Sitting on the north coast of this lush, tropical island, San Juan is the second settlement founded by European settlers in the Caribbean, and the oldest city under US jurisdiction. The stocky walls and watchtowers here have stood the test of time, repelling notable invaders – such as Sir Francis Drake – and the pirates who historically looted these islands. With massive fortresses, airy plazas and sheer Caribbean beauty, San Juan is a beach-blessed star of these turquoise waters. With more than 500 years of European history, Old San Juan gleams In Puerto Rico’s sunshine, with sugar-almond painted facades and ankle-testing cobbled lanes. Decorative balconies and varnished wooden doors add everyday artistry to streets, dripping with history. Soak up the culture at rum-fuelled parties and salsa dances on this Spanish-culture infused island, or recline into afternoon relaxation sessions on sensational slivers of gleaming sand. Kick back on the beach, or satisfy a lust for adventure by exploring sprawling mangrove forests. The magic of sea kayaking after dark here is an experience you won't forget. Break the waves with your oar, and watch as the waters illuminate with neon colour, as bioluminescence creates a mystical, peaceful spectacle. Pocked limestone cliffs and karst landscapes add rugged contrast to the serenity of the beaches, and you can walk into folds of the earth in sea-carved caves, or across cliffs to hidden views of the Caribbean’s expanse. Enjoy a taste of the island’s cuisine by sampling Mofongo – a local concoction of green plantains and chicken. Why not indulge and wash it down with an iced mojito, made from crushed mint and locally distilled rum?