While many of the castles that can be toured in Sintra once belonged to royalty, Quinta da Regaleira belonged to a wealthy – and eccentric – Brazilian-Portuguese businessman. The property gets its name from its owner in the mid-1840s, the Baroness of Regaleira. In 1893, it was sold at public auction to Antonio Augusto Carvalho Monteiro. Carvalho Monteiro purchased adjacent properties to expand the estate and built the current mansion between 1904 and 1910. Quinta da Regaleira is perhaps the most intriguing property in Sintra. While other castles were built as fortifications or displays of wealth, Quinta da Regaleira was …

The bright and colorful Pena Palace sits high atop a hill, its bold structure popping out from the lush green trees and gardens below. Featuring a Romanticism style of architecture, colorful towers, and mythological statues, the palace feels like it belongs in the pages of a fairytale. It seems impossible that such a fantastical castle exists in real life, but there it is, visible from Lisbon on a clear day. With roots as a 12th century chapel, a monastery was built on this site in the 15th century. The original monastery structure sustained significant damage during the Lisbon earthquake of …

Our final stop on our transfer tour from Porto to Sintra was Óbidos. And what a great stop it was. We loved both Aveiro and Nazaré, and Óbidos made it 3 for 3 on this tour. It was amazing! Óbidos is a medieval walled city that makes you feel as if you have stepped back in time. The walls and castle date back to the Moorish occupation in the 8th century. The city was conquered and annexed into Portugal in 1148. Its charms were evident even at that stage, and King Dinis presented it to his wife Isabel as a …

The second stop on our Porto to Sintra transfer tour was Nazaré. Located on the Silver Coast in Central Portugal, Nazaré is best known for its record-breaking waves and the surfers who brave them. Nazaré is made up of two regions, Praia (the beach area) and Sitio (the old town built on top of the cliff), which are connected by a funicular. Our first introduction to Nazaré was navigating the narrow streets of the Sitio neighborhood in an attempt to find a parking spot. Igor lamented the many large campers visiting from Spain, clogging up parking lots and going the …

When we were looking at potential stops on our journey from Porto to Sintra, Aveiro was high on my list. Known as the “Venice of Portugal” the pictures of the moliceiro boats cruising through the city’s canals won me over. We haven’t made it to Venice yet so I figured this would be the next best thing. The drive from Porto took about an hour and we immediately headed to Ria Pao, a bakery and pastry shop, for a late morning snack. Igor had us try ovos moles (soft eggs). A sweet treat native to Aveiro, the wafers filled with …

After a great morning at Quinta da Pacheca, Igor took us to lunch at a local spot before heading to Pinhao to take a boat ride down the Douro River. The one hour boat tour headed upstream towards Romaneira before turning around and returning to Pinhao. The tour was on a rabelo boat, which is a traditional Portuguese wooden boat that was used for centuries to deliver barrels of port wine from the Douro Valley to Porto. The boats have a flat bottom, which allows them to pass through shallow sections of the river. Rabelo means “little tail”, referring to …

You should not go to Porto without also visiting the Douro Valley and its vineyards. The scenery is stunning and the wine first rate. Since we were traveling with our kids, we didn’t want to bore them with too many stops at wineries so we decided to only go to one. On the recommendation of our tour guide Igor from Porto Tours and Transfers, we chose Quinta da Pacheca. Wine has been produced in the Douro Valley for over 2,000 years. In 1756, the Douro Valley was named the world’s first demarcated wine region. It was declared a UNESCO World …

Located along the Douro River in Porto, Cais da Ribeira is a bustling waterfront promenade starting at the foot of Ponte Dom Luis I. The pastel tiled buildings house restaurants and bars whose seating spills out onto terraces lining the walkway. The area is bursting with activity, as tourists stop to eat or people watch and buskers serenade the passers-by and rabelos (flat-bottomed boats) float along the river. While Cais da Ribeira is a great place to take a stroll, it is actually the other side of the river that affords you the best views of the city. Before exploring …

Towering over the city at 250 feet high, Torre dos Clérigos offers an amazing view of the city. The Baroque church and its tower were designed by Italian architect Nicolau Nasoni in the 1760s. It was the tallest building in all of Portugal at the time of its completion and remained so until the late 19th century. Built on an uphill street, the tower was put at the back of the building so as to appear even taller. When we arrived, there was a line outside the church to purchase tickets. We weren’t aware until we got to the front …

Opened in 1906 by the Lello brothers, Livraria Lello is one of Porto’s most visited sites.  The bookstore’s grand staircase, intricate plaster designs, and stained glass skylight all make Francisco Xavier Esteves’ Neo-Gothic, Art-Nouveau style building truly stunning. Although relatively small, you can easily spend an hour or two wandering around admiring all the details. While the interior is the reason that most people visit, the exterior should not be overlooked. And trust me – you’ll have plenty of time to study it while you wait on line! Designed by Jose Bielman, the Neo-Gothic exterior facade of the bookstore features …