Highlights of Portugal & Spain: Lisbon to Madrid - 13 Days

Day 1: Arrive in Lisbon

Welcome to Lisbon! Upon arrival, you'll be greeted by your driver and transferred to your hotel in the city center. After checking in, you can unwind after your long journey or head out for a quick stroll. You'll find Lisbon to be an unheralded gem of a European capital. The hilly waterfront neighborhoods are dotted with grand plazas and pastel-colored buildings, many dating back hundreds of years. Old cable cars lurch up winding cobbled roads, and medieval castles sit perched atop the highest points in the city. 

The quickest way to acquaint yourself with Lisbon's culture is through its traditional cuisine. This includes pastéis de bacalhau (cod fritters), grilled sardines, squid stuffed with sausage and onions, queijo de azeitão (a creamy cheese made from sheep's milk), pastéis de Nata (egg custard tarts), and the quintessential street food, the bifana. This sandwich of pork marinated in white wine is pure heaven after one too many Vinho Verdes.

Day 2: Walking Tour of Lisbon

There's no better way to get to the heart of a historic city like Lisbon than by exploring it on foot. In the morning, you'll head out on a three-hour walking tour led by an expert local guide. The guide will point out the major sights of central Lisbon and recount anecdotes about local lore to help introduce you to Portugal's fascinating capital. 

The tour includes stops at many highlights, including the upscale shopping area around Chiado Square and the 12th-century Lisbon Cathedral, the oldest church in the city. You'll also visit the historic neighborhoods of Baixa and Alfama, then make your way to the Arco da Rua Augusta, a magnificent 18th-century arch located in the Praça do Comércio on the banks of the Tagus River. You'll end the tour with a tasting of ginjinha, Portugal's famous liquor made from sour cherries.

Day 3: Day Trip to Sintra & Cascais

Today you'll head out for a full-day tour of Sintra and its surroundings. Located just half an hour east of the city, this resort town in the Sintra Mountains is known for its forested hills, upscale villas, and Moorish palaces. Start with a visit to the Palacio Nacional da Pena (Pena Palace). This 19th-century romanticist castle mixes Moorish and Portuguese late-Gothic architectural styles with distinct features like gargoyles, ornate battlements, and colorful terraces. 

After touring the palace, you'll have a break for lunch, at which point you can also stroll through the historic village of Sintra and do some shopping or sightseeing. Then it's off to Sintra Cascais Natural Park. Some can't-miss locales in this area include the dramatic coastal cliffs of the Cabo de Roca, the wide and inviting Guincho Beach (a popular surf spot), and the glamorous towns of Cascais and Estoril. After a day of sightseeing, you'll return to Lisbon for the evening. 

Day 4: Explore Lisbon

Explore more of Lisbon at your own pace today. Wander the narrow streets and tiled sidewalks of its Old Town, enjoy the sights from famous viewpoints, and taste the delicious local gastronomy. Don't miss a visit to the Belém quarter, famous for its monuments from the age of the Portuguese Discoveries, the breathtaking Jeronimos Monastery, and one of the most renowned Portuguese delicacies, the pastel de Belém (custard tart).

The Museu Calouste Gulbenkian should be at the top of the list for any art lovers visiting the capital, while the fascinating Museu Nacional do Azulejo or National Tile Museum is one of the city's true hidden gems. Head to the LX Factory for cool street art alongside a selection of restaurants, bars, and shops, or treat your tastebuds to an afternoon at the Timeout Market, where the shining stars of Lisbon's gastronomy gather under one roof. 

Day 5: Transfer to Évora, Capital of the Alentejo

This morning, you'll meet your driver for the two-hour drive east to Évora, the historic capital of the Alentejo province. One of Portugal's oldest cities, this UNESCO World Heritage Site dates back to the Roman era and offers an abundance of beautiful architecture and sites, like the medieval Évora Cathedral, the 2,000-year-old ruins of Templo Romano, and the 16th-century Capela dos Ossos (Chapel of Bones). Join your guide for a fascinating walk through the city's history and highlights, then end your evening with a bite to eat and a drink in the bustling city square of Praça do Giraldo.

Day 6: Transfer to Seville

Bid Portugal farewell this morning as your driver transfers you across the border and into Spain. After a scenic journey of around four hours, you'll arrive in Seville. The largest metropolis in southern Spain and capital of the Andalusia region, this seductive city is known for flamenco and fiestas, with its own cultural flavor and strong local identity.

 

After settling in, you have the rest of the afternoon free to stretch your legs and get your bearings among its winding medieval alleys and peaceful, elegant squares. As evening falls, head to the atmospheric Old Town to enjoy a meal of delicious small plates in the birthplace of tapas.

Day 7: Tour Historic Seville, Evening Flamenco & Tapas Tour

Head off with a local guide today to explore this ancient hotbed of culture. Visit the Seville Cathedral, a 15th-century Roman-Catholic church that's home to the tomb of Christopher Columbus. It's a UNESCO World Heritage Site, the largest Gothic church in the world, and an awe-inspiring testament to pious grandiosity. You'll also see La Giralda, the cathedral's looming bell tower. There's a noticeable stylistic difference between the two structures, as this 12th-century pillar was originally built as a minaret for the Great Mosque when the Moors ruled Andalusia.

 

Prepare to travel back to the era of the Christian conquest when you visit the Alcázar of Seville, one of the finest examples of Mudéjar architecture in the nation. Continue to the fashionable Santa Cruz neighborhood, once the city's Jewish Quarter. It's a colorful and well-preserved part of the historic center, with many cafés and tapas bars—the perfect excuse to take a break and enjoy some small plates and local wine. You can also visit markets and local shops where artisans produce intricate silverwork and elegant garment embroidery.

In the evening, your guide will pick you up and take you to a live flamenco show while sharing some history about the masterful dance and music you are about to see and hear. After the show, you'll be able to carry on chatting about the performance with your guide—and about life in Andalusia—over some great local tapas served at some of Seville's lesser-known local haunts.

Day 8: Transfer to Granada via Ronda

Get ready for an incredible Andalusian road trip! Your driver will pick you up today for the journey east to Granada, stopping en route in the town of Ronda. Hemingway once said of this mountainside city, "The entire town and as far as you can see in any direction is romantic background." Join a local guide to explore the spectacular Bullring of the Royal Cavalry of Ronda, considered one of the most important in Spain, as well as numerous buildings, churches, convents, and palaces that belong to its long and illustrious Roman and Moorish history.

After marveling at the landscapes and allowing plenty of time for a good lunch, you'll hop back in the car for the final leg of the journey into the foothills of the Sierra Nevada Mountains to the famous city of Granada. 

Day 9: Discover the Alhambra & Generalife Gardens

Step back in time today with a tour of Granada's most famous landmark: the Alhambra. This imposing fortress overlooking the city dates to the 9th century and was rebuilt in the 14th century by the Nasrid Dynasty, serving as a Moorish palace until 1492 when it became the Royal Court of Ferdinand and Isabella. Today you can stroll the grand halls and intricate architecture of the UNESCO World Heritage Site and escape to the peaceful Generalife Gardens, which are filled with colorful flowers and fountains and offer panoramic views of the city below.

 

After your visit, use the rest of the day to relax or explore more of Granada, losing yourself in labyrinthine streets and perhaps stopping at the Granada Cathedral, Alcaicería (old silk market), or Madraza (medieval Koranic school). Finish your visit with a dinner of traditional Granadan food at a local restaurant, as the Alhambra lights up the skyline and the sun sets over the Sierra Nevada.

Day 10: Transfer to Córdoba, Train to Madrid

Your driver will collect you at your hotel this morning for the transfer northwest to Córdoba. Andalusia's "second city" boasts rich Roman and Moorish history and a picturesque Old Town home to four UNESCO World Heritage Sites. Today's guided visit starts at the breathtaking Mezquita. Originally a pagan temple, it was later converted into the great mosque of the Ummayad Caliphate and finally transformed into a Catholic church.

 

Other memorable stops include the Alcázar of the Catholic Kings, where Christopher Columbus gained approval for his voyage in search of the Indies, and the winding side streets of the old Jewish Quarter. Your guide will then drop you at a recommended restaurant for a Cordoban lunch, and you'll have more time to wander before meeting up with your driver for the transfer to Cordoba Train Station. From here, catch a train to Madrid.

Day 11: Get to Know Madrid & the Prado Museum

Make sure to have a hearty breakfast this morning to prepare for a day of exploring Madrid. At the designated time, your guide will pick you up from your hotel and take you on a four-hour walking tour—introducing you to the city's highlights while sharing interesting anecdotes to bring it all to life. Your guide will adapt to your speed and style, whether it's a leisurely, laid-back stroll or a brisk pace to squeeze in as many sites as possible.

 

At the end of the tour, enter the magnificent Prado Museum to discover one of the world's finest collections of European art, including works by Velazquez, El Greco, and Goya. Admire some of these gems with your guide before they leave you to discover more art at your own pace. The rest of the afternoon is free for you to get to know more of the city on your own. Alternatively, your guide can take you to a nearby restaurant or tapas bar—whichever option suits you best.

Day 12: Madrid Tapas Tasting & Segway Tour

Get a genuine feel for the city and enjoy the best local cuisine on today's two-hour city walk. After taking in the main sights, put your feet up and savor some delicious tapas in local bars of the Las Letras district, the historic heart of the city. This tour is an excellent introduction to Madrid and one of its most charismatic neighborhoods for traditional tapas.

Later in the afternoon, meet your guide and step onto a Segway to cruise around the streets of Madrid in comfort. Visit the Plaza de la Villa (home of the oldest remaining civil building in the city) and Plaza de Ramales (built on the former site of a church, where Velázquez, one of Spain's most famous artists was buried). Then head for the Almudena Cathedral and the colossal Royal Palace. End your explorations at the Debod Temple, an authentic ancient Egyptian temple in the middle of the city, or Madrid Río, a vast green space that revitalizes the former industrial riverside. 

Day 13: Depart Madrid

Enjoy a final leisurely morning in Madrid. When the time comes, your Iberian adventure draws to a close as your driver transfers you to the airport to catch your departing flight. Safe travels!

Looking for more inspiration for your trip to Portugal and Spain? Check out these other ways to spend 11 days, 12 days, and 14 days on the Iberian Peninsula.