Portugal, Spain & Italy Itinerary: 16 Days of Discovery

The beautiful city of Lisbon lies draped across a string of seven hills on the western Iberian Peninsula and is the westernmost and oldest city in western Europe. Its long and tumultuous history has resulted in an aesthetic characterised by a haphazard combination of old and new; however, the aesthetic chaos of Lisbon only adds to its appeal and its undeniable charm. Bright yellow centenarian trams rattle their way up steep, tree-lined, cobbled streets; ornate ironwork balconies overrun with bougainvillaea sit above elegant outdoor cafes housed in ancient whitewashed, red-roofed stone houses; and a flurry of detailed mosaics decorate the sidewalks. Ancient statues adorn grand squares and hidden gardens. A diverse culinary scene, a plethora of fascinating museums, and numerous castles make it easy to see why Lisbon is one of Europe’s most misunderstood and underrated cities.

Set on Portugal’s coast in the southern Algarve region, the once-sleepy fishing village of Albufeira has evolved into one of the area’s most alluring and vibrant holiday destinations, thanks to its outstanding beaches and dramatic scenery and lively social scene. There are over 20 beaches to choose from in Albufeira, including the main beach’s vast, crescent-shaped expanse of fine, pink-gold sand fringing a turquoise bay and sheltered by rugged cliffs. The streets of the old town behind it are frequented by street performers and scattered liberally with shops, bars and restaurants. On the glittering Albufeira strip, you will find some of Portugal’s wildest nightlife venues, including the renowned Kiss club, which usually opens after midnight and pulsates till after dawn.

The Algarve’s southernmost city, Faro, has an elegant marina backed by a historical quarter dotted with white-washed Portuguese buildings, stately Catholic churches and age-old Moorish architecture. Its atmospheric squares and boulevards are paved with white and grey stone and lined with boutiques, designer stores, cafes and bars. There is no shortage of entertainment in this university town - it has a lively nightlife and a thriving arts and culture scene that caters to a wide array of audiences. There is plenty of opportunity for swimming and sunbathing on the area’s golden coast, and nature lovers will be in their element in the nearby Ria Formosa Reserve, with its incredibly biodiverse lagoon and coastal zone.

Spain’s enormous central capital, Madrid, lies on the River Manzanares and is a city of contrasts. Historical monuments like the impressive Royal Palace stand in stark contrast to state-of-the-art skyscrapers; masterpieces by Picasso, Dali and Velazquez adorn the walls of the city’s world-class galleries alongside contemporary modern works; local chefs display a passion for Spanish food at traditional eateries while chic fusion restaurants operate next door. Madrid’s real attraction lies in the seductive lifestyle of its hedonistic inhabitants; indulging in tapas, hunting for treasures at the El Rastro flea market or partying the night away in one of the many lively nightclubs. Make sure to soak up the vibrant street life of the grand, historic Plaza Mayor, Madrid's central square, and spend a leisurely afternoon on the landscaped lawns at the Parque del Buen Retiro.

Valencia, a seaside city bursting with energy, offers an unbeatable mix of old-world charm and futuristic architecture. Home to the legendary paella, Valencia invites you to revel in its culinary delights, from the bustling stalls of the Mercado Central to the flavors of the local tapas bars. As you wander through the historic streets, discover the awe-inspiring Valencia Cathedral and the silk exchange, a UNESCO World Heritage site.

The City of Arts and Sciences, an architectural marvel, showcases Valencia’s modern edge with interactive exhibitions and a stunning oceanographic park. Whether you’re lounging on the golden sands of Malvarrosa Beach or losing yourself in the Fallas celebrations, Valencia promises a vibrant and diverse experience that captures the essence of Spain.

The vibrant metropolis of Milan is the capital of Italy’s Lombardy region in northern Italy. Always at the forefront of international fashion, Milan’s sleek, glamorous facade has earned it a reputation for superficiality and excessive consumerism. However, beneath the surface lies a treasure trove of historical and architectural wonders—from its magnificent Gothic churches, Baroque mansions, and Art Nouveau palazzos to the striking modern skyscrapers of the Porta Nuova financial district. Must-see landmarks include the spectacular Milan Cathedral (Duomo), the glass-vaulted Galleria Vittorio Emanuele II, and of course, La Scala—one of the world’s most renowned opera houses. Milan offers something for everyone: those in search of high-end designer shopping will be more than satisfied, as will visitors interested in fascinating historical sites and extraordinary architectural achievements.