Best Sailing Tours in Orlando – Discover Scenic Lake Adventures

Day Sailing Tour - Orlando on Lake Fairview
Guided Sailing Tour with a Licensed Captain

2-Hour Private Day Sailing Tours

Escape the crowds and sail Orlando’s Lake Fairview with a licensed captain and certified sailing instructor. Sunshine, fresh air, and zero stress. Relax or take the helm with your experienced guide aboard our 25-ft MacGregor sailboat. Our sailing tours are perfect for couples, small groups, and local adventure seekers.

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Sunset Sailing- Things to do in Orlando
Sunset Sailing Cruise with Sailing Orlando

2-Hour Private Sunset Sailing Tours

Skip the crowded tourist attractions and set sail on a private 2-hour sunset tour—perfect for date nights, celebrations, or just unwinding. Relax aboard a 25-ft sailboat with an experienced captain, or try your hand at sailing as part of the crew. Bring your favorite drinks, enjoy the music, and see a quieter, more beautiful side of Orlando from the water.

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What to Expect: Planning your Sailing Experience

Each private 2-hour sailing tour includes a USCG-licensed captain and experienced sailor -Captain Dan! There is comfortable seating for up to 5 on our a 25‑foot sailboat, life jackets, and bottled water. It’s a hands-on experience—you can relax or help sail under the guidance of Captain Dan.

Tours depart from the Lake Fairview Park boat ramp (2200 Lee Road, Orlando, FL). Free Parking. Meet your Captain at the boat ramp at your scheduled tour time.

Not at all! Your Captain handles everything. You’re welcome to take the helm or trim the sails and learn a few fundamentals of sailing. Or you can kickback, relax, sip on your favorite drink and enjoy the Florida sun. Totally up to you!

Absolutely! Guests may bring their own snacks, beverages, and playlists!

Scenes from the Water

Best Lakes for Boating
Best Lakes for Boating – Central Florida
Day Sailing Tour - Sailing Orlando
Day Sailing Tour – Sailing Orlando
Sailing Orlando Sunset Cruise
2-hour Private Sunset Tour
Most Romantic Thing to do in Orlando
Best Date Night in Orlando - Sailing Orlando
Most Romantic Thing to do in Orlando
Great Photos Ops in Orlando

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