Chicago Sailing trips & boat tours

Our most recommended Chicago Sailing trips & boat tours

Chicago: Tall Ship Windy Architecture & Skyline Sailing Tour

1. Chicago: Tall Ship Windy Architecture & Skyline Sailing Tour

See the sights of Chicago from a unique waterside perspective on this tall ship tour. Sail around Lake Michigan onboard the tall ship Windy, a 148-foot traditional schooner. Choose from an architecture and history-focused tour or a sunset sail. On the Architecture and Skyline Sail, immerse yourself in Chicago's history and architecture. Take in the skyline, enjoy spectacular views, and discover the Windy City from the water. Learn about the people and plans that shaped Chicago’s most famous sights from the live onboard narration. On the Sunset and Skyline Sail, enjoy panoramic views of the sunset across the Chicago skyline in the company of friends or family. enjoy live educational narration about the sights you see with both options.

Chicago: Wine & Cheese or Beer & BBQ Thursday Evening Cruise

2. Chicago: Wine & Cheese or Beer & BBQ Thursday Evening Cruise

Cruise from the DuSable bridge and go up the main branch of the Chicago River to Wolf Point before heading back past the Chicago Riverwalk out onto Lake Michigan. Choose from a wine and cheese tasting or beer and BBQ meal experience. Hop aboard a spacious and comfortable ship and find a spot on the open-air decks or in the comfort of the climate-controlled interiors. Admire views of the city from the water as glide over the water. Select the wine tour to indulge in tastings of 4-6 different wines from “Picnic Wine & Provisions,” a Chicago-based wine boutique. Savor items from a buffet-style cheese table, with an expert on hand to advise on the wine and cheese pairings. Pick the Beer tour For tasting 4-6 beers from local breweries, while “Blackwood BBQ” provides each passenger with a a light meal of delectable BBQ samples, along with some mouth-watering sides. Purchase additional drinks at the onboard cash bar where full servings of the sampled beers or wines can be bought. Have the option to buy other local beers, spirits, non-alcoholic beverages, and snacks from the bar.

Chicago: Lake Michigan Educational 'Tall Ship Windy' Cruise

3. Chicago: Lake Michigan Educational 'Tall Ship Windy' Cruise

Enjoy a hands-on sailing experience aboard the iconic 'Tall Ship Windy.' Glide over the shimmering waters of Lake Michigan and admire views of the Chicago skyline. Try your hand at sailing with this family-friendly outing. Discover how to make maritime knots, hoist sails, and shoot the canon. Hop aboard the 148-foot, traditional topsail schooner and gaze up at the towering 4 masts. Set off as your guide provides you with tidbits of local history from the decks of this floating classroom. This unique learning experience combines physics, ecology, history, and storytelling. Take an active part in sailing the vessel. Watch the kids’ faces light up with excitement as they turn theory into practice, have real fun, and engage with history. Make history come alive with an exciting educational adventure for curious minds of all ages.

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