Debod Temple in Madrid, Spain

Legacy of Old-World Iberia: Two-Week Historical Tour From Madrid to Lisbon

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist

Countries Visited

Portugal, Spain

Places Visited

Madrid, Segovia, Salamanca, Trujillo...

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Suggested Duration

14 Days

From Madrid to Lisbon, this luxury two-week Spain and Portugal tour will hop across the Iberian Peninsula and traverse the best of Castilla y Leon and Extremadura. The landscape is dotted with grand history from cities built by conquistadors’ wealth to local capitals that have maintained their glamour for millennia. Partially isolated from the world, the atmosphere here is doused in heritage and offers an immersion in cultural legacy.

Customizable Itinerary

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Trip Highlights

  • Discover the cities of the conquistadores with a day in Trujillo and two in Caceres as both cities offer an atmosphere that is unchanged since the glory days of the 16th century
  • Linger in the historical art scene of Madrid as you spend a day immersed in the world of Velazquez and Goya, Picasso and Dali
  • Explore an evocative collection of Roman relics, including the white arched bridge into Salamanca, the red-brick aqueduct that runs through Segovia, and the amphitheater and art left behind in Merida
  • Admire how the architectural styles have blended over the centuries, particularly in Salamanca, where the facades reflect a golden period that lasted more than 500 years
  • Journey to the heart of old-world Iberia during your time spent in the province of Extremadura, home of epic monasteries, elegant city squares, and historical chronicles stitched together through the quarrels of centuries of kings
  • Be welcomed to the Iberian Peninsula with two attractions on a monumental scale with Madrid’s royal palace and its softly illuminated main square
  • Complete your journey across the Iberian Peninsula in Portugal’s capital Lisbon that overflows with grand monuments and maze-like neighborhoods on the hills
  • Escape into the fairytale land of Sintra, the former royal sanctuary with a palace that is so old nobody knows when it was built

Detailed Description

On the isolated plains of Iberia is the legacy created when marauding civilizations decided to stay. Roman relics are astonishing in their scale, Renaissance, and Gothic cities remarkable in their golden stone detail. Dotting the wooded hills are fairytale royal towns and blissful monasteries while along the cobblestone streets you can feel the history of the conquistadors, art collectors, and aristocratic dreamers. From Madrid to Lisbon and across the plains, you will also find that history is not something found in a handful of monuments or stories. In this part of the Iberian Peninsula, you will find cities that reflect their ancient era, whether you are sipping local wine on a central square lit by iron lanterns or wandering through a maze of narrow streets packed with mystique.

This two-week luxury tour will follow the trail of the old kingdoms and conquistadors as you hop between Madrid and Lisbon via the historical cities of Castilla y Leon and Extremadura. The ten destinations featured on this itinerary have deep contrasts, each with their roots in a different century and a distinctive atmosphere, yet each is similar in their unique ability to celebrate a grand period of history. From those still dominated by Roman legacy to those that take you on a journey through 500 years of architectural styles, the focus is on an immersion in the history, rather than a touring of the sights. By spending your evenings on elegant squares, and taking your time in the lanes of the past, you get to feel what it was like when these cities experienced their days of glory.

Start with several nights in Madrid for an insight into the best of Spanish art plus a day trip to the white-walled 11th-century city of Avila. Move next to Segovia with its dramatic setting and Roman aqueduct, before two days spent inside the golden sandstone streets of Salamanca, which dates from somewhere between the 13th and 18th centuries. Stop at an incredible monastery in Guadalupe while on route to Trujillo, and then take a couple of days in Caceres, cities where so many conquistadors were born. Spend a day in first-millennium Merida before crossing the border to Portugal for several nights in capital city Lisbon with its mix of grand riverside districts and vibrant neighborhoods on the hills. You will travel with a mix of first-class high-speed trains and private chauffeured transfers, with local guides leading your discovery in each of the destinations.

Starting Price

$3,075 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.

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