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19data points analyzed by Sailpages.com to compile this ISLANDER 55 buyer’s report
ISLANDER 55

ISLANDER 55

from 1968
$5.6K – $15K est. annual maintenance
Bluewater CruisermonoMasthead SloopVariableFull/Long

Specifications

Hull

LOA54.67 ft
LWL36 ft
Beam14 ft
Draft11.33 ft/ 5.75 ft min
Displacement38,000 lb
Ballast6,000.2 lb
Hull speed1.34·√LWL8.0 kn

Rig & Sails

Iforetriangle height59 ft
Jforetriangle base21 ft
Pmainsail luff52.5 ft
Emainsail foot21.5 ft
FLforestay21 ft
Mainsail1,229 sq ft
Jib (100%)619.5 sq ft
Spinnaker1,053.2 sq ft

About the ISLANDER 55

Only a few were built by Islander/Wayfarer. It is believed that the molds for the hull were sold to Tradewinds Yachts which built at least three cruising versions as the TRADEWINDS 55. A kit version was sold as the YACHTCRAFT 55.

Sailpages Buyer's Take

The Islander 55 is a rare, large cruising sloop designed by Bruce King and built by Wayfarer Yacht Corp./Tradewinds Yachts (USA) with production years listed as 1968. With a build count of ?, this vessel represents a unique entry in the classic yacht market, characterized by its substantial 38000.0 lb displacement and 54.67 ft LOA.

Best for:
This boat suits experienced coastal cruisers and bluewater adventurers who prioritize spacious interior volume and heavy displacement comfort over high-performance racing metrics. It is well-suited for couples or families seeking a stable, comfortable platform for long-range cruising, provided they are prepared for significant maintenance.
Bluewater capability:
With a D/L ratio of 363.6 and a capsize ratio of 1.67, the Islander 55 is well-suited for offshore passage-making due to its heavy displacement and stable hull form. Its 36.0 ft LWL and full keel design contribute to a comfortable motion in heavy seas, though its age requires careful structural assessment.
Comparables:
Comparable boats include the Cal 50 and O'Day 50, which share similar eras and roles as large, comfortable cruising sloops with substantial displacement. These vessels offer similar interior volumes and offshore capabilities, making them direct competitors for buyers seeking a 50-foot+ classic cruiser.

Performance

Comfort42.0
Capsize1.67
SA/Disp16.8
Disp/Len364
Bal/Disp15.8

Pricing

We don't have market pricing data for the ISLANDER 55 yet. If you own one, help other buyers β€” what did you pay for it? Reports build a community price estimate over time.

Estimated Cost of Ownership

Based on 54.67ft LOA. Actual costs vary by condition, usage, and local rates.

$/ft/mo
Annual Maintenance
$5.6K – $15K
Hull, rigging, sails, engine service
Annual Docking
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Annual Insurance
N/A
No price data available

Known Issues & Pre-Purchase Inspection

20 reported issues across 9 systems for the ISLANDER 55, compiled from owner reports in sailing forums and owner-association material.

6 critical8 major6 minor
Structural4Rigging4Deck3Rudder2Hull2Engine2Plumbing1Keel1Electrical1

Unlock the full inspection report

Thinking of buying a ISLANDER 55? This is an in-depth report on the faults this model is known for β€” so you know exactly what to check when you walk the boat. For the price of a coffee.

  • βœ“ All 20 specific issues β€” severity, symptoms & fixes
  • βœ“ Model-specific pre-purchase inspection checklist
  • βœ“ Downloadable PDF to take to your surveyor β€” yours to keep

One-time $2.99 Β· secure checkout by Stripe Β· instant access Β· 30 days online, PDF yours to keep

Similar Sailboats

Which engine powers your ISLANDER 55?

We haven't confirmed the engine for this model yet. If you own or know one, tell us β€” as owners report in, we build an accurate picture over time.

Brands sometimes mentioned for this model: Yanmar, Westerbeke, Universal, Perkins β€” is it one of these?

Already know your engine? Search all engines β†’ to find its exact parts.

Used sails that fit the ISLANDER 55

Checking eBay for sails sized to this boat's rig…