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.

Bedecked with dramatic cliffs, fertile mountains and sun-gorged beaches, Madeira is a lush, colourful island of plants, paradise and Portuguese-flavoured pleasures. Bathing in year-round sunshine, Funchal - the lowkey capital of Madeira - is perfect for slowing the pace, and toasting the thrilling scenery with a bottle of the island's famous wine. Narrow, cobblestone streets line the old town, where whitewash buildings, iron-wrought balconies, and tiled patterns carry echoes of Lisbon. Rua de Santa Maria is the city's oldest street, and the doors have been vividly painted by local artists. Sit for a drink, to sample your choice of Madeira's renowned wines - Boal is the ideal option for those with a sweeter tooth. You'll also find Corpo Santo Chapel here, one of the few remaining buildings to have survived from the 15th century. Blossoming parks and gardens splash colour around, and the sweet smell of pollen lingers in Parque de Santa Catarina. Look out over Funchal harbour between the fountains and blooming flower beds, as ducks and swans enjoy leisurely days on the lake. Madeira Botanical Garden waits in the hills over the city, along with Palhero Garden – a sophisticated and elegantly landscaped English garden, 500 meters above sea level. For an even more dramatic view of this gorgeous setting, head up to Cap Girao – a rusty-red cliff with a cable car strung up to its sheer drop. The cliff falls away vertically to the vivid blue waters below. Or head down to the sea, to enjoy Funchal's gorgeous pebble beaches rustling, framed by colossal, craggy cliffs.

Volcanoes dominate the island of La Palma. The island sits over a hot spot in the Earth’s crust. Beginning on the seabed 4,000 metres below sea level, the volcanoes grew to emerge above the waves and through the clouds to form a mountainous island. The highest point is 2,423 metres (7,950 feet) above sea level. The peak flanks La Caldera de Taburiente, a giant collapsed volcanic crater with a canyon exiting it. The ridge extending south of the Caldera erupted as recently as 1971, when Teneguía volcano sent slow lava flows to the sea. Roads reach lookouts where further exploration on foot begins. The Spanish port town of Santa Cruz de la Palma began in 1493 and supported the sea route from Europe to the New World. In the 16th century Santa Cruz was the third most important port in Europe, after Antwerp and Seville. But it attracted trouble. The pirate Françoise Le Clerc or ‘Peg Leg’, ransacked the town in 1553, leading to the construction of the forts Castillo de Santa Catalina and Castillo de la Virgen. History buffs should walk the cobbled town streets amongst colourful colonial buildings. Several vegetation zones are traversed if you travel up the mountains. Dry coastal scrub gives way to a woodland with large Canary Palms, a plant now grown worldwide. Higher slopes catch moisture from clouds, creating the lush laurel zone of semi-tropical forest. Next is a Canary Pine forest and finally an alpine zone of shrubs. The highlight here is the tall pink flowering spikes of the La Palma Bugloss.

Although this busy port city is smaller, quieter and less attractive than Las Palmas in Gran Canaria, Santa Cruz has its own share of elegant monuments. Until 1837, the island's capital was La Laguna, not Santa Cruz, so there are only a few of the buildings in the city center that are any older than that. At the busy Plaza de España, there are several pedestrian streets leading north and to the area west of the port, where you'll find the city's stunning auditorium and maritime park. A real highlight of the city are its ramblas, long tree-lined boulevards that fall steeply from the north end of the city to the sea.

Located 300 miles (483 km) off the coast of West Africa, the Cape Verde archipelago comprises ten islands and five islets, most of them of volcanic origin. They are divided into the windward and leeward groups and cover an area slightly larger than Rhode Island. Colonised by the Portuguese in the 15th century, they first settled on the island of Santiago to the south of São Vicente and established the town of Cidade Velha. It was from here that the main slave trade developed between the Cape Verde Islands, Europe and America. While Praia on the island of Santiago is the archipelago’s largest and capital city, Mindelo, with its brightly coloured colonial buildings, is considered the island’s prettiest town. It boasts an excellent deep-water harbour, Porto Grande, which is in close proximity to Mindelo. The official language is Portuguese, while the national language is Crioulo, a Creole dialect of archaic Portuguese mixed with many African elements and adapted English words.

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.

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.