🎉 Our End-Of-Season Sale is Live! ⛵
Enjoy up to $300 off on remaining dates & times - Book Your Charter Now
NOW BOOKING SUMMER 2025
Chicago Sailing Charters & Cruises
37' luxury sailboat
Up to 7 guests
Privately book our 37' luxury sailing yacht for an unforgettable day with your crew!
Our Chicago sailing charters & cruises are perfect for summer birthdays, bach parties, romantic proposals, anniversaries, and more. Take in the sights, sounds, and breathtaking scenery of the Lakefront during summer.
USCG-Captain Included
📍Navy Pier Marina - Downtown Chicago
WE'VE DONE 700+ SAILING CHARTERS SINCE 2018
Trusted superhost to thousands of guests, each & every year.
CHICAGO SAILING EXPERIENCES starting at $799
No hidden fees. No surprise charges. 100% transparent pricing.
❌ NO hourly captain fees
❌ NO refueling costs
❌ NO docking fees
New in 2025: all-inclusive sailing packages!
Book any Sail & Swim Playpen Charter or Navy Pier Fireworks Cruise this season, and we'll throw in our welcome package at no additional cost. That means fewer coolers to carry, less ice to lug, and more time to focus on making memories with your favorites.
Your all-inclusive booking includes:
🥂 Complimentary Champagne Toast
🍻 (Pre-chilled) 12-pack of High Noon Vodka Seltzers
🥜 Unlimited Snacks & Non-Alcoholic Drinks
Golden Sail Money-Back Guarantee
Bad weather? Unexpected issues? We recognize things come up. Our money-back guarantee ensures you have the freedom to make adjustments with ease, providing peace of mind in the weeks and days leading up to your planned outing with us.
100% Refund up to Two Weeks From Departure
50% Refund up to 48 Hours From Departure
Full Refund for Weather Related Cancellations
Swap Dates With No Fees
Subject to Availability
Three easy steps to pre-book your private boat party this summer:
STEP 1 - Choose Your Adventure
Browse our all charters & cruises page. We offer something for everyone!
STEP 2 - Recruit Your Crew
Fire up those group chats and start recruiting. Summer weekends will sell out.
STEP 3 - Lock-In Your Big Day
Book with a 50% fully-refundable deposit. Remaining balance to be auto-debited 5 days ahead of reservation.
