The Best Sailboat Rentals Near Gary

50ft Catamaran Charter with Water Toys - Annapolis, MD

We intentionally booked a late afternoon cruise around the Chesapeake so we would return around sunset to get great views and photos. Kristal was super responsive in preparing us and Captain Wayne and his 'first mate' Mish were super helpful with capturing the perfect photos. We would definitely book again!

38-ft Hunter 376 Sailing Adventure in Annapolis

Captain Alberto and Grace are wonderful hosts and guides. They have a wealth of sailing and life experience to share during your trip. They were very flexible with us during a proposal event.

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!

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!

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

It was the perfect experience! Right from the beginning, I began steering, pulling the halyard and raising the main sail. I learned the basics easily and Ben is great to talk to because of his years of experience and pleasant demeanor. I very much enjoyed my time and even more so am happy to have learned so much so quickly. I highly recommend this for anyone trying to see what sailing is all about!

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

Our experience sailing with Ben was great. He is a pro and is clearly very passionate and knowledgeable about sailing. This passion is infectious, and we learned plenty from him. He also allowed us to take an active role in the process given our interest in sailing. Ben was also very personable, interesting, and pleasant to converse with, which is an important quality when sailing with someone! Would highly recommend!