Weekend Private Sailing Charter on 28' Sailboat

Take in the Chicago skyline from the water on this 2-hour Shannon Sailboat adventure! Join family and friends for a day of relaxing on the serene waters of Lake Michigan.

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 28’ Shannon 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 glisten in the sunshine. Pose with friends and family for selfies or group photos with the city shining 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 2-hour sailing adventure offers a comprehensive tour of the coastline with unrivaled views of the Chicago skyline. Your captain will take you to the best viewing points, so you get the best experience possible. You'll have plenty of 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.

Bask in lake-reflected sunshine on this 2-hour Shannon Sailboat adventure!