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

8 reviews
38 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. Rates as low as $150 per hour (minimum of 2 hours). Other rates available below: Rates: • 3 hours: $450 • Additional hours: $100 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 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.

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...


8 reviews

5.0 out of 5!

  • Listing Accuracy

  • Departure & Return

  • Vessel & Equipment

  • Communication

  • Value

  • Itinerary & Experience

1 photo has been added by reviewers who booked this listing.
  1. ND

    We had a wonderful time with Captain Joey! The weather was perfect for cruising around and sailing. The Captain showed us beautiful views of the city skyline and there was never a dull moment on board. I would definitely book again with Captain Joey and recommend others to do so too.

  2. am

    Captain Joey was so great! Friendly and full of knowledge about sailing. We were celebrating a birthday and it was just perfect! Highly reccomend..harbor is Easy to access and beautiful views!

  3. MB

    Captain Joey was awesome! Highly recommended :)

  4. RL

    This experience was amazing. Captain Joey took us to a thrilling tour around the lake ending in a beautiful sunset with a great view. The boat and Joey was a complete fun experience catered to our needs. A chill trip all around with great moments! Worth every penny. If you have a fun group, captain Joey will fit right in and make everything fun. 12/10 recommend!!

  5. MT

    Had a great first sailing experience with Captain Joey! Before the outing, I was very impressed by his clear and prompt communication, especially with our concerns about the weather. We are also not from the area and he gave us clear instruction, making it easy to find him. Additionally, he was very friendly and our group very much enjoyed our sail with him and appreciated his flexibility with the timing. If we had the chance to sail in Chicago again, we would definitely call Captain Joey first!

Features & Details

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

Approximate Location

You’ll get directions for the exact departure location when you make a booking inquiry.

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.

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