Two-Week Best of Iberia: Spain and Portugal Itinerary

A 16 day trip to Portugal & Spain 
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The unforgettable highlight of Iberia is the contrasts that are discovered between regions and destinations. Everywhere has its distinctive style and atmosphere, and each is made unique by historical icons and cultural traditions. This handcrafted tour celebrates seven idiosyncratic destinations in Spain and Portugal to connect everything that makes Iberia so alluring: food and wine, art and architecture, urban wonders, rural charms, compelling history and contemporary energy. 

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General Information

Detailed Itinerary

Places Visited 

Madrid, Playa Mayor, Granada, Alhambra, Seville, La Giralda, Alcazar, Lagos, Algarve, Meia Praia, Lisbon, Baixa, Alfama, Belem, Porto, Douro Valley, Santiago de Compostela, Galicia, Santiago Cathedral, Barcelona, Catalonia, La Sagrada Familia, La Rambla, Barrio Gothic

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Madrid – Coffee on the Terrace and Tapas in the Streets

Madrid is the perfect introduction to the Iberian Peninsula. Sip coffee on an al fresco terrace while admiring the grandeur of an 18th-century plaza. Wander past dazzling palaces, and then continue to narrow alleyways full of charm and intrigue. Take a stroll through streets that smell of chocolate and churros. As you explore, you will marvel at the tranquility around you as Madrid is far more laid-back than the other capitals in Europe. Madrid is a city that is emblematic of the wider Iberian experience with so much to see and do, but such a wonderfully relaxed rhythm to guide you at every turn.

You will be picked up from Madrid’s international airport and transferred to your boutique hotel in the heart of the city. The afternoon will be at your leisure, and there are many outstanding attractions within walking distance, including the royal palace and the Prado, Spain’s pre-eminent art museum. In the early evening, you can head out on a guided tapas crawl for a journey that will introduce many Iberian flavors. Each tapas bar has a specialty that could come from any corner of the country, so that you can sample authentic Basque pintxos, paella bowls from Valencia, Galician octopus, tasty pork stews from the Castilla plains and cheese from La Mancha – all on a single street. The outdoor terraces are also a great introduction to informal Iberian dining.

What’s Included: airport transfer, accommodation, tour

Days 2 – 3: Granada – The Evocative Legacy of the Moors

Granada is not postcard perfect, which is just one of the reasons it is such a unique destination. The final stronghold of the Moors is liberally filled with ancient art and architecture including the grand Mudejar palaces that stand above whitewashed lanes, old mosques that have become churches with mysterious décor and almost every doorway is a photograph. But more than just beautiful Moorish relics, Granada has a rhythm and a soul that is quick to impress on visitors. You can feel it in the tiny cafes, smell it on neighborhood streets, and hear it when church bells are followed by the elegiac Islamic call to prayer. You will be transferred to the airport for an early morning flight to Granada, where your hotel is within the pedestrianized center of the city.

A local guide will take you on a private tour to narrate a colorful history as you wander down lanes that are also full of the present. You will hear of fables and riddles that only Granada knows the answer to. You can explore a mixture of Arabic and bohemian subculture, and then spend the afternoon in the city’s ultimate icon, the Alhambra. Few buildings in Europe are as exquisite, and the mix of architectural styles reflects an almost mythologized past that takes half a day to explore fully. The next day is free, and Granada is a welcoming city that really rewards anyone who explores without a map. You may choose to make a day trip to UNESCO World Heritage Baeza and Ubeda rather than spending the day in Granada, but you can follow your own whims.

What’s Included: accommodation, airport transfer, domestic flight, tour, breakfast

Days 4 – 5: Seville – Enveloped by the Vibrant Colors of the Past and Present

A rural road weaves across the Andalusian plateau, hopping between white villages perched high on the cliffs. These are the Pueblos Blancos, the Moorish villages built in inaccessible locations to withstand pirates and pillagers. They are idyllic places to explore on the road between Granada and Seville and traveling with a private guide, you will make a leisurely journey through the heart of Andalusia to discover a heritage that has been expertly preserved. Wander to Mudejar castles, discover houses built into caves, inhale the silence that prevails, and feel the soothing serenity of a wild and remote route. You will have lunch in one of the villages and arrive into Seville around late afternoon, which leaves just enough time to freshen up before getting involved on the vibrant city streets.

Seville has an old historic center larger than almost any other in Europe. But Seville is also about the here and now, a city of effervescent energy that implores you to keep discovering. The next day, a local guide will take you to both the famous sights and the unknown attractions, picking a route from the cathedral to hidden plazas and alleyways of Andalusian life. The afternoon will be at your leisure before a unique tapas and flamenco experience. Seville is the home of the musical art form: a guitar stirs, a melancholic voice wobbles as it cuts through the air, the dancer twirls with effortless elegance, and you will sit transfixed by the show. Tapas is served throughout the three-hour flamenco performance as Andalusia is also the true home of this culinary style.

What’s Included: accommodation, tour, breakfast

Days 6 – 7: Lagos – Charms of the Cliffs and Tranquility of the Coast

After the energy of Andalusia will come the tranquility of the Algarve, the old Moorish stronghold on the southern coast of Portugal. Villages are almost uniform in their whitened facades while marble city streets have been polished smooth by centuries of footsteps. It will be a half-day drive from Seville to Lagos, and the views will be incredible as you wind along sandstone cliffs, travel through cute rural towns and stop to watch the waves crash down below. Lagos is one of the largest Algarve towns, and while it is tailored to modern vacation tastes, it is also firmly rooted in tradition. You will be staying at a small coastal hotel just outside the city with a suite that overlooks the ocean. Within a two-minute walk, you can be standing on golden sand that continues uninterrupted for three miles.

The mysterious Algarve coastline provides a compelling experience the following day. The sandstone cliffs are crumbling as waves and wind create a unique series of caves and holes. Entire sections have broken off, leaving pinnacles and peaks that stand isolated in the ocean. Rugged cliffs have created beaches inaccessible by land, so you can choose between a boat or kayak tour and explore this remarkable coastline in the morning, entering up to a dozen caves as well as stopping at a deserted beach. Compared to the boat tour, the kayaking requires more effort but allows you to go deeper into the caves. The afternoon is at your leisure, and there are various beaches within easy reach of Lagos.

What’s Included: accommodation, transfer, tour, breakfast

Days 8 – 9: Lisbon – A Capital City With Many Styles and Atmospheres

On a high-speed train, you will cut north through Portugal, crossing the beautiful Alentejo plains. Tiny villages stand amid grape vines, castles watch down from the highest hills, and there will be a faint sense of wilderness seen through your train window. The train arrives in the center of Lisbon, and you will be greeted by a representative for the ten-minute walk to your boutique hotel. Another advantage of Portuguese train travel is that you can depart and arrive so close to your accommodation. Go for a traditional Lisbon lunch with your guide and discuss the city’s history and heritage. Your guide will then tailor the rest of your time in Lisbon to your interests. The city is too big to see it all, however, with a couple of days, it is incredible how many contrasting experiences you can include.

Every corner of Lisbon has its own atmosphere. Belem is full of grand monuments and iconic examples of the Manueline architectural style. Alfama is packed with energy and color, an old working-class neighborhood that is becoming quite fashionable. Bairro Alto is full of surprise, a maze of lanes that never disappoints. In Baixa, you will see some of Lisbon’s celebrated attractions, while in nearby Sintra, you will find a romantic old-world atmosphere. Public transport is the quickest way to travel, and it is comfortable with your private guide. Take a tram across the seven hills, then take a train to a seafood restaurant made famous by royalty, and embrace the atmosphere as you travel on your own two feet. Lisbon is such a distinctive city that it really requires a private guide and an individualized program. Lunch is included on both days, and the guide can make dinner reservations based on your preferences.

What’s Included: accommodation, transfer, train, tour, breakfast, lunch

Days 10 – 11: Porto – The Iconic Blue of Porto and the Vineyards of Douro

The train to Porto takes less than three hours, and your first impression will be otherworldly. Mosaics of blue ceramic tiles are the trademark of Porto and cover the exterior of many buildings. The most magnificent mosaic fills the train station, a scene painted on individual blue tiles and then pieced together to cover more than 150 square meters. As in Lisbon, your centrally located hotel is just a few minutes walk from the station, and a representative will assist with carrying your bags. You will be staying within the UNESCO World Heritage part of the city, with a balcony looking out on the Douro River and the port cellars beyond.

Spend the next day getting to know Porto. The mosaics that shimmer in the afternoon sun, the cobbled streets that excite an inquisitive eye, the terraces and traditions that seem omnipresent are all yours to explore. Porto is a relatively compact city, and you can explore many neighborhoods and attractions in a single afternoon. Of course, this being Portugal, you will explore at a relaxed pace, and there will always be time to stop for an espresso or energizing glass of port. With your private guide, you will also cross the river to the famous cellars to admire the endless rows of barrels, inhale the musty scent of oak aging, and then taste the vintages that make Port famous. You will end the day with a dinner reservation at an award-winning restaurant perched just above the water.

Explore a different UNESCO World Heritage Site the following day. On a private tour, you will meander into the Douro Valley. Baroque buildings stand amid ancient vineyards, castles, and palaces are left in a redolent state of ruin, lavish green landscapes lead you down towards the Douro River and its soothing charm. Spend the morning on the roads, and then stop at two vineyards. One is for tasting the variety of wines produced here, the other for a picnic and wine tasting surrounded by vines. You ca then travel back to Porto on a Douro River cruise, on a gentle journey beneath cliffs and vines.

What’s Included: accommodation, train, transfer, tour, breakfast

Days 12 – 13: Santiago de Compostela – A Cathedral City Frozen in Time and the Style of the Galicians

The far north of Portugal is the country’s cultural heart and where cities carry their history with pride while preserving the past with stoic dedication. Braga, the magnificent city of churches and saints and Guimaraes, the first Portuguese capital, where architectural opulence lines the streets, will engage your senses. On the road north, you can also stop at small market villages with the exact village dependent on the day you travel, as each hosts a market once or twice a week so you will time your arrival accordingly. It is an incredibly beautiful drive north into Spain as you cross over hills that will begin to feel more and more remote. Descending into Galicia, you can sense the change in rhythm and tradition as this is Spain’s most old-world region, and you will have a chance to stop at some of the cute fishing villages along the coast. The world’s finest grilled octopus is served here, and it is so fresh and so abundant that a plate comes free with almost every drink you order.

Your base in Galicia is Santiago de Compostela, an ancient cathedral city built upon the burial place of Saint James. It is the pilgrimage destination of the Camino de Santiago, a city where cathedral bells ring proud and true throughout the day. You will be led around by your guide, as Santiago de Compostela is a jigsaw piece of architectural styles. Romanesque, Baroque, Gothic, Renaissance styles are all here, held together in harmony by the unwavering hue of the local sandstone. Your afternoon is free, and you may choose to take a walk into the surrounding hills for stunning views over the city as the line of pilgrims make their daily arrival.

What’s Included: accommodation, tour, breakfast, lunch

Days 14 – 15: Barcelona – Beyond the Modernistas: Insider Discovery of the Catalonian Capital

Much like Lisbon, Barcelona is a city without a single defining image. Fly here in the morning to meet your private guide, an insider who will customize your journey of discovery. The work of Gaudi often feels unmissable, his Sagrada La Familia and Park Guell icons of the city. But Gaudi was not the first Modernista, and your guide can take you to the works of his master, the astonishing public buildings of unusual design. Take a stroll through Barrio Gothic, and you will find a Romanesque past. Follow this paradigm further by traveling out to a monastery on the outskirts of the city, where choir song has been repeated every lunchtime for many many centuries.

Explore the opulence of Eixample, where Modernista houses stand above tree-lined boulevards and designer shops. Spend a morning on a terrace loved by locals, an afternoon on the coast, then an evening at a palace overlooking the city. But these are just suggestions as your guide can make a program to suit, handpicking destinations that reflect your interests: art, history, wine, culture, architecture or anything more niche. Other options include visiting other parts of Catalonia, with half and full-day routes able to piece together a series of destinations.

What’s Included: accommodation, international flight, transfer, tour, breakfast

Day 16: Barcelona – Departure

Enjoy a day at leisure with your baggage safely stored at the hotel. Barcelona is a city full of attractions and experiences, and you can enjoy every minute until your plane departs. A private airport transfer is provided, and the hotel offers facilities for you to freshen up as needed before your departure.

What’s Included: airport transfer, breakfast 


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.