12 Medieval Cities and Towns in Portugal So Beautiful, You’ll Think You’ve Stepped Into a Fairy Tale

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When people think of Portugal, their minds often picture sandy beaches, sunny skies, vibrant cities, and delicious cuisines. However, this European nation offers much more than good weather, beach resorts, and world-class cuisines. Portugal is also famed for its strong cultural heritage and rich history.

This history and culture can be summarized perfectly in the country’s fascinating medieval cities and towns, many of which exist. To learn more, we’ve compiled a list of 12 beautiful medieval cities and towns in Portugal. These locations allow travelers to explore the past, admire impressive architecture, experience medieval Portugal, and learn more about Portugal’s unique history and culture.

Lisbon

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It makes sense to start this list with Portugal’s bustling capital city, Lisbon. The capital is believed to be one of the world’s and Europe’s oldest cities, with a history that can be traced back centuries. Luckily for us, many of the city’s oldest parts still retain much of their old-time charm and medieval layout.

You can experience medieval Lisbon at various landmarks and neighborhoods across the city. Fine examples include Castelo de São Jorge and the Mouraria neighborhood, known as the Moorish Quarter. You can’t miss Castelo de São Jorge as it sits proudly above the city, offering spectacular views and beautiful medieval ramparts. As for the Moorish Quarter, expect picturesque pastel-colored houses, vast squares, and medieval towers.

Sintra

Sitting above the pine-covered foothills of the Serra de Sintra mountains, a 30-minute drive from Lisbon, lies a Disney-esque medieval destination famed for its colorful castles, lush gardens, fairy tale vibes, and stunning natural scenery. Adored by architecture enthusiasts, history buffs, and storybook lovers, you can easily spend days exploring Sintra’s remarkable buildings and medieval streets.

The town’s crowning glory is the breathtaking National Palace of Pena, a Romanticist palace and UNESCO World Heritage Site. The palace is beautiful, but its landscape views are exceptional, too. Other key highlights of a trip to Sintra include Quinta da Regaleira, the Moorish Castle, Sintra Old Town, and Casa Hans Christian Andersen.

Coimbra

Coimbra is a gorgeous riverbank city in Central Portugal. Despite being conveniently located between Porto and Lisbon, it’s a lesser-visited Portuguese city, which is a shame because it has much to offer, starting with a mesmerizing Old Town. As you stroll through the city’s medieval cobblestone streets, you’ll discover fascinating landmarks, epic viewpoints, and historic buildings.

You don’t want to miss the University of Coimbra, Porta e Torre de Almedina, Praça do Comércio, and Torre de Anto. The university is a must-visit attraction because it’s one of the world’s oldest, founded in 1209. Once you’ve explored the city’s vibrant streets, we recommend walking along the river for the city’s best viewpoints.

Tavira

Tavira is an excellent vacation destination if you want to discover medieval Portugal and enjoy the Algarve coast. This small city, best known for its rich history and picture-perfect beaches, straddles the Gilão River in Southern Portugal. Unlike other tourist destinations in the Algarve, Tavira has retained much of its charm and distinctive character.

Brimming with history, the city boasts impressive hilltop castle ruins, Gothic and Renaissance churches, Roman bridges, and museums packed with medieval exhibits. Built on the ruins of a Moorish mosque, the Igreja de Santo do Castelo is one of our favorite landmarks in the city. Interestingly, warrior knights are entombed in the church. Other noteworthy attractions include Porta de Dom Manuel, Núcleo Islâmico, Tavira Old Bridge, and Castelo de Tavira.

Monsanto

Despite being relatively unheard of, Monsanto is arguably the most fascinating medieval town on our list. Nestled in the rocky hills of Central Portugal’s Castelo Branco District, this town is home to the ruins of a medieval castle and castle walls. However, the biggest draw to the area is Monsanto’s beautiful yet bizarre medieval rock houses.

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While the ruins of Monsanto’s former Templar Castle are intriguing, Monsanto’s rock houses offer the most mystery. Remarkably, many of the homes in the town sit underneath huge boulders, appearing to have been squashed. However, this isn’t a mistake. Monsanto residents decided to build their houses into the rock, and many locals still live in the homes today. This isn’t a sight you want to miss.

Sortelha

Sortelha is one of Portugal’s most beautiful and historic ancient Portuguese towns. It’s also one of the most well-preserved medieval towns, offering tourists a glimpse into the nation’s rich history. The town retains most of its medieval alleyways and traditional houses, all guarded by defensive walls and a towering castle.

The best way to explore Sortelha is to start at the castle. Built in the 13th century, this Romanesque castle sits on a rocky outcrop above the town, offering scenic views and well-preserved walls and towers. Afterward, get lost in Sortelha’s maze of cobblestone streets, keeping your eyes peeled for medieval tombs, the Renaissance Church, and the Gothic gateway.

Belmonte

Admittedly, Belmonte, a small town in Central Portugal, isn’t as easy to reach as other medieval destinations, with it being a three-hour drive from Lisbon. However, the extra effort required to get to the town will be rewarded with stunning natural scenery, rich history, and medieval architecture. Seems like a fair deal, right?

Besides its Jewish heritage, Belmonte is known for its medieval castle, stone walls, and traditional houses. In the town center, you’ll find many examples of medieval architecture, the Jewish Museum, the Museum of Discovery, and souvenir shops. Meanwhile, Castelo de Belmonte sits on a small hill overlooking the town. You can also find the 1st century Torre de Centum Cellas just outside the town.

Tomar

Tomar, or Thomar in English, is a small medieval city in Portugal’s Santarém district. If you want to follow in the footsteps of the Knights Templar, it’s a fantastic place to visit. This colorful city was once the headquarters of this mysterious group, and many of its medieval buildings still stand today.

One of the key Templar landmarks in Tomar is the 12th-century Convento de Cristo, a medieval fortress and church where Templar would meet for gatherings and religious ceremonies. Other medieval points of interest in the city include Castelo de Tomar and Igreja de Santa Maria dos Olivais. Other significant attractions in the city you don’t want to miss include the Church of São João Baptista, Aqueduto dos Pegões, and the Synagogue of Tomar.

Guimarães

Another fairy-tale medieval destination in Portugal is Guimarães, a beautiful city in Northern Portugal. Appearing as though it has been frozen in time, Guimarães is an incredibly well-preserved city famed for its medieval buildings, vibrant town center, and three-tier properties.

You’ll likely spend most of your time in the city, meandering the winding cobblestone streets of the Historical City Center. You’ll find enchanting landmarks here, such as Padrão do Salado, Largo de Donães, and the vibrant Old Quarter. You’ll also spend much time at the 10th-century Castelo de Guimarães, the birthplace of Afonso Henriques, the first king of Portugal. You don’t want to miss the Dukes of Bragança Palace and its museum, either.

Trancoso

Like Guimarães, Trancoso is a medieval delight that’s loved for its well-preserved architecture and rich history. This small city in Eastern Portugal features a labyrinth of medieval cobbled streets, a Jewish quarter, and a 10th-century castle. Declared a National Monument, Castelo de Trancoso dates back to Moorish occupation but was taken over by the Portuguese crown in the 12th century.

Today, the castle stands above the city, offering panoramic views from its tall stone-walled tower. In the city below, you’ll enjoy a pleasant stroll through the streets, quickly discovering charming medieval buildings and places to grab something to eat. Make sure you visit Praça Dom Dinis Square and the Portas do Prado gateway, and don’t forget to walk along the historic quarter’s town walls.

Chaves

The penultimate medieval destination on our list is Chaves, a historic city in Northern Portugal close to the Portugal-Spain border. Artifacts discovered in the city reveal the earliest human settlement in the area, dating back to the Stone Age. However, Chaves is better known for being ruled by the Romans in the 1st century.

Even today, travelers can admire the beautiful architecture the Romans left behind, including a Roman bridge connecting the city’s two sides across the Tâmega River. The city is also loved for its medieval square and 14th-century fort. However, our favorite landmark in Chaves is Castelo de Chaves. Here, you can find the Torre de Menagem and Jardim do Castelo. The breathtaking Praça de Camões is just outside, too.

Braga

The final medieval city for you is Braga, Portugal’s third largest city behind Lisbon and Porto. Braga is also one of Portugal’s oldest cities, so you can expect to find many historic landmarks. For example, the Castle of Braga and Braga Tower were built in the 2nd century. Both of these landmarks can be found in the city center.

Iconic historic sites, such as the Roman Thermae of Maximinus, Antigo Paço Arquiepiscopal, and Arco da Porta Nova, can also be found in Braga’s historic center. However, arguably the most famous medieval landmark in the city is Braga Cathedral. This beautiful monument, built from the 11th to 13th century, features a Gothic design. The 16th-century Bom Jesus do Monte is also worth visiting.