Olson's Classic Yachts - A Better Way to Rent a Boat in Chicago
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  • Home
  • Our System
  • Our Boats
    • Paper Tiger - Morgan 42
    • Wind Gypsy - Morgan 384
    • Scrimshaw - C&C 35MkIII
    • Sea Dancer - C&C 33MkII
    • Aquavit - Morgan 33
    • Playful Tiger - Morgan 321
    • Puffin - Tanzer 29
    • Little Darlin' - Catalina 27
  • Dining Aboard
    • Breakfast
    • Date Night
    • Tailgate on the Lake
  • Who We Are
    • Who Sails With Us?
  • Contact
  • Monroe Harbor
  • FAQs
  • Customer Login
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 We offer for lease restored classic sailing yachts that have been updated with modern equipment yet maintain the classic lines and ease of sailing our customers seek. We have focused on acquiring boats that were produced by legendary designers and builders that are time tested and proven vessels.  We believe that these classic designs give our customers the best mix of comfortable sailing while enjoying the sailing performance and beautiful aesthetics that make the best sailing experience for customers and their guests. 

Each of our boats has a story of its own. Come explore why Chicago has fallen in love with each of them...


Paper Tiger - Morgan 42
​Wind Gypsy - Morgan 384

​ Scrimshaw - C&C 35
Sea Dancer - C&C 33 
Aquavit - Morgan 33

Playful Tiger - Morgan 321
Puffin - Tanzer 29
​   Little Darlin' - Catalina 27
Killer Queen - Beneteau 42
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