The Best Sailboat Rentals Near Osage Beach

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

Amazing time! Ben is a very experienced and knowledgeable captain , he taught us how to steer the boat and answered all our questions. Hes very nice and made the ride great! You also get an amazing view of the city that you can’t get anywhere else I brought my boyfriend as a birthday present and it was perfect!

Sailing on Lake Pontchartrain with 52ft Shannon Sailing Yacht!

We had a wonderful sailboat ride on the lake with Captain Jim for my husband's birthday. It was a beautiful evening and the weather was perfect! His sailboat is huge and beautiful! Thanks for a great time!

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

Ben was an awesome captain and a pleasure to be around during our two-hour trip. His boat is the perfect setting for a romantic date night, and I highly recommend experiencing the sunset on board, the views were absolutely amazing!

Charter this beautiful Catalina from Milwaukee, WI - Captain Included

Patrik was so kind! We absolutely loved our sunset cruise around Milwaukee. He was so friendly and had great areas to go by! We loved every part of our engagement session and can’t think of a better skipper 🥰

41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.

John recently took my family out on Lake Michigan and he made the trip a great experience - communicative, nicely kept boat and very competent as a captain! I appreciated how he answered my youngest questions and was so thoughtful with them. Would recommend.

Hunter 'Legend' Sailboat, 36ft in Seabrook, Texas

The girls had such a great time! They appreciated the upgrade (when y'all found out it was a bachelorette party they got the upgrade) and said the boat driver was very attentive and super nice! It was the best part of their bachelorette weekend! Thank you!