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

Day 2: Explore Porto 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

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

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

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

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 8: Guided Visit of Monsaraz, Stargazing Experience

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.

Day 9: Transfer to Seville (Spain) via Aracena

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. 

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

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