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1996 Schooner 4 Masted Gaff Rigged

Chicago, Illinois



****2021 Has Been The Best For Windy In The Past 14 Years ****

The majestic, 4-masted schooner “Windy”, longtime icon of the Chicago skyline, is available for sale. The owners have been running her for some time and are ready to retire.

Located in downtown Chicago, Windy is a working Top Sail Schooner with COI valid through 2023,  capacity for 150 day passengers and 36 overnight.

 Windy has been a successful business, entertaining the public, groups and students, since 1996. The owners, looking to kick back and relax a little, have decided to retire and offer their operation and/or boat depending upon the buyers interests.   Described by her builder, Windy is " made from modern materials, but has all the character and charm of the great Age of Sail".

This US built, steel hull schooner, can be delivered by the current Captain to your location of choice, should you have another destination in mind.

The ship is equipped with 12 cabins, sleeping 36, with 4 electric heads, 2 with showers.

Decking has non-skid material applied to all walking areas. Several well maintained 
wood boxes are strategically placed on the decks to allow for on deck storage as well
as additional seating.  
Secure, built-in bench seating provides for customer safety and comfort.

The masts are constructed of aluminum, sitting on welded steel plates over the keel.

An inventory of 11 sails with deck fed roller furling makes for ease of sail trim when necessary.

New in 2021

Jib, Staysail, Foresail, Main and Mizzen

All lower cabin areas have at least two access and egress stations fore and aft. 
The aft main salon has one water tight door allowing passengers to enter and exit the galley.

The galley and gift area are located in the aft salon of the vessel. Facilities include sinks, 
refrigeration units,
commercial grade stove/oven, microwave oven and all the equipment needed for a working "Ships Pub, the bar.

There is a state of the art sound system allowing for communication between decks as well as piping the latest sailors' songs (or your choice) throughout the ship.

The engine and principal equipment are housed in the engine compartment in the aft section of the vessel. The 300 hp Cummins had a complete rebuild in Jan 2019 and has only 890 hours since the rebuild.

She has a 35 KW Onan generator along with two 2 KW Inverters and a 300 AMP High output alternator to enable full 110 operation without generator. 

 This is your chance to own a classically styled Tall Ship, and operate her as a public sailing vessel, charter, educational training vessel, or perhaps just to cruise the seven seas.

Please contact the listing broker for an appointment,

Basic Boat Info

Boat Name: Windy
Make: Schooner
Model: 4 Masted Gaff Rigged
Year: 1996
Condition: Used
Category: Sail
Construction: Steel
Boat Hull ID: SC001DSI
Has Hull ID: Yes


Length: 148 ft
Length Overall: 148 ft
Beam: 24'8 ft
Max Draft: 9'6 ft
Displacement: 93,000 lb
Cabins Count: 12

Engines / Speed

Engines: 1
  • Make: Cummins
  • Drive Type: Direct
  • Fuel: Diesel
  • Engine Power: 300hp
  • Type: Inboard
  • Year: 1996
  • Engine Hours: 890


Fuel Tanks: 3
Fuel Tank Capacity: 615 gal
Water Tanks: 3
Water Tank Capacity: 533 gal
Holding Tank Count: 1
Holding Tank Capacity: 1,200 gal


Heads Count: 4
Drive Type: Direct
Boat Class: Schooner, Commercial Boats


Larry Rutter
Rudders & Moorings Yacht Sales, LLC


Rudders & Moorings Yacht Sales LLC
83 Windward Lane
Bristol, Rhode Island, US, 02809



Sail Inventory:

11 sails – Foresail, mainsail, mizzen, (2016)
Spanker sail (NEW in 2020).
Jib and Jib staysail            
Uppers: Foretop, main top, mizzen top, spanker top –

Roller furling, deck fed.

All running rigging included. Sail inventory is removed, inspected, cleaned, and maintained by the originator’s sail loft each year.


Double VHF at helm station icom 745’s

Garmin chart plotter and full complement of software (AIS, Stedy Cast, Weather Monitor)


State of the Art sound system installed 2016

Safety Equipment:

PFD’s   200+ Type 3 Plus

Life rings

Life floats All above per USCG inspected vessel regulations for Subchapter T boat

Fire Suppression system

Generator: 35 K Onan Admiral Model 35MCGBA 4 BT

Electrical system Upgrade:   USCG approved

2019 – Installed two 2 KW Inverters and a 300 AMP High output alternator to enable full 110 operation without generator.

Engine Specifications:

890 hours (Complete Rebuild, January 2019) . Operating hours prior to rebuild = 9081.

Cummins 300 HP 6 cylinder Diesel , transmission Model :ZF Drive

Single screw

Structural improvements:

Vertical rigging (stainless steel shrouds) replaced 2015

Aluminum spreaders   replaced 2015

Boarding and between-deck ladders (formerly wood), all replaced 2018-19 with galvanized steel custom fabricated and fit ladders.

Galley and Bar/concessions:    

Galley is fully furnished with sinks, commercial grade stove, built in microwave, refrigerator (27cubic feet) plus freezer located below decks, (14 ‘ new in 2018)

All galley furnishings of cutlery, dishware, cookware and appliances are included with the sale

Other :

Guest blankets
Salon furnishings
Toolroom equipment  
All working tools/hardware are included in sale
All Docklines and fenders
Heavy winter docklines - 2 ¼” 600 feet total







The Company offers the details of this vessel in good faith but cannot guarantee or warrant the accuracy of this information nor warrant the condition of the vessel. A buyer should instruct his agents, or his surveyors, to investigate such details as the buyer desires validated. This vessel is offered subject to prior sale, price change, or withdrawal without notice.
Additional Contact Information

Please call the listing broker, Larry Rutter for an appointment


Cell: 401-338-3554

Disclaimer This calculator is intended solely for general informational purposes, and to provide a rough estimate based on the information you provide. You should not base your decision on this estimate alone.