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Charter a 31' Pearson Cruising Sloop, ChicagoCharter a 31' Pearson Cruising Sloop, ChicagoCharter a 31' Pearson Cruising Sloop, ChicagoCharter a 31' Pearson Cruising Sloop, Chicago

Charter a 31' Pearson Cruising Sloop, Chicago

4.4(30 reviews)
·
140 bookings
·
Estimated price
$200 / hour (2 hours minimum)
Captain Joey

Captain Joey

140 total bookings
Superowner

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.  My rate is $200 per hour (minimum of 2 hours). Rates: • 3 hours: $600. • Additional hours: $200 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.
Capacity
6 guests
Sailing
Sloop

Check Availability

Reviews

4.4 (30 reviews)
  • Listing Accuracy

    Awesome
  • Departure & Return

    Awesome
  • Vessel & Equipment

    Good
  • Communication

    Awesome
  • Value

    Good
  • Itinerary & Experience

    Awesome
  1. Charter a 31' Pearson Cruising Sloop, Chicago
  2. Charter a 31' Pearson Cruising Sloop, Chicago
  3. Charter a 31' Pearson Cruising Sloop, Chicago
  4. Charter a 31' Pearson Cruising Sloop, Chicago
  5. Charter a 31' Pearson Cruising Sloop, Chicago
5 photos have been added by reviewers who booked this listing.
  1. Anthony
    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!

  2. 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.

  3. 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!

  4. Cassie
    Cassie

    Our group of 5 ladies had a wonderful time on Lake Michigan with Captain Joey! The sailboat is beautiful, spacious and well maintained. From the directions to the dock to the actual sailing, Captain Joey knew how to make our trip great experience. The option to bring on drinks and snacks was very nice, and we enjoyed using the “picnic table” on the deck. This is a great way to enjoy the beautiful summer weather outdoors any time, but especially during the pandemic. We felt very safe on this private charter. We highly recommend sailing with Captain Joey!

  5. ND
    Nancy

    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.

Captain Joey

Captain Joey

140 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

Length
31ft
Year
1987
  • Bluetooth
  • Galley Stove & Oven
  • Life jackets/required safety gear
  • BBQ
  • Furling Mainsail
  • Furling Headsail
  • Fuel type: Diesel
  • Dinghy
  • CD Player
  • Autopilot
  • Wheel steering
  • Inboard Engine
  • Head
  • Cabin

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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