About this Experience
What you'll do:
Step aboard Chicago’s largest private sailing yacht for a personalized luxury cruise with breathtaking views of the skyline. Your private captain will tailor the trip to your group’s vibe—whether that’s anchoring for a swim or sailing past iconic landmarks. Enjoy the expansive deck space, perfect for lounging, dancing, or capturing insta-worthy moments. Bring your own drinks and snacks to enjoy while the premium sound system sets the mood. This is the ultimate BYOB celebration on the water.
Why we love it for your party:
BYOB: Bring your favorite drinks and snacks and we’ll have coolers, storage, and serving space ready.
Customizable: From swimming stops to sunset sails, your itinerary is designed around your group’s preferences.
Expansive: Chicago’s largest private sailing yacht offers multiple lounge areas, generous deck space, and room for everyone to relax or party.
Private captain: An experienced, USCG-certified captain ensures a safe, smooth, and unforgettable cruise.
Additional information:
We are BYOB but also offer provisioning with your favorite drinks and snacks—just ask.
For custom events or special celebrations, we can curate a unique, personalized experience.
About this experience partner:
At Sailing Chi, we prioritize safety, fun, and fully personalized experiences. Yacht Guppy combines world-class sailing with upscale amenities so you can celebrate stress-free while your captain handles the rest.
Favoriting lets this partner send you exclusive deals!
Book This Experience
Visit the experience booking site to check availability and book your experience.
LocationChicago, IL
797 E Grand Ave, Chicago, IL 60611, USAChicago, IL
Reviews
Frequently Asked Questions
What food and drink can I bring on the boat?
You may bring any food and beverages of your choosing including beer, wine, champagne, or hard seltzers. We have alcohol for purchase on board or ahead of time and can provide catering/provisioning of food and drinks for an added fee.
What if there is bad weather?
If there is current or forecasted lightning or high wind, we make a weather cancellation one hour before your scheduled departure and provide a full refund.
Is a Captain included?
Yes, a USCG-certified Captain is included in the price at checkout. Groups larger than 7 require an independently hired Captain. Upon booking we will send a curated list with available captains and instructions for contacting. Gratuity is appreciated for exceptional service!
Is there a bathroom on board?
Yes, you and your crew will have full access to our in-cabin bathroom.
Where do we get on the boat?
Navy Pier Marina 797 E. Grand Ave. Chicago, IL 60611
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What is your BYOB & Alcohol Policy?
Guests are allowed to bring alcohol in the form of beer, wine and hard seltzer drinks. We have a no hard liquor policy while on the boat for our guests safety. We do not provide or sell alcohol on board unless arranged through our catering or provisioning service. All beer must be in cans, not glass. Wine bottles are acceptable. We have wine openers and acrylic wine glasses on board. We provide use of our fridge for keeping drinks cool and have ice available. If extra ice is desired let us know ahead of time to ensure we have some on board before you arrive.
What else should our group bring?
Good things to bring include a bathing suit or change of clothes, towel, sunglasses, hat, light rain-jacket and layers for cooler days. Keep in mind, temperatures on the Lake will ALWAYS be cooler than on land. We humbly request no dark rubber soled shoes as they can scuff up the boat. We provide lifejackets, pool floats, blankets, sunscreen, bug spray, and full first-aid.
Where is your full list of FAQs?
You can see all of our FAQs here on our website https://www.onaboatsailing.com/faq
