Why Choose Us?

First-Class sailing

One of our beautiful sailboats.

First-Class Semi-Private Sailing

Our First-Class sails are designed to provide the experience of a top-notch private sail at a Semi-Private level. Only our larger boats participate in the program, and we limit the number of guests on board to 6. This is a great option for a group of 2 or 4 that wants to get out on the water on a big beautiful sailboat, without the cost of a private charter. Below is a list of several of the reasons why we believe that you should choose us.
  • Service – Our commitment to safety and service are head and shoulders above the rest as indicated by our reviews on Yelp!
  • Sailboats – ALL sailboats are at least 36-39′ long, and built for First-Class comfort and speed.
  • Availabilty– With 4 full time charter boats eligible for this program, there is a great deal of availability
  • Longer Sails – Most of our First-Class sails are 2 hours (some upgrades sails are 2.5 or 3 hour sails).
  • Comfort – Our boats are designed with passengers in mind, not 30 yr old cramped race boats converted to charter boats.
  • Value – there is no match for the boats you will sail on and the service you will receive for this price or anything close to it, this is simply the best value in town.
  • Parking – Park right next to our gated docks, or a 10 minute walk away for free most days.
  • Public Transportation – a modest walk away.
  • Belmont Harbor – This is the most sought after harbor in Chicago due to its location, parking (both free and resonable cost), beauty, attached picnic grounds and park, and 5 minute boat ride to the wide open lake (that is why there are plenty of vacant moorings at Monroe, Burnham, and 31st street harbors all summer long, but none at Belmont). We have spent many years getting several 40-45′ moorings in the private gated docks of Belmont Harbor so that we can offer the premier experience.
  • Booking – Online booking and reservation management 24/7 (check your reservation, re-email your confirmation, cancel or change your reservation and book a new one).
  • Repeat Guest Discounts – Sail again during the season for $79 per pair of seats (plus taxes and any upgrades chosen), and get 15% off Private Sails as well (must sail first before taking advantage of any discounts).
  • Options – We often make upgrades available like fireworks sails, weekend afternoons, evenings, and more.
  • Flexibility – Three free schedule changes if more than 10 days in advance, and you wont forfeit your voucher for shorter notice changes or missed sails like with other operations, instead there are partial change fees.
  • Peace of Mind – choose the Cancellation Insurance option for just $15 per pair of seats reserved and know that if you miss your sail, have a personal emergency, or your plans change, you can reschedule at no charge.
  • Most of all – Summer in Chicago goes by in a flash, and our staff genuinely wants to show you the beauty of the Chicago Skyline from Lake Michigan on one of our gorgeous sailboats.