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85data points analyzed by Sailpages.com to compile this ISLANDER 29 buyer’s report
ISLANDER 29

ISLANDER 29

$4,250 avg$3,500 – $5,000 (2 listings)1968–1969
$1.4K – $3.7K est. annual maintenance
Offshore CruisermonoMasthead SloopFin

Specifications

Hull

LOA29.08 ft
LWL23.33 ft
Beam8.83 ft
Draft3.67 ft
Displacement7,800 lb
Ballast2,499.9 lb
Hull speed1.34·√LWL6.5 kn

Rig & Sails

Iforetriangle height33.18 ft
Jforetriangle base11.25 ft
Pmainsail luff30 ft
Emainsail foot13.67 ft
FLforestay11.3 ft
Mainsail408.1 sq ft
Jib (100%)186.6 sq ft
Spinnaker317.3 sq ft

Engine

UniversalAtomic 430 hpSee all 6 parts →

About the ISLANDER 29

Also called the WAYFARER 29. A raised deck version was called the ISLANDER 30.

Sailpages Buyer's Take

Designed by J.H.McGlasson and built by Wayfarer Yacht Corp. / Islander Yachts (USA) between 1968–1969, the Islander 29 is a classic masthead sloop with a displacement of 7800.0 lb. While the exact hulls built count is unknown, the fleet is characterized by a comfort ratio of 26.43, suggesting a stable ride suitable for its era.

Best for:
This boat suits coastal cruisers and weekend sailors who prioritize a comfortable, stable motion over high-speed performance, as indicated by its moderate D/L ratio of 274.22 and SA/D ratio of 16.0.
Bluewater capability:
With a capsize ratio of 1.78 and a fin keel, the Islander 29 offers moderate offshore capability, though its age and specific structural vulnerabilities require careful evaluation for serious bluewater passages.
Comparables:
Comparable boats include the Cal 2-29 and O'Day 28, which share similar production years, displacement ranges, and the role of comfortable, family-oriented coastal cruisers from the late 1960s.

Performance

Comfort26.4
Capsize1.78
SA/Disp16.0
Disp/Len274
Bal/Disp32.0

Estimated Value

Limited Data
Based on 2 listings
Low
$3,010
Estimated Value
$3,302
High
$3,593
Inflation-adjusted to 2026 USD

Estimated Cost of Ownership

Based on 29.08ft LOA. Actual costs vary by condition, usage, and local rates.

$/ft/mo
Annual Maintenance
$1.4K – $3.7K
Hull, rigging, sails, engine service
Annual Docking
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Annual Insurance
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Known Issues & Pre-Purchase Inspection

15 reported issues across 8 systems for the ISLANDER 29, compiled from owner reports in sailing forums and owner-association material.

7 critical3 major5 minor
Structural3Rudder3Deck3Safety2Plumbing1Hull1Engine1Keel1

Unlock the full inspection report

Thinking of buying a ISLANDER 29? This is an in-depth report on the faults this model is known for — so you know exactly what to check when you walk the boat. For the price of a coffee.

  • All 15 specific issues — severity, symptoms & fixes
  • Model-specific pre-purchase inspection checklist
  • Downloadable PDF to take to your surveyor — yours to keep

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

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Engine Parts & Maintenance

The engines most commonly fitted to this model. “All parts” opens the engine's full catalogue; each part links to a matching listing on Amazon or eBay matched to its part number.

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Used sails that fit the ISLANDER 29

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