Lisbon to San Juan

A glorious mosaic of beauty, freedom and authenticity, Portugal’s capital is a stirring artwork of a city. Known for the seven hills it spreads across, and its stirring fado music, Lisbon is a pastel-coloured blend of houses and beautiful tile artworks - and this creative city strikes a perfect harmony between natural and manmade beauty. Stroll along Alfama's steep, cobbled streets as you explore one of the city’s oldest neighbourhoods - where each house and door could be its own photograph. Look for the decorative tiles, with the distinctive blues and whites of Azulejo ceramics, and visit the dedicated museum to learn more. Afterwards, wind up to São Jorge Castle, where views out across Lisbon’s red rooftops unravel. Just one of many majestic viewpoints, you can also seek out Miradouro da Graça for perhaps Lisbon's finest panorama, with the copper-coloured suspension bridge stretching over sparkling water beyond the sea of buildings. The elegant Tower of Belém rises in the Tagus estuary and is a historic defender of these shores. The grand, carved cloisters of Jerónimos Monastery spread out close by, and there's another UNESCO recognised location close by at Sintra, where a colourful town is set amid thick gardens and towering mountains - capped by the royal Pena Palace. Later, relax and take a quick break to drink Ginjinha, a cherry liqueur made from chocolate cups instead of coffee. Lisboetas have a sweet tooth, and the famous Pastel de Nata's crumbling pastry and caramelised-custard topping is the essential accompaniment to any coffee stop.

Providing a gorgeous green welcome to sailors venturing on the long journey across the Atlantic, Ponta Delgada’s shoreline is a reassuring sight, as it emerges into view. Sat on Sao Miguel Island, the largest of Portugal’s Azores islands - which wait on an outpost of western Europe, some 1,100 miles from the mainland. Ponta Delgada is the island’s largest city, and a place of spectacular volcanic vistas, steaming hot springs and impressive landscaped gardens. The city’s signature trio of arches welcomes you to Ponta Delgada, and its island of verdant volcanic contrasts. Wander between monochrome churches like the Gothic Church of St. Sebastian, and up to the Convent and Chapel of Our Lady of Hope – which houses the revered icon of Christ that is paraded through the streets annually, and believed to have miraculous powers by locals. Or, head for beaches offering sanctuary on charcoal-coloured sands, or the tropical António Borges Botanical Gardens, where tropical plants add extra shades to the Green Island's scenery. Now extinct, the mighty Caldeira das Sete Cidades is a truly awe-inspiring sight - and the colossal collapsed volcanic caldera blooms with lush greenery and scattered wildflowers. The vast crater has been taken over by a glowing, picturesque lake, which reflects the blue sky above. A full three miles wide - and with a circumference of eight miles - it’s a vast panorama to take in. The Lagoa de Fogo – or Lake of Fire – is another of the island’s calderas – rise up to see the crumpled scenery encasing a beautiful lake. São Miguel Island’s geothermal activity has practical uses too, and you can harness the powers to unwind any tired muscles after a long day, by sinking into the hot springs of Poca Da Dona.

Cherry red roofs, yacht-sprinkled bays and a sophisticated French flavour all add to the gorgeous Caribbean allure of Gustavia. The island's capital rolls around a horseshoe-shaped harbour, where gleaming yachts hover and fancy boutiques, bars and restaurants fizz with life and clinking cutlery. Head up to red and white Gustavia Lighthouse to look down over the revered waters, which attract many a celebrity guest and diving enthusiast to these shores. Christopher Columbus was the first European to discover this volcanic island in 1493, giving it the name St Barthelemy in honour of his younger brother. The island has a unique history as a Swedish colony, following a deal with the French King Louis XVI to exchange the island with Sweden for better trading rights. It was returned to French control in 1878 and is now a French Overseas Collectivity. Learn more of the Swedish legacy at Fort Karl - which sits on a 29-metre-high hill above Shell Beach. The fort now lies in ruins, but you'll meet wandering iguanas, and the views down of sweeping sea and emerald coastline are some of the island's finest. Down below, a delightful spread of tiny pebbles and shell fragments are scattered like confetti and lapped by crystal-clear water. A little exploration uncovers countless other glorious beaches and natural wonders. Colombier Beach is a little out of the way but cradles silky-smooth sands and typically turquoise waters. If you have chance, find somewhere to settle and sip fruity rum cocktails as the sunset flares across the waves.

Glowing turquoise waters lazily bowing palm trees and pristine white sand beaches – it's all waiting for you in Jost Van Dyke's picturesque Caribbean splendour. Slip off your shoes you won't be needing them too much in these parts as you wander soft heavenly sands and paddle out into impossibly clear waters. If this is your first experience of the Caribbean's splendour you may be a little sceptical about the reality of those famed shockingly bright colours that you see in photographs. Splash into water that glows with a bright teal hue and is blotched with occasional swells of deeper royal blue. Snorkellers will adore the explosions of colourful fish beneath the waves. White Bay is a slice of island perfection with a neat hill of trees framing a sandy sweep of shaded beach bars. The wander up to Majohnny Hill is the most exertion needed to explore this four-square-mile island and it's worth it to see the heavenly beaches emerging from tranquil waters below. Even the natural sea formations here encourage you to unwind with waves gurgling and frothing over the rocks to create Bubbly Pool a natural jacuzzi. Jost Van Dyke has a reputation as the off-the-radar island getaway of choice for celebrities like Keith Richards. A lot of that comes down to the calypso charm of its rustic beach bars - especially the legendary Foxy's Bar which is run by island legend Foxy Callwood. Rum-drenched cocktails and icy buckets of beach beers await - sure to get you into the island’s party spirit in no time.

If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiating out from the bay on the Atlantic Ocean that was discovered by Juan Ponce de León. More than a third of the island's nearly 4 million citizens proudly call themselves sanjuaneros. The city may be rooted in the past, but it has its eye on the future. Locals go about their business surrounded by colonial architecture and towering modern structures.By 1508 the explorer Juan Ponce de León had established a colony in an area now known as Caparra, southeast of present-day San Juan. He later moved the settlement north to a more hospitable peninsular location. In 1521, after he became the first colonial governor, Ponce de León switched the name of the island—which was then called San Juan Bautista in honor of St. John the Baptist—with that of the settlement of Puerto Rico ("rich port").Defended by the imposing Castillo San Felipe del Morro (El Morro) and Castillo San Cristóbal, Puerto Rico's administrative and population center remained firmly in Spain's hands until 1898, when it came under U.S. control after the Spanish-American War. Centuries of Spanish rule left an indelible imprint on the city, particularly in the walled area now known as Old San Juan. The area is filled with cobblestone streets and brightly painted, colonial-era structures, and its fortifications have been designated a UNESCO World Heritage Site.Old San Juan is a monument to the past, but most of the rest of the city is planted firmly in the 21st century and draws migrants island-wide and from farther afield to jobs in its businesses and industries. The city captivates residents and visitors alike with its vibrant lifestyle as well as its balmy beaches, pulsing nightclubs, globe-spanning restaurants, and world-class museums. Once you set foot in this city, you may never want to leave.