Proposal & Engagement Cruises
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.
Wednesday • Friday • Sunday - Sunsets
Saturday • Sunday - Sunrise
ALL SUMMER LONG!
2 Hour Minimum
USCG Captain
Up to 10 Guests
NOW BOOKING - SUMMER 2024
OUR 37' LUXURY YACHT IS PERFECT FOR MAGICAL MOMENTS LIKE PROPOSALS & ENGAGEMENTS!
Guests:
Up to 10
Length:
37'
Private
Bathroom
Refrigerator
Access
Kitchenware
Available
S/V DRAGONFLY - 2003 JEANNEAU SUN ODYSSEY
Jeanneau is a French luxury brand of cruising class yachts made for day cruises & entertaining. Our yacht offers comfort & extra seating compared to other sailboats. The bimini in the cockpit provides shade while the dodger 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 salon seating area.
We sail out of
Monroe Harbor
in Downtown Chicago
Engagement Cruise
dates & times:
400+ FIVE STAR REVIEWS
7 years of unforgettable experiences, stunning photos and saying "yes!"
Bailey
We had such a good time taking our engagement photos on the boat. Greg was so accommodating to us with positioning the boat where we needed it. Would 100% recommend to anyone looking to take some amazing photos and have a great time on the lake.
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Sara
Greg was so flexible at rescheduling with us due to weather. He made us feel very comfortable and gave tips on how to take the most beautiful photos with the scenery of the city. By the way, the boat was spotless, so clean and so so beautiful😍
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Ryan
Incredible people offering an incredible service! Proposed to my high school sweetheart and wouldn’t have wanted to do it any other way! It is a must do!!!
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 + 6% booking fee
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
Start planning your summer sail now!
