From ancient castles to modern art museums, Portugal is filled with timeless treasures to explore. We’ve partnered with Anne & Mike Howard of HoneyTrek, as they share their timeline to the city’s top attractions.

Sintra Portugal Pena Palace HoneyTrek.comSet high in the mountains, just 20 miles from the capital with cool temps and views to the ocean, Sintra has always been in fashion. From the Moors to medieval royalty to the European jet-set, people have flocked to this seductive locale for more than a millennium. Each group left their stylistic mark, from foreboding fortresses to over-the-top summer palaces, turning this village into a veritable Architecture 101. Start early and see 1,000 years of Portuguese history before the sun goes down.

10th Century: Moorish CastleMoorish Castle Sintra-Portugal HoneyTrek.com

Using massive granite boulders and the sheer mountain cliffs, the powers of Muslim Iberia built one of the most foreboding (and scenic) forts. Wander between the double walls, along the battlements, and into the castle keep for the best views of Sintra. For extra credit, check out the Old Stables where an archeological dig is revealing signs of life back to Roman times.

14th-16th Century: National Palace of SintraNational Palace - Sintra Portugal HoneyTrek.com

In the heart of Sintra village, this palace stands as the country’s best preserved example of medieval architecture and its many facets: Gothic, Mudéjar, and Manueline styles. Playing off the area’s Moorish roots, King Dinis used intricate geometric motifs in the original chapel from 1395. Heading into the King João I Wing, you’ll find hand-painted ceilings of whimsical magpies, mermaids, and caravels. By the time Manuel I came to reign, Portugal was a world superpower and he flaunted it with countless maritime references and the dazzling domed Coat of Arms room.

16th Century: Convent of the CapuchosConvento dos Capuchos Sintra Portugal HoneyTrek.com

Tucked into the hills of Sintra, away from worldly delights and distractions, the Franciscan monks built one of the purest monasteries. Flowing with the contours of the landscape and using only the surrounding materials, they created stone and cork structures with subtle dashes of embellishment, like seashell and broken tile mosaics. Even if you can only go for an hour, its serenity will leave a lasting impression.

18th Century: Queluz PalacePalacio de Queluz Sintra Portugal HoneyTrek.com

Having traveled the world over by the mid-1700s, the Portuguese tastes were growing more and more international. King Pedro III drew on baroque, rococo, and neoclassic style (particularly from France and Italy) for a palace and gardens, said to be the “Versailles of Portugal.”

19th Century: Pena PalacePena Palace Sintra Portugal HoneyTrek.com

The best example of Romanticism in Portugal (if not the world), Pena Palace was the fantasyland of the creative King Ferdinand II. Nostalgic for times of yore, he began building on the ruins of a medieval monastery and expanded with architectural elements across the ages and globe. Notice the intense detail of the fully-furnished palace and the 200-hectare gardens, planted with over 500 hand-selected species of trees.

19th-20th Century: Quinta da RegaleiraQuinta Regaleira Sintra Portugal HoneyTrek.com

After Ferdinand made Sintra the epicenter of Romanticism, the style carried on for another ~75 years with the international elite building dozens of opulent mansions on the mountainside. A fan-favorite is the conceptual garden of Quinta da Regaleira. Descend the spiral staircase into the Iniciatic Well, hop from stone to stone in the grotto, down the Promenade of the Gods and through a chapel laden with Masonic references. Be sure to go with a guide … even the incinerator has symbolism.

20th-21st Century: MU.SA (Museu das Artes de Sintra)Museu das Artes de Sintra HoneyTrek.com

Previously a grand 1920s casino, the city’s main art museum is a great way to get in touch with its modern side and see some of country’s top contemporary artists.

Rent Bikes in Sintra Portugal HoneyTrek.com

Sintra Mini Guide:

Where to Stay:
Sintra Bliss House: A sleek hotel on the main drag with a fabulous breakfast buffet.
Casa do Valle: On the terraces of a former vineyard, this self-catering hotel is supremely peaceful and only a short walk from the bustling city center.

Where to Eat:
Tacho Real: No tourist gimmicks here, this is authentic Portuguese food in a historic setting of stone arches and vibrant tilework.
Casa Piriquita: A classic Sintra café serving the city’s famous queijadas (sweet cakes) and travesseiros (aka almond pillows). For something salty, they have a phenomenal grilled cheese.

What to Do:
Park E Bike: Zip to the more remote monuments, down to the beach, and back up the mountainside on these super-charged electric bicycles — without breaking a sweat. It’s the most scenic and fun way to tick off 1,000 years of sightseeing in one day.
Nature Hike to the Castles: Skip the tourist bus to Pena Palace and the Moorish Castle, and take the historic walking paths through the forest. Follow Santa Maria trail up and Lapa Trail down for a scenic loop back to town.

Mike & Anne Howard are official Travelocity Gnomads. Gnational Gnomads is an exclusive group of high-profile travel and lifestyle experts who offer tips and inspiration on behalf of Travelocity. For more information visit TravelocityGnomads.com.

Travelocity compensates authors for their writings appearing on this site; such compensation may include travel and other costs.

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