Private 3-Hour Weekday
Sunset Sail on 36' Sailboat

See Chicago at its best with this 3-hour Catalina Sailboat sunset cruise! Join family, friends, or a romantic partner for a cozy evening on the water.

Arrive at Monroe Harbor, just East of Lake Shore Drive, where you'll meet your Coast Guard licensed captain and receive an overview of the experience. This flexible charter can be fully customized depending on your interests, from the guest list to the music and even the route you'll sail. Any questions about the experience are best asked at the harbor, but your captain will be there to assist throughout.

Board a luxurious 36’ Catalina Sailboat and settle in for a cozy cruise across the lake. Your captain will guide the sailboat out of the harbor, then unfurl the sails and shut off the engine for a wind-fueled adventure. Stretch out on the spacious sailboat and take in the stunning views of Chicago’s skyline. Capture photographs of the iconic buildings as they are colored gold, pink, and a silky lavender by the setting sun. Watch as the first stars peek out from the sky above you. Get together for joyous group photos with the glittering city in the background. Put together a playlist of your favorite songs and then connect to the bluetooth speakers for the perfect musical accompaniment to your cruise.

This 3-hour private sailing adventure offers a comprehensive tour of the coastline with unrivaled views of the sparkling Chicago skyline. Your captain will take you to the best viewing points, so you get the best experience possible. You'll have ample time to capture all the photos that your heart desires and to ask any questions about the art of sailing you like. This experience is perfect as a romantic adventure, for family gatherings, or even as a treat for your clients and colleagues.

A magical evening awaits you on this 3-hour Catalina Sailboat sunset cruise!