Best Road Trip Route for a Spain and Portugal Itinerary

A road trip lets you enjoy winding coastal roads and hidden gems at your own pace while enjoying the culture, food, and scenery along the way. At I Spy Spain, we’re all about helping travellers make the most of their trips. Need a little direction? Here’s a sample 14-day Spain and Portugal itinerary to inspire your adventure! All transportation is provided, so you don’t have to worry about

Day 1–3: Madrid – Your tour begins at Madrid Barajas Airport, where a hotel transfer will take you to Hotel Pestana Plaza Mayor to check in and freshen up. On the second day, explore Madrid on a 2.5-hour Segway tour starting at Plaza San Miguel, followed by lunch at Casa Lucio nearby. On the third day, start with a guided tour of El Prado, then enjoy lunch at Adrede before some free time to wander local streets, shop, or visit El Retiro Park.

Day 4: Toledo & Caceres – Begin the day with a tour of Toledo, followed by lunch at a local restaurant, then drive to Caceres while enjoying the scenic sights along the way.

Day 5: Caceres – Spend the day exploring Caceres on a guided tour. Try a couple of hiking trails, then finish the day with dinner at a local restaurant.

Day 6: Dehesas & Montanchez – Spend the day touring the Dehesas region, learning about Iberico pigs, visiting traditional jamón drying facilities, and tasting local products, with a lunch stop along the way.

Day 7–9: Mérida & Zafra – Spend the first morning exploring Mérida’s theatre, amphitheatre, and other sights before driving to Zafra for a two-night stay. Enjoy free time to relax, explore the town, or take a scenic bike tour of the Dehesas region, including visits to historic sites and wildlife spots. End each day with dinner at local restaurants and soak in the charm of this historic town.

Day 10–12: Seville – Drive to Seville and explore Barrio de Santa Cruz, enjoy guided tours of the city and Casas Palacios, and take a boat ride along the Guadalquivir. Learn to cook paella in a hands-on class, visit an olive grove with tastings of olive oil, cheese, and wine, and end the evenings with Flamenco and local dinners.

Day 13–14: Madrid – Take the train back to Madrid and check in at your hotel, then enjoy some free time to explore nearby sights or relax at the hotel before your final dinner at La Malontina. On the last day of your Spain and Portugal itinerary, check out early and take a pre-paid shuttle to the airport for your departure.

Contact us today and let us design a custom Spain and Portugal itinerary.

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