Up to 6 guests
Your boat. Your crew. Your afternoon.
A floating picnic with sails. Bring your favorite snacks and drinks, take a dip, or take the helm. We handle the boat and the skyline does the rest.
The experience
Bring the party aboard.
We sail when you want to sail, based on availability. Reservations are required, so lock in your date early — especially for fireworks, the Air & Water Show, and summer weekends.
- Up to six guests
Bring your people. Larger groups can book multiple boats or move up to the catamaran.
- Hands-on if you want
Help hoist the sails, take the helm, or just sit back. Kids love steering; the skipper loves company.
- Swim, grill, chill
Pack a swimsuit and towel. There is a grill on board, and Lake Michigan is right there.
- BYOB and snacks
Bring your favorite food and drinks aboard.
Rates
Simple pricing.
Two‑hour cruises start at $500. Three or more hours are $200 per hour. All cruises include a USCG-licensed captain and crew.
| Option | Details | Rate |
|---|---|---|
| 2-hour private cruise | Up to 6 guests; captain and crew included | $500 ($250/hr) |
| 3+ hour private cruise | Up to 6 guests; custom route and pace | $200/hr |
| Private lesson | Up to 6 people; 3‑hour minimum; any skill level | Contact us |
| Larger group | 7–30 people; multiple boats or catamaran | Contact us |
Please remember to tip your captain and crew. Cruises are subject to the cancellation and weather policy; a 50% deposit holds your date for group and special-event cruises.
More than six?
Step up to the catamaran.
Our 38' Lagoon catamaran, Latitude Adjustment, carries up to 12 guests with a galley, grill, refrigerator, Bluetooth radio, and room to spread out.
- 12-person capacity
Equivalent to a 70' monohull in deck space. Options for 12+ are available.
- Yacht concierge
A concierge caters to your group, from drinks to dinner aboard.
- Custom itinerary
Lessons, a tour, a chill-out, or a party cruise — build the day you want.
Reserve a date
Tell us about your crew.
Send the date, time, and group size and we will confirm availability. For same-day requests, call the office.
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Departure
Monroe Harbor
400 E Monroe St (approx.), Chicago -
Season
May–October, seven days a week
Good to know
Before you board.
Can we bring our own food and drinks?
Yes. Think of it as a floating picnic. Bring snacks, drinks, and a towel if you plan to swim. There is a grill on board if you want to cook.
What if the weather is bad?
The captain decides. If we cancel for weather, you will hear from us at least two hours before your cruise and can reschedule. See the weather policy.
Can we choose where we sail?
We will build the route around your group, the wind, and the time of day. Popular runs include the lakefront, the Playpen, Navy Pier, and the river when conditions allow.
What is the cancellation policy?
Private cruises canceled with less than 48 hours' notice forfeit the sail. Groups and special events require a 50% deposit, with the balance due 45 days before the event. Full details are in the cancellation policy.
Do we need to sign a waiver?
Yes. Everyone must complete a liability waiver before sailing. Parents may sign for children.