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Sail and Sip on Lake Michigan
Sail and Sip on Lake Michigan
Sail and Sip on Lake Michigan
Sail and Sip on Lake Michigan
Sail and Sip on Lake Michigan
Sail and Sip on Lake Michigan
Sail and Sip on Lake Michigan
Sail and Sip on Lake Michigan


best price

location_on Monroe Harbor, CHI

Sail and Sip on Lake Michigan

$700 $630

10% off

Bucket Listers is excited to partner with On a Boat Sailing to offer you exclusive ticket pricing:

💰Price List:
Sail and Swim Skyline Cruise: $900 per boat, up to 6 people (originally $1000)
Fireworks Cruise: $900 per boat, up to 6 people (originally $1200)
Labor Day Firework Cruise: $1350 per boat, up to 6 people (originally $1500)
Sunset Cruise: $630 per boat, up to 6 people (originally $700)
🗓️Multiple dates
⏰ Multiple times
📍Monroe Harbor: 400 E Monroe St, Chicago, IL 60603

About The Event:

You can Sail, Swim & Sip while renting your own sailboat! Charters are 3 hours long for you to enjoy a Day Sail, Sunset Sail and the Navy Pier Fireworks on select dates. All charters fit up to 6 guests and include beer, wine or champagne, soft drinks and snacks. Guests are also welcome to bring their own food and beverages in addition, no hard liquor on the boat. The boat is equipped with glasses, plates, silverware, towels, floaties, and blankets

"Dragonfly" is a 37' foot long, French-built Jeanneau Sun Odyssey luxury sailing yacht. Unlike most sailboats, this boat is designed for comfortable cruising, with a spacious open cockpit for seating, a folding table, and a surround sound Bluetooth stereo system that you can play from your phone. Keep your drinks cool in the fridge that we stock with ice-no lugging of coolers necessary. The boat is also equipped with a bathroom, full set of cocktail glassware, plates, silverware, towels, floaties, blankets, an assortment of beer, wine, soda, water, and packaged snacks. Dragonfly is fully insured and certified every year to operate as a legal charter in the city of Chicago. We carry onboard all necessary safety equipment including USCG life jackets and your captain is first aid CPR certified.

What Should You Bring:

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

Weather Cancellation Policy:

We will not accept any refunds unless due to weather. The Partner will notify each patron 1 hour before each charter. If the charter is canceled we will offer a full refund to patrons. We sail in the rain and advise guests to dress accordingly, this is an outdoor activity! If there is lightning or high waves, we make a weather call 1 hour before each charter. If the charter is canceled we will contact you and offer a full refund.

All sales are final, no refunds or exchanges.

Parking Info:

The closest parking is the underground Millennium Lakeside Garage- price is $15-$30 depending on the day. The entrance ramp is off of Columbus Dr. between Monroe St. and Randolph St. Look for signs for the Lakeside half when you enter.
1. Once through the ticket gate, drive straight forward until you see a ramp down, 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 and doors in the corner, called section 117. Park here.
4. Go through the 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.

Where to meet info:

Google "Monroe Harbor Public Dock", see map below. Please plan ahead to arrive on time. The closest drop-off point is 400 E. Monroe and from there it is a 2-minute walk north of the Chicago Yacht Club along the Lakefront Trail to get to the dock. If you are over 15 minutes late, the time will not be made up to you, we have other charters. Look for our boat Dragony no earlier than 15 minutes prior to departure as this is a pickup dock only.


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