Freedom Sail Charters

Thrilled to discover a charter company that’s a gem like this one! Freedom is a gorgeous, spotless boat with a crew that has always given us a warm welcome. And I’m always looking for something that’s more than just a booze cruise. Sure, it’s BYO food and beverage.
Bonus:
They always provide an extra crew member to help guests aboard + serve food and bevs so we can relax and enjoy the views of the Chicago skyline without a lot of boat traffic.
Crew also provides bottled water, cooler space, ice and plastic plates and drinkware aboard.
I’ve sailed with several Beneteux racing boats and have recently been converted to luxury cruising of Catalina 375’s. But it doesn’t matter whether know sailboats or not — the boat is very spacious and perfect for 6 guests. They also happen to offer «prince/​princess seats» with cushions in the corners, and a Bose sound system so you really feel like you’re sailing in style.
Capt Jim and Capt Geoff are the ideal blend of professional, accommodating, informative, patient and entertaining. I know Capt Jim from sailing on Tall Ship Red Witch, so it’s especially fun to get to see him out on the water again and to hear some great Mac race stories. He’s great about getting the sails up as soon as possible. He really knows the conditions and give you a heads up if there are weather concerns. He will also check with guests for comfort level (sporty or leisure sail + some sailing tips if you want to take the helm).
Our last sail was especially lively with up to 30 mph gusts, so we were able to heel, hang on and harness the wind! Conditions change, so I don’t believe you can really Unilocal about «no wind». This crew makes the best of whatever Mother Nature offers up.
They mostly do 2 or 3 hour sails: daytime, sunset, fireworks — probably moonlight sail and swimming if the conditions are right. No online booking, but they’ve been very quick to return calls and emails.
Sure, I’m already a fan of 31^st Street Harbor, beach and the southern-​Chi skyline. Some northside friends think it’s a hike to come south. That’s fair. We sail with different boats based on the harbor and where guests are coming from.
But it’s the captains and crew of our favorite sailboats that make us want to come back!
Thanks for making us feel like VIP’s.