3rd Coast Cruising – Legend 31 

New
 400 East Monroe Street, Chicago, IL 60601, United States

3rd Coast Cruising – Legend 31 

Chicago, IL, United States
31 feet
6
Just listed

Sail Chicago with one of the city’s most established sailing schools.

3rd Coast Cruising has been introducing people to sailing on Lake Michigan for more than 25 years. Whether you want a relaxing private cruise, a hands-on sailing lesson, or a little of both, our experienced team will customize the experience around your group.

You’ll sail aboard a Hunter Legend 31, a comfortable and responsive sailboat that accommodates up to six guests. Enjoy Chicago skyline views, learn the basics of sailing, take the helm, or simply relax with friends and family.

Guests are welcome to bring food and drinks. Swimming may be available when conditions allow, and all required safety equipment is provided onboard.

From first-time sailors to experienced guests looking to sharpen their skills, 3rd Coast offers much more than a typical boat ride; it’s a genuine Chicago sailing experience.

Sail Chicago with one of the city’s most established sailing schools.

3rd Coast Cruising has been introducing people to sailing on Lake Michigan for more than 25 years. Whether you want a relaxing private cruise, a hands-on sailing lesson, or a little of both, our experienced team will customize the experience around your group.

You’ll sail aboard a Hunter Legend 31, a comfortable and responsive sailboat that accommodates up to six guests. Enjoy Chicago skyline views, learn the basics of sailing, take the helm, or simply relax with friends and family.

Guests are welcome to bring food and drinks. Swimming may be available when conditions allow, and all required safety equipment is provided onboard.

From first-time sailors to experienced guests looking to sharpen their skills, 3rd Coast offers much more than a typical boat ride; it’s a genuine Chicago sailing experience.

3rd Coast Cruising & 3rd Coast Charters
Charter Operator
3rd Coast Cruising & 3rd Coast Charters
21 years of experience
ID & credentials verified
responds within an hour

Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
September 2026
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Number of days
1
Group Size
2 adults • 0 children
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2 Hour – Sailing Trip, Monohull
FREE Cancellation 14 days notice
2 hour trip multiple starting times (10:00 AM, 12:00 PM, 2:00 PM, 4:00 PM, 6:00 PM)
+2
US $500
Private tour: up to 6 people
3 Hour – Sailing Trip, Monohull
FREE Cancellation 14 days notice
3 hour trip multiple starting times (10:00 AM, 1:30 PM, 5:00 PM, 7:00 PM)
+2
US $600
Private tour: up to 6 people
4 Hour – Sailing Trip, Monohull
FREE Cancellation 14 days notice
4 hour trip multiple starting times (10:00 AM, 1:30 PM, 5:00 PM, 7:00 PM)
+2
US $800
Private tour: up to 6 people
There is 1 person looking at this charter.

Customer reviews

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FAQs about 3rd Coast Cruising – Legend 31

3rd Coast Cruising – Legend 31 offers the following trips to customers:
  • US $500 per group - 2 Hour – Sailing Trip, Monohull (2 hours)
  • US $500 per group - 2 Hour – Sailing Trip, Monohull - 12:00 PM (2 hours)
  • US $500 per group - 2 Hour – Sailing Trip, Monohull - 2:00 PM (2 hours)
  • US $500 per group - 2 Hour – Sailing Trip, Monohull - 4:00 PM (2 hours)
  • US $500 per group - 2 Hour – Sailing Trip, Monohull - 6:00 PM (2 hours)
  • US $600 per group - 3 Hour – Sailing Trip, Monohull (3 hours)
  • US $600 per group - 3 Hour – Sailing Trip, Monohull - 1:30 PM (3 hours)
  • US $600 per group - 3 Hour – Sailing Trip, Monohull - 5:00 PM (3 hours)
  • US $600 per group - 3 Hour – Sailing Trip, Monohull - 7:00 PM (3 hours)
  • US $800 per group - 4 Hour – Sailing Trip, Monohull (4 hours)
  • US $800 per group - 4 Hour – Sailing Trip, Monohull - 1:30 PM (4 hours)
  • US $800 per group - 4 Hour – Sailing Trip, Monohull - 5:00 PM (4 hours)
  • US $800 per group - 4 Hour – Sailing Trip, Monohull - 7:00 PM (4 hours)
When you book a trip with 3rd Coast Cruising – Legend 31, you can expect the following amenities onboard:
  • Anchor
  • Wheel Steering
  • Life Jackets
  • Outside Speakers
  • Ice Box
  • Grill
3rd Coast Cruising – Legend 31 offers the following activities:
  • Sailing, Catamaran & Gulet Tours
  • Sunset Dinner Cruises
  • Birthday Celebrations
  • Bachelorette & Bachelor Parties
  • Proposal & Engagement Trips
  • Corporate & Group Events

Your operator

3rd Coast Cruising & 3rd Coast Charters
3rd Coast Cruising & 3rd Coast Charters
3rd Coast Cruising & 3rd Coast Charters

Chicago, Illinois, United States

ID & license verified
Member since July 2026

Captain Jim has more than 30 years of sailing experience and has taught thousands of students on Lake Michigan. As the founder of 3rd Coast Cruising, he's helped complete beginners become confident sailors, boat owners sharpen their skills, and experienced crews prepare for bigger adventures. His style is hands-on, relaxed, and tailored to each group, whether you want to learn, take the helm, or simply enjoy an unforgettable sail.

ID & license verified
Member since July 2026

Captain Jim has more than 30 years of sailing experience and has taught thousands of students on Lake Michigan. As the founder of 3rd Coast Cruising, he's helped complete beginners become confident sailors, boat owners sharpen their skills, and experienced crews prepare for bigger adventures. His style is hands-on, relaxed, and tailored to each group, whether you want to learn, take the helm, or simply enjoy an unforgettable sail.

What the boat is like

Boat category
Other
Boat type
Sailing
Boat manufacturer
Hunter
Boat Model
Legend 31
Year built
1985
Boat length
31 ft
Capacity
6 persons
Engine model
Yanmar
Max crusing speed
5 knots
Powered by
1 x 13HP
Engine Type
Inboard
Fuel Type
Diesel
Boat category
Other
Boat type
Sailing
Boat manufacturer
Hunter
Boat Model
Legend 31
Year built
1985
Boat length
31 ft
Capacity
6 persons

Which kind of activities are offered

Sailing, Catamaran & Gulet Tours
Sunset & Dinner Cruise
Birthday Celebrations
Bachelorette & Bachelor Parties
Proposal & Engagement Trips
Corporate & Group Events

Which amenities are available onboard

Anchor
Wheel Steering
Life Jackets
Outside Speakers
Ice Box
Grill

What's included in the trip price

What’s allowed on the boat

Child Friendly
Alcohol
Glass Bottles
Shoes
Swimming

What additional terms you should be aware of

Security deposit is not required

A refundable deposit is not required by the charter operator.


How cancellations work

Free cancellation up to 14 days prior to trip

You can cancel or modify your booking up to 14 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.

More details

How you can pay

Reserve with a 10% booking deposit, pay the captain the rest

When the captain confirms your trip, BoatBooker charges your credit card a 10% booking deposit to guarantee your reservation.

The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:

 Visa

 Mastercard

 American Express

 PayPal

When paying the remaining balance with a credit card, an additional 4% charge will apply.