.png)
PROPOSAL
CHARTER
Make your proposal memorable with Windy City Sailing!
An engagement proposal is something that both of you will remember for the rest of your life. So, what better way to create this fantastic memory than sailing on a private proposal charter from the comfort of one of our exquisite yachts with the beautiful Chicago skyline as your backdrop?
Your proposal charter with Windy City Sailing can occur under the colorful canopy of the bursting fireworks. Or, you could choose a more intimate setting on a relaxing morning, afternoon, or evening excursion. Either way, it will be a memorable occasion.
What do we need to bring on the proposal sailing charter?
We provide our guests with all the amenities needed to make their night a night to remember. On all of our excursions, guests will be provided with bathrooms, comfortable seating areas, bottled water, ice, and a cooler that can store any of the treats you decide to bring with you on your journey. Feel free to bring along your own music to enhance the viewing experience with surround speakers on the topside. Our experienced crew and captain will handle getting you and your party to the show and you don’t have to worry about anything except for having a good time.
WINDY CITY SAILING HAS PROUDLY BEEN OFFERING EXCEPTIONAL SERVICE FOR TWO DECADES AND WE HAVE THE SATISFIED RETURNING CUSTOMERS TO PROVE IT!
Marriage Proposal Sailing Charter
Frequently Asked Questions
How can a sailing charter help plan a surprise proposal?
Our team can help coordinate timing, scenic locations, and pacing so your proposal unfolds naturally and feels effortless while cruising on Lake Michigan.
Can the proposal experience be customized?
Yes. Sailing routes, departure times, and onboard details can be tailored to create a proposal that reflects your relationship and vision.
When is the best time to plan a sailing proposal in Chicago?
Sunset sails are especially popular due to dramatic skyline views and softer lighting, though daytime proposals offer a relaxed atmosphere and clear city views.
Can friends or family be part of the proposal experience?
Proposals can be planned as an intimate moment for two or shared with a small group, depending on your preferences and the yacht’s guest capacity.
Why choose a sailing charter for a marriage proposal?
A private sailing charter offers privacy, breathtaking scenery, and a memorable setting that turns a proposal into a once-in-a-lifetime experience.