At the end of World War II, John was stuck in Panama, trying to join his wife, Mary who was in Australia. After few months, he decided to buy an old sailing boat, PAGAN, and sail to Australia, whatever he had absolutely no experience of sailing. After a lot of adventures, described in his book "Desperate voyage" he was finally wrecked on FIJI Island by a hurricane. Rescued by locals, he succeeded to meet Mary in Australia.

Few months later, they returned to the US, where John graduated from the University of California. On the proceeds of his book, they bought a 36' ketch,"Tropic Seas", and sailed with their son Johnny, five years old, across the Pacific to Sydney, Australia. Their second son Roger was born on Tahiti, on the way.

The couple then decided to build a new boat "Outward Bound" to complete a circumnavigation.  They departed Sydney in July 1958. After sailing the Indian Ocean, the Red Sea, the Mediterranean and the Atlantic, they arrived at Barbados in 1960.

Once in Caribbean, they were pioneers in chartering up and down the islands, planting coconut trees here and there, (Coconut Johnny was soon his nick name) with regular anchoring at Palm Island.

In 1966, he succeeded to lease the island to the government for 99 years and just a dollar a year. With no or very few cash, the couple began the tremendous enterprise of clearing the island of its bushes and swamps. They even set up the very first airport of the Grenadines.

Out of just a charter stopover in the beginning, they built a small resort, which they improved years after years. In order to collect more cash, they sub-leased some lots of land for villa building.

The hotel became successful enough and received a lot of repeat guests joining themselves for thirty years.

In November 1998 John Caldwell died, still strong and valid at 80 years old.

Palm Island Resort Company was then sold in March 1999 and the hotel closed for works.