The 4 Best Sailing Experiences in Orlando
Orlando isn’t just about theme parks and roller coasters. Thanks to its many lakes and warm Florida sunshine, it’s also a surprisingly good spot for sailing. Whether you’re looking for a peaceful afternoon on the water or a romantic sunset cruise, Orlando offers options that let you enjoy the area from a different perspective. These sailing tours bring you close to nature, with some even offering hands-on sailing lessons or private excursions — perfect for putting a unique twist on your visit.
If you’re craving a break from the hustle of major attractions, a sailing trip can provide tranquility and fresh air, all while soaking up scenic views of Lake Fairview. No matter your experience level or interest, there’s a tour here that fits your style. Let’s explore the top options, complete with details, reviews, and what makes each one special.
1. Private 2-Hour Day Sailing Experience
At number 1 on our list, the Private 2-Hour Day Sailing Experience offers a personalized way to enjoy Lake Fairview. For $85 per person, you hop aboard a comfortable 25-foot MacGregor sailboat and set out into a peaceful slice of Orlando’s natural landscape. This tour is ideal if you’re looking for a quiet escape, away from the crowds, with the flexibility to relax or get involved in sailing.
What sets this trip apart is the private nature of the tour, allowing for complete customization. You can simply unwind on the deck, soak up some sun, or even learn the basics of sailing from your friendly crew. Reviewers love the relaxed atmosphere and personalized service, with many describing it as “a blissful, peaceful trip,” and praising Captain Dan for his friendly, knowledgeable guidance. One guest noted, “Dan was great at explaining sailing nuances and making us feel at home.” The tour’s length and intimate setting make it perfect for couples or small groups wanting a calm, engaging experience.
Bottom Line: If you’re after a private, flexible trip with the chance to learn some sailing in a relaxed setting, this tour is a great choice. It offers excellent value, especially for those who want a personal touch.
2. Private 2-Hour Sunset Sailing Tour on Lake Fairview
Number 2 on our list is the Private 2-Hour Sunset Sailing Tour on Lake Fairview. For $89 per person, this tour is perfect for those seeking a romantic or scenic experience that captures Orlando’s beautiful sunset. Meeting at Lake Fairview Park, you’ll board a 25-foot sailboat and drift into the evening, watching the sky turn shades of orange and pink reflected on the water.
This trip excels at offering a personalized experience, allowing you to bring your own food and drinks along. It’s ideal for couples celebrating special occasions or families wanting a memorable outing. Reviews highlight the cozy atmosphere, with one guest noting, “The sunset views were stunning, and Captain Dan made us feel very comfortable.” The tour’s focus on sunset vistas makes it stand out, especially since most visitors miss this view from the water.
Bottom Line: For a romantic, tranquil evening that includes spectacular sunset scenery and the freedom to bring snacks, this tour delivers a memorable experience at a fair price.
3. Orlando: Private Sunset Sailing Trip on Lake Fairview
Coming in at number 3, the Orlando: Private Sunset Sailing Trip on Lake Fairview offers a similar sunset experience but emphasizes the chance to get involved and learn. For $89 per person, this 2-hour trip combines the beauty of Lake Fairview with a hands-on approach. You’ll climb aboard a 25-foot MacGregor sailboat and enjoy the reflection of the sunset on the water.
What really makes this trip special is the opportunity to become part of the crew and receive a sailing lesson from an experienced guide. Guests have praised Captain Dan’s friendly demeanor and the high level of engagement. One remarked, “This was the best part of our vacation; I loved how involved we were in sailing.” The focus on learning makes it a good fit for those interested in understanding sailing basics while also enjoying a peaceful sunset.
Bottom Line: If you want a personalized sailing lesson combined with sunset views, this tour provides both in a relaxed setting, making it ideal for curious travelers or those celebrating a special evening.
4. Sailing Tour with Certified Sailing Instructor
Rounding out the list, the Sailing Tour with Certified Sailing Instructor offers a more instructional experience for $72 per person. This 2-hour tour is perfect for anyone interested in learning to sail with a professional instructor guiding the way. The focus is on providing a calm, educational environment aboard a 25-foot MacGregor sailboat, with the chance to get involved in maneuvers and sailing fundamentals.
An excellent choice for beginners or those wanting to gain confidence on the water, this tour has received enthusiastic reviews. One customer shared, “My mom, celebrating her birthday at 80, had her first sailing experience, thanks to Dan’s help and patience.” The emphasis on instruction makes this a value-packed option for travelers eager to pick up a new skill while enjoying the Florida sun.
Bottom Line: For an affordable, educational sailing experience tailored for beginners, this tour combines learning with relaxation—good for solo travelers or groups wanting to boost their sailing skills.
How to Choose the Right Sailing Tour in Orlando
When deciding among these options, consider your budget, interest level, and what kind of experience you’re after. If peace and privacy are your priorities, the Private 2-Hour Day Sailing Experience offers a serene escape. For romantics or sunset lovers, the Sunset Tours and Sunset Trip with Learning provide stunning views and personal touches. Budget-conscious travelers or those eager to learn should consider the Sailing Tour with Certified Instructor, which combines instruction with a peaceful outing.
Booking early is advisable, especially for sunset tours, which tend to fill quickly in peak season. Think about what experience aligns best with your interests—whether it’s simply relaxing under the sun, celebrating a special occasion, or picking up sailing skills—and you’ll find the perfect trip.
Final Thoughts
From private daytime sails to engaging sunset cruises, Orlando’s sailing options cater to a variety of tastes. For a quiet escape, the Private Day Sailing does the trick, while the Sunset Tours provide a romantic backdrop. Those eager to learn can dive into a sailing lesson with an instructor, gaining confidence on the water.
Whatever you choose, these trips add a unique dimension to your Orlando visit, giving you a chance to see the city’s lakes in a whole new light. Be sure to book early, and enjoy a peaceful day on the water in this vibrant Florida city.