Our On-Water Training, Close Quarters service offers professional instruction for individuals looking to enhance their boat handling skills in tight spaces. Whether you are a seasoned boater wanting to sharpen your abilities or a beginner looking to build confidence in close quarters navigation, our experienced instructors provide personalized guidance to help you navigate challenging situations with ease. With a focus on safety and precision, our training program ensures that you are equipped with the knowledge and skills necessary to maneuver your vessel confidently in confined spaces such as marinas or busy waterways. Elevate your boating experience with our comprehensive Close Quarters training. (Limited to 4 students per vessel)
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Nightime Navigation Training on Your Boat
Learn how to navigate in and out of your Chicago Harbor at night without electronics. Learn how to negotiate the Chicago Locks in the dark and finally gain confidence in operating on the Chicago River’s Central, South, and North Branches without spotlights. This training also includes insider tricks and professional tips on navigating around sightseeing tour boats and that fireworks barge! The sooner you book, the sooner you can have your training!
Class taught by an elite Boat Safe Chicago National Safe Boating Council Instructor.
Book online at www.BoatSafeChicago.com
On-Water Training on Your Boat (Intro & Docking)
Our On-Water Training. This session includes Introduction to Powerboating, Close Quarters Maneuvers, and Docking. This session provides professional instruction for individuals looking to enhance their boat-handling skills in tight spaces. Whether you are a seasoned boater wanting to sharpen your abilities or a beginner looking to build confidence in close quarters navigation, our experienced instructors provide personalized guidance to help you easily navigate challenging situations. With a focus on safety and precision, our training program ensures you are equipped with the knowledge and skills to confidently maneuver your vessel in confined spaces such as marinas or busy waterways. Elevate your boating experience with our comprehensive training. Up to 4 family members may attend on your boat.
On-Water Training, Close Quarters, & Docking (Your Boat)
Our On-Water Training. This session includes Introduction to Powerboating, Close Quarters Maneuvers, and Docking. This session provides professional instruction for individuals looking to enhance their boat-handling skills in tight spaces. Whether you are a seasoned boater wanting to sharpen your abilities or a beginner looking to build confidence in close quarters navigation, our experienced instructors provide personalized guidance to help you easily navigate challenging situations. With a focus on safety and precision, our training program ensures you are equipped with the knowledge and skills to confidently maneuver your vessel in confined spaces such as marinas or busy waterways. Elevate your boating experience with our comprehensive training. Up to 4 family members may attend on your boat.
Elite Captains at Boat Safe Chicago
$150/hr (including gratuity)
Master captains with National Safe Boating Council certifications
Able to captain an array of vessels
Professional, friendly, and elite
Bartender/specialty pre made drinks
I offer bartender services, or pre made drinks sealed in plastic container
Chicago Sailboat & Yacht Charters
We offer two beautiful powerboats that can take a total of 25 people out together on Lake Michigan. A 51′ Searay Sundancer and a 35′ Searay Sundancer boat that can accommodate a lot of guests. We can bring both of our boats together so you and your entire group can do a “Tie-Up in the Playpen”. Summer in Chicago without spending time with all your friends in the Playpen should not be missed. Please book your group trips early before we get all booked up
Charters can range from going to the world-famous “Playpen” where we can anchor and crank up the sound system and go for a swim or chill on our rafts to cruising along the lakefront and by Navy Pier. You can also take a trip through the “Locks” and down the Chicago River or some blue water cruising past the Chicago Lighthouse, the cribs of Chicago, and into the deep blue waters of Lake Michigan and taking in some of the best views of Chicago.
Chicago Sailboat and Yacht Charters provide our guests with exclusive, private charters that offer complete luxury, flexibility, and customization. Take your friends & family on a cruise and experience Chicago like you never thought was possible a priceless adventure.
On Wednesday & Saturday nights we offer Sunset & Fireworks cruises just off of Navy Pier.
Experience firsthand the relaxing beauty of a peaceful sail on our 4+ hour and all day Private boat Charter. Boating in Chicago is the perfect way to end the day with friends. Maximum of 12 guests on a boat.
Come enjoy the beauty of Chicago in the lap of luxury. Our Lake Michigan boat charters include many points of interest around Chicago such as: The Playpen, Navy Pier, Chicago River Locks, Chicago lighthouse, Adler Planetarium, Shedd Aquarium, Soldiers Field, Buckingham Fountain and many more.
On Wednesday & Saturday nights we offer Sunset & Fireworks cruises just off of Navy Pier.
Our cruises are perfect for these special occasions:
- Bachelorette or Bachelor Parties
- Anniversary Cruises
- Special Occasions Cruises
- Chicago Scene Boat Party
- Birthday Parties
- Corporate events
- The World Famous “Playpen” we anchor, turn up the music, crack open the drinks and dive into the water
- Chicago River Cruise – Hanging out at City Winery
- Chicago Air & Water Show (Friday, Saturday & Sunday middle of August)
- Holiday Weekends (Memorial Day, 4th of July, and Labor Day- Book early they book up fast)
- Lollapalooza- Listening to the concert from Monroe Harbors
The owners Ted Widen, the owner of ChicagoScene.com & Mark Kaplan started the world Famous Chicago Scene Boat party in the “Playpen” over 20 years ago. We know how to show people a great time in Chicago.
Our Boats: We offer two beautiful powerboats to choose from. We have a Searay Sundancer 51′ and a Searay Sundancer 35′ cruiser. Between both boats, we can take out a total of 25 guests and do a “Tie-Up in the Playpen” just off Lakeshore Drive. Please book those larger trips early before we get all booked up.
Fireworks from Navy Pier: On Wednesday & Saturday nights we offer Sunset & Fireworks cruises that take place just off of Navy Pier about 1 hour after the sun sets.
Experience firsthand the fun and beauty of the city on a Private boat Charter with all your friends and family members. Summer in Chicago is short and boating on Lake Michigan is the perfect way to spend a day with friends in Chicago.
Time of Operation:
Mid-May through September, we host private charters every day of the week.
Our weekends book up very fast so please don’t wait. We offer discounts for weekday bookings Monday – Thursday.
Time slots:
We offer 4, 6, and 8-hour private charters out of Burnham Harbor. Our charters normally start at 10 AM, 2:30 PM, or 7 PM for our Sunset and fireworks cruises.
* We took Chance The Rapper and his family & Matt Forte and his kids for a Sunset & Navy Pier Fireworks show
Private, Luxurious, and Affordable Yacht Charters in Chicago, IL
Chicago Sailboat and Yacht Charters offer an exclusive and unforgettable experience for those who want to explore Chicago’s magnificent, river, shoreline or the Playpen in the lap of luxury. With our private and affordable yacht charters, you can indulge in the ultimate photo-worthy experience, where our fleet of premium powerboats will take you and your friends on a breathtaking adventure. Each of our boats is tailored to meet your unique needs, with comfortable seating and premium sound systems, all at an affordable cost. Our charters are perfect for impressing clients, hosting unforgettable gatherings, or simply indulging in a romantic evening watching the sunset. If you are looking for a boat or yacht rental in Chicago, IL, to have a great time in the Playpen, look no further than Chicago Sailboat and Yacht Charters. We are one of the premier boat charter companies in Chicago, offering services and amenities that are designed to impress and delight.
Bring a Group to Party in the Playpen!
We know that the best things in life are meant to be shared. That’s why we offer a range of options for group charters, so you can bring together your friends, family, and business colleagues to have a blast in the Playpen. Our fleet of premium powerboats, including a 51′ Searay Sundancer and a 35′ Searay Sundancer, together they can accommodate up to 25 people, allowing you to experience the ultimate in-group fun and adventure. With our Tie-Up in the Playpen option, you can stop and anchor in the world-famous playpen, where you can crank up the sound and chill on our rafts or take a dip in the crystal-clear waters. A group charter with Chicago Sailboat and Yacht Charters is the perfect way to create lasting memories and share unforgettable moments.
The Playpen – Chicago’s Popular Boating Place
If you’re looking for a thrilling boating adventure, look no further than the Playpen. With its breathtaking view of the city it’s the perfect location to anchor your boat, jump into the refreshing water, and soak up some sun while sipping on your favorite drink.
The luxurious amenities on our boat will amplify your experience as you feel the breeze blowing through your hair. The dazzling blue waters are ideal for swimming, and you can even climb aboard a floating island to take a break from all the action.
Whether you’re looking for some relaxation or some excitement, the Playpen is the ultimate destination for boating enthusiasts.
Chicago Sailboat and Yacht Charters Offer Priceless Pampered Yachting Experiences
At Chicago Sailboat and Yacht Charters, we pride ourselves on providing our guests with priceless, pampered yachting experiences. We go above and beyond to offer complete luxury, flexibility, and customization, tailoring each of our charters to your unique desires. From taking a cruise down the Chicago River to partying in Lake Michigan’s Playpen to watching the sun go down over the city, our yacht charters will help you do it all in style. At Chicago Sailboat and Yacht Charters, we believe that our guests deserve the absolute best, and we promise to deliver unforgettable, priceless yachting experiences that you’ll treasure for years to come.
Bad Beaches Only Boating Charters
COME ENJOY AN AFFORDABLE LUXURY BOAT RENTAL EXPERIENCE ON LAKE MICHIGAN WITH BAD BEACHES ONLY BOATING https://www.badbeachesonlyboating.com/
THE EXPERIENCE: This is a 32′ Maxum SCR that can comfortably accommodate up to 12 guests. Perfect for bachelor[ette] parties, birthdays, fireworks, corporate events, pride events and other celebrations!
AMENITIES: The smoke-free vessel features three entertainment zones (rear deck, bow, and cabin) for guests to enjoy. The bow of the boat is perfect for your Instagram and TikTok moments. Additional amenities include a top of the line sound system that you can control via Bluetooth, Aux, or USB. There are several exterior and interior lounge areas, wet bar, dining area, living room, and bathroom. We also offer a complimentary cooler for additional beverage storage.
RATES [please note the harbor (boating) season is from May 1 – Oct 31 each year]: Flat Rate of $250 / hr (boat rental only)
**Longer rentals available upon request. Please inquire for holiday/special events pricing and special requests, including Memorial Day + weekend, Black Yacht Weekend, 4th of July + weekend , BLVCKSCENE, Chicago Party Boat Scene, Air & Water Show weekend, Labor Day + weekend, etc.**
The Captain fee is a separate transaction between you (the renter) and the Captain. Upon booking we will provide you a list of approved United States Cost Guard (USCG) captains for hire. Captains charge between $100-$150 per hour, plus gratuity. Fuel and clean-up are NOT included in the hourly rate; however, it will be added to your booking at a $150 flat fee.
LAUNCH TIMES: Weekend times are 10A-11A; 2P-3P; 6-730P, unless otherwise indicated and for charters exceeding 5+ hours. Weekdays offer additional flexibility for start times (excluding holiday and special event days).
Fireworks show at Navy Pier every Wednesday and Saturday night, between Memorial Day and Labor Day!! Book 7pm+ before all gone!
LOCATION: We are docked at 31st Street Harbor, which is a 10 minute ride from downtown. There is paid parking available nearby (in and outdoor parking).
After booking your charter, our team will provide you with directions, safety information, and a list of approved captains available for hire for your charter.
We are happy to answer any and all questions. Just send us a written message for a custom offer. Complimentary cooler and floaty pad included for each charter.
You could be anywhere in the world but you’re here with us! We can’t wait to host you!!!
WHAT TO BRING:
Snacks
Beverages (Alcohol is allowed-no red liquids)
Towel
Sunscreen
and good vibes! 🙂
ABOUT US
WE ARE A BOAT CHARTER COMPANY OWNED BY FOUR WOMEN, WHO WANT TO SHARE OUR LOVE FOR WATER AND NATURE WITH OUR GUESTS. OUR DESIRE IS FOR OUR GUESTS TO EXPERIENCE BOTH THE BEAUTY AND ADVENTURES OF OUR CITY ABOARD OUR VESSEL.
Cruise Chicago in Style: Unforgettable Lakefront Experiences
This yacht is a 35-foot Maxum 3300 SCR, designed to comfortably accommodate gatherings of up to 12 guests. Whether it’s for bachelor / bachelorette parties, birthdays, corporate gatherings, just friends getting together or any other special occasion, this yacht promises an unforgettable experience. We specialize in cruising the Chicago River, viewing the fireworks and partying in the Playpen. We pride ourselves on delivering a unique yachting experience that surpasses all expectations.
Our yacht boasts state-of-the-art technologies and amenities. From a fully equipped galley to top-of-the-line entertainment systems, multiple lounge areas, plush seating, a modern sound system, high-speed internet via WiFi, microwave, refrigerator, bathroom facilities, and more, we ensure your comfort and enjoyment. We also have the one and only very large inflatable duck, better known as DaDuck, that can fit 12 adults. The rental cost covers fuel, taxes, and cleaning, and we are happy to accommodate BYOB preferences, allowing you to bring your own food and beverages. Please no red wine.
Rates: Weekdays (MON-FRI): $275 per hour (minimum 3 hours)
Weekends / Holidays (SAT-SUN): $300 per hour (minimum 3 hours) We offer weekend time slots from: Saturday – 10 am to 2 pm, 3 pm to 6 pm, and 7 pm to 11 pm. Sunday – 1pm to 3 pm, 4 pm to 7 pm, and 8 pm to 11 pm.
CAPTAIN DISCLAIMER: We ONLY provide captained charters. We can provide a list of USCG certified captains from which you can choose to caption the yacht. Please note the captain’s fee is not included in the boat rental price and is directly payable to the captain. Upon booking, our team will furnish you with detailed directions, safety guidelines, and a list of approved captains available for hire for your charter. For any inquiries or assistance, please don’t hesitate to reach out to our team. We eagerly anticipate the opportunity to host you aboard our yacht!
On A Boat Sailing
Your own Chicago Playpen boat rental on our sailing yacht, a Jeanneau Sun Odyssey 37. Don’t miss out on the most exclusive spot for sunshine, swimming and jammin out to your favorite tunes. We even provide the pool floaties!
The Boat
Our sailboat “Dragonfly” is a 37′ foot long, French built Jeanneau Sun Odyssey. Unlike most sailboats, this boat is designed for comfortable cruising, with a spacious open cockpit for seating, folding table, surround bluetooth stereo system that you can play from your phone, and full galley below. Keep your drinks cool in the fridge, no cooler necessary. The boat is equipped with glasses, plates, silverware, towels, floaties, blankets, an assortment of drinks 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.
The Crew
Captain Greg Scannell is a certified USCG Master Captain and sailing instructor. He is committed to providing you a great time, keeping you safe, and helping you create positive lasting memories. Together, Greg and Cait have sailed over 10,000 miles around the country through its waterways on the Great American Loop, sailed the Bahamas for two months on Dragonfly, and have captained luxury catamarans in the Caribbean.
Cait Scannell will join charters as her schedule permits as she runs a professional solo architecture practice. When she’s along she will often take the helm where she’s most comfortable. Cait bought Dragonfly in 2016 after taking lessons from Greg. At the time, she was the youngest female boat owner in the Chicago Harbors. She earned the nickname “Lady Dragonfly” from Monroe Harbor tender captains.