Luxury Sailboat with Private Captain: Navy Pier Marina, downtown Chicago

5 (14)

4hr
Starting at $170/person, $1,299/party

About this Experience

What you'll do:

Meet us on the all-new docks at Navy Pier Marina in Downtown Chicago and step aboard your private 37’ luxury sailboat with a USCG-certified captain for a 4-hour BYOB cruise along Chicago’s iconic Lakeshore. Enjoy spacious cabin and on deck seating, a swim platform, Lily Pad, and fun pool floaties for the ultimate on-water party. The boat is stocked with complimentary snacks, beverages, Bluetooth speakers, kitchenware, refrigerator with ice and a private bathroom—everything you need for a seamless and convenient celebration. Anchor at the lively Playpen or choose a quieter cove for swimming and relaxing with your crew. Soak in picture-perfect scenic views of the skyline while sipping your favorite drinks in VIP style.

Why we love it for your party:

BYOB and food: Bring your favorite drinks and bites—we’ll have ice, glassware, and storage ready. Catering packages are also available.
Luxury AF: A sleek 37’ private sailboat with plush seating, top-tier amenities, and your own licensed captain. Departing from the conveniently located all-new Navy Pier Marina in Downtown Chicago- 10 minute boat ride to and from the playpen compared to 30-45min from other harbors!
Complimentary features: Snacks, beverages, Bluetooth speakers, kitchenware, refrigerator, and private bathrooms—all included for no extra fee.
Scenic views: Cruise past Chicago’s most Instagram-worthy skyline spots for unforgettable group photos.

Additional Information:

What's included:
- USCG-certified Captain trained in First Aid and CPR (no separate Captain’s fee)
- Private use of our fully permitted, fully insured sailing yacht (no fuel or docking fee)
- Complimentary beverages and snacks on board (with BYOB or catering/drink packages available)
- Fully stocked kitchenware, fridge, and bathroom (no damage/cleaning deposit)
- Surround sound Bluetooth speakers
- Swim platform with Lily Pad, life jackets, noodles, & pool floaties
What to pack:
- Bathing suit and towel
- Sunglasses, hat, sunscreen
- Rain jacket or layers for cooler days
- Boat shoes, sandals, light-soled tennis shoes
- Comfortable, breathable clothes

About this experience partner:

On A Boat Sailing is the premier purveyor of sailing charters & cruises for intimate group celebrations in Chicago. We have over 500 five-star reviews in our ninth season in business.

Provided by On A Boat Sailing

Joined February 2025

Book This Experience

Visit the experience booking site to check availability and book your experience.

Visit Website

Location
Chicago, IL

797 E Grand Ave, Chicago, IL 60611, USA

Reviews

See All

5 (14 Ratings)

Alicia

August 2024 • Birthday Party

When I say I celebrated my 36th birthday on this beautiful boat, it was AMAZING!! Cait was so incredibly helpful and prompt with any questions I had. Her husband Greg was the coolest captain you could possibly meet. I wish I could rate this 10 stars, for it was truly a wonderful experience! You can’t go wrong if you book with them!! Thank you again!!

Maura B.

August 2024 • Bachelorette Party

Charles customized a boat day for my friend's bachelorette weekend. When we talked about our favorite part of the whole weekend, we all agreed, hands down, the boat experience was the best part. Skilled captain, fun vibes, and amazing overall experience. SailingChi is a MUST

Caroline

July 2024 • Bachelorette Party

Amazing experience, wonderful people, best boat trip possible. Greg and Cait were so professional and accommodating as well as kind and considerate.

Arina

June 2024 • Birthday Party

We rented Greg’s yacht to celebrate my birthday and it was truly amazing!! The yacht itself was very clean and beautiful and Greg was accommodative and helping us with any requests we had. Thank you!

Natalie H.

June 2024 • Bachelorette Party

We booked the Guppy for an afternoon as part of my bachelorette party and had the absolute BEST time! Charles was very knowledgeable and really let us customize the experience for our group. Truly the highlight of our weekend; 15/10 recommend!!

Pat

June 2024 • Birthday Party

Couldn’t have been better! My family celebrated a birthday and two big wedding anniversaries onboard the Dragonfly on a lovely Sunday. Captain Greg guided us out into the beautiful waters of Lake Michigan, showing us views of the Chicago waterfront all the way. It was an afternoon filled with great conversations, many laughs and relaxing times. Smooth sailing for three wonderful hours. Captain Greg is the best!

Brad

August 2023 • Birthday Party

OAB Sailing provided the perfect venue for my wife's 40th birthday party! Greg was hyper-responsive to questions in the weeks prior and very thorough. The boat arrived in immaculate condition and ready to go on the time promised. The downstairs cabin with fridge, kitchenette, head, and table worked great to hold our trays and drinks. Greg was a skilled captain, navigating a bunch of chop from other boat traffic, and we felt comfortable and unrushed the entire time. Parking is easy in the MilPark garage; follow his handout instructions to keep the walk to a few minutes! Would definitely book again!

Oscar

August 2023 • Group-Trip Party

Wow! Absolutely grateful for Greg and the dragonfly . Always courteous and always a great time . Blessed my group with a trip to the playpen Chicago . Perfect ride and tour . Thank you so much for being a genuine good soul.

Abby

June 2023 • Bachelorette Party

I cannot recommend "On A Boat Sailing" enough! My friends and I booked this experience with Greg & Cait for a bachelorette excursion and it was amazing. Weeks prior to our day trip our group received a thorough email with all of the information we needed for a seamless arrival...making it so easy to find the boat on the marina, etc. We had a group of 7 girls on the trip and the boat was so spacious, incredibly clean, and a great atmosphere to have fun (& relax). Greg was the best captain and built in tour guide for us girls who had never been out on the lake before. I will definitely be back to book with them again! Thank you so so much!!

Natalie

July 2022 • Girls-Trip Party

This is a great price for a big group! We had the whole boat to ourselves and had a blast for 4 hours in the playpen! A great alternative for a private group!

Rose

July 2022 • Bachelorette Party

Definitely recommend Greg and his sailboat for a nice day out on the lake! He was absolutely accommodating for our bachelorette party! Very prompt at answering any questions we had.

Kailey

May 2022 • Girls-Trip Party

The boat ride with Greg was the highlight of our trip to Chicago! Greg is an experienced sailor and was kind, entertaining and accommodating. It was a great way to admire the architecture of Chicago and to relax with friends. Cannot recommend enough.

Rachel

July 2018 • Birthday Party

This is a MUST! I booked this trip for a surprise for my boyfriend’s birthday and it did not disappoint! Greg is a wonderful host and his girlfriend Kate was amazing. They were both very knowledgeable, experienced and accommodating. Such a relaxing experience I would recommend to anyone. My original trip was scheduled for Friday and it was pouring so Greg rescheduled immediately and responded very quickly to any questions I had. It’s a must-do!

Reviews

Frequently Asked Questions

🍾 What food and drink can I bring on the boat?

You may bring any food and beverages of your choosing including beer, wine, champagne, or hard seltzers. We have alcohol for purchase on board or ahead of time and can provide catering/provisioning of food and drinks for an added fee.

⚡ What if there is bad weather?

If there is current or forecasted lightning or high wind, we make a weather cancellation one hour before your scheduled departure and provide a full refund.

👨‍✈️ Is a Captain included?

Yes, a USCG-certified Captain is included in the price at checkout. Groups larger than 7 require an independently hired Captain. Upon booking we will send a curated list with available captains and instructions for contacting. Gratuity is appreciated for exceptional service!

🚻 Is there a bathroom on board?

Yes, you and your crew will have full access to our in-cabin bathroom.

📍Where do we get on the boat?

Navy Pier Marina 797 E. Grand Ave. Chicago, IL 60611

+ View 3 More

🍻 What is your BYOB & Alcohol Policy?

Guests are allowed to bring alcohol in the form of beer, wine and hard seltzer drinks. We have a no hard liquor policy while on the boat for our guests safety. We do not provide or sell alcohol on board unless arranged through our catering or provisioning service. All beer must be in cans, not glass. Wine bottles are acceptable. We have wine openers and acrylic wine glasses on board. We provide use of our fridge for keeping drinks cool and have ice available. If extra ice is desired let us know ahead of time to ensure we have some on board before you arrive.

🕶 What else should our group bring?

Good things to bring include a bathing suit or change of clothes, towel, sunglasses, hat, light rain-jacket and layers for cooler days. Keep in mind, temperatures on the Lake will ALWAYS be cooler than on land. We humbly request no dark rubber soled shoes as they can scuff up the boat. We provide lifejackets, pool floats, blankets, sunscreen, bug spray, and full first-aid.