The Best Sailboat Rentals Near Me

Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise

Sailing with Captain James was a dream!! You will not regret this experience! Not only is he hospitable, he is full of life and passion which only made our trip better. We enjoyed every part of our trip the only sad part was that we didn’t book longer. 100/10 would book with Captain James again!!

38-ft Hunter 376 Sailing Adventure in Annapolis

Our family of four, who are experienced sailors, appreciated the opportunity to sail with Alberto and his lovely wife, who shared lots of great stories and reflections of sailing on the Bay. The boat was perfect for a day of sailing, and exactly how described on the website. It was clean and comfortable and we felt completely welcomed, and were able to participate in sailing activities as we desired, while also relaxing and enjoying some downtime. Great time sailing!

38-ft Hunter 376 Sailing Adventure in Annapolis

Captain Alberto and Grace were amazing, and helped with a very romantic sunset sail. The were ver gracious, accommodating, and knowledgeable. If we get the chance we will definitely come back and hire them again!

Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise

Lovely experience, James was really patient and understanding. Boat was clean and had everything we needed. 10/10 experience will definitely book again.

Charter this Classic Shannon Sailboat w/ Professional Captain in Chicago

Michael was incredible!!! He was so friendly and made our experience so comfortable, relaxing, and fun! I wish he was the captain of every boat I go on moving forward because he was such a wonderful person to have around! Thank you so much Michael! We appreciate your help!

Set Sail with 36' Sailing Boat in Downtown, Chicago

Went on a 3 hour cruise with Captain Dawn and Ted and wow did we have a great time. It’s well worth it to see Chicago from the lake, and no better way to get out on the water than on a sailboat. Will definitely reach out to this group again when I return to Chicago.