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The British
Leeward Islands - Antigua, Dominica, Montserrat, Nevis, St. Christopher (St. Kitts) and
the Virgin Islands - all used postage
stamps inscribed "LEEWARD ISLANDS" between 1890 and 1 July 1956,
often concurrently with stamps inscribed with the colony's name.
http://en.wikipedia.org/wiki/Leeward_Islands
Scott: #128O (CD308)
Issued: 10.10.1949
UPU Issue
Inside #128: Stamp on Envelope
Best website related:
Sandafayre – Stamp Atlas
http://www.sandafayre.com/atlas/carrib.htm