Tours and Activities

The boat is over 35’ feet long and very wide and heavy which makes the ride even smoother in all conditions. The boat has A/C, 1 Bedroom, 1 large Bathroom, 2 refrigerators as well as two sinks, plus a large cooler out in the seating area.

A SPECIAL EVENT SAIL! Treat yourself to an Independence Day Sail from the best seat in town! Order a cool drink from our bar, then relax and enjoy a leisurely evening listening to patriotic music and enjoying the Chicago skyline. The City of Chicago MAY also have fireworks on July 3th, but officially this has not been announced. (probably not, but we can hope!) Chicago’s weekend kick of the Fourth of July celebration is one of the best in the nation. Enjoying this event from Chicago’s official Schooner, Tall Ship Windy, this is truly a VIP event. This event sells-out early.

We’ll help you chase your Monday BLUES away aboard the 148-foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of Lake Michigan accompanied by the sweet sounds of the blues. Whether you’re a long-time fan or a newcomer to the blues, you’re sure to be transported by the talent and passion of each amazing artist. With a full bar and a friendly, knowledgeable crew, you’ll be able to relax and enjoy the music in comfort and style.

Wakesurf Chicago is the best option for boat rental in downtown Chicago. Our boat rental service in Chicago includes gas and a captain to guide you through your experience whether you want to do a river cruise or party in the playpen.

We have a Mastercraft X24 inboard boat that is specifically outfitted for wake surfing. We also have top of the line equipment from Phase 5 and Doomswell available to make your experience that much better.

An experience you don’t want to miss! Chicago’s famous Air and Water Show aboard the 148′ Lakeshore Sail Charters is truly a magical event. While the official schedule has yet to be announced, we anticipate another year of thrill and excitement.

A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in town! Grab a cool drink from our bar, relax, and enjoy a leisurely evening sail past the brilliant and beautiful Chicago skyline. Our Capt and crew will bring you out under power, to watch the fireworks, for the best location, out on the water! We will play the accompanying music, that the show is set to! This is one of the most popular events of our summer season!

Watch the Chicago fireworks from one of our boats offering a stunning, panoramic view of the city skyline illuminated by vibrant bursts of color. As you cruise along Lake Michigan, the gentle waves and open air create a relaxed, unforgettable atmosphere—perfect for celebrating a summer evening or special occasion away from the crowds onshore.

Experience the thrill of riding across Lake Michigan with our brand new premium fleet of Yamaha VX Waverunner rentals in Chicago—adventure, speed, and stunning skyline views await! Book now for an unforgettable ride on the water.

We offer a great Party Cruise- daytime, evening and night cruises for groups from 1 up to 13 in Paradise -spacious luxury Motor Yacht. Playpen Party Cruises! Pets and kids are welcome.

Please note, we provide a captains list for you, once you select captain you must pay captain in person for his/her services (captains do require a deposit)

The Yacht has a huge front of the boat that can fit the entire group plus a sun pad. The back seating area of the boat has a plenty of room and turns into a lounger. She is a two bathroom, two bedroom sailboat with a great dining and lounging area below and a large refrigerator and freezer. We also have a four person blow up raft for people to enjoy while swimming in the playpen.

Leave the hustle and bustle behind! Explore Chicago’s shoreline, with a leisurely trip on Lake Michigan. Take in the world-famous skyline, enjoy spectacular views and discover the Windy City from the water.

Embark on a captivating journey through the heart of the Windy City with a unique Chicago River cruise! Discover hidden gems and gain an entirely new perspective as you navigate the bustling waterways, where architectural marvels rise majestically along the banks. Imagine gliding past the lively Chicago Riverwalk, catching glimpses of its inviting patios and restaurants buzzing with energy and offering tempting access right from the water.

Set sail with Poseidon Chicago Charters for an unforgettable daytime experience on the magnificent Lake Michigan! The Chicago skyline provides a stunning backdrop to your special occasion. Whether you’re celebrating a momentous bachelor or bachelorette party, marking a milestone birthday, orchestrating a romantic engagement, hosting an intimate wedding celebration, toasting years of love on an anniversary, joyfully declaring a new chapter at a divorce party, commemorating a hard-earned graduation, capturing picture-perfect moments on a photoshoot cruise, or hosting any other unique private event, our daytime charters offer the perfect setting to create lasting memories with your cherished companions.

Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treats and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more!

Chicago has it all – amazing architecture, great food, and iconic sights both old and new. This tour takes you to some of the city’s best spots alongside a local guide where you’ll get the inside scoop on what makes Chicago so special. Not only that, we’ll throw in a couple of sweet, local treats to keep you going as we explore on foot and via local transportation.

Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treats and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more!

Chicago has it all – amazing architecture, great food, and iconic sights both old and new. This tour takes you to some of the city’s best spots alongside a local guide where you’ll get the inside scoop on what makes Chicago so special. Not only that, we’ll throw in a couple of sweet, local treats to keep you going as we explore on foot and via local transportation.

We offer a great Party Cruise- daytime, evening and night cruises for groups from 1 up to 13 in Paradise -spacious luxury Motor Yacht. Playpen Party Cruises! Pets and kids are welcome.

We offer a great Party Cruise- daytime, evening and night cruises for groups from 1 up to 13 in Paradise -spacious luxury Motor Yacht. Playpen Party Cruises! Pets and kids are welcome.

We offer a great Party Cruise- daytime, evening and night cruises for groups from 1 up to 13 in Paradise -spacious luxury Motor Yacht. Playpen Party Cruises! Pets and kids are welcome.

Welcome aboard the luxurious 32 ft Larson Cabrio, a spacious cabin cruiser designed for ultimate comfort and enjoyment. Relax in a cozy bedroom, prepare meals in the fully equipped kitchen, and freshen up in the convenient bathroom. Our amenities include two fridges to keep your refreshments cool and a selection of fun floaties for endless water enjoyment.

To understand the city of Chicago, you need to know its river. Hop aboard a private boat with a Windy City local to hear how the Chicago River has shaped the city’s skyline and its very identity, taking in its beautiful architecture from a truly unique perspective!

If you’ve taken an architecture boat tour in Chicago, you’ve most likely heard a smattering of common urban myths and legends masked in “truth” because the tour guide supposedly knows best. But most tours are little more than regurgitated scripts that unfortunately perpetuate these myths. And then the guests who take those tours spread those myths to their local friends, and the myths become “truth”…but they’re not true.

Enjoy cruising the beautiful Chicago River for 2 hours

You are the driver! Our dock crew will train you or someone in your group when you arrive.

Gas Powered, automatic. simple to drive.

BYOB and snacks are welcome or we will be happy to cater to you.

Have an awesome charter experience with a captain who is also a licensed commercial pilot, serial entrepreneur, fluent in French, English, a little bit of Spanish and Mandarin, who travels the world constantly !

Green & Yellow Jet Car, Water jet cars blends the iconic design of exotic supercars with thrilling aquatic performance!

Blue & Black Jet Car, Water jet cars blends the iconic design of exotic supercars with thrilling aquatic performance!

Red Jet Car, Water jet cars blends the iconic design of exotic supercars with thrilling aquatic performance!

Make a splash in style with the Barbie Jet Car. The ultimate ride for fun, fashion, and adventure on the water! With room for 4–5 passengers, this eye-catching pink jet car is perfect for groups who want to cruise, laugh, and live the dream.

A SPECIAL EVENT SAIL! Treat yourself to an Independence Day Sail from the best seat in town! Order a cool drink from our bar, then relax and enjoy a leisurely evening listening to patriotic music and enjoying the Chicago skyline.

Capt. Rich hails from the midwest. He lived in the Caribbean for over 20 years captaining everything from sailboats, motorboats, ferries, catamarans, to mid-sized yachts. He currently holds a 100 ton International Masters license, VSO, STCW-95, and a dozen other endorsements.

I’m Captain Mike, and the water has been my second home since I was a little kid. With over a decade of experience navigating the waters of Lake Michigan, I’ve honed my skills to ensure every voyage is not just enjoyable, but also safe. Whether it’s soaking up the Scene party vibes or catching the breathtaking Air and Water Show, I’m dedicated to making your time on the water unforgettable. Join me for a voyage where safety meets excitement, and let’s create memories that’ll last a lifetime.

Hi I’m Matt! I’ve been captaining in Chicago for five years but have been in the boating industry much longer. In the past I studied biology with intent of going into the medical field however I decided to stop going to school to pursue a life on the water. In my free time I enjoy going out to eat, music shows and snowboarding. On boats under 40′ my rate is $100/hr and $120/hr on those over.

Hello! I’ve been boating most of my life, the last 15 years on Lake Michigan in the Chicago area. I’m familiar with all the hot spots such as the playpen, Monroe Harbor, and the Chicago river. Look forward to facilitating a safe and enjoyable boating experience for you.

Cześć! Jestem Kapitanem Mike imówię po polsku! I’m your trusted skipper for private boat charters. I’ve always found my heart anchored in the world of boating, growing up on the serene waters of the Channel Lakes, the vibrant Lake of the Ozarks, and the majestic Lake Michigan.

Today, I offer premier private charter services, where my aim is to curate a unique and memorable experience for you. Whether it’s a special event like a bachelor or bachelorette party, a birthday celebration, or just a tranquil day out on the water, I’m here to cater to your specific needs and make your boating adventure an extraordinary journey.

Hello!! Im capt. Tanner, i’ve been onboats since I was little. In 2020, I started as a technician and work on 30′ to 75′ yachts, I ran with a friend of mine who has been a Capt. For 17 years, which has taught me a lot on the water, along with U.S captain training. Chicago is close to one of the best spots with great people! The boating community is outstanding and the playpen is the party spot, as far as skyline view on the way you can’t beat it!!! If partying isn’t your ideal scene, take a cruise down the river, which planning ahead we can dock and order portfinos and eat right off the river and go for a cruise!!

Hey there, I’m Captain Tony!

With experience that spans over 15 years I am passionate about creating unforgettable moments for my clients. As a dedicated professional in the vibrant world of yachting, I strive to go above and beyond, ensuring that every voyage is a remarkable experience. My goal is to create memories that will last a lifetime. So, if you’re dreaming of a breathtaking adventure out on the water, rest assured that I will be there to steer you towards an extraordinary journey.

Ready to make some waves in Chicago? I’m Captain John Brown, I have been running boats for 15 years, and I’m here to make your Chicago boat charter absolutely epic! From fun-filled family adventures to unforgettable bachelor and bachelorette boat bashes, or just a fantastic party with your closest friends, I’ve got the experience to ensure smooth sailing and good times. My priority is always your safety and maximum enjoyment. Let’s get this party started!

What’s up, Charterers? I’m Taylor, your go-to yacht expert! Hailing from sunny Florida, I’ve been on boats for most of my life, so you can trust you’re in good hands. I’m all about making your charter experience amazing—I’m outgoing and friendly, and I love meeting new people. But don’t worry, if you prefer some privacy, I’m more than happy to give you space and let you enjoy your time on the water. Let’s make you some unforgettable memories!

Have an amazing charter with a captain who is more than just a sailor, but a certified EMT fluent in Spanish and Portuguese, as well as someone who can show you the wonders of Chicago’s magnificent waterfront.

Instagram: @captain.ianbarbosa

I appreciate the opportunity and look forward to serving as your captain!

Book me and you are getting someone who genuinely loves what I do.. I have a natural ability to read a group and adjust to the vibe so your charter feels just right. I come prepared with free seasick patches that often save the day, and I take a keepsake photo and print one for everyone on board at no cost, which is always a hit. I bring my own Insta360 for fun photo and video content for your group and I am learning to fly my drone to capture some unique footage too.

At Believe Tours Charter Chicago, we offer the ultimate yachting experience on our luxurious Sea Ray 50 ft!

The yacht comes equipped with a spacious living area, full kitchen, two bathrooms, and a comfy bedroom. Our experienced team of professionals goes above and beyond to ensure you and your guests are comfortably accommodated and entertained while on board. Allow us to help you create the perfect yachting experience of a lifetime.

At Believe Tours Charter Chicago, we offer the ultimate yachting experience on our luxurious Sea Ray 50 ft!

The yacht comes equipped with a spacious living area, full kitchen, two bathrooms, and a comfy bedroom. Our experienced team of professionals goes above and beyond to ensure you and your guests are comfortably accommodated and entertained while on board. Allow us to help you create the perfect yachting experience of a lifetime.

This tour is the answer to many requests for an Art-Deco-specific tour because — let’s face it — we all LOVE the elegance, glam, and glitz of the 1920s. This 2-hour walking tour explores the interiors and exteriors of gorgeous buildings from this surprisingly brief architectural period in Chicago, with some interesting details and stories about life in that era. Flappers, gangsters, jazz, speakeasies — we’ll pepper those throughout our larger exploration of Chicago’s magnificent Art Deco buildings in order to truly set the context for you!

With a lifetime of experience on the water, starting from the sun-drenched coasts of South Carolina to the expansive waters of Lake Michigan. After 5 years of navigating the waters of Chicago, I have amassed a wealth of experience across various different vessels. I am committed to excellence in customer service and I hold myself to a high standard of care for not only the vessel, but my guests as well.

Step aboard Montauk, a Hamptons-inspired 57’ power catamaran designed for private charters of up to 49 guests. Perfect for any celebration, the Montauk features a full-service bar, private bathroom, bluetooth JL Audio surround sound, and an optional DJ booth. Your experience is fully private, with a USCG-licensed captain and a professional crew—including bartenders and event planners—dedicated to creating a seamless, unforgettable outing.

Discover Chicago by Water: History, Architecture & Firefighting Legacy

Step aboard and let our expert docents guide you through the fascinating story of Chicago—told from the best seat in the city: the deck of our historic fireboat.

In my younger years, I fell in love with the water and boats. In my college years, I loved the energy of the city and the clubs where I bartended. I have now combined them into yachting. Being a 50-ton captain and helping people enjoy the water from a relaxing cruise to a day at the playpen to fireworks at night. Let’s see which one is right for you and your family, friends, or co-workers. Look forward to a great time and memories on the water.

Hello, I am Captain Dave Krell. I am a US Coast Guard licensed 50 Ton boat captain. I have over 40 years of power boating experience operating on Lake Michigan, US Rivers, Intercoastal Waterways, Gulf of Mexico, and the Atlantic Ocean. I grew up on boats, and I have spent every summer of my life on the water. It’s my Zen Zone. Whether it’s going to party in the Play Pen, seeing the fireworks, or just seeing the sites of the city. With 100’s of charters completed, it will always be a safe but great time with me as your captain!

Hello! I would be thrilled to captain for you. Although born in Chicago, I was raised in Florida spending much of my free time on the water. After graduating from Florida State University (Go Noles), I spent years working in the fitness industry. That career ended up relocating me back to Chicago, where I then pivoted to working in the marine industry. I took up captaining as a fun way to gain experience on the water and meet all kinds of new people!

Step aboard the Sophisticated Lady – Chicago’s Largest 49 Passenger Yacht. This tastefully restored classic Chris-Craft showcases rich cherry wood and teak finishes, a spacious open floor plan across three levels, and multiple outdoor areas including a flybridge with panoramic views and bow seating.

Equipped with one of Sea Ray’s widest beams, this yacht is most popular for its large open cockpit and cabin floor plan, making it phenomenal for social events, birthdays, bachelorette parties, and corporate groups.

Equipped with an upgraded JL Audio Bluetooth Audio, starboard facing U-shaped seating area, and full sized cabin with bathroom. This express style cruiser is great for both family outings and entertaining.

One of Sea Ray’s most popular models, this yacht features a fully upgraded JL Audio bluetooth system, and wetbar in the cockpit. Below deck, the cabin includes a dinette, two beds, kitchen, and a bathroom.