Portugal & Spain Luxury Vacation

What to expect on this itinerary
This handcrafted journey will take you through the legacies of Iberia, as you trace the route of the great explorers and the unprecedented civilizations. From Lisbon to Madrid you’ll enjoy an in-depth exploration of what has made Iberia so special including azulejo tiles, olive oil and wine, Moorish design, fado, and flamenco, plus art, architecture, and passion. These 11 days will celebrate the delicate and the decadent, to create a unique impression of a region that remains as authentic as ever.
Customizable Itinerary
Lisbon – Evocative Impressions of the Portuguese Capital
Upon your arrival, Lisbon will delight you from the first impression. Almost every building seems to hold you captive and every plaza has its own energy and style, which will encourage you to linger. Each neighborhood presents a different side to the city, and the contrasts between Baixa and Alfama will be just one example on your first day. You’ll be greeted at the airport by a guide and transferred to a 19th-century palace turned guesthouse, where the gardens are a tranquil place to relax and unwind. Spend the late-afternoon hours on an orientation tour, as you stroll through the Portuguese capital and get to know what makes it so unique. For the evening meal, you will have a choice of legendary Lisbon chefs, who each serve an iconic local dish at the vibrant Time Out Lisbon Market.
What's Included:
Lisbon – Manueline Beauty and the Haunting Art of Fado
Lisbon – Day Trip to the Royal and Poetic Landscape of Sintra
Evora – Exploring the Vast Beauty of Alentejo
Seville – Gourmet Olive Oil Tasting and a 2000-Year History
Seville – Strolling the Old City and Learning the Flamenco
Granada – Pre-Medieval Villages and the Jewel of the Moors
Granada – The Extraordinary Legacy of the Moors
Madrid – Delicate and Decadent – Two Contrasting Spanish Cities
Madrid – An Art Historian Leads You Through the Prado and a Foodie’s Tour of the City
Madrid – Departure
Trip Highlights
- Explore art for the soul by learning the flamenco and experiencing a fado performance, elegiac expressions from Andalusia and Lisbon
- Savor the architecture of the ages as you get up close with the Manueline style of Belem and the exquisite design of the Moors
- Travel into the royal legacies of Spain and Portugal with a day in Sintra complemented by Europe’s largest palace in Madrid
- Escape into the villages of yesteryear, from Andalusian Ronda to medieval Evora, both timeless insights into a place and century
- Taste your way through the best of regions, like gourmet olive oil near Merida and an Andalusian tapas crawl
- Visit some of the great art museums, including the Calouste Gulbenkian collection in Lisbon and the Prado
- Wander along the lanes of history in vast old quarters like Seville and Granada
- Gain a detailed insight into local design, such as azulejos tile production as an expert guide leads you through the Alhambra
- Explore with private guides and stay in a handpicked collection of Iberia’s boutique hotels
Detailed Description
Iberia’s great legacies are impossible to replicate, from the soulful passion of flamenco and fado to Manueline and Moorish design, with poetic palaces and azulejos tiles. In both Spain and Portugal, you will find destinations that don’t merely preserve the past but maintain history as the proud starting point for now. Hilltop villages still move to a medieval beat, exotic smells drift over the landscapes, and the cities are cast in swathes of color. This handcrafted tour of Spain and Portugal goes in search of the legacies that are too unique to copy, those legacies that haven’t been exported but are used as tenets for the 21st century.
Travel from Lisbon to Madrid on this 11-day journey that is a celebration of time and space. You’ll follow in the footsteps of the explorers of old, trace the style of the great pre-medieval civilizations, uncover the legacies of art and design, and encounter some of the planet’s greatest architecture. Seven UNESCO World Heritage Sites are part of the route but this isn’t a tour of museum pieces, more an expedition to destinations where the history is very much alive. Watch how hand-painted Portuguese tiles are created, learn the art of flamenco and fado, stay at ageless properties, and taste your way through tradition. All tours will be private and you’ll travel mostly by privately-chauffeured vehicle, other than the high-speed train to Madrid.
Start with an eclectic experience in Lisbon consisting of a fado performance, private art collection, Manueline architecture and the royal palaces of Sintra. Then, cross the Alentejo region to visit Setubal and Evora, two very different impressions of past legacies. Jump across the border to Roman Merida and enjoy private olive oil and wine tasting on route before you lose yourself in the city of Seville. Flamenco has its home here, as do conquistadors stories. Travel across Andalusia, where the legacy of the Moors is found in Ronda, Granada, and Cordoba. Each destination will reveal a wide sphere of history and design. Then take the train to Madrid, where the Spanish capital will be a grand final stop for this handcrafted private tour.
Starting Price
$9,900 per person (excluding international flights)
Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.
What's Included
- Accommodations
- In-country transportation
- Some or all activities and tours
- Expert trip planning
- 24x7 support during your trip
Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.
Verified Traveler Reviews
Based on 3558 reviews
I couldn’t say enough positive things about Zicasso's travel specialists, from top to bottom. Airport service was excellent, daily guides were excellent, and management was excellent, a rare combination.
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Zicasso’s travel specialist is absolutely A+—BEST IN CLASS!!!
Planning the trip with him was delightful. He listened carefully during our initial call and we had several conversations and emails to design the itinerary. His recommendations were spot-on and he was very flexible and supportive of our requested modifications, and incredibly responsive. It was an excellent experience planning the trip!
We LOVED the travel app he uses—it was truly helpful during the time we were in Spain. Everyone in our family really appreciated it!
When on the ground in Spain, we were in texting contact with him throughout the trip, including requesting additional add-on experiences the day before, which he made happen, and other small and meaningful adjustments! All of the drivers and guides selected were on time, professional, with deep knowledge, and delightful and fun to be with.
We absolutely loved our trip and it was just fabulous to work with a travel partner as excellent as him!
We highly recommend!!
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Zicasso’s travel company was very professional; great communicators and super-responsive. We would highly recommend using their services.
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My trip to Portugal was absolutely amazing. Zicasso’s travel company went above and beyond my expectations. The itinerary was amazing and all the guides were incredible. Everything was on time, the accommodations they booked were five-star and in great locations, and enough time was built in for me to be able to explore on my own. I feel the cost was well worth the value. Should I ever go back to Portugal, I would certainly use this travel company again, and I would highly recommend them to anyone looking to have a great experience on a Portugal vacation.
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Zicasso’s tour company did a fabulous job in providing us with an exceptional Portugal vacation over the Christmas and New Year’s holiday. They provided us the 24/7 coverage they promised over the holidays without a glitch, including addressing our weather-delayed arrival and multiple itinerary updates that this required without missing a step. We will be using this travel company again and recommend them without reservation.
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We enjoyed a relaxing trip to Portugal in December 2025. Zicasso’s travel company and their team were awesome, very present, tailored the trip based on our needs, and we got to explore much of the country, given the time of the year. The itinerary suggested was wholesome, relaxing, and covered most of the sights and sounds. I would highly recommend them to friends and family.
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