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Charter a 31' Pearson Cruising Sloop, Chicago

Charter a 31' Pearson Cruising Sloop, Chicago

With Captain

4.5(36 reviews)

158 bookings

the United States,Illinois,Chicago,Sailing

Capture 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. The minimum charter is 2 hours at $500. My rate for 3 hours or more is $200 per hour. Rates: • 2 hours: $500 • 3+ hours: $200 per hour 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

Currently Snoozed(Off-Season)

This listing will be active on 17 Mar 2025.

You’ll be able to get in touch with the owner when they return.

Captain Joey

158 total bookings

Superowner

Capacity: 6 guests

Sailing: Sloop

Reviews

4.5 (36 reviews)

Listing Accuracy
Awesome
Departure & Return
Awesome
Vessel & Equipment
Awesome
Communication
Awesome
Value
Good
Itinerary & Experience
Awesome

6 photos have been added by reviewers who booked this listing.

AD
Alejandro

Great overall experience. I must advice that I had to adjust my plans from what I initially had in mind. I had to get props for the experience on my own, which complicated the planning and fortunately resulted all right. Also, it wasn’t until after booking my experience that I realized that Captain Joey was thinking of going out for a motorboat ride rather than for a sail, which would’ve been a total bummer - I had to talk him into this plan and he kindly agreed to doing so.
SV
Sabrina

Captain Joey is incredible. He went above and beyond to ensure that my partner and I had perfect wedding portraits. He perfectly mapped out sunset and found us the perfect views. Would not have been possible without out Joey! Cant wait to come back again soon!
Anthony

I contacted Captain Joey back in February of 2022 for a June 2022 engagement charter. Long story short, my partner said YES! Everything about the trip was amazing with the only exception being that I got motion sickness about 20 minutes into the charter (be sure to take CJ’s advice when he talks to you about what to do to prevent this). CJ is a very laid-back, jokster type who really put me at ease while I was: 1. overcoming motion sickness and 2. Preparing to propose to my partner. He is batting 1000 when it comes to engagement charters so I’ve you’re looking to propose on a boat, CJ is your captain!
AM
Andrew

I booked this rental for a surprise wedding engagement and Captain Joey did a great job working with me. He helped come up with game plan to pop the question and he was easy to work with even when plans changed. He was also nice enough to play along with the charade before the question was asked to keep it a surprise. I was very happy with how everything turned out and would definitely recommend to others.
LK
Linda

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!

Captain Joey

158 total bookings

Superowner

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...

Features & Details

Make: Preston
Model: 31

Length: 31ft

Year: 1987

Life jackets/required safety gear
Wheel steering

Approximate Location

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

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.