$399—Lake Michigan private sailboat cruises for up to 8
Why We Love This Deal
Set sail on Lake Michigan this summer. These private chartered sailboat cruises are the perfect way to spend a summer day. Up to eight guests can enjoy a day of sun and salt-free surf. When viewed from the lake, the Windy City is nothing but spectacular.
What's Included
- $399 for a two-hour private sail for up to eight people ($249 voucher + $150 captain fee; reg. up to $988), available on the following days and times:
- Morning sails: Saturdays and Sundays at 9 a.m.
- Weekday sails: Mondays–Thursdays at 9:30 a.m., 12 p.m. and 3:30 p.m.
- Sunset sails: Mondays, Tuesdays and Thursdays at 6:30 p.m. and 7 p.m. (times may vary)
- Note: You will purchase this voucher for $249, then pay the required captain fee of $150 and gratuity directly to the captain. Taxes will be paid separately at time of booking (this is standard for all purchases). Once a reservation is confirmed, a 10-day rescheduling and cancellation policy applies; read full terms and conditions
- Not valid on: July 3–5, August 15–16
More Reasons to Go
- Sailboats feature an expansive sun pad and deck, onboard bathroom, swim ladder and interior seating
- Each boat is piloted by a professional captain, so you can focus on the fun
- Cruises depart from a private dock in Belmont Harbor
Travelzoo tip: Make this deal a gift when completing your purchase. Check the "Is this a gift?" box at the top of the checkout page. Then, enter the gift recipient’s information and select the delivery option.
Have a Question?
Member Services available
Mon-Fri, 9am-6pm ET
Sat-Sun, 12-5pm ET




