1992 Caliber 40 Cutter (Florida)

S/V Michael Leslie — a 1992 Caliber 40 Cutter located in Green Cove Marina, Florida, for sale by broker. Responses to inquiries may come from a broker who is representing the owner as a fiduciary.

Michael Leslie is a well-equipped 1992 Caliber 40 Convertible Cutter offering the solid construction, comfortable accommodations, and practical cruising systems that have made Caliber yachts popular with serious cruising sailors.

Her current owner has cared for the vessel since 2001, cruising extensively throughout New England before bringing her south to Florida. Over more than two decades of ownership, she has been outfitted and maintained for comfortable, self-sufficient cruising, with meaningful updates to her rigging, electrical systems, and onboard equipment.

The Caliber 40 was designed as a capable offshore cruising yacht with a solid fiberglass hull, protected cockpit, skeg-hung rudder, and versatile cutter rig. Her sail plan provides several combinations to suit changing conditions while remaining manageable for a cruising couple or shorthanded crew.

An important update was the replacement of the standing rigging in 2020, at which time the mast was also rewired. These improvements address two significant areas for anyone evaluating an established cruising sailboat and complement the boat’s practical cutter configuration.

Auxiliary power is provided by a Yanmar diesel with approximately 3,600 hours, paired with a three-blade Max-Prop. The feathering Max-Prop provides efficient propulsion under power while reducing drag when sailing.

For extended cruising and comfortable time aboard, Michael Leslie is also equipped with a diesel generator, air conditioning, and Starlink connectivity. Her electrical system has received recent attention as well. New AGM batteries were installed in 2024 along with a new battery charger in 2025.

Below deck, the Caliber 40 offers a comfortable and practical cruising interior with accommodations that work particularly well for extended stays aboard. The owner’s stateroom features a private ensuite head with a separate stall shower, a desirable feature not always found aboard cruising sailboats of this size. A second head is positioned near the companionway, providing easy access for guests while maintaining privacy for the owner’s cabin.

The aft cabin provides additional sleeping accommodations for two, allowing the boat to comfortably accommodate family or guests while maintaining separation between sleeping areas. The main salon serves as a spacious central living area, while the galley and storage arrangements reflect Caliber’s emphasis on practical cruising rather than simply maximizing interior volume.

She would be well suited to a buyer considering coastal cruising, the Bahamas and Caribbean, seasonal liveaboard use, or longer-distance passagemaking.

Michael Leslie is available for inspection in Florida.