Islander Freeport 38 Information, Review, Specs

Sailing Performance & Handling

The Freeport 38 is a heavy-displacement cruiser, and its performance characteristics reflect Robert Perry’s mandate to prioritize comfort over raw speed. With a Displacement-to-Length (D/L) ratio typically hovering around 285 and a modest Sail Area-to-Displacement (SA/D) ratio of approximately 14.5, the boat requires a stiff breeze—ideally 12 knots or more—to truly wake up. Because it lacks the high-aspect rig of its cousin, the Islander 36, it is not a "pointing" machine; it performs best on a reach or a run where its weight provides a stable, predictable motion in a seaway.

The hull features a modified fin keel and a large skeg-hung rudder, a configuration Perry frequently utilized to ensure tracking stability and protection for the steering gear. According to design notes from Robert H. Perry Yacht Designers, the Freeport series was intended to feel "shippy" and secure. While the high freeboard and voluminous cabin trunk create significant windage, making docking in a crosswind a maneuver that requires practice, the boat’s heavy mass allows it to carry momentum through a tack even in choppy conditions.

Interior Comfort & Variations

The interior is the Freeport 38's defining feature. At the time of its release, the "Great Room" layout was revolutionary for a boat under 40 feet. The most popular configuration features a "Pullman" berth forward (positioned against the side of the hull rather than a V-berth) which allows for a much larger, private head in the forepeak. The main salon is remarkably wide, taking full advantage of the boat's 12-foot beam.

The "B" layout, often preferred by liveaboards, utilizes the massive stern area for a wrap-around settee situated directly beneath the iconic rectangular stern windows. This creates an airy, sun-drenched lounge that is virtually unmatched in other 1970s-era monohulls. Materials are typical of the Islander "Golden Age," featuring heavy teak joinery and plywood bulkheads with teak veneers.

Regarding siblings, the Freeport 36 and 38 are virtually identical in hull form. The Freeport 38 is essentially the "Mark II" version of the 36, often featuring an integrated bowsprit and minor cockpit refinements. It should not be confused with the Freeport 41, which was a Charlie Davies-designed center-cockpit ketch with a much more traditional, heavy-full-keel profile.

Known Issues & Buyer’s Checklist

Prospective buyers should approach a Freeport 38 with a focus on three specific areas of concern common to the Islander builds of this era:

• The Stern Gallery Windows: While they provide excellent light, the large rectangular windows in the transom are notorious for leaking. Over decades, the seals perish, and because of their size, they can be a point of structural vulnerability if not properly re-bedded or replaced with modern tempered glass or acrylic.
• Fuel Tank Corrosion: Many Freeports were built with black iron fuel tanks located deep in the bilge. If water has sat against the exterior of the tank, they are prone to pinhole leaks. Replacing these tanks often requires significant "surgical" removal of cabin soles or furniture.
• Chainplate Inspection: The chainplates on many Islanders were glassed into the hull or hidden behind cabinetry. Owners on various technical forums have noted that inspecting the stainless steel for crevice corrosion is difficult, yet vital, as the 38-foot rig puts significant load on these points.
• Deck Delamination: Like many boats from the late 1970s, the Freeport uses a balsa-core deck. Moisture ingress around stanchion bases or the windlass often leads to soft spots that require expensive core replacement.

Community & Resources

Owners of the Freeport 38 often find common ground within the broader Islander yachting community. The most prominent resource is the Islander 36 Association, which, while focused on the 36, maintains extensive technical archives and historical data that overlap with the Freeport builds, particularly regarding engine mounts and fiberglass layups.

The Verdict

The Islander Freeport 38 is a specialized tool. It is not designed for the sailor who wants to win Wednesday night buoy races, but it is an exceptional platform for a couple looking to live aboard or cruise coastal waters in comfort. It offers the interior volume of a much larger vessel without the associated slip fees.

Pros:

• Exceptional Volume: Feels more like a 42-footer below deck.
• Robert Perry Design: Balanced handling and a seaworthy hull shape.
• Aesthetic Character: The "pirate ship" windows offer a unique, classic look.

Cons:

• Light Air Performance: Struggles to move in winds under 10 knots.
• Windage: High profile makes it challenging to handle in tight marinas.
• Maintenance Intensity: Large windows and aging iron tanks require vigilant upkeep.