Take a Virtual Tour!

Sailboat Cruise Pensacola Beach

View our 28 ft. wide Condor: spacious side-decks, super-comfy seats, and tons of room to explore!

Condor Flying & Surfing!

Condor Flying & Surfing Pensacola Beach

Only on our Condor! Feel like you’re surfing & flying while riding the bows. Click to watch the video.

Meet the Captain

Michael “Captain” Kirk

Captain Kirk will welcome you aboard his craft and you and your friends will boldly go on a memorable adventure.


Sailboat Wedding Pensacola Beach

Enjoy your wedding on the waves and swap vows on deck while the captain himself conducts the service.

Pensacola Sailing & Pensacola Beach Sailing Tour, Sunset Cruise, and Sailboat charter

Go Fast. Have Fun. Relax! This is no ordinary sailboat. Join us for the experience of a lifetime aboard our incredibly stable, world-class Condor racing trimaran, Dare II. 40 ft. long and 28 ft. wide, our trimaran is super-comfortable, spacious, and absolutely a fun, relaxing adventure for kids and grandparents alike!

Testimonials and reviews

“Incredibly stable” May 19, 2014 – A TripAdvisor Traveler Read 84 reviews of Condor Sailing Adventures

Condor Sailing Adventures

TripAdvisor Traveler Rating:
5.0 of 5 stars
Based on 84 traveler reviews

Most Recent Traveler Reviews:
  • May 19, 2014: “Incredibly stable”
  • May 14, 2014: “AMAZING Sunset Cruise”
  • May 6, 2014: “An Amazing experience!!”
  • May 5, 2014: “Awesome”
  • Apr 27, 2014: “Ahmazing!!!!!”

© 2014 TripAdvisor LLC

Write a review

Rare: only 21 Condor trimarans in the world. And only in Pensacola can you enjoy sailing on one.

Safer than ordinary sailboats: Condors were designed to be stable racing around the world in 40-50 ft. seas. And Dare II’s amazing stability means no leaning, which means none of the typical rocking, rolling ordinary sailboat-motion.

No leaning = no seasickness.

Dare II is perfect for people who get seasick standing on a dock, or can’t swim, or are pregnant. So smooth and relaxing, it’s like sitting beside the pool!

Gorgeous: People whip out cameras when Dare II sails into view. You instantly get excited and happy just seeing her, knowing this is going to be an amazing, unforgettable experience that you’ll want to tell everyone about.

More fun and safer for kids: kids are not stuck in a seat. Instead they have a huge amount of space to safely explore. Kids have a blast sitting on the sides, getting splashed, surfing/flying on the bows, driving, and watching for marine life. Plus, kids 12/under are $15 off on any Two-Hour Cruise.

More relaxing: Literally stretch out in super-comfy seats, on the two spacious side-decks. Dangle your feet in the water. Sunbathe on the floats. Or drive a racing trimaran, and learn how to sail! Guests tell us that Dare II is more relaxing than a massage.

Easier boarding: 2 easy steps get you aboard, ready to plop into a super-comfy seat. Perfect for seniors with cranky hips and knees. Plus, Dare II allows for some handicapped access.

Uncrowded: No more than 6 guests max.

Peaceful: we sail on quiet, peaceful Pensacola Bay. Unlike Pensacola Beach, there are rarely any jet-skis and powerboats. Just us, dolphins, and shrimp boats!

It all adds up to the experience of a lifetime. So skip the ordinary Pensacola sailing charter, and join us on our world-class Condor racing trimaran, for a fun, relaxing, adventure that you’ll fondly remember forever…

Contact Us!
(850) 637-SAIL (7245)

Book Your Cruise Online