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Orange Beach Sailing Charters

Sailing Charters In Gulf Shores, Alabama

Welcome To Orange Beach Sailing Charters...

We are excited about this upcoming summer and we are ready to take you, your loved ones and family on the best “private” sailing charter on the Alabama Gulf Coast. Come along with Captain Ryan or Captain Randy on our fabulous sailing yachts, “Sailob” and “Attitude“. We are the premier sailing cruise line serving Orange Beach and Gulf Shores, Alabama. Take one of our Gulf Shores sailing charters out on the water today!

Book Your Sailing Charters Online!

Book Your Orange Beach Sailing Charters Online!


All day and overnight adventures give you time to relax and take in the beautiful coastline.

Dolphin Sightings

We see dolphins! No noise from the engine means more happy dolphins in the water.

Family Day Trips

Children love our two and four hour day trips. Perfect escape from the beach and shopping.

Romantic Sunsets

Sunset trips make for an unforgettable experience on the Alabama coast.

a large ship in the water

About Us

Orange Beach Sailing Charters

Our Gulf Shores sailing charters are professionally operated with an experienced crew. We offer convenience and save you time by allowing you to book your sailing charter online. We are also conveniently located in Orange Beach so it does not take long to get you offshore and sailing the calm seas of the Gulf of Mexico. We make your life easier than it was before you found us. Don’t panic if you forgot drinks, we have water to keep you hydrated. We encourage you to bring your camera, bathing suit, and sunglasses.  Flip flops are always optional with Orange Beach Sailing Charters.

Our sailing yachts can accommodate up to six passengers while sailing in Orange Beach and Gulf Shores. Orange Beach Sailing Charters specializes in small group sailing charters and family eco tours. Young and older couples also frequent our yachts to share romantic moments together. Your kids will love our Orange Beach sailing charters. Children enjoy learning about local marine life like dolphins, sea turtles, seagulls, pelicans, cormorants, manatees and gain nautical knowledge about sailing the boat. When you charter your sailing trip with us, you are chartering the boat for only your group. Book your charter to start your sailing in Gulf Shores, Alabama today!

500+ 5-Star Reviews Of Our Excursions In Orange Beach, Al!

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Sunset and dolphins

Excellent trip with Captain Randy. We did the sunset cruise which was excellent. We even saw several dolphins in the bay. Highly recommend as Captain Randy runs a professional and safe operation.

– John T. | Tripadvisor
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Great Sailing Charter!!!

Having previously sailed with Captain Ryan and loved it; we got the opportunity to sail with Captain Randy on a 4 hour charter. Highly recommended. Focused on making sure you have the experience you are looking for. Very knowledgeable and enjoyable to chat with. Orange Beach Sailing Charters is great!

– Mike H. | Tripadvisor
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This was our first private sailboat ride in Orange Beach Al. And we had a blast! Captain Randy was great. Funny, informative, and very accommodating. There were six of us. Mema, gramps, mom, dad, and two teenagers. Captain Randy showed us some of the most valuable properties in Alabama. We were very happy with our sunset cruise. And we highly recommend This sailboat experience.

– Mur018 | Tripadvisor
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Great sunset cruise

Great sunset cruise the other night. Randy is a fantastic captain and host. We booked the private sunset cruise for our anniversary. Our 1st try was rained out, but Randy was great at trying to accommodate and we made it at the end of the week. Thanks Randy. We will be back.

– Jim T. | Tripadvisor
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Best Tour of Orange Beach

Would recommend anyone new to sailing to try the Orange Beach Sailing Charters. They provided good customer service up front and a better experience out on the water. My wife and I selected the 2 hour tour during the afternoon and thoroughly enjoyed being out on the water. Captain Randy was an excellent guide and offered much information about the area. Hope to get out there again in the future for a longer session.

– Brian H. | Tripadvisor
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Perfect Relaxing Sunset Cruise

Great experience. We took the sunset cruise. Private charter for 6 people. Hard pressed to find a better value. This was a relaxing cruise in the Gulf. Captain Randy is friendly, entertaining, and professional. So much better than riding in a boat with 60 strangers. Zero complaints. Couldn’t have been better.

– VRG | Tripadvisor
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We had a wonderful time sailing with Captain Randy. What an experience! We enjoyed his knowledge and great stories. We will see you next time we are in town Capt!

– Ashley W. | Tripadvisor
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Wonderful Sailing

Captain Randy was a delight to sail with. He was very knowledgeable and had lots of experience. We all felt extremely comfortable and safe in his hands. Our trip was mid-day and we had a bit of an un-sure weather pattern. But, Captain Randy still made our trip adventurous and fun!! We can't wait to sail with Captain Randy on our next trip.

– balzermv | Tripadvisor