Hugh Alphonse Duffy – a brief history

Designer, builder and founder of Duffy’s Esperanza (1), now known as Tradewinds, La Compesina, Bananas, El Gringo Loco, Chez Shack and most recently, Duffy’s Esperanza (2). Although Duffy has been the moving force in the restaurant/guest house business in Vieques for over 35 years, his notorious and varied career stretches back to his New York roots.

Born a god zillion years ago (November 6, 1921), Duffy was the son of a shipbroker and worked on merchant ships in his youth. As a 19-year-old engineer, he found himself with a lieutenant’s commission in WW II. Ask him about the 3 ships he was on that were sunk by the Germans.

Duffy resided in New York City, where he first opened an antique store, Duff’s Stuff, and then became a fashion photographer. Landing the Studebaker car account in the early 50’s, he invested all his capital in a car elevator just in time for the auto manufacturers (or more exactly – the public) to decide the model was a dud. There was nothing left to do but to dump everything and move his first wife, Tanya (the countess), and 2 young children to San Juan. There, he built his first Guest House in Isla Verde, creatively christening it Duffy’s. You can still get a room there, though they’ll tell you it’s the cat that’s named Duffy.

Never able to resist turning an easy profit, or the allure of travel and adventure, the next stop for Duffy was St. Thomas in the Virgin Islands. There he created his next place, or “store” as it’s called in the biz. Located in Creque Alley, it was the birthplace of the Mamas and Papas, as in “Duffy’s good vibrations and our imaginations can’t go on indefinitely, and California dreamin’ is becoming a reality.” You can find the story in John and Michelle Phillips’ separate biographies.

On to southern Spain, Duffy and Tanya, now up to 3 kids, moved to the happening southern coastal town of Torremolinos. It was the mid-sixties, Rock and Roll was king, and southern Spain was the playground of music makers like the Rolling Stones. Duffy’s son Tim (of Love Shack fame) had his first bar there at age 15.

Repatriating to the U.S., Duffy perfected his culinary skills at Bradley’s, the renowned New York City jazz club. Then back to Puerto Rico to open Tiffany’s, which became a popular nightspot in Old San Juan. During this time the Duffy family, finding a welcoming hippy culture in Key West, again relocated. Here Duff and Tonya parted ways and he was again in search of the next adventure. Contacting his Old San Juan friends, Myrna and Charlie Connolly in Vieques, he paid them a visit and decided that the sleepy fishing village of Esperanza was perfect for his next store. At this time he met his second wife, Donna. Duffy signed a 20-year lease with Miguel Torres for his colmado on the then almost completely residential beachfront road in Esperanza. Duffy’s Esperanza was a tremendous success before the paint dried.

In the next dozen years, Duffy designed, built and operated the first Duffy’s Esperanza (aka Tradewinds, then The Island house), La Campesina in La Hueca and Bananas, as well as fathering two children with Donna. After the sale of Bananas in 1980, Duffy and family moved to St. Thomas, Key West and St. Croix. Duffy returned to Vieques in 1991 to establish El Gringo Viejo (now who might that be?) and Chez Shack, where you can still find him holding court Wednesday – Monday during “season.”

With the opening of Duffy’s Esperanza in January 2007, Duffy’s youngest son Mikey is doing a fine job of carrying on the family legacy.