10 years since we launched Free Spirit Yacht Cruises. Hard to believe.

10 years. Hard to believe.

It’s been ten wild, where-did-they-go? years since Joe and I launched our version of Free Spirit Yacht Cruises.

The company was originally founded by Joe’s parents in 1983 and was thriving. Joe worked there for eighteen years as a captain. But his parents were retiring, and we had our own plans.

Our first plan was to get married. As it turns out, that was a great decision! Right, Joe (wink, wink)? Next, we would buy the company.


Joe and I work well together and our backgrounds and skill sets complement one another — important because even though we both had a lot experience in the yacht charter industry, we were basically building a new company.

Our Free Spirit Yacht Cruises Journey

One particularly challenging issue – the year we launched followed on the heels of the Great Recession. Yacht charters were not exactly high on the list of necessities. People who had lost jobs were thinking about finding new ones and putting food on the table. Marketing yacht charters would require a lot of energy, creative marketing and patience.

Free Spirit Cruises

Fortunately, Joe and I both like a challenge. We didn’t let the economy deter us. Chicagoans love summer and Free Spirit Yacht Charters is a service that our clients love.

Company Cruise

Free Spirit Yacht Cruises

So we put one foot in front of the other (in deck shoes) and moved ahead. We did some redesigns on both the Free Spirit and the Gypsy Spirit. New finishes. New furniture. Lots of paint. And lots of elbow grease.

Meanwhile, we ramped up the catering, adding themed buffets and premium bar options and bringing in topnotch catering companies. We wrote a marketing plan and implemented it. Joe and I hired experts to help us in areas where we needed assistance.

At the same time, we went out and introduced ourselves to concierges and hotel managers. We joined a few chambers and did some networking (Joe was always the guy in the Hawaiian shirt, summer or winter). We passed out lots of cards and brochures and redesigned our website. A lot of work but well worth the effort.

Captain Joe

Today we are the proud owners of a company we love. And we get to spend every April through October out on Lake Michigan. Pretty sweet deal if you ask us!

So even though we’ll occasionally join in the Chicago sport of complaining about the cold, we know it’s just a matter of time before our yachts are back in Burnham Harbor.

We’re looking forward to the 2017 yachting season. We’ve already nailed down dates for some upcoming events. Merlot and Massage Cruise, anyone? Yacht yoga? Fireworks cruises? Never too early to sign up for these.

Yacht Yoga

Yacht Yoga

We’re excited about getting back on the water and hope to see you on an upcoming charter for your company meeting, client appreciation cruise, family party, wedding, shower, anniversary……you name it….if you’re celebrating an event or entertaining clients, we hope you’ll do it on a Free Spirit luxury yacht.

Merlot and Massage Cruise

Merlot and Massage Cruise

Free Spirit Yacht Cruises is already booking charter cruises well into 2017, so don’t wait too long if you’ve got specific dates in mind.

Learn more about Our Story.









Yoga Six Flow & Free Spirit Cruise!

We’re partnering with Yoga Six for a super fun and relaxing afternoon of yoga and yachting. Join us for a Yoga Six Flow in the park and a Free Spirit Cruise!

Free Spirit Cruise

A few months ago we shared the news about a new program called Yacht Yoga. It was so well received that we extended it through Oct 2nd.

Yoga Six Flow & Free Spirit Cruise!

Now we’ve got more good news for yoga lovers!

We’re partnering with Yoga Six for a super fun and relaxing afternoon of yoga and yachting.  Enjoy an outdoor Yoga Six Flow in the park and continue flowing thru the afternoon cruising aboard our Free Spirit Luxury Yacht.

Experience a magical afternoon of connection and sea natural beauty from the other side of Chicago on Lake Michigan;)

Sunday, August 14th
11a – 3p

Yoga on land at Gold Star Memorial Park next to Burnham Harbor.
Followed by a 3-hr cruise on our Free Spirit Luxury Yacht.

Enjoy a delicious post-yoga catered lunch on-board – subs, salad and snacks, icy cold beer and soda and wine.

Sign-up now!


Special discount for Free Spirit friends and fam.

Save $15 when you sign up with promo code yogasix15.

Sound like fun? We thought you’d like this!

Be sure to share this post with any yoga loving friends.

Yoga Six Flow





















Highlight of the 2016 Summer. So far. Chicago Fireworks Cruise.

We don’t mean to play “can you top this?” Chicago fireworks cruise. But how did you spend your 4th of July weekend?

One of the fun things we did was host a private yacht charter for the cast and crew from The Sponge Bob Musical, War Paint and The Book of Mormon!

Chicago Fireworks Cruise

Can you say magical night? We got feedback like this:

“We had the best 4th of July ever!…..Their (the Free Spirit Yacht crew) hospitality is amazing. We felt at home and happy. Also, Captain Joe is funny (Joe loved that)!” – Vasthy Mompoint

As you can see from some of the photos we took, guests had a blast. The weather cooperated (lucky us). Cast members hammed it up. And everyone enjoyed being out on Lake Michigan with the spectacular Chicago skyline as a backdrop.

We cruised past Navy Pier and the big new Ferris Wheel. And then Captain Joe found one of his perfect fireworks watching spot.

And then there were FIREWORKS! The pictures pretty much tell the story.

Fourth of July Cruise

If you’ve been looking for a fun way to entertain clients or host a company party or Chicago fireworks cruise, a private luxury yacht charter might be just the thing. We offer delectable catering options (food and bar) in a luxurious setting that make it oh-so-easy to mix business with pleasure.

That’s why many of our corporate clients book private yacht charters with us season after season.

“This is the 4th time I rented the Gypsy and keep coming back because we have had such a wonderful experience! I guarantee we will rent again in the future and have provided information to other friends looking for boat rentals. Thanks again!” – Katie Freund

Sound like something you’d like to do before the season ends? Here’s how to reach us: call 708.361.2220 or request a proposal.

Check out a snippet from this Free Spirit Chicago Fireworks Cruise!






Treat your staff. Wow your clients.

This photo pretty much says it all. Late afternoon cruise. A glimpse of the world-famous Chicago skyline in the background. Relaxed and happy group enjoying a Chicago summer cruise on the Chicago River and Lake Michigan.

Company CruiseThis summer, we’ve already had more than a few charter cruises that looked like this. Company outings to treat staff to something special. Or companies entertaining clients on a corporate charter that says: “We value your business and want to show you how much!”

Whether you’re doing a company party, a corporate meeting or a client appreciation party, few venues can top a private luxury yacht charter.

Three hours relaxing as you cruise Lake Michigan. The spectacular Chicago skyline in the distance. A delectable buffet. Music in the background (live, DJ or iPod). Hanging out with people you like and enjoying a summer afternoon (or morning brunch or evening). Your call – we do them all.

After being cooped up all winter, hosting a company meeting on a luxury yacht is probably the nicest thing you can do for your staff. And from what we hear from corporate clients who book with us year after year, the payback in employee engagement is huge.

This is the kind of feedback we get:

“Thank you – everyone on the team had a great time at our outing! The service, experience and everything exceeded expectations. The #1 surprise was how good, helpful and organized all the staff on the boat were. We never had to ask for anything – they were always one step ahead.

Thank you for helping me organize the outing! Hope to do another one again in the future.”

Dean Gordon
FTI Consulting

Want to do something really special for your team or clients? Call us today to find out how to book a private charter for your group.




Guess what we got? Yacht Yoga.

Yacht YogaNo kidding. Yacht Yoga. Just like it sounds. We’re practicing yoga on a yacht. Our Free Spirit yacht, to be exact.

Offering special relaxation-themed cruises is a vision we’ve been exploring for a couple of years now. Now the time seems right. As some of you know, Angela has been teaching YogaSculpt since April, 2015. She’s earned her 200-hour teaching credentials for Vinyasa yoga, and it’s changed her life. Now she wants to share some of the wonderful benefits with others.

Who Should Sign Up

Anyone who could use a little “me” time. Or anyone who puts others before themselves way too often.

What’s The Class Like?

Vinyasa yoga is a series of poses that flow breath with movement. The practice helps you relax, unwind and breathe. In Yacht Yoga, you’ll focus solely on yourself and your internal conversation – the one you’ve been having with yourself lately. Good or bad.

In addition to yoga flow, we’ll explore concepts from The Four Agreements, by spiritual teacher and bestselling author, don Miguel Ruiz. A blend of ancient wisdom and practical common sense, these are designed for “seekers of truth and personal authenticity”. If that sounds like you….or the you that you want to be…..sign up now.

We’re only offering 2 classes per week starting May 1st and ending May 24th. And we’re keeping classes very small so space is limited. If this sounds like fun, don’t wait to sign up.

The Free Spirit will stay dockside at Burnham Harbor.

Free Spirit Yacht Yoga

In Chicago, one thing is certain. The weather won’t be.

Wednesday, July 1st dawned way cooler than we would’ve liked. And it never went higher than 66.

Not exactly ideal summer weather…..especially when you’re running private yacht charters on Lake Michigan.

But hey, this IS Chicago. And if there’s one thing we can always be sure of, it’s that the weather is never predictable. So we roll with it. And we have heat on the yachts.

A few years ago, during a particularly cold run, we stocked up on blankets. Just in case anyone forgot to bring a sweater on the boat and wanted to be out on deck.

Private Yacht Charters

This year when July 1st brought chilly weather, we prayed that it wouldn’t dampen the charters we were running that night.

We wanted them to enjoy it as much as they had the first two times.

So we were very happy to get this feedback…..

Angela and Joe,

“Everybody enjoyed it very much….good comments on the food, as well as the crew and how friendly everyone was. They also liked the DJ, the fireworks and the dancing.  Thanks to you and your crew for a memorable event.”

Shane Swanson, New York Life, Managing Partner

We may not be able to control the weather, but we can make sure your guests are well attended to when you charter with us. And find you a great DJ. Cause who doesn’t like to party on a yacht!

Have a happy and safe 4th of July weekend;)

Thank you to our Free Spirit Partners!

It was another fantastically fun Merlot and Massage Cruise this year!  And a huge “Thank You!” to all that helped make this year’s event a big success.

Stivers Coffee treated us with delicious fruit smoothies and exceptional coffee creations.  Starting this year, you can add their service to your Free Spirit Cruise!

Stivers Coffee


Mary is a holistic health professional offering a variety of therapies.  Thank you Mary and Jessica for the soothing hand and foot massages.

Holistic Health


Delos Wellness introduced and provided amazing treatments for muscle relief for chronic pain and stiffness.  If you have never tried Delos therapy, you can schedule a complimentary Delos therapy session at their 600 West Chicago Avenue location.  Or you can create your own private cruise and add a Delos therapist to your event for an additional fee.

Delos Therapy


We had so many Super Stars pampering and sharing great energy with our Free Spirit charter guests.  Thank you Chris Ramsey and her team of massage therapists.



We love Rickey Gold! Rickey has been working with Free Spirit Yacht Cruises since Joe and I took over in 2007.  She is a master copy writer and excellent marketer. Thank you for adding list checker to your resume;)

Rickey Gold


Thanks to Catered by Design for their tasty treats, Jansco Promotional Products for delivering our new Free Spirit wine glasses on time, VoFotos for capturing so many beautiful moments and Windy City Silkscreening for our Fun Free Spirit t-shirts!

Free Spirit T-Shirt


And “Thank You” Mother Nature:)

Free Spirit Cruise

How are we going to top this for next year’s Merlot and Massage Cruise?


Free Spirit Yacht Cruises Giveaway

We’re giving away goodies.

It’s spring. We’re happy. You’re happy. What better way to celebrate than with a GIVEAWAY! So that’s what we’re doing.

The Free Spirit Yacht Cruises Giveaway runs May 1st – May 31st.

It’s safe and secure to enter. 16 lucky people will win prizes. And there are multiple ways to enter.

What can you win?

  • 3 Lucky Winners will each get 2 Merlot & Massage Cruise Tickets
  • 5 Lucky Winners will receive either a Free Spirit or Gypsy Spirit T-shirt
  • 8 Lucky Winners will receive a Free Spirit Wine Glass

“How do I enter?” It’s easy!

  1. Go to this link: Free Spirit Yacht Cruises Giveaway
  2. Use your Facebook login or enter your email address.

Merlot and Massage CruisePrizes

Merlot & Massage Cruise

You can’t buy tickets anymore, but you CAN win 2 of them in our raffle!

Free Spirit Yacht Cruises had it’s first Merlot & Massage Cruise in May, 2010. It was a big hit and is the only open cruise we run all season. This year we have the Free Spirit and the Gypsy Spirit going out with groups to relax and unwind.

Here’s a quote from Now You Know Events blog post about their Merlot & Massage Cruise experience, “Guests were treated like royalty by Captain Joe Donofrio and family as they enjoyed cocktails and good company.”

Free Spirit or Gypsy Spirit T-Shirt

With the help of our friends at  Windy City Silkscreening, we’ve created fun new t-shirts for our clients.  We won’t be selling these t-shirts. Yes you can enter our raffle to win!

Gypsy Spirit T-Shirt

Free Spirit Wine Glass

If you’ve ever chartered the Free Spirit or Gypsy Spirit, you know, we give every charter client a gift bag with our Free Spirit Wine Glass.  Below is a photo one of ouour clients shared with us:) Guess what?  You can enter Free Spirit Yacht Cruises May Giveaway to win!

Free Spirit Wine Glass

Signature Free Spirit Wine Glass

You can enter multiple times, so don’t stop at just one. And be sure to tell your friends.

Winners will be selected randomly on June 1st. We’ll announce winning names on social media and email winners directly.

Good luck, Everyone!

Any questions, shoot us an email: info@freespiritcruises.com

Free Spirit Yacht Cruises will be back in Burnham Harbor!

Have you noticed? Despite the cold, snow and ice, spring is quietly peeking around the corner. The days are getting longer, and it’s still light after 5:30. Could there be better news?

Actually, there could.

Cause it’s time to start planning your summer fun. And in Chicago, summer fun is synonymous with Lake Michigan and our glorious lakefront. So we’re excited to share the news that we’re launching the Free Spirit and Gypsy Spirit in April. Free Spirit Yacht Cruises will be back in Burnham Harbor!

Captain Joe and the crew have been hard at work making sure everything is immaculate and in perfect working order aboard the Gypsy Spirit and Free Spirit. Angela and her team are busy booking charters and designing mouthwatering menus for the 2015 season. Come April, our yachts will be ready to cruise Lake Michigan for your private events, company outings, meetings and more.

To get you in the spring spirit, here’s a video we put together. It’s our “Taste of Chicago” but with cruises, featuring our clients and friends with images of Chicago’s magnificent skyline, Navy Pier fireworks, the Air & Water Show and of course a gorgeous Chicago sunset (remember those  😉 ) Watch ‘til the end to meet our captains and crew.

Please share the video with your friends, colleagues or anyone who’s looking forward to summer and may want to experience Chicago’s most inviting yachts.


What are 5 things you would give thanks for this Thanksgiving?

Thanksgiving always makes us stop to think about all the things we’re grateful for – our health, our family, our friends…

Focusing on gratitude and giving thanks can really enhance our daily lives. It can be a struggle to keep an optimistic outlook with the cold, grey winters, traffic jams and the holiday hustle-bustle. However, starting the day writing out 5 things to be grateful for shifts our mind into a state of gratitude.

Good Times

Here are the top 5 things we are grateful for at Free Spirit Yacht Cruises this Thanksgiving!

  1. At the top of our list are clients and friends like you!
  2. Running a business where our goal is to make people happy
  3. Providing an exceptional & wonderful experience
  4. Beautiful days and magnificent sunsets
  5. Good times and smiles


On a personal note to practice this exercise of gratitude on a daily basis, opens us up to see how much we have and less focused on the things we don’t. It’s amazing!

Happy Thanksgiving
All of us at Free Spirit Yacht Cruises wishes you and your family a blessed and wonderful Thanksgiving!!