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

Proposal & Engagement Cruise

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.

Wednesday • Friday • Sunday - Sunsets 

Saturday • Sunday - Sunrise
ALL SUMMER LONG!

 

2 Hour Minimum

USCG Captain 

 Up to 10 Guests

NOW BOOKING - SUMMER 2024

REAL REVIEWS FROM THE NEWLY ENGAGED!

7 years of unforgettable experiences, stunning photos and saying "yes!"

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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!!!
2 Hour Min
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 + 6% booking fee
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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


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

Welcome to the crew!

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