USCG-Certified Captain
37' Luxury Yacht
Up to 7
Guests
Birthdays • Graduations • Reunions • Bachelor(ette) Parties • Engagements • Photoshoots • Wedding Groups • Summer Getaways • Romantic Dates
312.619.7858
for exclusive pricing & fee-free booking
OVER 500 PRIVATE SAILING CHARTERS IN CHICAGO SINCE 2018
CHOOSE YOUR CHICAGO SAILING EXPERIENCE BELOW!
SAIL & SWIM | FIREWORKS | LAKEFRONT | SUNSET
4-Hour Experience
Chicago's famous lakefront party is back! This 4-hour private chicago sailboat rental is designed for you & your crew to party by water! We will depart from Monroe Harbor, sailing Chicago's lakeshore to begin your voyage. On nice days, you & your guests can drop anchor to swim & float anywhere on the Lakefront. Whatever you do - don't forget a bathing suit, some sunscreen & something cold to sip on!
Starting at $1,399 | Up to 7 guests
FRI • SAT • SUN
10AM & 2:30PM DAILY
This 2.5 hour Chicago sailboat cruise will split your time with us between sailing Lake Michigan & watching the famous Fireworks show at Navy Pier. These are the best seats you can possible have for a world-class fireworks show. We've all seen fireworks - you've never seen anything like this before. Our guests say this is an unforgettable experience.
$999 | Up to 7 guests
7PM WEDNESDAY'S
8PM SATURDAY'S
3-Hour Experience
This 3-hour Chicago sailboat cruise will take you & your guests on a favorable sail down the gorgeous coastline of the City's lakeshore, giving a unique perspective on Chicago's world-class architectural landscape. If you're looking for a private & intimate way to experience Chicago - this is the cruise for you.
Starting at $899 | Up to 7 guests
WED • FRI • SAT • SUN
10AM, 1:30PM & 5:00PM DAILY
Relax and enjoy a captained Chicago sunset cruise from our 37' luxury sailing yacht, Dragonfly. We will cast off from Monroe Harbor in downtown Chicago and set sail to a favorable course on Lake Michigan. Bring your own food and drinks, listen to your favorite music, and take in the views of our city’s iconic skyline as the sun sets before you. You won't believe the photos!
Starting at $799 | Up to 7 guests
FRI • SUN
6:30PM DAILY
“I rented [Dragonfly] to celebrate my bday with 6 close girlfriends. Greg was very communicative before the trip. He answered all my questions in a very timely manner. The boat is very spacious!
Dyna, Chicago, IL
WHAT MAKES ON A BOAT SAILING DIFFERENT
We're a one boat, one captain small family business sharing our passion for sailing with our customers. Our boat, S/V Dragonfly, has played host to thousands of guests since our first private sailing charter in 2018.
Unparalleled Sailing Expertise
Captain Greg Scannell and First Mate Cait Scannell share a combined 25 years of sailing experience, including an 8-month, 5,500 nautical mile voyage from Chicago to the Bahamas and back in 2021.
500+ private charters later, we're actively curating the best experiences for our guests looking to explore the joys of sailing on Lake Michigan. Let us show you!
Luxury & Comfort Aboard S/V Dragonfly
Our 37' sailing yacht was designed for entertaining & comfort. Guests love the flexibility of luxury sailing along with dropping anchor & swimming or floating with a cold one, should the weather permit.
Bluetooth connectivity to play your own music, onboard bathroom facilities, and ample space above and below deck makes stepping aboard Dragonfly for the day an absolute breeze.
