My 40 foot sailboat can fit up to 10 passengers. Ask about cheap weekday specials!! We have beanbag chairs you can lounge in, coolers, and you can hire a captain if you like.
EARLY BIRD PRICING IN EFFECT! Only 15% of our bookings will sell at this rate so lock in our best rates of the season today!
Enjoy Lake Michigan aboard a spacious 40 sailboat! Please contact me even if the schedule shows that the boat is unavailable as it probably is still available!!
If you aren't an experienced sailor we can recommend a captain for you but please note that you will pay the Captain directly, and their rate is not included in the Boatbound price. Please assume $60/hour for a Captain rate (plus gratuity). By US Coast Guard law the Captain is your employee and although we can recommend captains that we have worked with in the past you can hire whatever Captain you like.
My 40 foot sailboat is equipped with coolers for your drinks, and a full bathroom. This is your most affordable option to get up to 10 guests out on Lake Michigan this summer!
Chris was great and the boat was amazing. Look forward to my next cruise on this boat
Chris was absolutely incredible with helping me re t his beautiful sailboat. My friend and I had a blast on the boat. Chris’s was so accommodating. The boat is stunning also. Cannot wait for another trip !
Chris was so great! From my questions at the beginning, leading up to my rental, before and after our trip - communication was seamless. The boat was incredible! We had such a good time. Thank you so much for everything Chris! I would highly recommend renting from him.
Chris was fantastic coordinating our rental and very easy to work with. Will rent from him again!
Chris was so helpful and respectful and gave step by step and clear directions on expectations and ways for us to have fun. Would recommend to everyone!
Our group had a great day sailing on Chris's boat. He was responsive, professional, and the boat was in fantastic condition. Looking forward to next time!
The boat, time and captain that was designated to us made this day one for the books. I highly recommend this boat to anyone that wants a nice day on the lake.
Chris’s boat was everything we wanted! My friends and I had a great time and can’t wait to go back out again.
Chris's sailboat is beautiful and very fun to be on. In terms of logistics, Chris was very prompt in answering questions and found a great captain. We were a group of 9 guys for a bachelor party and it was a great experience!
Loved sailing on the advantage! Can’t wait to do it again!
Thx Chris..!! You were great with everything! We enjoyed our evening very much !
This was my first time using Boatsetter. I was planning my parents 50th anniversary celebration and I couldn't screw up the event or I never would have heard the end of it. Chris answered all of my many questions patiently and promptly. He also set us up with an amazing captain. The boat was perfect for our group of 8. I would highly recommend this experience.
Chris was extremely helpful throughout the entire process and found a fantastic captain to raise the sails and man the wheel while we had one of the best weekends of the summer. The boat was fantastic and very roomy for 10 people. Highly recommended!
I would 10/10 recommend Chris, his beautiful sailboat and captain Marty! Chris was extremely responsive and helpful with all my questions. We took his boat out for a birthday with 8 girls - all the age of 24 - it was an absolute blast. No complaints!! Would book again in a heart beat.
Chris was great! Very responsive and the boat was as advertised. It really added to our 4th experience. Request Captain Marty! He is the best
What an amazing experience my friends and I had celebrating my 30th birthday! Chris' boat was absolutely beautiful & Captain Chuck was great. We will definitely rent again!
Excellent experience on Chris' boat! Very clean and plenty of room for 10 plus a captain
Beautiful boat and a great ride around the lake. The captain was very professional and made sure we all had a great time. Definitely will be renting from Chris again!
My friends and I did the sunset/night cruise...Highly recommend for anyone who wants to see some pretty cool scenery of the Chicago skyline. From the beginning, Chris was very responsive and helpful when figuring out the best day and time to book. Once we got our time set, the directions of getting to and on the boat were simple. Our captain Chuck was very professional and often pointed out the big boats he sailed around the area. My friends and I left wanting to do it all over again! Highly recommend!
Had a really great time sailing on this boat with the captain Chris he did a great job provided 2 coolers with ice for us, helped us carry stuff into the boat and answered all of our questions...would really recommend it for anyone, a group of 10 people is perfect for this boat...me and my friends really loved it and will probably do it again this year before the summer ends.
It was a great experience. Chris was our captain -- he sailed us off the coast into the Lake for a couple of hours. After which, he let us just hang out by the dock for remainder of our time.
Had a great time on Chris' boat over labor day weekend. The crew and boat were on-time and ready for us. Plenty of room for the group of 10 of us and a great time on the lake.
The boat was really awesome and Captain Bill was fantastic! There was plenty of space to move around the cabin and we never felt crammed. Chris was very helpful throughout the booking process and helped us whenever we had questions. We had a slight weather delay and the captain was very communicative throughout the process. Would rent this boat again.
Me and my friends rented Hunter 40 from Chris on August 13, 2016 and it was a delightful experience. We also got to see the Navy Pier fireworks which was an added bonus. Our captain was Bill Mintz who was also very professional and experienced. Chris was very responsive throughout the process and answered all our questions with sufficient clarity. I highly recommend this boat to other Boatbound users.
My friends and I had so much fun on our beautiful sunset sail aboard Chris' boat! Captain Bill was very knowledgeable and friendly. He showed us the ropes and kept things light and fun. The boat was comfortable and easy to move around on. We will definitely be booking another sail with Chris!
Chris was very responsive and made sure that I got the best deal possible. The boat was beautiful and very reasonably priced for what's out there. Really enjoy the experience and everyone else on the boat did too. Thanks again Chris!
Incredible and easy experience, would rent this boat again in a heartbeat. Thanks Chris!
Chris was fantastic during the entire booking and scheduling process. We had Captain Bill on our rental and he was terrific. Everyone in the group of 8 had an amazing time and can't wait to rent the boat again!
Chris was a great host. The boat was exactly as listed clean and fun to sail. He did a great job helping us understand the boat and systems. Location is perfect right next to soldier filed and museums
Chris's hunter was well maintained and sailed great, would definitely rent from Chris again.
We had a wonderful day on Chris' Hunter 40. The boat was beautiful and spacious and Chris was easy to work with through the booking process. Captain Bill, who spent the day with us chartering the boat truly made the experience memorable. He was knowledgable, friendly, interesting and someone you just wanted to spend time with. He taught us about sailing and spent time to explain everything we had questions on. The group felt like they were spending time with an old friend. Thank you so much Captain Bill and Chris for a fantastic day on the Hunter 40!
My group and I had a wonderful time sailing on Chris's Hunter 40. We enjoyed out day tremendously and it was made better by the helpful insight from both Chris and Captain Bob. Chris is quick to respond and made sure that all questions were answered prior to setting sail. The boat is clean, well kept, and has character. Would recommend to others.
It was a great day!
Chris did everything to make the rental comfortable.
The boat was easy to use.
We sailed with more than 20 knots of winds and we had no problems.
The boat was very reassuring and Chris learnt us how to do the docking.
It was a great day. Don't hesitate.
Nice, clean cruiser with plenty of room our 6-person day sail. The boat could easily accommodate 2-4 more on board.
Chris was very good about communicating throughout the process. I performed a quick "checkout" sail a few weeks in advance, which mostly consisted of a basic walkthrough of the boat and some docking practice. No matter how many boats you've sailed, docking is a new boat for the first time can be a challenge and Chris was a patient instructor.
The boat performs reasonably well (8kts of speed off the wind with ~13kts of breeze) and the cockpit layout is a good balance between size and access to the controls. I was able to single-hand most of the time when needed without too much help from my inexperienced guests.
Overall, a solid value for a well-kept boat in the city.
We had an amazing time on Chris's boat. It was very spacious, clean, and came equipped with everything we needed for a day on the lake. There was an aux cord and speakers so we could play music and there were coolers for food and drinks. The captain (Jeff) was GREAT! He taught us about sailing and made the trip really fun. I would recommend this boat to anyone!
We had the best day on Chris's boat! It's the perfect size boat for a small group of people. The boat was very nice and clean, & had a small bathroom. The captains were very accomodating & respectful of us. It was a great day for sailing and the captains knew exactly where to take us and taught us a little about how to sail, they made it really fun.
Chris was great to work with, easy to communicate with, and even gave us a 1/2 day rate. I have already forwarded his info onto some friends of mine looking to charter a sailboat.
I have nothing negative to say about the whole expierence-thanks Chris!!!
I recently bareboat chartered a Hunter 40 from owner Chris over the 4th of July weekend. Wow what a great time! The owner Chris has a nice mid 1980's Hunter 40 that seems pretty well maintained. He came and made berths and made sure all was clean before leaving us the first evening. He came back the following day for our shakedown cruise since the wind was blowing to 30 knots the day prior. He made sure we could get in and out of the slip without crashing into his neighbors and we did a short sail to his satisfaction. We had a great time sailing along the Chicago shoreline for the next few days and then going to the GD concerts in the evenings. Truly epic! All the dock neighbors were pleasant and welcoming.
If you are looking for a pristine sailing yacht this isn't the boat for you but if you are looking for a good value and a good sailing boat that is located perfectly for sailing the Chicago shoreline and being home base for adventuring into Chicago, Advantage is perfect.