Expansive Luxury BYOB Yacht Cruise with Private Captain

Cait was a lifesaver! Another captain canceled on me less than 40 hours from a booking on a Saturday! The horror of potentially having 10 guest in my crew with that time of letdown was so disappointing. Luckily Cait answered my bat signal and things happen for a reason because we got her amazing sailing yacht and awesome husband, captain Greg, to take care of us which was such a great upgrade! Thank you for taking such good care of us! We will be back and recommending you to all our friends!

When I say I celebrated my 36th birthday on this beautiful boat, it was AMAZING!! Cait was so incredibly helpful and prompt with any questions I had. Her husband Greg was the coolest captain you could possibly meet. I wish I could rate this 10 stars, for it was truly a wonderful experience! You can’t go wrong if you book with them!! Thank you again!!

Amazing experience, wonderful people, best boat trip possible. Greg and Cait were so professional and accommodating as well as kind and considerate.

We rented Greg’s yacht to celebrate my birthday and it was truly amazing!! The yacht itself was very clean and beautiful and Greg was accommodative and helping us with any requests we had. Thank you!

Couldn’t have been better! My family celebrated a birthday and two big wedding anniversaries onboard the Dragonfly on a lovely Sunday. Captain Greg guided us out into the beautiful waters of Lake Michigan, showing us views of the Chicago waterfront all the way. It was an afternoon filled with great conversations, many laughs and relaxing times. Smooth sailing for three wonderful hours. Captain Greg is the best!

OAB Sailing provided the perfect venue for my wife's 40th birthday party! Greg was hyper-responsive to questions in the weeks prior and very thorough. The boat arrived in immaculate condition and ready to go on the time promised. The downstairs cabin with fridge, kitchenette, head, and table worked great to hold our trays and drinks. Greg was a skilled captain, navigating a bunch of chop from other boat traffic, and we felt comfortable and unrushed the entire time. Parking is easy in the MilPark garage; follow his handout instructions to keep the walk to a few minutes! Would definitely book again!

Wow! Absolutely grateful for Greg and the dragonfly . Always courteous and always a great time . Blessed my group with a trip to the playpen Chicago . Perfect ride and tour . Thank you so much for being a genuine good soul.

I cannot recommend "On A Boat Sailing" enough! My friends and I booked this experience with Greg & Cait for a bachelorette excursion and it was amazing. Weeks prior to our day trip our group received a thorough email with all of the information we needed for a seamless arrival...making it so easy to find the boat on the marina, etc. We had a group of 7 girls on the trip and the boat was so spacious, incredibly clean, and a great atmosphere to have fun (& relax). Greg was the best captain and built in tour guide for us girls who had never been out on the lake before. I will definitely be back to book with them again! Thank you so so much!!

This is a great price for a big group! We had the whole boat to ourselves and had a blast for 4 hours in the playpen! A great alternative for a private group!

Definitely recommend Greg and his sailboat for a nice day out on the lake! He was absolutely accommodating for our bachelorette party! Very prompt at answering any questions we had.

The boat ride with Greg was the highlight of our trip to Chicago! Greg is an experienced sailor and was kind, entertaining and accommodating. It was a great way to admire the architecture of Chicago and to relax with friends. Cannot recommend enough.

This is a MUST! I booked this trip for a surprise for my boyfriend’s birthday and it did not disappoint! Greg is a wonderful host and his girlfriend Kate was amazing. They were both very knowledgeable, experienced and accommodating. Such a relaxing experience I would recommend to anyone. My original trip was scheduled for Friday and it was pouring so Greg rescheduled immediately and responded very quickly to any questions I had. It’s a must-do!