Highlights of Spain & Portugal: Cities, Beaches, & Culture - 16 Days

Day 1: Arrival in Lisbon

Welcome to Portugal!

After touching down at the airport in Lisbon, a private driver will be waiting for you outside the terminal to transfer you to your hotel in the historic center. After checking in, you'll have as much time as you'd like to unwind after your long journey. Still, we recommend heading out for a quick stroll around the city. 

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 of which date back hundreds of years. Old cable cars lurch up winding cobbled roads, and medieval castles sit perched atop the highest points in the city. In their heyday, they served as defensive outposts protecting the Port of Lisbon and all those Portuguese galleons returning from the New World laden with pilfered gold and silver.

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: Private Tour of Lisbon

There's no better way to get to the heart of a historic city like Lisbon than by venturing from neighborhood to neighborhood on foot. In the morning you'll head out on these winding streets on a three-hour walking tour led by an expert local guide. Along the way, the guide will point out all the major sights of Central Lisbon and recount anecdotes about local lore. It's a great introduction to the culture of this fascinating city. 

The tour includes stops at many highlights, including the upscale shopping area around Chiado Square, and the Lisbon Cathedral, which dates to the 12th century and is the oldest church in the city. You'll also visit Baixa, located in the historic heart of the city. Its central square, Rossio, has been one of Portugal's main plazas since the middle ages.

Another famous square is the Praça do Comércio, which is located on the banks of the Tagus River and is the location of the Arco da Rua Augusta, a triumphal arch that dates to the 18th century and features six impressive columns. You'll then cap the tour with a tasting of Ginjinha, Portugal's famous liquor made from sour cherries.

Day 3: Day Trip to Sintra & Cascais

Sintra has long been one of the most popular day trips from Lisbon. 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.

Located to the south of Sintra, the fishing town of Cascais is the premier beach destination for holidaymakers from Lisbon, and it was once the coastal playground of Portuguese royalty. You can still see evidence of its heritage in the form of the many lavish mansions still here. 

You can opt for a private guided tour or with a small group. Regardless, the day begins with a half-hour drive to the Palacio Nacional da Pena (Pena Palace). This 19th-century romanticist castle mixes Moorish and Portuguese late-gothic architectural styles. You'll notice a number of distinct features including gargoyles, ornate battlements, and colorful terraces. From Lisbon, on a clear day, you can see all the way to the Palace's canary-yellow towers perched above the pine forests of the Parque de Pena. 

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 and/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. 

Day 4: Private Transfer from Lisbon to Porto - Coimbra City Tour

After breakfast, your driver will meet you in the lobby of the hotel for a road trip north. The ultimate destination is the city of Porto but after two hours you'll stop en route in Coimbra. This is one of the most stunning cities in Portugal, which is why it's a shame that many visitors overlook it on their way from Lisbon to Porto.

Upon arrival in Coimbra, you'll meet an expert guide who will lead you on a three-hour tour of this historic city. Perched atop a hill, Coimbra affords panoramic views of the Mondego River down below. Your guide will lead the way to major highlights, like the medieval old town and Sé Velha, a romanesque cathedral dating to the 12th century.

Throughout the tour, your guide will regale you with tales of Coimbra's rich history and local lore. One interesting tidbit: Coimbra was once the capital of Portugal but is now best known for its university. The University of Coimbra was founded in the year 1290, which makes it the oldest educational institution in Portugal and one of the oldest in all of Europe.  

At the end of the tour, your guide will drop you at a great local restaurant for lunch. After some more time to explore, you'll meet up with your driver and continue another 1.5 hours until you reach Porto. Upon arrival in this singularly beautiful city, you'll check into your hotel and have the evening free to relax.

Day 5: Private Tour of Porto

Your day begins with a three-hour tour of this UNESCO World Heritage city led by a local expert guide. Porto has been a key locale in much of Portugal's rich history, which you can still see on its streets and in its architecture. It has been the site of Celtic, Roman, and Moorish occupation, an invasion by Napolean and Spanish troops, and even a civil war.

You'll learn about this history as you tour Porto's historic center, including the Praça da Liberdade (Liberty Square), which is the largest and most impressive plaza in the city. You'll visit Rua Santa Catarina (the main shopping thoroughfare), Gomes Teixeira Square, and the baroque Igreja dos Clérigos church, which dates to 1750.

From there, head to the iconic São Bento Railway Station (built in 1900 on the site of a former convent) and the riverfront Ribeira neighborhood, which is the heart of Porto's nightlife scene. You'll also learn the history of Porto's emblematic Dom Luís I Bridge, a double-decked iron arched bridge that stands 279 feet (85 m) over the Douro River. It's on this waterway that colorful wooden Rabelo boats line up in front of the old port wine cellars.

At the end of the tour, your guide will drop you at a local hotspot café or restaurant for a hearty lunch and give you some tips on how to enjoy the rest of the day in the city.

Day 6: Day Trip to the Douro Valley - Wine Tour & River Cruise

In the morning you'll embark to the Douro Valley, a fertile grape-growing region that produces some of Portugal's best wines. Your guide and driver will pick you up in Porto for the 1.5-hour trip outside the city to the heart of the region.

This full-day tour includes a visit to a quinta (winery) where you'll tour the vineyards and production facilities, and enjoy a wine tasting. You will then drive to a nearby country town where your guide will recommend the perfect restaurant for a leisurely lunch of traditional Portuguese cuisine, followed by another wine tasting.

Then it's time to hop aboard a riverboat for an hour-long cruise down the tranquil Douro River. Relax and admire the beautiful scenery of the valley and the rolling hills along the riverbanks.  

Day 7: Fly from Porto to Madrid

This morning, you'll take an hour-long flight from Porto to Madrid. On arrival at the airport, you'll be greeted by a private driver who will transfer you to your hotel in the city center. Take some time to settle in and get your bearings before heading out to explore this diverse marvel of a city.

Perhaps you could go see a show. Gran Vía is Madrid's answer to Broadway, and on it, you'll find plenty of theaters showcasing plays and musical productions. Needless to say, the options for culture in this city are vast, and you could also visit museums, art galleries, and live music venues if the mood strikes.

When night falls, be sure to indulge in Madrid's world-class culinary scene. If you want to dine amid history, head to Botín in the city center. No less than Ernest Hemingway described it in his seminal novel The Sun Also Rises as the best restaurant on earth. 

Day 8: Private Tour of Madrid - El Prado Museum

Make sure to have a hearty breakfast to prepare for your full day of exploring Madrid. A private guide will pick you up from your hotel and take you on a four-hour walking tour of the city highlights. Your guide will adapt to your speed and style, whether you prefer a leisurely stroll or a brisk pace to squeeze in as many sites as possible. 

At the end of the tour, you'll visit the magnificent El Prado museum, which features one of the finest collections of European art in the world. This includes works by Velazquez, El Greco, and Goya. Your guide will lead you through some of these exhibits before leaving you to continue exploring on your own.

Should you choose, before parting ways your guide can recommend a good nearby restaurant or tapas bar—the perfect spot to cap your day in Madrid.

Day 9: Private Walking/Segway Tours of Madrid - Tapas Tasting

Today you'll embark on two separate tours of Madrid. The first is a two-hour walking tour where you'll immerse yourself in the local culture while also enjoying the best cuisine. Head first to Barrio Las Letras: known as the "literary quarter," this historic neighborhood in the city center was once home to Spanish lit legends like Cervantes and Quevedo. Stop on Calle Huertas for a quick bite at one of the many tapas bars that line the street.

Later that afternoon, you'll meet your guide again for a Segway tour in the streets of Madrid. Zipping along, you'll visit major highlights including two of the oldest plazas in the city. Plaza de la Villa dates to the early Middle Ages and is surrounded by old government buildings, while Plaza de Ramales is built on the site of a former church that's said to be where Velázquez—one of Spain’s most famous artists–is buried.

You'll continue to let the segway do the hard work as you ride to the Almudena Cathedral (the seat of the Catholic archdiocese in Madrid) and the Royal Palace. The latter is the official Madrid residence of the Spanish royal family and boasts a not-so-modest 3,114 rooms. Other highlights include visits to the Debod Temple, an ancient Egyptian temple rebuilt in the city center, and the Parque del Retiro and/or Paseo del Prado.

Day 10: Day Trip to Toledo

In the morning, your driver will pick you up from the hotel for the hour-long trip from central Madrid south to Toledo. This historic city was the capital of Spain in the 16th century, and enjoys a dramatic location atop a gorge overlooking the Río Tajo.

In the Middle Ages, Toledo was known as the "City of the Three Cultures," a place where—legend has it—Christian, Muslim, and Jewish communities peacefully coexisted. You can see remnants of this in the old Arab, Muslim, and Christian monuments that still stand. These include the 15th-century Monastery of San Juan de los Reyes, the former Roman palace Alcázar de Toledo, and the Moorish Synagogue of Santa María la Blanca, which dates to the 12th century.

Accompanied by an expert guide you will visit these historic landmarks as well as others, including the grand 13th century Toledo Cathedral and the 12th century Church of Santo Tomé. Throughout it all, you'll tour the ancient streets of an incredible city that could aptly be described as an open-air museum. After all, Toledo does enjoy UNESCO World Heritage Status. 

Day 11: Train from Madrid to Barcelona

In the morning you'll leave Madrid on a high-speed train bound for Barcelona. After a three-hour trip, you'll arrive at the Mediterranean coast and the beautiful capital of Catalonia. Make no mistake, Barcelona abounds with as much energy and excitement as it does culture and history. Upon arrival at the train station, you'll transfer to your boutique hotel in the city's historic Old Town. After settling in, you'll want to head back out and experience Barcelona's kinetic energy first-hand.

We recommend visiting Mt. Montjuic. This famous hill stands 1,988 feet (606 meters) high and overlooks the Port of Barcelona. Take the Montjuic Cable Car from the metro station near Olympic Park, which takes you up to the 17th century Castle Montjuic and offers panoramic views of the city. You can also access Montjuic via cable car from Barcelona Beach and by funicular elevator adjacent to the cable car. 

The Poble Espanyol is also fun to visit. Constructed in 1929, this open-air museum features over 100 recreated buildings in the style of traditional Spanish villages. When the sun goes down over the city, make sure you're near the Magic Fountain of Montjuic, which is named for the dazzling display of water and colored lights that occur after dark. It's the best free show in the city, one whose effect is heightened by the hundreds of spectators and a communal atmosphere.

Day 12: Visit Park Güell & Sagrada Família

After breakfast at the hotel, you'll meet a local guide who will whisk you away in a chauffeured vehicle for a half-day tour. The destinations are two of the most impressive works by the legendary Catalan architect Antonio Gaudí: Park Güell and the Sagrada Família.

First, you'll visit Park Güell. Located atop Carmel Hill in north Barcelona, this UNESCO World Heritage Site is a fine example of Gaudí's boundary-pushing modernist style. The park takes up 42 acres and you'll be able to marvel at every building as you stroll the walkways and gardens. There are also incredible views at many points in Park Güell that look out over the city.

Next up is the Sagrada Família, the iconic Roman Catholic basilica with an impressive mix of gothic, Catalan-modernism, and Art Nouveau architectural styles. Despite construction on the church beginning in 1882, it's still technically under construction and was only consecrated in 2010. Upon arrival, the guide will reveal insight into the Sagrada Familia's fascinating history, and you'll glean even more info as you explore the interior. 

Around lunchtime, you will part ways with your guide. On your own, you can visit Ciutadella Park. Open since 1881, this green lung of Barcelona takes up 70 acres and features sculptures, lakes, gardens, playgrounds, and the Barcelona Zoo. You could easily spend the remainder of the afternoon here and not run out of things to do and see.

Day 13: Hiking the Costa Brava - Transfer to Begur

After breakfast at your hotel, a private guide will pick you up and you'll embark on a 90-minute drive north of the city along the Costa Brava. This beautiful coastal area stretches between Barcelona and the French border and offers incredible hiking opportunities along routes that pass through coastal villages, secluded beaches, and hidden coves ideal for swimming and snorkeling.

Your guide will select a suitable trail according to your fitness level. Then, it's off for a brisk hike along coastal cliffs flanked by olive orchards and oak forests on one side, and the turquoise and sapphire-blue waters of the Mediterranean on the other. Your reward will come in the form of a three-course meal at the end of your hike, featuring local Catalan specialties.

The last leg of this day trip involves a transfer to your hotel in the coastal town of Begur, known for its postcard beaches. This is where you'll overnight.

Day 14: Free Day on the Costa Brava - Beaches & Hiking

Today, you'll be free to explore the beaches and trails of the Costa Brava. This region is a favorite holiday spot with locals from Barcelona as well as those from Southern France who come for the scenery and leisure activities.

A great way to start the day is by enjoying the fresh air on a coastal hike. The best route is the Gran Recorrido (GR) 92, also known as the Camino de Ronda, which runs from the town of Blanes, in the region of Girona, up to the border with France. This rugged trail hugs the shoreline, passing through many cities, towns, beaches, and bays for over 100 miles.

The nice thing is you can pick up the path anywhere you like and hike it for as long as you prefer. There's a good day hike that runs about 11 miles from the town of Palamós, near Begur, south to the town of Sant Feliu de Guixols. It passes stunning coastal cliffs featuring prime views as well as by many lovely beaches that beckon you to take a dip.

Day 15: Wine Tasting in the Empordà Region

In the morning, a driver will pick you up from your hotel in Begur and drive you to a small wine producer in the Costa Brava's Empordà region. This area stretches from the town of Figueres, in Catalonia, to the French border. Although not as big as other viticulture regions in Spain, Empordà is known to produce delicious wines like White Grenache, Tempranillo, Macabeu, and Syrah. There's a long wine-producing legacy here—historians say that vineyards have been in this area since the 5th century BCE. 

This five-hour excursion includes private transport and a stop for lunch in a nearby town before you return to your hotel in Begur later that afternoon. You'll have the rest of the day free to relax and, if you so choose, head to the beach for a refreshing swim before dinner.

Day 16: Private Transfer to Barcelona - Departure

It's time to say farewell to Spain! At the designated time, a driver will pick you up at your hotel for the transfer to Barcelona. Upon arrival in the city, you'll be dropped off at either the airport or train station to connect with your onward journey. Adios!