Angela's Charter Service

Call Website Contact the business

Angela's Charter Service Operating from Navy Pier. And as it turned out… marriage made on Lake Michigan. What better place to fall in love!

Angela Motola is the founder of Angela’s Charter Service, a women-owned Chicago yacht charter company focused on creating elevated private experiences aboard the Gypsy Spirit on Lake Michigan and the Chicago River. After eleven wonderfully rewarding years running Angela’s Charter Service, I am working with my husband, Joe Donofrio, managing our own luxury yachts in our company, Free Spirit Yacht Cruises. Between Joe’s eighteen years as a private yacht charter captain and my expertise running a thirty-boat yacht charter broker company, we decided this could be a great joint venture.

10/03/2026

Chicago! There’s still time to get outside—and on the water. ⚓️🍂

A quick Halloween update: Because Navy Pier Marina closes for the season on October 31, Haunted on the Lake will not sail as planned.

But the spirit of the celebration doesn’t have to end. The Gypsy Spirit is still cruising on select dates before the marina closes, giving you time to create your own private Spirited Cruise.

Bring up to 49 guests and make it your own:

🎃 Costumes or a custom theme
🎶 Your music and atmosphere
🍽️ Food designed for your gathering
🥂 Bar packages or cash bar
🏙️ Beautiful Chicago views

Perfect for birthdays, corporate outings, fall celebrations and end-of-season gatherings.

Availability is limited and subject to confirmation. Visit angelascharters.com to start planning.

09/27/2026

Still making memories on the water!

🛥️✨ From skyline views to celebrations to corporate functions, Gypsy Spirit is cruising from Navy Pier. Come aboard while the season is still going strong.

📍Chicago | angelascharters.com

Something spirited is coming to Chicago’s waterfront. 🎃🌙Join us aboard the Gypsy Spirit for Haunted on the Lake—an eleva...
09/22/2026

Something spirited is coming to Chicago’s waterfront. 🎃🌙

Join us aboard the Gypsy Spirit for Haunted on the Lake—an elevated Halloween yacht experience featuring:

🎧 Music and dancing
🍴 Light bites
🍹 Full bar and welcome rum punch
🏆 Costume contest
🌃 Indoor and outdoor decks with Chicago skyline views

Saturday, October 31
Boarding: 7:30 PM
Cruise: 8:00–10:30 PM
21+ | Limited to 40 guests

Early-bird tickets are $88 for the first 10 guests. General admission is $93.

Reserve your spot:
https://angelascharters.com/haunted-on-the-lake/

09/16/2026

★★★★★

Just when you think you’ve experienced it all… 💍🛥️Their guests arrived expecting a surprise proposal party—but the real ...
09/14/2026

Just when you think you’ve experienced it all… 💍🛥️

Their guests arrived expecting a surprise proposal party—but the real surprise was a wedding aboard the Gypsy Spirit.

We were honored to help bring every detail together while keeping the celebration completely confidential. Seeing the moment their guests realized what was happening was something we will never forget.

And then we received these incredibly kind words:
“Absolutely flawless experience for our wedding ceremony… Communication was excellent from start to finish, every detail stayed confidential, and the crew was professional, warm, and completely unflappable on the day.”

Thank you, Shane, for trusting Angela’s Charter Service with such an extraordinary moment—and for sharing this beautiful photograph and five-star review.

Some celebrations deserve a venue as unforgettable as the occasion. ⚓️

Read the full review: https://maps.app.goo.gl/7xNcNjHrhNYXkvxe8

What a beautiful day for a wedding on the water. 🤍Just when I think I’ve experienced it all after so many years in this ...
09/13/2026

What a beautiful day for a wedding on the water. 🤍

Just when I think I’ve experienced it all after so many years in this business, a day like this reminds me why I still love what I do.

There is something incredibly special about being invited to share in one of the most meaningful days of a couple’s life. The joy, the family, the friends, the Chicago skyline—and a yacht filled with people celebrating love.

So much gratitude to this beautiful couple for choosing the Gypsy Spirit to be part of their story.

Here’s to a lifetime of adventures together. 🥂⚓️

From workday to lake day.Good company, an open-air cruise and Chicago at sunset made for a memorable evening aboard the ...
09/11/2026

From workday to lake day.

Good company, an open-air cruise and Chicago at sunset made for a memorable evening aboard the Gypsy Spirit.

No packed agenda. Just time for the team to unwind, connect and enjoy the city from a completely different perspective. ⚓️

09/08/2026

Oh, what a night! ✨ Great people, beautiful Chicago views, and unforgettable moments aboard the Gypsy Spirit. ⚓️🥂

Address

Chicago, IL

Telephone

+18777517175

Website

Alerts

Be the first to know and let us send you an email when Angela's Charter Service posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Business

Send a message to Angela's Charter Service:

Shortcuts

Share

Category