Delve deeper into Portugal and southern Spain as you visit iconic cities and explore lesser-known towns and villages over two epic weeks. Tick off Porto and Lisbon, stopping at the Templar city of Tomar and a charming village en route. Journey deep into the Alentejo countryside where ancient Évora and fortified Monsaraz await, then continue to Spain, where you'll stop at small Andalusian towns on the way to Seville and Granada.


  • Soak up the culture and culture of Portugal's biggest cities, Porto and Lisbon
  • Unearth mysterious Knights Templar history in Tomar
  • Visit a cork tree forest, tour an olive oil farm, and go stargazing
  • Hike the Caminito del Rey near Seville
  • Explore the incredible Alhambra with a guide in Granada

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Porto (Portugal), Foodie Experience in Porto Porto
Day 2 Explore Porto by E-Bike Porto
Day 3 Free Day in Porto Porto
Day 4 Transfer to Lisbon via Tomar & Constância Lisbon
Day 5 Lisbon Guided Tuk-Tuk Tour Lisbon
Day 6 Day Trip to Sintra & Hike Lisbon
Day 7 Train to Évora, Cork & Olive Oil Jeep Safari Évora
Day 8 Guided Visit of Monsaraz, Stargazing Experience Évora
Day 9 Transfer to Seville (Spain) via Aracena Seville
Day 10 Self-Guided Walking Tour of Seville, Flamenco Experience Seville
Day 11 Transfer to Granada, Hike the Caminito del Rey Granada
Day 12 Tour the Alhambra, Explore Granada Through Scent Granada
Day 13 Free Day in Granada Granada
Day 14 Depart Granada  

Detailed Itinerary

Day 1: Arrive in Porto (Portugal), Foodie Experience in Porto

Portugal is famous for its grilled fish and fresh seafood dishes

Bem-vindo (welcome) to sunny Portugal! A driver will be waiting for you at Porto's airport, ready to transfer you to your hotel in the city center. Drop your bags, refresh, and start exploring Portugal's second-largest city.

This afternoon you'll join a 3.5-hour walking tour of the historic downtown. A local guide will share a firsthand look at Porto's culinary renaissance, including the rebirth of specialty food shops and new restaurants adopting old methods. Stop at old-school family-run businesses to taste simple, quality products and traditional Portuguese recipes made with love. Learn why these spots are an integral part of what makes gastronomy in Porto unique. Finish the experience with an introduction to Porto's famous drink, port wine, and taste three different styles.

Day 2: Explore Porto by E-Bike

Get to know Porto by E-bike
Get to know Porto's hilly neighborhoods by e-bike

Those who know Porto's hilly landscape and narrow cobbled lanes may think that a bike tour around the city is something worthy of an Olympic feat... But today, you'll take to the streets in the form of electric bikes. E-bikes make it surprisingly easy to ride and explore the historic center. Your private ride will take in some of the most iconic places and highlight the best historic architecture in town over three hours.

This afternoon is yours to explore at your own pace—and on two legs. Start in the Ribeira neighborhood, which sits right along the Douro River. Famed for its narrow and colorful dockside houses and its views of the iconic double-decked Dom Luís I Bridge, this UNESCO World Heritage Site is simply a must-see. Sit on a café terrace with wine and people-watch, or even venture to the river's south bank for a port wine tasting at one of Gaia's famous cellars.

Day 3: Free Day in Porto

The Paiva Walkways follow the river in Arouca Geopark

Today is yours to explore as you wish. Continue trekking the cobbled narrow streets of Porto, or escape to the countryside for an immersive day trip experience.

The Paiva Walkways are considered one of the most beautiful riverside hikes in Europe. An incredible 5-mile (8 km) boardwalk follows the Paiva River, providing glorious views of Arouca Geopark, recognized by UNESCO as a Geological Heritage of Humanity. Your guide will share insights about life and traditions in Portugal as you explore geologic, natural, and archaeological places of interest. Stop for a traditional lunch and try the local posta Arouquesa, a hearty steak, before visiting a local distillery where Pinguça, a great Portuguese liquor, is produced.

Alternatively, venture into the famous Douro Valley wine region. Spend the day visiting traditional wineries and learning about the region's fascinating UNESCO-protected wine heritage. After a wine tasting at two magnificent vineyards, enjoy a traditional lunch at one of the valley's famous quintas (estates), followed by an hour-long cruise down the tranquil Douro River. Relax and admire the beautiful scenery of the valley, where the vines roll down to the riverbank while sipping on a glass of port wine.

Day 4: Transfer to Lisbon via Tomar & Constância

Tomar's picturesque setting
The Convent of the Order of Christ in Tomar

Today you'll be picked up at the hotel for a private transfer to Lisbon, Portugal's colorful capital city. Along the journey, your driver will stop at Tomar, known as the "Templar City." Visit the 12th-century Convento de Cristo, which was once the headquarters of the legendary Knights Templar and is a curious example of Gothic, Manueline, and Renaissance architecture. On your self-guided visit, you could also explore the 15th-century Tomar Synagogue, which became a haven for the Jewish population expelled from Spain in 1492.

After Tomar, Continue on to Constância, a small, charming village where Luis de Camões (one of the most famous Portuguese poets) lived and used to write some of his lyrical poems. Then stop nearby at Almourol Castle, a famous postcard castle from the 12th century that sits at the center of a small granite island in the middle of the Tagus River, before continuing on to Lisbon.

Day 5: Lisbon Guided Tuk-Tuk Tour

Guided Tuk-Tuk Tour
 Iconic trams wind through Lisbon's colorful, cobbled streets

Explore the "City of Seven Hills" in style today by electric tuk-tuk. Led by a knowledgeable guide, you'll zip through the charming capital's modern and historic districts, from the neoclassical avenues of Baixa to the cobblestone alleys of bohemian Bairro Alto. Discover the city's fascinating history and hidden corners, and stop at stunning panoramic viewpoints such as São Pedro de Alcântara, Parque Eduardo VII, Senhora do Monte, and Santa Luzia.

Use the rest of the day to explore at your own pace. The LX Factory is one of the city's coolest destinations, where the former textile factory is now a hub of street art, restaurants, bars, and boutiques. Choose to explore Lisbon's artistic heritage at the National Azulejo Museum, where you can learn about the history of Portugal's colorful hand-painted tiles. Or visit picture-perfect Belém to see the Jerónimos Monastery, one of the few buildings to survive Lisbon's devastating 1775 earthquake, and to try the Portuguese custard tarts at the historic Pasteís de Belém bakery.

Day 6: Day Trip to Sintra & Hike

Sintra Heritage Hike: Hidden Secrets
Views of Pena Palace from the Moorish Castle in Sintra
Plan your trip to Spain
Chat with a local specialist who can help organize your trip.

UNESCO World Heritage-listed Sintra and its mystical hills, dotted with fairy-tale palaces and extravagant villas, have enchanted visitors for centuries. Here castles, palaces, and romantic gardens dot the landscape. This place inspired poets and writers, such as Lord Byron, and now it's your turn to fall in love.

More than a day trip, today you'll hike through amazing scenery up to the incredible Moorish Castle, which dates back to the eighth century, and admire the marvelous Pena Palace at the top of the mountain, a favorite of the region. This 6-mile (10 km) hike will venture through the dense forest and the exotic natural environment, discovering the best trails and places in this fascinating region.

Day 7: Train to Évora, Cork & Olive Oil Jeep Safari

Jeep Safari through a Cork Fork & Visit to an Olive Oil Estate
The small ancient city of Évora is surrounded by farmland

Board a train destined for Évora, a UNESCO World Heritage site and the cultural and gastronomic capital of the Alentejo region. Swap cobblestones for countryside when you journey the iconic landscapes of the Alentejo on a Jeep safari. The pace of life here slows as golden plains dotted with cork trees, olive groves, and whitewashed villages take over. Sitting in the back of a Jeep, you'll drive through a cork forest to learn about one of the few trees that can be harvested without cutting.

After, visit an olive oil farm to learn about the production and sample a variety of zesty, fresh olive oils. Stop for a traditional Alentejo lunch where you'll have the chance to try regional dishes before returning to Évora to check into your hotel. Wander the compact, historic center to explore a city founded 2,000 years ago. Connect with the past at Roman ruins, medieval churches, and the chilling 17th-century bone chapel, Capela dos Ossos.

Day 8: Guided Visit of Monsaraz, Stargazing Experience

Historical village of Monsaraz
Admire the region from the medieval hilltop village of Monsaraz

Today you'll visit Monsaraz, a small fortified medieval village that sits high above the Alentejo plains and overlooks the expansive Alqueva Reservoir. This tiny hilltop town is surrounded by ancient walls and a castle that dates back to the 13th century. You'll climb the castle walls to soak up panoramic views of the surrounding countryside, including the vineyards and olive groves, before exploring nearby villages to visit local terracotta pottery workshops and more.

When night falls, you have the opportunity to join a special stargazing experience. The Alqueva Dark Sky Reserve in the Alentejo was the world's very first reserve of its kind. Discover firsthand why this area with extremely low light pollution has optimum conditions for celestial observation. You'll explore the universe both with your naked eye, with binoculars, and with state-of-the-art telescopes.

Day 9: Transfer to Seville (Spain) via Aracena

See how pigs are reared in the mountainous area of Sierra of Aracenal

A private driver will take you from your hotel in Évora to Seville, making a special stop en route. Iberian or ibérico ham is well known as the best ham in the world, especially if it is the top-tier jamón made from acorn-fed black pigs. Visit a family-run farm in the mountainous area of Sierra of Aracenal to see how the pigs are reared. Then visit a production site to see thousands of hams slowly curing. Many people consider Iberian ham the jewel in the crown of Spanish gastronomy, and you'll have the opportunity to taste it with a glass of the best fino or manzanilla.

Afterward, venture to Aracena for a seasonal gourmet lunch at a local restaurant. With your guide, all you need to do is sit down, and the friendly hosts will bring a parade of plates—maybe asparagus, artichokes, wild mushrooms, cheese, acorn-fed Iberian pork, and more, depending on the season. Take a short walk up to the castle after lunch before continuing to Seville. 

Day 10: Self-Guided Walking Tour of Seville, Flamenco Experience

Seville's Plaza de España
Seville's Plaza de España is filled with beautiful ceramics

Today is yours to indulge in a self-guided walking tour of Seville. Start at the stunning Plaza de España, admire the Moorish architecture of the Real Alcázar, and visit the majestic Seville Cathedral—three key historic sites in Seville. Walk above the city on the Metropol Parasol, an impressive wooden structure that looks like a mushroom and offers panoramic views across Seville. Then cross over the Guadalquivir River to explore the lively Triana district and visit the local market hall.

In the evening, you'll experience one of Spain's unmissable cultural experiences: flamenco. This musical style dates back to the ninth century, when the music and dances of immigrants in Andalusia mixed with the cultures of local Moors and Jews to produce the style that defines Spanish folkloric music today. Seeing a special performance of this colorful and fascinating art form is a cultural must-do. Enjoy an unforgettable evening at one of the city's most famous flamenco tablaos in the heart of Andalusia, where the quality and authenticity of the flamenco is at its best.

Day 11: Transfer to Granada, Hike the Caminito del Rey

Private Transfer Seville to Granada, Hike the Caminito del Rey
Hike the Caminito del Rey on the way to Granada

Today's road trip to Granada involves a pit stop for an adrenaline-pumping adventure. The Caminito del Rey, once considered the world's deadliest path (due to its deteriorated state), is a narrow network of walkways that run along the steep walls of the El Chorro gorge. This 4.8-mile (7.7 km) hike isn't for the fainthearted, with parts of the trail suspended some 400 feet (120 m) above the ground. You'll arrive at the northern entrance to put on safety equipment before embarking on the track, which offers incredible views down the gorge.

After the three-to-four-hour hike, you'll continue to Granada, passing through some of Andalusia's most enchanting locales. Take in the views as your driver passes olive groves, rolling meadows, cork forests, and rocky mountains. Once in Granada, enjoy the rest of your day at leisure. 

Day 12: Tour the Alhambra, Explore Granada Through Scent

Generalife Gardens of the Alhambra in Granada
Generalife Gardens of the Alhambra in Granada

Granada was once the last bastion of Al-Andalus (Muslim Spain) when the Moors ruled it, and today you'll see striking examples of this ancient history. Dramatically topping a hill overlooking Granada, the imposing Alhambra was a Moorish palace until the Christian reconquest in 1492. It's now a UNESCO World Heritage Site, and today you'll explore the building's history and the beautiful Generalife park and gardens. Alhambra receives more than two million visitors annually, but your small group tour will offer extraordinary insights with a knowledgeable guide.

Later today, take a unique and unexpected guided visit around Granada via scents. Travel through history via various smells and scents that tie Granada to different places and times. Discover the Bañuelo, a hammāam or Arab bath from the Ziri period, the grand Granada Cathedral, built in the 16th century, or the colorful Alcaicería, once the traditional Moorish bazaar that's now full of colorful Andalusian treats, trinkets, and souvenirs. At the end receive a little box of the fragrances you've discovered during the route and take memories of Granada home with you.

Day 13: Free Day in Granada

El Torcal
The unusual landforms and impressive karst landscapes at El Torcal

Today you can choose your own adventure near Granada. Embark on a full-day trip to the idyllic and time-trapped Las Alpujarras mountains, just an hour away from Granada. Pass through some of the 50-odd mountain villages and witness the area's abundant birdlife, including the distinctive hoopoe with a haunting cry. Learn about the locals' rich traditional way of life and the area's history as the last stronghold of the Spanish Muslims, or Moors, from your guide. Enjoy lunch in one of the villages to sample the region's cuisine before returning to Granada in the evening.

Or choose to explore El Torcal on a privately guided hike through the Sierra del Torcal mountain range. Marvel at the unusual landforms and impressive karst landscapes. After the hike, stop at a local restaurant for lunch before visiting two dolmens (stone tombs), including a megalithic burial mound called a tumulus and a long barrow form of dolmen, dating back to 3,000 BCE.

Day 14: Depart Granada

The Alhambra in Granada
The Sierra Nevada mountains rise behind the Alhambra in Granada 
Your two weeks in Portugal and Spain have come to an end. A private driver will pick you up from your hotel and transfer you to Granada's airport for your flight home. Safe travels!

More Great Spain Itineraries

Looking for more inspiration for your trip to Portugal? Check out these other Spain itineraries, explore different ways to spend two weeks in Spain and Portugal, or discover the best time to visit Spain.


Map of Off-The-Beaten-Path Portugal & Southern Spain - 14 Days
Map of Off-The-Beaten-Path Portugal & Southern Spain - 14 Days