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Anniversary Celebration Cruise

Last year, it was dinner and a movie. The year before? More of the same. This year, why not treat yourself and your sweetie to a private anniversary sailing charter with Windy City Sailing?

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Whether it’s watching the sunset over Chicago’s magnificent skyline, enjoying the fireworks of Navy Pier from the lake, or simply enjoying each other’s uninterrupted company as you sail and relax, our crew is here to make your anniversary memorable. We offer a variety of sailing packages in the morning, afternoon, and evening to accommodate any occasion. 

Anniversary Charter with Windy City Sailing

About Our Yacht

Our yacht, a 40-foot sloop, is an intimate yet luxurious way to celebrate. Below deck, it provides a full kitchen galley, salon, and two full staterooms. Above, the Nebula has a spacious foredeck, cockpit, and bow area that gives our guests plenty of room to kick back, relax, and enjoy their cruise.

FIVE STAR RATINGS ON TRIPADVISOR AND GOOGLE

WINDY CITY SAILING HAS PROUDLY BEEN OFFERING EXCEPTIONAL SERVICE FOR TWO DECADES AND WE HAVE THE SATISFIED RETURNING CUSTOMERS TO PROVE IT!

Frequently Asked Sailing Questions

Dine, Drink and Sail in Style

Want to bring your favorite bottle of wine or a special meal on board to celebrate? Prefer to have a chef prepare something special? We’re pleased to accommodate both! Additionally, guests are welcome to bring along appetizers, meals, and drinks of their choice. We also work with a private chef that can create your favorite dishes on board - a memorable experience for all our guests.

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It’s simple, charming, and EXTREMELY memorable.

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