This trip takes you from north to south, discovering Portugal's Jewish heritage with city tours in Porto, Lisbon, Évora, and Tomar, plus a visit to Sintra with its National Palace of Pena and the Portuguese Riviera. Relax in the Douro Valley with a wine tasting and a river cruise, and then explore the monasteries of Batalha and Alcobaça, the castle in Amourol, and the synagogue and old Jewish quarter of Castelo de Vide. Other highlights include the community museum in Belmonte, the Amoreira Aqueduct in Elvas, and Amarante's iconic stone bridge.


  • Explore the architecture of Porto and the Jewish heritage of Lisbon
  • Discover the Jewish history in Évora, Belmonte, Monsanto, and Sortelha
  • Visit the monasteries of Batalha and Alcobaça
  • Sip wine and ride a traditional Rabelo boat in the Douro River Valley
  • Enjoy a guided tour of Sintra and the Portuguese Riviera

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive at Lisbon Airport - Transfer to Évora and explore the city Évora
Day 2 Explore Évora's Jewish history with a walking tour Évora
Day 3 Day trip to the villages of Monsaraz and Elvas Évora
Day 4 Drive to Belmonte via Marvão and Castelo de Vide Belmonte
Day 5 Discover the villages of Belmonte, Monsanto, and Sortelha Belmonte
Day 6 Transfer to the Douro Valley with stops in Casa do Passal and Trancoso Peso de Régua
Day 7 Enjoy a wine tasting in the Douro Valley Peso de Régua
Day 8 Transfer to Porto - Visit the famous bridge in Amarante Porto
Day 9 Explore Porto with a private walking tour Porto
Day 10 Drive to Tomar and visit the Almourol Castle Tomar
Day 11 Transfer to Lisbon via the Batalha and Alcobaça monasteries Lisbon
Day 12 Join a Jewish Heritage walking tour in Lisbon Lisbon
Day 13 Explore Sintra and the Portuguese Riviera with a guided tour Lisbon
Day 14 Depart Portugal  

Detailed Itinerary

Day 1: Arrive at Lisbon Airport - Transfer to Évora and explore the city

White Houses of Évora
White Houses of Évora

Welcome to Portugal!

Upon arriving at Lisbon Airport, your host will greet you with all the necessary documentation and assistance. Then, you'll transfer about 1.5 hours east to the city of Évora

After settling into your hotel, stave off any jetlag with a stroll through the city. Although you'll enjoy a guided walking tour of Évora tomorrow, check out some of its main sights. Start in the center of the Old Town, at Praça do Giraldo which is surrounded by beautiful architecture. Meander the square with its large fountain and views of the Church of Santo Antão, then make your way to the viewpoint, Miradouro do Jardim Diana, which is near the Cadaval Palace. Enjoy the views over the city's rooftops and the ancient ruins of Templo Romano Évora.

There are plenty of restaurants in the city's Old Town. Grab a seat at a terraced cafe in one of the main squares, or peruse the side streets for a cozy bistro.

Day 2: Explore Évora's Jewish history with a walking tour

Roman Ruins of Évora
Roman Ruins of Évora

After a leisurely breakfast, your guide will lead you through the city of Évora on a walking tour. With narrow, Moorish-style streets contrasting with lively, open squares, you'll understand why this city is a beloved UNESCO World Heritage Site. As you wander along the medieval walls, stop to visit some of the city's churches, such as the 18th-century Cathedral of Évora and the Graça Church. You can't miss the Gothic-style São Francisco Church, with its curious Chapel of Bones

After an initial introduction to the city, you'll explore Évora's interesting Jewish history, including some of the most important Jewish quarters in the country. Starting in the 14th century, in an attempt to limit the interaction between Christians and Jews, the Jews in Portugal were forced to live in neighborhoods named Judiarias (Jewish Quarters). Meander through these old neighborhoods as your guide divulges stories of daily life for the Jewish communities throughout the centuries. Enjoy lunch at one of the traditional taverns in the neighborhoods.

Aside from its many Judiarias, Évora holds other significant Jewish histories, which your guide can tell you more about during lunch. The city became the headquarters of one of the seven ouvidorias jurídicas (Portuguese-Jewish Courts). It was also home to the Holy Inquisition Court, which processed the most accusation cases for Judaism in Portugal. As your tour comes to an end, you'll pass by Giraldo Square, where you'll find a memorial honoring of the victims of Portuguese Inquisition

After your tour, the rest of the day is yours to relax or continue exploring the town's historic streets. In the evening, enjoy dinner in the lively town square or at one of the quieter bistros in the Jewish neighborhoods.

Day 3: Day trip to the villages of Monsaraz and Elvas

Church in Monsaraz, Portugal
Church in Monsaraz, Portugal

Today you'll enjoy a day trip through the region's plains to visit the historic towns of Monsaraz and Elvas

Your first stop will be Monsaraz, a medieval, hilltop town of whitewashed buildings and schist facades. Start with a visit to the castle, which offers extensive views over the town, the plains, and Alqueva Dam, the largest artificial lake in Europe. 

Next, visit the Inquisition House, a museum dedicated to the Jewish memory of Monsaraz. The museum has an area dedicated to the heritage and history of Monsaraz, with several thematic rooms. Start in the “Religion and Man” room, which focuses on the different religious texts that influenced the town, including those of Christianity, Judaism, and Islam. Then head to the "Judaism in Monsaraz” room, a space dedicated to the Jewish history and presence in the town.

After lunch in Monsaraz, you'll continue your day trip to the town of Elvas, which sits near the border with Spain. Upon arriving in the city, you'll quickly notice the Amoreira Aqueduct, which acts as a gateway into the city's walled Old Town. The 16th-century aqueduct is over 20,000 feet long, running from a spring in the Serra do Bispo mountains to the fountain in Elvas.

The rest of the Old Town is just as impressive, with its fortress, Forte de Santa Luzia, recognized as the largest walled fortification in the world. Its defensive structures are shaped like a star, which is a testament to the development of military strategy up to the 19th century. Today, the fortifications of Elvas are a UNESCO World Heritage site. 

Explore the historic center, walking along its town walls, viewing its various arched gateways, and enjoying its lively core, Republic Square. Tour the Castelo De Elvas and peruse some of its churches, such as the Our Lady of the Assumption Cathedral. At the end of your visit, check out the Elvas Jewish History House to learn more about the Jewish communities that once lived in the region.

In the late afternoon, you'll return to Évora, where you'll have some time to rest at your hotel before dinner.

Day 4: Drive to Belmonte via Marvão and Castelo de Vide

Castle-Dominated Town of Marvão
Castle-Dominated Town of Marvão

In the morning, you'll leave Évora and start your 3-hour trip to the hillside town of Belmonte. Along the way, you'll stop in the towns of Marvão and Castelo de Vide.

Marvão sits between Castelo de Vide and Portalegre near the border with Spain and on the highest crest of the Serra de São Mamede mountain range. Inside the walls of this historic town are narrow streets lined with the beautiful houses featuring architecture typical of the country's Alentejo Region. You'll find Gothic arches, Manueline windows, wrought-iron balconies, and other embellishments made from the local granite.

Twenty minutes away is Castelo de Vide, a historic walled town dominated by its castle. Explore the old Jewish Quarter and find hidden treasures like the medieval synagogue, Sinagoga de Castelo de Vide, which was beautifully restored and now functions as a museum. It features a rare, 14th-century stone ark for its Torah. Here you'll learn about the Jewish community that settled in the town, as well as its influence and persecution by the Portuguese Inquisition.

In the evening, you'll settle into your accommodation in the town of Belmonte, where you can enjoy dinner in one of its restaurants under the castle.

Day 5: Discover the villages of Belmonte, Monsanto, and Sortelha

Red Roofs of Monsanto, Portugal
Red Roofs of Monsanto, Portugal

Your day begins with a walking tour in the town of Belmonte. You'll start at the Beit Eliahu Synagogue, which was inaugurated in 1996, precisely 500 years after the decree prohibiting Judaism in Portugal. It sits along Fonte da Rosa Street, in a small promontory on the valley facing toward Jerusalem. Here you can meet with the local Jewish community members and visit the cemetery.

Next, you'll visit the Belmonte Jewish Museum, which opened in 2005 as the first museum in Portugal dedicated to Jewish heritage. The exhibits focus on the experience of Judaism in Belmonte, particularly the fear that led to hidden practices. You'll learn about the prayers, tools, and modes of communication used by the Jewish community throughout the centuries.

Afterward, you’ll make your way to Monsanto, a quintessential Portuguese village. Although many are free-standing, most of the houses in the town use the area's granite boulders for walls and roofs. Enjoy views of the surrounding hills and valleys from atop the Castle of Monsanto, which is where you'll find the ruins of the São João Chapel. Wander into the center of Monsanto to enjoy tapas for lunch and visit the landmark, Torre de Lucano.

On your way back to Belmonte, you'll stop in another village, Sortelha. Here you'll also find granite rocks used for building materials, but you'll notice that Sortelha has a more medieval feel to it, as its historic center is surrounding by old walls. Enjoy walking along the cobbled streets and make your way up to the castle. Your guide will detail the history of the village, with many Jewish descendants still living in Sortelha. 

In the evening, you'll return to Belmonte.

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Day 6: Transfer to the Douro Valley with stops in Casa do Passal and Trancoso

Douro River Valley and Peso de Régua
Douro River Valley and Peso de Régua

After breakfast, you'll start your journey to today's destination, the beautiful Duoro Valley. Along the way, you'll stop in the town of Carregal do Sal and visit Casa do Passal, a former residence of Arístides de Sousa Mendes, an unsung Portuguese hero. While working as a diplomat in Bordeaux, Sousa Mendes issued approximately 30,000 visas for those fleeing Nazi persecution. For his act of defiance, he was severely punished by the Portuguese government, stripped of his diplomatic position, and forbidden from earning a living. 

Your next stop is the town of Trancoso, which was home to an extensive Jewish community in the 15th century. During the Inquisition, Trancoso’s Jewish heritage essentially became extinct. You can still find traces of its past Jewish identity, however, in some of its buildings and written documents. You'll visit the town's Jewish Interpretation Center, as well as the Castle of Trancoso.

In the evening, you'll arrive in the Douro Valley in the town of Peso de Régua. After settling into your accommodation, take some time to rest before enjoying dinner on the banks of the Duoro River.

Day 7: Enjoy a wine tasting in the Douro Valley

The Douro Valley Wine Region
The Douro Valley Wine Region

Awake early for your full-day tour of the Douro Valley, a UNESCO World Heritage Site that sits within rocky hills. Despite its reputation as one of the country's most fertile wine regions, the area originally lacked quality soil needed for winemaking. Throughout the centuries, however, locals revitalized the region, planting vineyards one at a time. 

Start the tour with a scenic drive, admiring the passing landscapes of deep valleys, sharp turns along the Douro River, and terraced vineyards that seem to go on forever. You'll have the opportunity to visit one of the many estates that produce the region's famous wines and ports, tasting the different varietals while enjoying lunch.

The Douro River is also known for its difficulty in navigation, challenging boats with its natural barriers. The Rabelo boat, a unique and ancient vessel, is the only one able to take on the river. Nowadays, these types of boats are used for tourism, offering 1-hour river cruises. Enjoy the views of the valley from a different perspective. 

In the late afternoon, you'll return to Peso de Régua.

Day 8: Transfer to Porto - Visit the famous bridge in Amarante

Bridge of S. Goncalo in Amarante
Bridge of S. Gonçalo in Amarante

After breakfast at your hotel, you’ll start your journey toward Porto. Along the way, you’ll stop in Amarante, a city full of history and tradition. Amarante is particularly known for its iconic bridge, the Ponte de São Gonçalo. During the second French invasion, known as the Peninsular War, the bridge played a significant role in helping the Portuguese army to defend its city for as long as possible.  

As you walk through the streets of Amarante, you'll notice the Serra do Marão mountains creating a dramatic backdrop against the city's red roofs and stone streets. As you walk toward the river, stop into some of the city's churches, such as the Igreja de São Pedro and Igreja de São Gonçalo. Cross the bridge and grab lunch at one of the bistros overlooking the town and the Tâmega River.

In the evening, you'll arrive in Porto. Settle into your hotel and then explore the city's nightlife. There are plenty of bars, restaurants, and wine cellars down along the bank of the Douro River. Or you can wander through the historic Vitória district, where you'll find lively restaurants spilling out into the streets.

Day 9: Explore Porto with a private walking tour

The Riverfront of Porto, Portugal
The Riverfront of Porto, Portugal

Enjoy breakfast at your hotel before embarking on a guided tour of Porto. Start at the São Bento Station, well-known throughout the world for its atrium lined with about 20,000 blue tiles. Nearby is the Romanesque Porto Cathedral and the Clérigos Tower, a baroque bell tower worth the climb for its expansive views of Porto.

You can't miss Livraria Lello, a 19th-century bookstore that inspired parts of Harry Potter. Then pop into Café Majestic for a little rest and a cup of coffee while admiring its ornate interior. Continue to the neighborhood of Ribeira, navigating the steep steps and medieval streets through café terraces and picturesque corners. You'll have free time to browse the shops or simply relax at one of the main squares.

After lunch, enjoy a walk along the banks of the Douro River. Here you'll find many places to taste Portugal's famous wine, or you can take a short river cruise in one of the traditional Rabelo boats. Grab dinner at one of the restaurants lining the river while you watch the sunset behind the city.

Day 10: Drive to Tomar and visit the Almourol Castle

Convent of Christ Church in Tomar
Convent of Christ Church in Tomar

In the morning, you'll make your way to the historic Templar City of Tomar, stopping at the riverside Almourol Castle along the way. Located in the village of Vila Nova da Barquinha along the Targus River, the castle is dramatically set atop a small islet. You'll enjoy its views and the surrounding hills with a short boat ride, then explore its ancient walls.

Upon arriving in Tomar, you'll settle into your accommodation and then meet your guide for a walking tour of the city. Start at Templar Castle and discover the architecture of the Convent of Christ. Here you'll learn about the fascinating history behind how the Order of the Knights Templar became the Order of Christ, upholding their power, knowledge, and wealth in Portugal.

Next, you'll dive a bit deeper into the Jewish heritage of the city with a visit to Tomar Synagogue. Despite its discreet facade, the Synagogue's interior is full of symbolism. Its four columns—each decorated with motifs—represents the Matriarchs of Israel: Sarah, Rachel, Rebekah, and Leah. The columns are linked to twelve arches, symbolizing the twelve tribes of Israel.

The Synagogue was used for various purposes over the centuries. Samuel Schwarz, a Portuguese Jew of Polish origin, discovered it and it soon became a national monument. After acquiring the building a few years late, Schwarz created a museum with his collection of tombstones and Hebrew inscriptions. He named it the Abraão Zacuto Luso-Hebraic Museum, which your guide will help you explore.

Excavation work in the museum has uncovered several interesting relics, including coins from the reign of King Afonso V in the 15th century, confirming the probable date of the Synagogue's construction. You'll also view other remains, including domestic ceramics and the water-hearing system for the Mikvah, the ritual purification bath.

After the tour, you'll have the rest of the day to enjoy Tomar on your own. You can stroll through the gardens of the Seven Hills National Park, or the main square, visiting its dominating church, Igreja de São João Baptista. In the evening, you'll find plenty of restaurants throughout the old town offering tapas and traditional Portuguese cuisine.

Day 11: Transfer to Lisbon via the Batalha and Alcobaça monasteries

Monastery of Alcobaca
Monastery of Alcobaça

Today you'll say goodbye to Tomar and make your way to the Portuguese capital, Lisbon. Because you'll drive through the heart of the county, take time to visit the beautiful monasteries of Batalha and Alcobaça.

Just 40 minutes from Tomar is the Batalha Monastery. Consisting of a yellow-hued limestone, the monastery was erected in the late 14th century, dedicated to Our Lady of Victory and a symbol of Portugal’s resistance to Castille (modern-day Spain). Because it was built over 150 years, some portions of the buildings took many years to complete, including the popular Unfinished Chapels. Also known as the Pantheon of King Duarte, the construction of the chapels was stopped after the king's death, only to be finished over a century later.

After lunch in Batalha, you'll continue to the Alcobaça Monastery, which was Portugal's first Gothic building. It has its simplistic beauty, influenced by the Cistercian monks who used to live there. The monastery was created in the 12th century by Portugal's first king, Afonso Henriques

In the afternoon, you'll finish your journey to Lisbon. After settling into your accommodation, head out into the city to find dinner. There are plenty of eateries in the historic center, particularly in the Bairro Alto and Alfama neighborhoods.

Day 12: Join a Jewish Heritage walking tour in Lisbon

The Red Rooftops of Alfama, Lisbon
The Red Rooftops of Alfama, Lisbon

Enjoy a leisurely breakfast before meeting your guide for a walking tour focused on the city's Jewish heritage. You'll start at the Shaare Tikvah Synagogue, a truly hidden treasure. Inaugurated in 1904, it was the first synagogue built in Portugal for nearly 500 years, due to the expulsion ordered by King D. Manuel I in 1496. When it was built, the law prevented any temple that was not Christian to have a facade facing the street. So despite its central location, you won't find its entrance on the main street.

The architect of the synagogue, Ventura Terra, was one of the most renowned architects of the time. It's a humble building with two gender-specific floors facing toward Jerusalem. It created an important community for the Jewish families in Lisbon, as well as Sephardi families from North Africa and Gibraltar who, after the extinction of the Inquisition in 1821, started returning to Portugal.

Your next stop is the 1506 Jewish Massacre Memorial, a tribute to the victims of intolerance and religious fanaticism. The memorial is in the location where the massacre started, in the square opposite the St. Dominic Church.

In the afternoon, you'll explore the neighborhood of Alfama, the oldest quarter of Lisbon where you’ll find St. George’s Castle perched atop one of the city's hills. Nearby, you'll also visit the Judiaria (Jewish Quarter) of Lisbon, filled with narrow streets and small houses where the Jewish population once lived.

Next, head to the downtown area of Baixa, completely rebuilt after the devastating earthquake of 1755. Stroll in Chiado, a bohemian area, where 19th-century writers and thinkers gathered to discuss intellectual matters in the cafes. You'll find plenty of restaurants for lunch in either neighborhood.

Later, head to Belém, the quarter of Lisbon most associated with the time of the Portuguese Discoveries. There you’ll find monuments such as the Jerónimos Monastery, the Monument to the Discoveries, and the Belém Tower, a great place to watch the sunset.

Now that you know the city's layout, enjoy your evening in Lisbon by exploring the neighborhoods on your own and finding a lively restaurant for dinner.

Day 13: Explore Sintra and the Portuguese Riviera with a guided tour

The Pena National Palace in Sintra
The Pena National Palace in Sintra

Awake early for a group tour to the popular tourist destination of Sintra, home of the National Palace of Pena and its surrounding greenery. The town and the northern slope of the Serra de Sintra (Sintra Mountains) have wonderful natural characteristics and impressive historic landmarks.

It's difficult to see all that Sintra has to offer in one single day, so it's best to focus on one of the most romantic palaces in Portugal, the Pena Palace. The castle's history starts in the 15th century, but its current state is a prime example of Romanticist architecture, brought back to life in the 19th century by King Ferdinand II. Enjoy wandering the grounds with views out to the forest, the valley, and the sea.

After exploring the castle, take some time to enjoy the town of Sintra. Many tourists overlook Sintra itself, but it's home to charming, winding cobblestone streets, colorful facades, and quaint shops, all nestled into the surrounding hillside.

On the way back to Lisbon, stop at the westernmost point of mainland Europe, Cabo da Roca (Cape Roca), for views over the Atlantic Ocean. Continue your journey towards the Portuguese Riviera in the towns of Cascais and Estoril. It’s worth stopping for a quick stroll around the towns and along the beach.

You'll return to your hotel in time for a little relaxation before dinner.

Day 14: Depart Portugal

Unforgettable views of Lisbon
Unforgettable views of Lisbon

It's time to say goodbye to beautiful Portugal. In the morning, your driver will transfer you to the airport in time to catch your flight home, or onto your next destination.