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FROM MONROE HARBOR - DOWNTOWN CHICAGO

Engagements & Proposals

2 or 3 Hour Cruise

USCG Captain 

 Up to 10 Guests

WED • FRI • SAT • SUN
SUNRISE & SUNSET AVAILABLE

Enjoy your own private sailboat rental to capture the perfect moment for you and your loved one. Whether you're popping the question, taking engagement photos or just celebrating the happy occasion with friends and family, On A Boat Sailing is the way to go - intimate, timeless and memorable.

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OVER 500 PRIVATE CHARTERS IN CHICAGO SINCE 2018

ONE BOAT. ONE CAPTAIN. ONE UNIQUE EXPERIENCE.

Guests:

Up to 10

Length:

37'

Bluetooth

Speakers

Private
Bathroom

Refrigerator
Access

Kitchenware
Available

S/V Dragonfly offers world-class sailing with comfortable amenities, encouraging you & your guests to focus on the adventurous day ahead.

The bimini umbrella in the cockpit gives ample shade and some light rain protection in our main seating area. Willing guests are welcome to relieve our captain and try their hand at the helm!

Lounging space for sunbathing and lake-gazing is available on the foredeck. This will be a popular locale for photo opportunities on beautiful days! Those camera rolls are no match for these views.

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foredeck

Down below, the teak interior cabin has two private changing rooms, a bathroom with shower, kitchen and comfortable salon seating area. The perfect place to store your bags, keep your drinks cool and prepare the days provisions.

400+ FIVE STAR REVIEWS

7 years of fresh waters, exclusive parties & unforgettable experiences.

OUR 37' LUXURY YACHT IS PERFECT FOR MAGICAL MOMENTS LIKE PROPOSALS & ENAGEMENTS!

2 or 3 Hours

USCG Captain 
Up to 10 Guests

Escape the city and enjoy the privacy and beauty of sailing on Lake Michigan. This 2-hour private charter is a one-of-a-kind romantic setting for you and your loved one. We will depart from Monroe Harbor and curate a route to your desired experience. Pop the question from our 37' luxury sailboat!

Starting at $699

WED • FRI • SAT • SUN
SUNRISE & SUNSET AVAILABLE

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Plan your Engagement Cruise now!

flexible booking plan

Flexible Booking Plan - 50% Deposit, Fully-Refundable

We recognize that plans change, so we've designed our booking options to be incredibly flexible. This ensures you have the freedom to make adjustments with ease, providing peace of mind for your experience with On A Boat Sailing.

100% Refund up to Two Weeks From Departure

50% Refund up to 48 Hours From Departure

Full Refund for Weather Related Cancellations

Swap Dates With No Fees-Subject to Availability

chicago sailboat cruise


STEP ABOARD
Be first for private sailing offers & special event happenings on Chicago's famous Lakefront. 

Welcome to the crew!

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