Jaffa, the ancient city just south of Tel Aviv, is awash in hip restaurants, trendy galleries and glowing nightlife.

Many inhabit neo-Gothic and neo-Renaissance buildings, making for an irresistible pairing of old-meets-new. At the heart of it sits the Jaffa Hotel. This towering presence of a stone building overlooks the Mediterranean and was once a 19th-century monastery and French hospital. Repurposed and transformed by architect Ramy Gill and British designer John Pawson, the former chapel is now a swanky cocktail lounge with vaulted ceiling and stained glass windows. In the lobby, artefacts from 13th-century crusades are flanked by work from Damien Hirst. The food program tapped Big Apple powerhouses Major Food Group (Carbone, THE GRILL), who conjured an all-day deli, turning out Manhattan staples like bagels and lox, and a classic Italian-American red-sauce joint. What’s life without contrast?