Day 1 (AUG 20): Lisbon, Portugal

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-colored 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 neighborhoods - 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. Afterward, 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-colored 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-recognized location close by at Sintra, where a colorful 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 caramelized custard topping is the essential accompaniment to any coffee stop.

Day 2 (AUG 21): Day at Sea

Day 3 (AUG 22): Casablanca, Morocco

Immortal lines from the silver screen may have imprinted a warm, fuzzy visage of old Casablanca into our minds, but this thriving city is a curious example of what Morocco's modernity looks like. Glistening white art deco buildings line the wide pathways that sweep through Casablanca, as the sea sparkles like a thin mirage on the horizon. There's an aura of creativity amid Casablanca's culture and chaos, helping to make the city one of Morocco's most curious and compelling. The Hassan II Mosque took a staggering seven years and 10,000 artists to craft its legacy as the country's largest mosque, and to bring the world's tallest minaret to sky-high reality. A vision of cool-to-the-touch marble, cavernous prayer rooms, and intricate inlays, the mosque is extraordinary in scale and ambition. Retractable roofs let the sun flood in, while dizzying glass floors dazzle, and the blue Atlantic waves surge below your feet. After that humbling visit, stroll along La Corniche - where surfers glide across rough and tumble waves, and chic cafes offer front-row seats for sweet peppermint teas with a side of people-watching. Casablanca is a diner's city - boulevards laced with French-fusion restaurants, buzzy beachfront joints, and raw seafood bars provide gem-like offerings fresh from the boat. Those seeking a slice of that golden-age Hollywood romance can wander through the medina, with its unabashed ramshackle feel, and maze of alleyways punctuated with busy barber shops and butchers.

Day 4 (AUG 23): Tangier, Morocco

Set on the Maghreb coast, Tangier is Africa's outstretched hand to Europe. With its bustling markets and lively waterfront, this city on Morrocco’s north is an energetic and invigorating place and an exciting immersion into an incredible continent. The location, on the highly strategic narrowing of the Strait of Gibraltar, made Tangier a vital Phoenician trading town - and the resulting city is an invigorating mesh of cultures and curiosities. Part of the fun of Tangier is the well-rehearsed dance, as you dodge good-natured hawkers, and this is certainly a place to stroll with confidence and purpose. Delve into the mayhem of the walled Medina of Tangier for a rush of stimulation, as bartering and bantering echoes along the tight alleys. Crowded, noisy, and busy, you'll be sold to with a smile as you wander between stands of colorful spices, dried fruits, and fabrics in this authentic Moroccan marketplace. Refresh and escape the sun with a fresh orange juice - or a sip of mint tea. Close to the city, you can find the Caves of Hercules, a coastal hollow that opens at both ends. The Phoenicians cut a window in the shape of the African continent, which reveals views of the Atlantic's waves, and legend says Hercules rested within its confines. From Tangier, you can also venture inland to the Rif Mountains, where gorgeous Chefchaouen - a village of bright blue alleyways - waits. Punctuated by blooming flowers, the entire town is a beautiful, molded artwork of color, spilling down the mountain like a waterfall.

Day 5 (AUG 24): Cádiz, Spain

More than a hundred watchtowers gaze out across the waves surrounding this ancient Andalusian city. Sprinkled with evocative cobbled side streets, you'll explore 3,000 years' worth of history, while stumbling across palm-tree-lined plazas of shaded coffee sippers. Cádiz claims the mantle of Western Europe's oldest city, and every piece of architecture - and every wrong turn - offers a chance to discover fascinating new tales. Founded by the Phoenicians in 1100 BC, Christopher Columbus used the city as a base for his exploratory, map-defining voyages of 1493 and 1502. The port grew in importance and wealth as Cadiz's strategic location close to Africa's northern tip helped it blossom into a center for New World trade. Catedral de Cádiz, is a display of the city's wealth and importance, looming spectacularly over the Atlantic's waves, with cawing seagulls sweeping between its twin bell towers. Inside, treasures from the city's trading exploits in the West Indies and beyond - which helped fuel the growth of this historically prosperous city - are on display. Enveloped by ocean on almost every side, Cadiz has something of an island feel, and you can cool off from southern Spain's unrelenting sunshine on the sweeping golden sand beach of Playa Victoria. The two towers of the new El Puente de la Constitución de 1812 mark a contemporary landmark in this most ancient of cities, in the form of a spectacular new road bridge. Torre Tavira, meanwhile, is the most famous of Cádiz's army of watchtowers, and the highest point in the city. Reach the top for a view of the ocean fringing the city's expanse, and to learn about the towers - constructed so trading merchants could survey the harbor from their lavish homes. The Central Market is a chaotic place of bartering, where flashing knives dissect fresh fish. Stop in at the orbiting bars to enjoy tapas, freshly prepared with the market's produce.

Day 6 (AUG 25): Gibraltar, Gibraltar

A curious slice of Britain - picked up and plonked into the sun, sea, and sand of southern Spain - Gibraltar is a unique and historic peninsula, crowned by the iconic Rock of Gibraltar mountain. Bright red phone boxes gleam, Union Jacks flutter in the breeze, and cones of fish and chips are scoffed in the sun in this most British of outposts. At times a surreal and strange juxtaposition, you can be gazing at the African shoreline from the beach one moment, and carefully treading across the runway of a crammed-in international airport the next. Gibraltar's cathedral-like Rock towers 400 meters above the waves and the stark limestone mountain watches out across a narrow, strategic strait between the European and African continents. The pointed Rock is a symbol of this unique place, and you can hike it - or take the convenient cable car - to enjoy the views and meet the mischievous colony of Barbary macaques who live on its slopes. Europe's only wild monkeys roam free and loose on the mountain - so be sure to hang onto your sunglasses and cameras. The Siege Tunnels bring to life the struggles for this land, with the plucky British boring tunnels through the rock by hand, effectively converting it into a giant watchtower, capable of defending the distant territory. Natural caves inside droop with stalactites, while a squat Moorish castle stands proudly at its summit. Gibraltar packs a lot into this two-and-a-half square miles of territory, which has fallen under British jurisdiction since 1713. Grand Casemates Square is a sunbathed plaza, and drizzly old Britain feels a world away, as you sit back and sip ice-cold beers and cocktails in Gibraltar's historic center.

Day 7 (AUG 26): Malaga (Costa del Sol), Spain

Bathing in the Sunshine Coast's stunning subtropical climate, and laying out endless spectacular beaches, it's no surprise that Malaga is one of Spain's most popular cities. The already impressive cultural appeal of this holiday city has skyrocketed over recent years, and with a storied old town and Moorish fortifications, Malaga has a lot to offer. Nearby, you can recline on the renowned beaches of the Costa del Sol, or venture inland to discover the Moorish treasures of Granada and Cordoba. La Malagueta beach is Malaga's spacious urban beach, perfect for a sunbathe and a dip in the warm water, before enjoying seaside cocktails or seafood tapas in the restaurants nearby. Malaga and the Costa del Sol may be best known for glorious weather and beaches, but Malaga can now stake a genuine claim as an artistic powerhouse too. Visit the renowned Picasso museum - housed in the artist's birthplace - before exploring the freshly opened outpost of the Pompidou Centre. The art also spills out onto the streets in the colorful Soho district - splashed with vibrant street paintings. Known as La Manquita - or the one-armed woman - the city's cathedral rises over the historic old town. Its huge bell tower stands tall, but an accompanying second tower was never completed - hence the nickname. The Alcazaba fortress palace looms over the waterfront and forms a spectacularly preserved remnant from the era when the Moors controlled the Andalusia region. Discover more of the Arabic influence by visiting Granada's Alhambra palace, or Cordoba's La Mezquita mosque. Together with Seville's converted cathedral, the cities form Andalusia's Golden Triangle of Moorish wonders.

Day 8 (AUG 27): Cartagena, Spain

On the crossroads of mighty cultures, this Murcian port has endless ancient stories to share. A valuable natural harbor attracted many civilizations to this sun-bathed, southeasterly setting - following its foundation by the Carthaginians in 227 BC. Blending the imprints left by countless cultures on this global junction, the presence of everyone from the Vandals to the Phoenicians and Moors can be felt as you explore, walking between ruins and celebrated modernist architecture along Calle Mayor. Cartagena is crowned by the soaring Castillo de la Concepcion - rise to the stout castle aboard a panoramic lift. Inside, look through reams of archaeological treasures, or admire the rolling views down over the port and across the waters. Watch out for the electric blue peacocks who strut flamboyantly. Cartagena's emergence as a visitor destination coincided with a stunning discovery in 1988 - the bowl of a gloriously preserved Roman Theater. Enter to sit among the grandiose ancient venue, so evocative, you can't help but imagine the historic performances that have graced its stage. Wander the breezy waterfront, looking across the narrow strait towards Africa's distant haze, and spotting gleaming warships. Cartagena's perfect harbor means it has been one of Spain's oldest strategic navy positions since the 16th century. Settle to enjoy the joys of tapas in lively bars - sampling crisped paella, squid and honeyed-eggplant. Easter's Semana Santa festivities are typically lively here, as hooded processions, lavish floats, and somber fiery displays roll through the streets.

Day 9 (AUG 28): Palma de Mallorca, Spain

A rugged Mediterranean gem, arising out of the rich blue haze, Mallorca is a Spanish island of cuisine, culture, and sun-gorged beaches. Palma de Mallorca is the island's dominating capital and a sand-colored mirage of glorious buildings and living history. Conquered and liberated countless times over the years, since its Bronze Age founding, the city is your gateway to ceaseless Mediterranean beauty, buzzy markets, and intense flavors. Cafes and bars wait close to the sweeping coastline, where you can enjoy strong espressos to kick start the day, or splashes of red Mallorcan wines to round it off. Bicycles trundle up and down the promenade, which invites you to wander in the morning sunshine beside the waves. Dominated by the indefatigable form of Santa María cathedral, which looms over the city and coastline, Palma de Mallorca is drenched in history and culture. The labyrinth of the old town is a cobbled haven, which bustles with dripping ice creams and sun-lashed squares. Settle to try the island's superb cuisine, and savor local ingredients with an exceptional depth of flavor. Something about the sunshine here makes tomatoes extra sharp and delicious, while the seafood is consistently juicy and plump. The creation of the mighty cathedral, Le Seu, began in 1229 and was eventually concluded in 1601. A perfect encapsulation of Palma de Mallorca's blend of the historic and the contemporary, even Gaudi lent his hand to it, and the interior features a spectacular modernist take on the New Testament from artist Miquel Barcelo, which is painted across the chapel's walls. The splendid Royal Palace of La Almudaina fortress stands nearby, a left-behind Moorish footprint of square towers and Arabic archways that now serves as an official summer residence for the King of Spain.

Day 10 (AUG 29): Barcelona, Spain

The infinite variety of street life, the nooks and crannies of the medieval Barri Gòtic, the ceramic tiles and stained glass of Art Nouveau facades, the art, and music, the throb of street life, the food (ah, the food!) - one way or another, Barcelona will find a way to get your full attention. The capital of Catalonia is a banquet for the senses, with its beguiling mix of ancient and modern architecture, tempting cafés and markets, and sun-drenched Mediterranean beaches. A stroll along La Rambla and through waterfront Barceloneta, as well as a tour of Gaudí's majestic Sagrada Família and his other unique creations, are part of a visit to Spain's second-biggest city. Modern art museums and chic shops call for attention, too. Barcelona's vibe stays lively well into the night when you can linger over regional wine and cuisine at buzzing tapas bars.