Miles Stair

Miles came to St. John in 1972 to work at the front desk of Caneel Bay Resort to “stay the winter and get a tan”. Advancing to Food & Beverage Manager at the resort, meeting his then wife-to-be Susan and his keen interest in outdoors activities cemented his love affair with St. John. Joining Holiday Homes of St. John in 1985 was easy – both his parents had held real estate licenses in Virginia while he was growing up. This natural progression led to enhancing his continuing real estate education (GRI, CRS, and CBB designations) and then purchasing the company in 1992.

As an active community leader, Miles’ affection for St. John has ingrained him into the island’s weave of education and business leadership. Miles’ many positions over the years include President of the St. John Board of Realtors, Chairman of the Board of Trustees of Gifft Hill School, Commissioner on the VI Territorial Governing Board of Hospitals and Health Facilities, President of Estate Chocolate Hole Landowners Association, Vice Chairman of Friends of the Virgin Islands National Park, President of the Friends of the E. I. Sprauve Library and as a Charter Member of the St. John Rotary Club.

An avid sports enthusiast, Miles can be found hiking, running and paddle boarding, taking advantage of St. John’s unique environment. True to being active in the community, Miles continually participates in the many of the islands sporting events including the 8 Tuff Miles, the St. John Landsharks annual triathlon and the Beach to Beach swim. Miles also pursues his athletic activities off island with such events as bicycling across America to raise funds for the Virgin Islands chapter of the American Lung Association, Boston and New York Marathons and hiking the length of the Appalachian Trail one summer.

The unique blend of knowledge of the island, love of the island and business experience gives his real estate clients a unique buying and selling perspective of St. John.