Looks Good
This date is available.
By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.
This date is available.
Whether you're an expert sailor or a newby looking to experience the beauty of traveling on the water, courtesy of Mother Nature, you'll love sailing on Helios. Please join us on our world class 40ft Pacific Seacraft sailboat! If you were choosing a sailboat to travel around the world, this would be the perfect sailboat for you! She is likely the most complex sailboat you'll ever experience. She's a real beauty, with lots of teak wood and ultra-leather, inside and out. This sailboat is an ideal, romantic place to pop the question. Or to take it a step further, the Captain can legally officiate weddings in Cook County. The Captain reserves the right to reschedule a booking, due to inclement weather. No-show customers will be charged the 2 hour minimum fee. For late-show customers, the hourly charge begins at the scheduled time rather than their arrival time. Safety is our number one priority, so customers will always be expected to abide by the Captain's instructions to ensure the safety of all. Customers may bring alcohol, although the Captain reserves the right to return to the dock if customers appear to be over-served, for safety reasons. *Important to know* Please note that we are unable to accommodate night charters. This is a world-class sailing yacht designed for guests who enjoy the sailing experience and is not a good fit for partying

HC
Bob and his wife Gabby are amazing. We had so much fun with them. The boat is gorgeous and Bob is clearly a seasoned captain. Thanks again!
TF
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.
AS
What a wonderful time out on beautiful lake Michigan with Captain Bob! First time my family and I have been on a sailboat and we learned so much! The views of the city coupled with the hospitality onboard made it a day to remember for sure! A+ Highly recommend!
AS
We had a wonderful time on Bob's boat! We felt safe and loved seeing the beautiful skyline! Would definitely do it again!
TW
I was impressed that everything went according to plan. Met Captain Bob right on time and boarded what looked like an almost brand new boat. Very well maintained and extremely clean. First mate was first of all and offered water and refreshments for myself and my guest. Leaving the marina was professional and uneventful. The wind was light and variable and made for rather slow sailing but it was a great opportunity to hear some of the fine stories connected to Helios. For anyone that wants a true sailing experience and an opportunity to talk to some people that have been there done that, charter this sailboat! Thank you Captain, maybe we can have another adventure later in the summer.

My wife, Gabby and I have sailed extensively throughout the Gulf of Mexico, Atlantic Ocean, Caribbean and now the Great Lakes. We spend the summers in Chicago and winters in Florida. I'm a retired engineer and licensed Captain, and Gabby is an abstract artist. We have 6 children and 8 grandchildren, some of whom are in the Chicago area.
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
Departure Location
Free cancellation up to 2 days before your trip.
If the Captain cancels due to weather or other unforeseen circumstances, the renter will receive a full refund. if the renter cancels less than 48 hours prior or is a no-show, there will be a 2 hour minimum charge The booking begins at the scheduled time even when the renter arrives late