Come Sailing, Inc.

09/03/2026

Beating the city heat, one beautiful sunset sail at a time. 🌇 While the pavement was baking ashore, a cool breeze kept CITY CAT purring along on the lake.
​Trade the sweltering concrete for some fresh air and relaxation on the water. Link in bio to book your escape! ⛵🐾

09/01/2026

The time has come! We are beyond excited to introduce swimming charters on CITY CAT, Chicago's only 49-passenger sailing catamaran.

​This is what sailing cats are so well known for—just walk down the bow stairs and straight into the water! It is a super fun experience to swim from a big charter catamaran in Lake Michigan with the beautiful Chicago skyline in the background.

​Swimming is available on select public sails and private charters.

​Ready to dive in? Book now at the link in our bio! ⛵🌊

08/29/2026

Reunion & Come Sailing present: Sail & Sip on Lake Michigan! ⛵️🍷

We’re teaming up with our friends at Reunion for an exclusive 2-hour premium catamaran cruise aboard CITY CAT!

Enjoy open bar, delicious light bites, and the absolute best skyline views in Chicago.

✨ What’s Included:
• 2-Hour Skyline Cruise aboard CITY CAT
• Open Bar & Light Bites by Reunion
• Unbeatable views of the Chicago skyline

🗓 Dates: Saturday, September 13 & Saturday, September 20

⏰ Times: 1:00 PM – 3:00 PM | 3:30 PM – 5:30 PM

📍 Departure: Navy Pier Marina, Chicago, IL

🎟 Tickets: $200 per person

⚠️ STRICTLY LIMITED TO 44 SPOTS PER SAIL!

Don't wait—lock in your tickets before they sell out!

👉 Reserve Your Spot Here: https://www.toasttab.com/catering/chefartsmithreunion.com/menu/reunion%20x%20city%20cat%20boat%20ride/

08/27/2026

Join us for a relaxing Sunset Sail this Friday evening or a spectacular Fireworks Cruise on Saturday aboard our 49-passenger catamaran, CITY CAT. Single tickets are available for both of these public sailing events at www.ComeSailing.us. Link in bio.

08/22/2026

Come sailing with friends, family, and colleagues! ⛵️

CITY CAT is Chicago’s only true commercial charter catamaran. At nearly 29 feet wide, she offers stability, wide-open deck space, and shaded seating with plenty of room for groups up to 49 passengers.

Quiet, stable, and powered by the breeze. Kick back on the bow trampolines, take in the iconic skyline views, and experience Lake Michigan by sail.

📍 Departing from Navy Pier Marina

🔗 Book your private charter or public sail today: www.ComeSailing.us

08/20/2026

Sunset sail on CITY CAT; Beautiful and Relaxing.

08/18/2026

Clear skies, crisp breeze, and the best seat in the house! ⛵🏙️

Step aboard CITY CAT for an unforgettable experience on Lake Michigan! Whether you're planning a private event, corporate outing, or just looking to kick back with the ultimate view of the Chicago skyline, we’ve got you covered.

Did you know that, outside of a 150-passenger tall ship, CITY CAT is the only USCG-inspected sailing vessel in Chicago certified to carry more than 13 passengers? Step aboard our 48-foot catamaran with spacious decks, smooth twin-hull stability, and front-row skyline views. There's room for up to 49 guests to sail together on one boat!

👉 Reserve your spot on board today: https://www.comesailing.us/

08/14/2026

Welcome to Chicago's Air and Water Show Weekend!! This year's headliners are the US Air Force Thunderbirds! And wow, they are LOUD! 😂 Individual tickets are still available for our Special Public Air and Water Show Sail on Sunday. So come on out and enjoy the show on Late Michigan from Chicago's only 49-passenger catamaran. See our website for details. https://www.comesailing.us/chicago-air-water-show.html

08/12/2026

The wait is over—CITY CAT has cleared all USCG approvals and is officially open for bookings! ⛵💨

​CITY CAT is our brand-new 48' sailing catamaran, offering a quiet sailing escape on Lake Michigan for up to 49 passengers. Featuring comfortable seating, plenty of shade from sun or rain, and trampolines over the water for a thrilling yet relaxing ride above the waves, she is the only sailboat in Chicago with this capacity!

​Regular public charter prices start at $75/adult Monday–Thursday and $90/adult Friday–Sunday.

​✈️ Special Air & Water Show Charters!

Looking for an unforgettable front-row seat to Chicago’s iconic Air & Water Show? We are running special extended event sails timed to catch all the action—including the headlining U.S. Air Force Thunderbirds right overhead from the water!

​Check out all the details, view our regular schedule, and book your Air & Water Show tickets before they sell out at www.ComeSailing.us!

08/08/2026