Free Spirit Yacht Cruises offers two impeccably maintained, luxury yachts for corporate events — the Free Spirit and the Gypsy Spirit. Both yachts are available for charters in Chicago during the warm months of spring, summer and early fall.

For corporate entertaining, it’s hard to top a Chicago dinner cruise on the spacious, multi-level, Free Spirit. Custom-built to accommodate up to 120 passengers, the Free Spirit yacht is perfect for client entertaining and company parties. Guests can mix and mingle in the warm and inviting salon, relax in the shade on the upper deck, or soak up some sun on the cushioned comfort of the front bow.

Some of our corporate clients make it an annual event, booking charters for summer celebrations, employee appreciation parties and staff outings.

Looking to impress a special client or entertaining potential clients in town for a tradeshow or convention? The Gypsy Spirit is the perfect venue for groups of 49 or less. Her custom-designed interior offers the comfort, elegance, and luxury required by the most discriminating Lake Michigan charter yacht guests.

Treat your colleagues to a memorable evening, delighting in the breathtaking views of Chicago’s world famous skyline while enjoying cocktails and an elegant dinner. Or host a casual breakfast cruise with mimosas and bloody mary’s while cruising along Chicago’s scenic lakefront or the Chicago River. Talk about mixing business with pleasure!

Of course, we suggest that you schedule a viewing prior to booking either yacht in order to understand the full experience awaiting you. Learn more about corporate events aboard the Free Spirit or Gypsy Spirit.

Chicagoans love their lakefront. Warm weather brings flocks of fans out to the glorious parks and beaches along Lake Michigan. We also love our special Chicago Celebrations, especially when they’re celebrated in style on a private yacht charter cruise. Here are some of the super fun yacht parties available for charter:

Twice a week, Memorial Day through Labor Day, Navy Pier hosts spectacular fireworks displays from a barge on Lake Michigan. With two luxury yachts, we can accommodate small and large Chicago fireworks cruise events and boat parties with ease. Both yachts are elegantly appointed and oh-so-comfortable. Your guests will be impressed with your entertaining expertise!

Navy Pier Fireworks Schedule

These book up crazy fast! So you’ll want to plan ahead to reserve this cruise.

Saturday, August 15, 2020 & Sunday, August 16, 2020

The Air & Water Show is one of the highlights of Chicago’s summer season. And there’s no better way to celebrate this exciting event than on a comfortable luxury yacht charter on the open water of Lake Michigan. Kick back, sip on your favorite drink and catch the thrills. “This year’s headliners include the U.S. Air Force Thunderbirds and new this year, the F-35 Heritage Flight.”

Cruising Time:
The Free Spirit cruises for 4 hours with a 100-person minimum private charter.
The Gypsy Spirit cruises for 4 hours with a 40-person minimum private charter.

Whatever you’re celebrating, hosting an event on one of our luxury yachts will make it even more special. We can accommodate just about any event – one that your guests will talk about for years to come. Private parties aboard our yachts offer a comfortable, elegant setting which works just as well for a casual, fun-in-the-sun outing as an upscale, sophisticated cocktail party.

Every detail of your cruise will be expertly managed. From helping you choose the perfect menu and bar package to making sure your guests are comfortable and attended to on board.

We offer a wide variety of catering options, all featuring delicious contemporary cuisine for your private parties. Let us help you select the perfect menu, whether you’re hosting a theme party (Chicago Blues Cruise) with a full dinner buffet or a simple birthday celebration with sandwiches and salads.

Entertaining clients or showing off Chicago to visiting friends takes on a whole new meaning when the venue is a luxury yacht on Lake Michigan. Cruising lazily on the shimmering blue water, with the Chicago skyline as a backdrop, makes conversation easy. Big groups or intimate gatherings. Free Spirit Yacht Cruises has you covered.

Birthday on a boat! The guest of honor will remember this special day for years to come. Whether you’re inviting a big crowd or a small group of close friends, we have the perfect yacht to suit your needs.

The Chicago River is a unique part of our city, and one that tourists and locals alike always find fascinating. Architectural gems, old and new, line the river bank. Condos, offices, hotels, restaurants and cafes. If you haven’t seen it, you’re in for a treat.

In addition to Lake Michigan cruises, the Gypsy Spirit also cruises the Chicago River. And if you want to really learn about our city, we have a list of tour guides to narrate your charter.

A few interesting Chicago River Factoids:

• The Chicago River System is 156 miles long and flows through downtown Chicago.
• 52 moveable bridges span the river.
• The river flowed directly into Lake Michigan until 1900, when the Chicago Sanitary District reversed the flow, using a series of canal locks. Today the river empties into the Chicago Sanitary and Ship Canal.
• Garbage filled the river until the 1990s when it underwent an extensive cleaning as part of Mayor Daley’s Chicago beautification program.
• On St. Patrick’s Day, the river is dyed bright green.

Sunset on Lake Michigan is glorious. Beautiful, peaceful, and romantic. For family celebrations, wedding receptions, dinner parties – you name the occasion, we’ll make sure you and your guests have a fabulous time.

Sunset cruises are especially well suited for celebrating your rehearsal dinner or a special wedding anniversary. For smaller events where you want to host close friends and relatives without the distraction of a restaurant venue, a private yacht is the perfect solution. Intimate, cozy and very private.

We invite you to have your Wedding Ceremony and Wedding Reception aboard the Free Spirit or Gypsy Spirit.

If a banquet hall or hotel ballroom is not your idea of a dream wedding venue, we offer a private luxury yacht – an incredibly romantic setting for an elegant, intimate affair.

The Free Spirit (or the Gypsy Spirit) is an excellent place for you to begin your lives together. After the nuptials, your guests can begin to enjoy the reception immediately. No need to book two venues and shuttle guests between locations!

On the day of your wedding, our captain and crew will attentively handle every detail, execute your plans and warmly welcome you and your guests. All you have to do is enjoy your very special day, toast your new spouse, and celebrate with people dear to you.

Chicago and blues are synonymous. Ours is the town where the blues were born.

If you’re a blues fan, it doesn’t get much better than hosting (or being a guest on) a Free Spirit Yacht Charter Blues Cruise. Three hours of pure musical joy. Cruising Lake Michigan, the knock-em-dead Chicago skyline as a background, enjoying a custom Chicago-style menu, and listening to true Chicago blues.

Create and bring your own playlists. Or better yet, book the real thing – like Vino Louden, lead guitar and bandleader for many years for Chicago legend and “Queen of the Blues” Koko Taylor. Vino’s been around long enough to have toured with B.B. King and Bonnie Raitt. On land, you can hear him at Buddy Guy’s Legends. But you can also book him for your Free Spirit Blues Cruise. Here’s a clip of Vino playing on the Free Spirit. Talk about memorable parties!