Yankee Clipper III Review: Pros, Cons, and Insider Advice

Yankee Clipper III — History: From Launch to Modern Voyages

Original identity: Built in 1927 in Kiel, Germany as the steel-hulled private yacht Cressida (yard: F. Krupp Germaniawerft).
Early names: Cressida → Crimper (brief) → Pioneer (under Vanderbilt ownership).
Conversion & service: Rebuilt after WWII for passenger cruising; acquired by Windjammer Barefoot Cruises in 1965 and renamed Yankee Clipper (often listed as Yankee Clipper III in Windjammer materials).
Type & rig: Three-masted staysail schooner (stag-sea rig), steel hull, sail area ≈ 950 m², length ≈ 59.5 m (197 ft).

1927–1940s: Private yacht with long-range voyages; wartime service/ownership changes during WWII.
Post‑ WWII: Reconstructed and operated as a cruising vessel for private owners (Vanderbilts as “Pioneer”).
1965–2007: Celebrity period — Caribbean sailing cruises under Windjammer Barefoot Cruises, popular for casual barefoot-style voyages with multiple cabin types and informal onboard life.
2007 onward: Windjammer’s bankruptcy ended regular service; the vessel was retired and has been laid up/parked (reported permanently docked in Trinidad or laid up in a shipyard).

Year built: 1927
Builder: F. Krupp Germaniawerft, Kiel, Germany
Length: ~59.5 m (197 ft)
Beam: ~9.1 m (30 ft)
Draft: ~5.1 m (17 ft)
Tonnage / sail area: reported ~327 GT and ~950 m² sail area
Crew capacity: historically ~30; passenger accommodations included multiple cabin classes (standard, deck, captain’s cabin, admiral suite).

Widely remembered among tall‑ship and Caribbean cruise enthusiasts for Windjammer’s informal “barefoot” style.
After Windjammer folded in 2007 the Yankee Clipper ceased commercial operation; most sources report it laid up or permanently docked (reports vary on exact location/status).
Historical records and ship databases list her ex‑names (Cressida, Pioneer) and technical specs; she appears in tall‑ship registries and maritime histories.

Sources: Wikipedia (SV Yankee Clipper), tallship-fan ship profile, maritime articles and archival pages (last consulted Feb 7, 2026).