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VIP Bach Experience: Chicago's Largest Private Sailing Yacht  image 1
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VIP Bach Experience: Chicago's Largest Private Sailing Yacht

About this experience

What you'll do:

Enjoy the best yachting experience with Chicago's sexiest captain! For starters our yacht Guppy is huge so no matter what the sea-state is her generous size and location in Chicago guarantees you will host a great party. Our captain is a passionate sailor but also goes out of his way to make this a memorable experience in the best way for everyone. We’ll soak up the fresh breeze from the lake and enjoy one of the world's great skylines. You couldn't ask for a more memorable experience than sailing in The Guppy along the Chicago coast!

Why we love it for your party:

  • Chicago’s best captain (He’s passionate about being out on the water and loves to pump up the party jams and enjoy the finest of yachting has to offer)

  • Stunning skyline views (Your group gets to cruise Lake Michigan on a luxurious 50-foot yacht Guppy, soaking in Chicago’s iconic skyline—perfect for photos and a memorable backdrop that elevates any celebration, from birthdays to bachelorette parties)

  • Customizable fun (Whether you want to anchor at the Playpen for swimming and music or sail past Navy Pier for fireworks, Sailing Chi tailors the trip to your vibe—ideal for keeping everyone in your group entertained and engaged)

  • Insta-worthy (Guppy has many lounge spaces for sunbathing and lake-gazing is available on the foredeck - a popular locale for photo opportunities on beautiful days!)

  • Spacious luxury (With room for your crew on a well-equipped yacht, there’s space to dance, relax, or mingle, plus amenities like a huge sound system for your best playlist—making it the best private party venue on the water)

About this experience partner:

At Sailing Chi, we emphasize client enjoyment, safety, and a tailored experience to bring only 5-star events for you and your guests. Yacht Guppy offers world-class sailing with comfortable amenities, encouraging you & your guests to enjoy the day ahead. Our professional captain handles everything, letting your group focus on celebrating—no stress, just good times, whether it’s a corporate outing or a family reunion.

Additional information:

  • We are BYOB but we also offer the ability to have the boat provisioned with all your favorites. Just let us know!

  • If you're interested in a more customized, special event, reach out to us directly and we can curate a unique experience for your party.

Book with Confidence!

Generous Cancellation

Generous Cancellation

This experience offers a full refund on cancellations with 7+ days notice.

Lowest Price Guarantee

Lowest Price Guarantee

If you find it cheaper, we’ll refund the difference.

Check Availability

Book Your Experience

  • Private Yacht with Sailing Chi - Thur/Fri/Sundays at 11:30AM

    Starting at$2,999per party

    4hr

    You have now arrived at Chicago best bach yachting experience. All-inclusive boutique experience on Chicago's largest private sailing yacht available for parties up to 13 guests. We'll start in the early afternoon depending on your needs. Ideally we will sail out for some photo moments along the Chicago skyline. We will ultimately end up in the Chicago Playpen where the party starts! We will stay there till about 4 or 5 and then make our preparations to land back at the harbor around 6pm.

  • Private Yacht with Sailing Chi - Saturdays at 11:30AM

    Starting at$3,499per party

    4hr

    You have now arrived at Chicago best bach yachting experience. All-inclusive boutique experience on Chicago's largest private sailing yacht available for parties up to 13 guests. We'll start in the early afternoon depending on your needs. Ideally we will sail out for some photo moments along the Chicago skyline. We will ultimately end up in the Chicago Playpen where the party starts! We will stay there till about 4 or 5 and then make our preparations to land back at the harbor around 6pm.


Location

Chicago, IL

111 N Jean Baptiste Pointe du Sable Lake Shore Dr, Chicago, IL 60601, USA

Cancellation Policy

Green shield with a checkmark in the center

generous Cancellation Policy

Full refund on cancellations with 7+ days notice. No refund within 7 day window.

Reviews

See All

5 (12 Ratings)

R

Raymond

August 2024 • Group-Trip Party

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!

A

Alicia

August 2024 • Birthday Party

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!!

C

Caroline

July 2024 • Bachelorette Party

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

A

Arina

June 2024 • Birthday Party

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!

P

Pat

June 2024 • Birthday Party

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!

B

Brad

August 2023 • Birthday Party

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!

O

Oscar

August 2023 • Group-Trip Party

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.

A

Abby

June 2023 • Bachelorette Party

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!!

N

Natalie

July 2022 • Girls-Trip Party

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!

R

Rose

July 2022 • Bachelorette Party

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.

K

Kailey

May 2022 • Girls-Trip Party

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.

R

Rachel

July 2018 • Birthday Party

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!

Check Availability

Book Your Experience

Private Yacht with Sailing Chi - Thur/Fri/Sundays at 11:30AM

Starting at$2,999per party

4hr

You have now arrived at Chicago best bach yachting experience. All-inclusive boutique experience on Chicago's largest private sailing yacht available for parties up to 13 guests. We'll start in the early afternoon depending on your needs. Ideally we will sail out for some photo moments along the Chicago skyline. We will ultimately end up in the Chicago Playpen where the party starts! We will stay there till about 4 or 5 and then make our preparations to land back at the harbor around 6pm.

Private Yacht with Sailing Chi - Saturdays at 11:30AM

Starting at$3,499per party

4hr

You have now arrived at Chicago best bach yachting experience. All-inclusive boutique experience on Chicago's largest private sailing yacht available for parties up to 13 guests. We'll start in the early afternoon depending on your needs. Ideally we will sail out for some photo moments along the Chicago skyline. We will ultimately end up in the Chicago Playpen where the party starts! We will stay there till about 4 or 5 and then make our preparations to land back at the harbor around 6pm.

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