Proposal Cruise
Proposal Yacht Charters in Chicago
This is the most important question you will ever ask — and the setting should match. A private proposal cruise on Lake Michigan gives you the Chicago skyline, a golden sunset, and complete privacy for the moment that changes everything.
Find your perfect proposal cruise vesselWhy celebrate on the water?
Complete privacy — just you, your partner, and the captain (who knows to stay discreet)
Sunset timing coordinated for the perfect golden-hour moment
Optional hidden photographer to capture the surprise
Champagne-ready vessels for celebrating afterward
Typical Proposal Cruise Experience
Duration
1.5–2 hours
Group Size
2–6 guests
What's Included
Private intimate vessel, credential-verified captain, fuel, and all platform fees. Photography and champagne arrangements available as add-ons.
Popular for proposal cruises
These vessels are frequently booked for this occasion.
Make Your Proposal Perfect
Add professional services to make your charter extraordinary. Our curated provider network handles every detail.
Proposal on the Water
Intimate vessel, on-board photographer, floral arrangement, champagne setup, and sunset route planning.
Custom quoted based on your vessel, guest count, and service level.
Request This Package →Photographers
Capture the moment (discreetly or not)
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Florals & Decor
Rose petals, florals, and romantic styling
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Champagne Service
Champagne and celebration bites
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Want a custom package? Our concierge team can design the perfect experience for your proposal cruise.
Speak With a ConciergeProposal Cruise FAQ
Can the captain help coordinate the timing?
Suggested captains who frequently handle proposal cruises know exactly how to position the boat for the best skyline backdrop at the right moment.
Can I have a photographer hiding on board?
Yes! Our photography add-on can be arranged discreetly. The photographer boards before your partner arrives and captures the moment naturally.
What if she/he says yes and we want to extend?
Subject to availability, many captains can accommodate a charter extension. Discuss this possibility with your captain before departure.
Ready to plan your proposal cruise?
Browse available vessels and see transparent pricing for your dates.
Find your perfect proposal cruise vessel