All private bookings are approved for up to 7 guests. Our booking partner, Sailing Chi, offers a Sail & Swim+ booking for up to 13 guests. This is a great solution for larger groups wanting to stay out on the water for a bit longer!

Yes, a USCG-certified Captain is included in the price at checkout. Gratuity is appreciated for exceptional service!

It is often very difficult to predict the conditions on the Lake as they can be very different compared to the city and surrounding suburbs of Chicago. We do our best to communicate expectations of poor weather ahead of your sail. We will sail in the rain and advise guests to dress accordingly or request to reschedule when possible. If there is current or forecasted lightning or high wind, we will make a weather cancellation one hour before your scheduled departure. If your charter is cancelled, we will contact you and offer a delay, rescheduled booking or a refund that aligns with our booking policy.

We have a recommended age minimum of 5 years old. Children under 12 will be encouraged to wear a life jacket at all times. We love having kids onboard, but please be advised of the risks of boating and the range of conditions from smooth sailing to rough and choppy waters. It is 100% the parent's responsibility to monitor children and ensure that they stay within designated safe areas of the boat. Conditions will be unstable at times!

We do not encourage bringing pets on board without prior boating experience. If you do wish to bring a cat or small to medium sized dog we encourage you to bring a pet life jacket. We do not provide pet life jackets. Of course a parrot on the shoulder is always welcome on the high seas, arrrr matey!

Lake Michigan is subject to a wide range of conditions, from calm to rough seas depending on the weather which will cause the boat to be unbalanced at times. As such, some passengers may experience seasickness. Please see below for our tips to prevent seasickness: • Be well rested and do not drink alcohol excessively the night before • Take antiemetic drugs (Dramamine) the night before to get it in your system and again 30 minutes before the cruise • Be sure to have plain foods ahead of the cruise. An empty stomach or foods that do not sit well (greasy, spicy, dairy etc.) are not good ideas • Wear an acupressure wristband such as sea-band

Yes of course! Our sailing experiences for perfect for all forms of celebration. We are happy to discuss special needs ahead of your booking date & time. We provide catering, provisioning and or decorations for an additional fee, too.

Yes, you and your crew will have full access to our in-cabin bathroom.

You may bring any beverages of your choosing including beer, wine, champagne, or hard seltzers. No hard liquor on the boat please per our own safety precautions. Please do not bring red wine or other items that may stain the boat if spilled. We provide glassware for our guests. We have a fridge onboard to keep things cool, along with utensils, glasses and dish-ware.

If its a hot day and you want to swim, bring a bathing suit and towel! We have a few spare towels onboard the guests may share. Other good things to bring include sunglasses, hat, light rain-jacket and layers. Temperatures and wind on the Lake will ALWAYS be cooler than on land. We humbly request no dark rubber soled shoes as they can scuff up the boat. We provide lifejackets, pool floats, blankets, sunscreen, bug spray, and full first-aid.

Boat shoes are great but not a requirement. We humbly ask for no black soled shoes or high heels as these can scuff or scratch the boat. Guests are welcome to remove shoes and go barefoot while on the boat if desired.

Yes, we customize a fee for catering and provisioning pending on the size of the group and order. Generally the fee starts at $199 plus cost of goods.

No dress code for our yacht club! We want guests to be comfortable and come as they are. We recommend casual athletic wear that is quick drying and no denim. Please be advised the Lake is always cooler than the city by about 10 degrees so bring layers if sailing with us in the Spring or Fall months.

Guests are allowed to bring alcohol in the form of beer, wine and hard seltzer drinks. We have a no hard liquor policy while on the boat for our guests safety. We do not provide or sell alcohol on board unless arranged through our catering or provisioning service. All beer must be in cans, not glass. Wine bottles are acceptable. We have wine openers and plastic wine glasses on board. We provide use of our fridge for keeping drinks cool and usually do have ice available. If ice is desired let us know ahead of time to ensure we have some on board before you arrive.

📍 Navy Pier Marina 797 E. Grand Ave. Chicago, IL 60611 Keep an eye out for S/V Dragonfly where Captain Greg will be waiting for your group!

The closest parking is the underground Millennium Lakeside Garage- price is $20-$35 depending on the day and special events in the area. The entrance ramp is off of Columbus Dr. between Monroe St. and Randolph St. Look for signs for the Lakeside entrance gates when you get to the bottom of the ramp. 1. Once through the ticket gate, drive straight forward until you see a ramp down to level 2, stop. 2. Turn right, in front of the ramp, drive forward all the way until you reach a concrete wall, 3. Turn left, drive forward all the way, you should see a group of parked cars, boat trailers and pedestrian doors in the corner, the columns will say section 117. Park here. 4. Go through the pedestrian doors, walk down the ramp. On your left there will be glass doors. 5. Walk up the stairs to the crosswalk on Lake Shore Drive. 6. See map below for the directions to the dock.

Your private charter includes: ✅ USCG-Certified Captain ✅ Complimentary snacks and drinks ✅ Fridge with Ice ✅ Kitchenware including acrylic cups and stemware ✅ Pool floaties, life jackets and pool noodles

No! We offer 100% transparent pricing on all bookings. ❌ NO hourly captains fees ❌ NO refueling costs ❌ NO docking fees

You may bring any food and beverages of your choosing including beer, wine, champagne, or hard seltzers. No hard liquor is allowed on the boat per our company safety policy. Please do not bring red wine and other food or drinks that may stain if spilled. We provide kitchenware and non-breakable acrylic glassware for our guests. We have a fridge with ice onboard to keep things cool. Ahead of the cruise or while onboard guests may purchase our bottles of white wine, rose, champagne, packaged cases of beer or seltzers. We do provide complimentary packaged snacks, water, gatorade and sugar free sodas.