Arawak Indians settled the British Virgin Islands around 100 BC, migrating from the Orinoco Basin in South America. A peace loving tribe, they were hounded out by the more aggressive Caribs, who arrived from South America in the mid-15th century. It was only a few decades later that Columbus stopped by on his second trip to the New World and crashed the party. Columbus, perhaps feeling the lack of female company shipboard, named the islands Las Vírgenes in a somewhat obscure reference to St Ursula and her 11,000 virgins. He also gave Virgin Gorda (Fat Virgin) and Anegada (Sunken Island) the names that remain today.

The Spanish didn't think much of the islands, settling only to mine copper on Virgin Gorda in the early 17th century. The Europeans were harassed by Caribs and by pirates who attacked galleons carrying riches back to Spain. An assortment of colorful characters sailed through the surrounding waters, including pirates Henry Morgan, Sir John Hawkins and Blackbeard, and English sea dog Sir Francis Drake. As Spain declined as a colonial power, ownership of the islands shifted about until the Dutch established a permanent settlement on Tortola in 1648.

The English ousted the Dutch from Tortola in 1672, and from Anegada and Virgin Gorda in 1680. The new rulers introduced the two quintessential features of the colonial era in the Caribbean: sugar cane and slaves. At first, most of Tortola's 'planters' were more interested in piracy and smuggling than agriculture, but by the 18th century they were displaced by a new wave of experienced planters and a settlement of hard working Quakers. Between the mid-18th and early 19th centuries, the islands prospered, producing sugar, cotton, rum, indigo and spices.

Slave unrest and ideological doubt brought an end to slave auctions in 1803. By the 1830s, slaves had been emancipated. Abolition and the introduction of sugar beet in Europe and the USA were disastrous for the islands: capital and settlers departed for more buoyant economies, and for the next 100 years the islands' economy stagnated.