Lisbon to Bridgetown

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.

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.

Bridgetown, the captivating capital of Barbados, combines faded colonial history, captivating tradition, and vivid white beaches plucked directly from your richest imagination of Caribbean perfection. Recently listed as a UNESCO World Heritage site, thanks to its beautifully preserved colonial architecture, Bridgetown’s mask of modernity covers a core of complex history and fascinating culture. Sherbet coloured buildings line up to overlook the waterfront of the Constitution River at the ‘The Careenage’ - where gleaming ships bob on the blue water, and peaceful strolls along a wooden boardwalk await. Stop for a sobering moment at the commemorative plaque honouring the people traded at this spot, when Bridgetown was the British Empire’s most important harbour, and first stop on the Transatlantic Slave Trade crossing. Just five minutes’ stroll from here is Carlisle Bay - a postcard-perfect place where you'll find crystal-clear, turquoise seawater glowing in the Caribbean sun, and a mile of soft white powder sand. A treasure trove for divers, the shipwrecks scattered below the shallow water’s waves are now inhabited by turtles and swirling, rainbow-coloured tropical fish. Head to the backstreets, where street food vendors serve up spicy chicken soup, barbecued pigtails and thirst-quenching coconut water. There are bargains aplenty to be had on Broad Street, where duty-free malls and souvenir stalls cram together, vying for your attention. Roebuck Street is the spot where one of the Caribbean’s favourite drinks, rum, was discovered - having been created here from the by-products of the island’s booming sugarcane trade. Nowadays, it’s lined with bars splashing every variety of the deliciously spicy dark libation imaginable into glasses. For a touch more culture, visit one of the oldest synagogues in The Americas - Nidhe Israel Synagogue, which was built in 1654. The adjoining museum tells the story of Barbados’ Jewish immigrants, who were instrumental in the island’s development.