1. Charter a 31' Pearson Cruising Sloop, Chicago
  2. Charter a 31' Pearson Cruising Sloop, Chicago
  3. Charter a 31' Pearson Cruising Sloop, Chicago

Charter a 31' Pearson Cruising Sloop, Chicago

17 reviews
74 bookings

Rapture in the breathtaking Chicago skyline as we sail out on our Pearson 31' Cruising Monohull sloop. We can accommodate up to 6 passengers on your charter.  My rate is $150 per hour (minimum of 2 hours). Rates: • 3 hours: $450 • Additional hours: $150 per hour at 5+ hours. What To Expect On Board: We offer flexible scheduling to accommodate your group when it's most convenient. Our cruises are skippered by Certified Instructors and Crew.  If you are interested in learning how to sail, we are happy to let you take a more active role. If not, just sit back and enjoy the cruise and the spectacular views. Bring your favorite food and beverages to enjoy a picnic on the water.  We even have a grill on board for your convenience. Don't forget to bring your swimsuit and towel if you'd like to take a dip! Our 31-foot Cruising Monohull boat can accommodate up to 6 people. Boat Specialties: • Private Cruises • Group Outings & Bachelorette Parties • Corporate Team Building Events • Sailing Lessons If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Request to Book” and send us an inquiry for a custom offer.

Captain is included.
A captain is provided by the listing owner to host and operate the trip.
6 guests

Super OwnerCaptain Joey

Sailing since 1988. USCG licensed captain. The reason we charter is to make sure your experience is an extraordinary one so you will come join us again and again...

Check Availability

April 2021
May 2021
June 2021
  • Select a date to check availability.


17 reviews

4.8 out of 5!

  • Listing Accuracy

  • Departure & Return

  • Vessel & Equipment

  • Communication

  • Value

  • Itinerary & Experience

5 photos have been added by reviewers who booked this listing.
  1. EE

    Captain Joey was great! Really fun boat ride.

  2. LK

    We chose Captain Joey for my first sail. There were 4 of us, plus our experienced captain. We had a 2 hour sail and he took us by motor power inside the breakwater and then outside the breakwater for sailing. It was everything I thought it would be - peaceful and a fresh breeze with beautiful views of the Chicago skyline. I would do it again, and I highly recommend it!

  3. RP

    Best part of our summer so far!

  4. GC

    My wife & I celebrated our 1 Year Anniversary and we had an awesome time . The view was amazing and we definitely enjoyed the vibe of the Captain !

  5. JP

    We had a great time with Captain Joey! He listened to what I wanted and we had a safe and fun trip. Will definitely charter again!!!

Features & Details

  • Life jackets/required safety gear
  • BBQ
  • Bluetooth
  • Galley Stove & Oven
  • Cabin
  • Wheel steering
  • Inboard Engine
  • Autopilot
  • CD Player
  • Dinghy
  • Fuel type: Diesel
  • Head
  • Furling Headsail
  • Furling Mainsail

Approximate Location

You’ll get directions to the departure location when you make a booking.

The boat's approximate location on a map

Cancellation Policy

Full refund up to 5 days prior.

Additional Terms & Information

Children 12 or under must wear life jacket. 2020 ALL PASSENGERS MUST COME WITH A MASK. Cancellation Policies for Private Cruises and Sailing Lessons: • Cancellations/Rescheduling made by you with at least 5 days prior to the day of the trip incur no penalty and may be rescheduled with no additional fees. • Sailing Lesson cancellations made by you with less than 5 days prior, no notice or no-shows will result in loss of lesson time and a $50 rescheduling fee. • Private Cruise cancellations made by you with less than 5 days prior, no notice or no-shows will result in loss of sail with full fee. • Cancellations made by our company incur no penalty and may be rescheduled with no additional fees.   • Behavior that is detrimental to the safety and well-being of the vessel, crew or individual, e.g., excessive alcohol consumption, will not be tolerated and may result in a non-refundable, non-credited, early departure from the vessel.

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