7–36 people
More boats. More stories.
Bachelorette parties, birthdays, company outings, and two-boat regattas. We will put your group on the water, keep everyone safe, and make it the part of the summer people talk about.
Multi-boat parties
Your own marina in the middle of the lake.
For groups of seven or more, book two or more boats. You get multiple skippers, music setups, and room to move. Guests can hop between boats, stretch out, or tie up together at the Playpen.
- Up to 36 people
Six guests per monohull. Add boats as your group grows.
- Regatta or flotilla
Race for bragging rights, or connect the boats and float together.
- Swim, grill, BYOB
Bring your own drinks and food. We will help you plan the details.
Rates
Group pricing.
Group sails are priced per boat, per hour, with a three‑hour minimum and a two-boat minimum for groups of seven or more.
| Option | Details | Rate |
|---|---|---|
| Multi-boat party | 3‑hour minimum, 2-boat minimum, up to 6 per boat | $200/hr per monohull |
| Teambuilding regatta | 3‑hour event, 2-boat minimum, lessons + racing | $250/hr per monohull |
| Catamaran committee boat | Up to 12 guests, 3‑hour minimum, concierge | $600/hr |
| Groups over 36 | Custom multi-boat plan | Contact us |
A 50% deposit holds the date and boats; the balance is due 45 days before the event. See the cancellation policy for rescheduling terms.
Teambuilding
Forget the golf outing.
Nothing builds a team faster than trying to make a sailboat move. Add a race and your group will be hooked — communication, adaptability, and a little friendly pressure.
- Three‑hour event
Basic sailing lessons first, then a race to determine the best team. No experience needed.
- Licensed captains
Every boat has a USCG-licensed captain who teaches at all levels.
- Committee boat option
The 38' catamaran is perfect for teammates who would rather chill, cater, and watch the race.
Occasions
Built for a good story.
Bachelorette & bachelor
Float, swim, take photos, and let someone else drive. Multiple boats for bigger crews.
Corporate outings
A regatta, a sunset cruise, or a catered catamaran afternoon. We can host 36 across the fleet.
Fireworks & events
Fourth of July, Air & Water Show, and summer fireworks — book early, these dates go first.
Everyone must complete a liability waiver before sailing. Parents may sign for children.
Start planning
Tell us about the group.
Send the occasion, date, and headcount. We will come back with a boat plan and a quote. For dates inside two weeks, call the office.
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Departure
Monroe Harbor
400 E Monroe St (approx.), Chicago
Good to know
Group questions.
How many people fit on a boat?
Six guests per monohull. For groups of seven or more we add boats. The 38' catamaran carries up to 12 guests, with options for larger groups.
Can we race?
Yes. Our teambuilding format starts with a sailing lesson and then runs a race. You can also book a multi-boat regatta without the formal lesson.
Can we bring food and drinks?
Yes. Bring your own food and drinks. The catamaran has a galley, grill, refrigerator, and cooler; the crew can help you plan catering for larger events.
What is the payment schedule?
A 50% deposit holds the date and boats. The remainder is due 45 days before the event. Rescheduling at least two weeks out carries a $100 fee per boat; fewer than two weeks is non-refundable. See policies.
Do you sail in the rain?
Light rain is usually fine. The captain makes the call on lightning and unsafe conditions. If we cancel, you will be notified at least two hours before and can reschedule.