ALL CHICAGO CHARTERS & CRUISES
Soak up the sights of our city’s iconic skyline! This 3-hour Chicago sailboat cruise will take you & your guests on a favorable sail from Monroe Harbor down the gorgeous coastline of Chicago's lakeshore, giving a unique perspective on the city'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 $149pp + 6% booking fee
Chicago's famous lakefront party is back. This 4-hour private sailboat charter is designed for you & your friends to party in luxury. We will depart from Monroe Harbor, anchoring the boat in the party zone. Whatever you do - don't forget a bathing suit, some sunscreen & something cold to sip on!
Starting at $179pp + 6% booking fee
This 2.5 hour Chicago sailboat cruise will take you & your group to the closest possible viewing area for the famous Navy Pier Fireworks show. We've all seen fireworks - you've never seen anything like this before.
Starting at $129pp + 6% booking fee
MEET YOUR SAILING YACHT FOR THE DAY
S/V DRAGONFLY
Guests:
Up to 10
Length:
37'
Bluetooth
Speakers
Private
Bathroom
Refrigerator
Access
Kitchenware
Available
Our 37' sailing yacht offers comfort & style compared to other sailboats. The bimini umbrella in the cockpit provides shade while the dodger windshield provides a wind break from the cool breezes on the Lake. Lounging space in the sun is available on the foredeck. Down below, the teak interior cabin has two private changing rooms, a bathroom with shower, kitchen and comfortable salon seating area.
We sail out of
Monroe Harbor
in Downtown Chicago
All sailing charters
dates & times:
400+ FIVE STAR REVIEWS
7 years of fresh waters, exclusive parties & unforgettable experiences.
STEP ABOARD
Be first for private sailing offers & special event happenings on Chicago's famous Lakefront.