About this Experience
What you'll do:
Step aboard your private 37’ luxury sailboat with a USCG-certified captain for a 4-hour BYOB cruise along Chicago’s iconic lakeshore. Enjoy spacious deck seating, a swim platform, a Lily Pad, and fun floaties for the ultimate on-water party. The boat is stocked with complimentary snacks, beverages, Bluetooth speakers, kitchenware, refrigerator, and a private bathroom—everything you need for a seamless and convenient celebration. Anchor at the lively Playpen or choose a quieter cove for swimming and relaxing with your crew. Soak in picture-perfect scenic views of the skyline while sipping your favorite drinks in VIP style.
Why we love it for your party:
BYOB and food: Bring your favorite drinks and bites—we’ll have ice, glassware, and storage ready. Catering packages are also available.
Luxury AF: A sleek 37’ private sailboat with plush seating, top-tier amenities, and your own licensed captain.
Complimentary features: Snacks, beverages, Bluetooth speakers, kitchenware, refrigerator, and private bathrooms—all included for no extra fee.
Scenic views: Cruise past Chicago’s most Instagram-worthy skyline spots for unforgettable group photos.
Additional Information:
What's included:
USCG-certified Captain trained in First Aid and CPR (no separate Captain’s fee)
Private use of our fully permitted, fully insured sailing yacht (no fuel or docking fee)
Complimentary beverages and snacks on board (with BYOB or catering/drink packages available)
Fully stocked kitchenware, fridge, and bathroom (no damage/cleaning deposit)
Surround sound Bluetooth speakers
Swim platform with Lily Pad, life jackets, noodles, & pool floaties
What to pack:
Bathing suit and towel
Sunglasses, hat, sunscreen
Rain jacket or layers for cooler days
Boat shoes, sandals, light-soled tennis shoes
Comfortable, breathable clothes
About this experience partner:
On A Boat Sailing is the premier purveyor of sailing charters & cruises for intimate group celebrations in Chicago. We have over 500 five-star reviews in our eighth season in business.
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