Embark on an unforgettable evening aboard Guppy, Chicago's largest private sailing yacht, offered by Sailing Chi. From the heart of downtown Chicago at DuSable/Monroe Harbor, you and your loved ones are invited to experience Lake Michigan's magic.

To learn more, visit them on Google Maps or visit SailingChi.com.

This voucher grants you a three (3)-hour evening sail (Monday, Tuesday, Thursday, Friday, Sunday) scheduled at your convenience, hosted by a yacht captain and an attentive steward.

Bring up to 10 guests-family, friends, or a mix of both-and let them craft a bespoke adventure just for you. Picture this: gliding across the waves as the Chicago skyline glows against a watercolor sunset, the breeze carrying laughter and serenity alike.

Whether you'd like to marvel at the city skyline's architectural wonders, anchor in the Playpen for a refreshing swim, or simply bask in twilight's embrace, they're here to make it extraordinary.

At Sailing Chi, their passion is creating cherished moments on the water-tailored to your vision, wrapped in the beauty of Lake Michigan's horizon.

Guests can bring provisions. They can also provide provisions for a charge. Service fee is the responsibility of the winner.

The fee amount for the captain and crew is 30% of the value of the winning bid or minimum $700.

Must redeem between April 15 and November 1, 2026