Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a lei... More

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. On this tour, you will travel through Chicago with an expert guide in a comfortable minibus, enjoy world renowned ... More

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air! Fun for all ... More

Elevate your evening with a delicious dinner and jaw-dropping panoramic views of the Navy Pier fireworks display illuminating the Chicago city skyline! On our Fireworks Signature Dinner Cruise on Lake Michigan, a dazzling show of ... More

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

This summer, marvel at jaw-dropping views of the Chicago skyline illuminated by Navy Pier’s dazzling fireworks display from Lake Michigan on our Seadog Lakefront Fireworks Cruise. Every Saturday and Wednesday during the summer m... More

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

Set sail for an unforgettable experience on the water with private boat tours and captained rentals along the Chicago River and Lake Michigan. Whether you're looking to explore the city’s historic waterways or enjoy a relaxing c... More

Fireworks Cruise Aboard Island Time – See the Sparks Fly the Island Party Way! Experience Chicago’s dazzling fireworks like never before—from the deck of our floating Tiki Bar, Island Time! Cruise along the scenic Chicago R... More

Save 20% when you bundle these two iconic Chicago experiences! Discover Chicago by road and river with a 48-hour Hop-on Hop-off Ticket and Shoreline Architecture Cruise combo! This ticket includes a 48-hour pass for our hop-on, ... More

A breathtaking evening of elevated dining and spectacular fireworks views awaits on our Fireworks Premier Dinner Cruise on Lake Michigan! There’s no better way to marvel at Navy Pier’s dazzling fireworks display than from an u... More

Set sail on our flagship vessel, where style meets comfort in a Tiki Chic atmosphere. Your adventure begins on the iconic Chicago Riverwalk, where you’ll board a beautifully appointed boat featuring two climate-controlled decks,... More

The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. We zip you to many sights around the local waterways including the Navy Pier, Soldier Field, ... More

Set sail for a memorable experience on Lake Michigan with a Signature Chicago Brunch Cruise that is as scenic as it is delicious! You'll savor a chef-prepared buffet and bottomless mimosas while in our comfortable indoor areas. Ma... More

Sunday Funday Mimosa Cruise – Chicago’s Floating Tiki Bar Adventure! Sundays are Fun-Days aboard our vibrant floating tiki bar, Island TIme, where the drinks are cold, the vibes are high, and the views are iconic! Cruise down... More

Enjoy the Navy Pier Fireworks from the Chicago River. A brief version of Wendella's Lake Michigan Fireworks Cruise, this experience is 45 minutes and does not go out to Lake Michigan.... More

Set sail for an exquisite evening of gourmet dining set to the backdrop of Navy Pier’s awe-inspiring fireworks show on our Fireworks Premier Plus Dinner Cruise on the Chicago River! A decadent plated dinner and craft cocktails w... More

Fine dining and unrivaled skyline views await from the moment you step aboard our Premier Plus Chicago Lunch Cruise. A selection of delectable plated lunch specials and craft cocktails will delight your palate while captivating pa... More

Chicago Air and Water Show 2025 Great for friends & family! PLEASE READ CAREFULLY Experience Chicago’s Air & Water Show from the Best Seat on the Lake! 10AM SAIL: Our first sail will depart at 10am sharp. Our first event wil... More

Enjoy a picturesque day dining on Lake Michigan with our Premier Chicago Brunch Cruise. You’ll indulge in a chef-prepared buffet meal featuring savory and sweet classics, bottomless mimosas, top-notch service, and breathtaking v... More