfect for travelers interested in gaining practical sailing skills in a supportive setting. The reviews highlight the friendly, professional guidance, and the chance to enjoy the Florida sun as you learn.
Bottom Line: Best suited for those wanting an educational, engaging sailing experience in Orlando.
How to Choose Your Perfect Sailing Experience
When selecting the best sailing tour in Orlando, consider your budget, interests, and how involved you want to be. For a peaceful, private ride with optional learning, the Private 2-Hour Day Sailing Experience is excellent. If you’re after a romantic sunset with a more personal touch, the Private Sunset Tours are fantastic. Want to learn sailing? The Certified Instructor Tour offers the most educational value. Budget-conscious travelers might prefer the more affordable sailing lessons which still deliver hands-on experience.
Booking early is recommended, especially for sunset tours or private experiences, which tend to fill up quickly during peak seasons. Always check the weather forecast—clear skies mean better views and safer sailing.
Final Thoughts
Orlando’s lakes are more than just scenic backdrops—they’re a fantastic setting for sailing adventures. Whether you want a serene daytime cruise, a romantic sunset sail, or a hands-on sailing lesson, there’s an option that fits your style. For balanced value, the private tours provide intimate, personalized experiences with lots of flexibility. If you’re traveling with a partner or small family, these are perfect choices.
For those eager to learn the ropes, the sailing lesson with a certified instructor offers a practical, engaging way to spend time on the water. Whatever your preference, booking early and planning around the weather will ensure your Orlando sailing adventure is smooth sailing.