Orlando’s sailing scene offers practical options for both novice and experienced sailors. The most worthwhile tours operate on 25-foot boats, keeping groups intimate with 4-6 passengers.
We especially like the 2-hour daytime tours for their combination of basic instruction and relaxed sightseeing, while the sunset tours earn our top rating for their unbeatable evening views and expert commentary from local captains.
The best operators provide all safety equipment and welcome hands-on participation for those interested in learning sailing basics.
Let’s look at our favorite sailing tours in Orlando.
Key Points
- Private 2-hour day sailing experience on Lake Fairview with an experienced guide, comfortable seating for up to 4 adults, and amenities like a cabin and bottled water.
- Small group sailing tours in Orlando with a certified instructor, hands-on sailing experience, and the opportunity to enjoy the Florida sunset.
- Private 2-hour sunset sailing tours on Lake Fairview, offering an intimate atmosphere, stunning sunset views, and the chance to learn from an experienced guide.
- Highly rated private sunset sailing trips on Lake Fairview, with a 25ft sloop-rigged MacGregor sailboat, amenities, and an experienced guide.
- Sailing experiences in Orlando that cater to various group sizes, offer accessibility, and provide flexibility with free cancellation and no upfront payment.
Private 2-Hour Day Sailing Experience
Set out on a private 2-hour sailing adventure on the serene waters of Lake Fairview in Orlando. This highly rated experience, with a 100% recommendation rate, invites you to relax on the comfortable 25-foot MacGregor sailboat while an experienced guide teaches you the basics of sailing.
With seating for up to 4 adults, you’ll have the opportunity to assist with rigging the sails or simply sit back and enjoy the peaceful surroundings.
The tour begins at the Lake Fairview Park public boat ramp, and you’ll return to the same location after your excursion. Along the way, you’ll have access to a cabin with additional seating and dry storage, as well as bottled water, life jackets, and towels.
This private experience ensures that only your group will participate, allowing for a personalized and engaging adventure. With a Badge of Excellence award, you can trust in the quality of this sailing experience.
Read our full review: Private 2-Hour Day Sailing Experience Review
Book now: Check availability
Orlando: Sailing Tour With Certified Sailing Instructor
Although Orlando is primarily known for its world-famous theme parks, the city also offers a serene sailing experience on the tranquil waters of Lake Fairview.
Set out on a 2-hour sailing tour with a certified instructor and a small group of up to 5 participants. This activity is wheelchair accessible, making it an inclusive experience for all.
During the tour, you’ll learn the basics of sailing as you help trim the sails and steer the 25-foot MacGregor sailboat.
Enjoy the Florida sunset and participate actively or simply relax and take in the picturesque scenery. The experienced captain and sailing instructor will provide all the necessary equipment, including a cooler for your personal beverages and snacks.
With free cancellation up to 24 hours and no upfront payment required, this sailing tour is a flexible and convenient way to explore Orlando’s natural beauty.
Based on 4 reviews, it has earned a perfect 5/5 rating, highlighting the calmness, friendliness of the captain, and memorable moments for families and friends.
Read our full review: Orlando: Sailing Tour With Certified Sailing Instructor Review
Book now: Check availability
Private 2-Hour Sunset Sailing Tour on Lake Fairview
Step aboard a 25-foot sailboat and set off on a private 2-hour sunset sail on the tranquil waters of Lake Fairview.
This 5-star rated experience, provided by Sailing Orlando, offers an intimate and romantic atmosphere for couples or families. With an experienced guide and sailing instructor at the helm, you’ll enjoy stunning sunset views often overlooked by visitors.
The sailboat features comfortable seating for up to 4 adults and a cabin with additional seating and dry storage, perfect for bringing your own food and beverages.
Throughout the tour, you’ll have the opportunity to engage in sailing activities, such as moving the rudder, while learning about the art of sailing from your knowledgeable guide.
Bottled water, safety equipment, life jackets, and towels are provided, ensuring a relaxing and carefree experience.
With consistently positive reviews praising the guide, Dan, and the overall tranquil atmosphere, this sunset sailing tour on Lake Fairview is a must-try for those seeking a unique and unforgettable adventure in Orlando.
Read our full review: Private 2-Hour Sunset Sailing Tour on Lake Fairview Review
Book now: Check availability
Orlando: Private Sunset Sailing Trip on Lake Fairview
You can set sail on a private sunset adventure across the tranquil waters of Lake Fairview in Orlando. Priced from $89 per person, this 2-hour sailing trip accommodates up to 4 participants, offering a personalized experience.
Aboard a 25ft sloop-rigged MacGregor sailboat, you’ll have the opportunity to get involved in sailing or simply relax and admire the sunset reflecting on the lake. The cabin provides additional seating and dry storage, while a cooler is available for your personal beverages and snacks. Bottled water, towels, and safety equipment are all included.
Meet your experienced guide at the public boat ramp and set sail 15 minutes before the activity starts. With an overall rating of 5/5 based on 10 reviews, travelers praise the exceptional sailing experience and the knowledgeable captain.
Don’t miss this opportunity to learn about the beauty of Lake Fairview at sunset.
Read our full review: Orlando: Private Sunset Sailing Trip on Lake Fairview Review
Book now: Check availability
Recap
Whether you’re seeking a relaxing day sail or a breathtaking sunset cruise, Orlando offers a range of exceptional sailing experiences. With skilled instructors and picturesque lakes, you’ll enjoy the tranquility of being on the water and create lasting memories of your time in this vibrant city. Embark on your sailing adventure and discover the beauty of Orlando from a unique perspective.