The Best Sailboat Rentals Near Glen Lake

Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

This is the boat to book for a sweet sailing experience in Chicago. Super family friendly. Ocean-worthy vessel and Capt Bob and Gabby have been all over the hemisphere with it. They're more than willing to share as much knowledge as you'd like to know. I even pulled up the main sail! Bob and Gabby were great with our young children. Just wonderful people. Swimming spot they chose was excellent. If you're looking for the real deal, this is it. Loved hearing their stories about open ocean sailing and traversing the Caribbean Islands. Kids loved the aqua chair floaty. Worth every penny and more.

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

The boat is exactly as listed. Had a great night out watching the navy pier fireworks. Communication was excellent. The weather wasn’t cooperating and the captain was quick to reach out with details. We ended up rescheduling twice. Chicago weather what are you going to do. But once we got in the boat everything was so lovely. And there is a boat dog named, Piper. Piper kept us all entertained! Highly recommend!

Sail in downtown Toronto

Dom was a great host. He went above and beyond. We have nothing but good things to say about our experience. Ot was a great experience and we would definitely recommend it for anyone visiting the area or locals just wanting to get out on the water and enjoy the beautiful views.

Sail in downtown Toronto

We had an amazing time sailing with Dom! The views of the Toronto skyline were incredible, and we learned so much about the Toronto Islands and about sailing along the way. What we especially appreciated was Dom’s ability to make sailing feel accessible and unintimidating—he cuts through the insider language and conventions and focuses on the practical knowledge that really matters when you’re getting started. It made sailing feel much more approachable and feasible for complete beginners like us. Dom was an incredibly warm and welcoming host, and the whole experience was relaxed, fun, and genuinely informative. We also loved how easy it was to bring our own snacks and drinks. Highly recommend!

Exclusive Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch

Highly highly recommend booking with Stephen! We had friends coming to visit from out of town and we had the most wonderful charter. Stephen was an excellent captain and very kind host. The boat itself is very cool, with plenty of room to hang on the bow (and a clean bathroom!). Can’t say enough about what a great time we had!!

Exclusive Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch

Not sure I can say enough about how absolutely incredible our experience was with Steve. Boat was perfect. Communication was perfect. But the experience was incredible! He took my wife, two sons and I out to the Wednesday night races in Annapolis, and we got to engage right into the races, feel the speed of the boats, see the tight turns, and it’s an experience my sons will not forget. Can’t recommend highly enough.