1. Private Cruise onboard Hunter Legend Sailboat in Chicago
  2. Private Cruise onboard Hunter Legend Sailboat in Chicago
  3. Private Cruise onboard Hunter Legend Sailboat in Chicago

Private Cruise onboard Hunter Legend Sailboat in Chicago

11 reviews
42 bookings

Cruise along Chicago harbor on aboard this 32′ Hunter Legend sailboat that seats up to 6 people! Book a Private Cruise with our Hunter Legend now! Rates as low $150 per hour and a minimum booking of 3 hours.  Get ready for a once in a lifetime tour where you chose the itinerary or let us help you craft the perfect boat tour. The boat is chartered with a captain for your convenience. This is the perfect boat to discover the region. it is comfy and convenient to go to places only accessible by the water. Your departure will be from Chicago and is nearby to many easy to access places. 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
Cruising Monohull

Owner:Captain Jim

We've had so much fun on our annual Bluewater Magellan trips over the years that we decided to invest in our own catamaran. We offer private sailing charters on Lake Michigan in the summer and in the winter we take the boat somewhere warm to offer multi-day cruises. Throughout all the growth and change, one thing will always remain the same: our commitment to providing the best sailing experience possible. Whether it's local or tropical—we want you to love sailing as much as we do and will do our best to make sure you have a great time!

Check Availability

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


11 reviews

4.9 out of 5!

  • Listing Accuracy

  • Departure & Return

  • Vessel & Equipment

  • Communication

  • Value

  • Itinerary & Experience

29 photos have been added by reviewers who booked this listing.
  1. VA

    Had an amazing time even got to drive the boat for a little.

  2. JT

    Best experience on a sailboat this far. They highly ensured our safety and entertainment.

  3. AH

    Captain Jim and his crew were so accommodating and kind!! They made sure we were comfortable and the boat ride was amazing!! 10/10 my favorite thing to do in Chicago!

  4. NL

    Great guy, great time. Highly recommended

  5. NS

    Great captain/crew! Had a wonderful time

Features & Details

  • Life jackets/required safety gear
  • BBQ
  • Bluetooth
  • Galley Stove & Oven
  • Cabin
  • Wheel steering
  • Inboard Engine
  • CD Player
  • Chart Plotter
  • Single Engine
  • Fuel type: Diesel
  • Inverter
  • Berth
  • 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

50% refund up to 14 days prior.

Additional Terms & Information

Rescheduling done by you with at least 48 hours' notice incur no penalty and may be rescheduled with no additional fees. Cancellations with at least 2 weeks' notice will result in 50% of total charge being retained and 50% refunded. Cancellations made with less than 2 weeks' notice will not be eligible for a refund. Cancellations made by our company incur no penalty and may be rescheduled with no additional fees.   Cruising Credits will be issued if there is inclement weather. 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. If your cruise was scheduled during an event (e.g., America's Cup or Air & Water Show), please keep in mind that you paid for a cruise. We cannot control the factors outside of our company. If the event is canceled but we are still able to safely sailor motor-sail, credits or refunds will not be issued.

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