2 Sailing Trips in Chicago Worth an Afternoon

1.Private Sailing on Beautiful Lake Michigan – Navy Pier, Chicago

★★★★★★★★★★5.0 · 70 reviews · 2 hours (approx.) Our pick

Sail Lake Michigan with your own group of up to six, departing from Navy Pier Marina for a two-hour private charter. Your captain adjusts the route to the wind and your interests, with possible views of the skyline, Adler Planetarium, Soldier Field, and Buckingham Fountain. Bring your own drinks and music, and ask captains such as Mike or Ulysses about sailing and Chicago.

“A great time out on the lake. Our captain was very capable and informative. I would recommend for just a fun experience or for a special occasion.”

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2.Chicago River Architecture Tour Aboard a Historic Yacht

★★★★★★★★★★5.0 · 45 reviews · from $49Best value

Settle aboard a historic wooden yacht for a roughly 90-minute Chicago River cruise with a docent explaining landmarks such as the Wrigley Building, Riverwalk, and Michigan Avenue Bridge. Soda, coffee, and snacks are included, with alcohol available to buy. The group is capped at 60, and the cruise returns to its starting point.

“Lots of info shared, small boat experience was awesome plus free soda! Felt very professional and safe.”

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