Lisbon, one of the sunniest cities in all of Europe, averages 2,800 hours — or about 117 days — of sunshine a year. With this in mind, Brian and I boarded our flight to Portugal, leaving behind a gloomy Chicago November and anticipating sun-drenched days in flowery summer attire and kitschy straw hats. Return home tanned and rejuvenated? Yes, please! 

Well … plans didn’t quite work out. 

During our four-day stay in Lisbon, Portugal’s capital city, it rained all day, every day. (Actually, it rained for most of our two-week vacation through Portugal and Spain, stomping on our dreams of having a positive travel experience to make up for our 2017 hurricane in Puerto Rico.) 

I’ll admit that we pouted a bit; yet we persisted, nonetheless. Rainy weather be damned, we swallowed our gloom, buried our flip flops in our suitcases and donned full-on winter gear, including mittens and wooly hats.  

We walked up cobblestone hills gushing with streams, explored Lisbon’s eclectic boroughs, gray with low-hanging clouds, and rode the city trams as thunder and lightning exploded around us. We attempted to dry soggy clothes via hair dryers and googled “How to operate European heaters” on more than once occasion. We watched a fado show, ate pastel de nata (Portugal’s famous custard tarts) and dove head on into Lisbon’s storied nautical history, all while planning excursions between rain showers (win!) and attempting to keep our umbrellas from turning inside out (fail). 

Although Portugal boasts a great climate (most of the time), a thriving food culture, and iconic storybook destinations such as the Douro Valley, the country was somewhat of an under-the-radar vacation spot until a few years ago. Unfortunately, the secret is now out and — despite the foul weather — we competed for sight-seeing space with hordes of tourist groups, many of which visited on the daily cruise ships that constantly disgraced the harbor. (Yes, I’m annoyed with overtourism.) 

    As one of Western Europe’s oldest cities, Lisbon evokes a delightful blend of old-world glamour and chic newness. Brian and I found a cute AirBnB in the Alfama neighborhood, an iconic district with rolling alleyways, weathered facades and humble ma-and-pa shops. Amid these timeless streets, kids kicked soccer balls along the cobblestones, men gathered to smoke and gossip outside storefronts, and the sounds of fado drifted through the air. 

    Built on seven hills, exploring Lisbon’s upper and lower neighborhoods involves navigating a network of staircases and “elevators,” or funiculars. Of course, given this terrain, Lisbon also boasts several excellent miradors for sunsets — Miradouro de Santa Luzia and Miradouro das Portas do Sol, to name a few. 

    Weather woes aside, we managed to see quite a bit of Lisbon, even if our spirits (and socks) were dampened. A few of the more popular landmarks included:

    • Mosteiro dos Jerónimos — Jerónimos Monastery. This expansive abbey dates back to the 16th century. Vasco da Gama’s tomb is inside the entrance to the church. (Belém)
    • Padrão dos Descobrimentos — Monument of the Discoveries. The original monument was built for the 1940 World Exhibition to honor the achievements of explorers during the Age of Discoveries. The current monument is a replica, built in 1960. (Belém)
    • Belém Tower. This elaborate tower was used to guard the entrance to Lisbon’s harbor. It was also the final image of Portugal many sailors and navigators saw as they set out on their voyages of discovery. (Belém)

    Day Trip to Sintra

    Another rainy day found us boarding a train at Lisbon’s Rossio train station on a journey to fairytale Sintra. Upon arrival,  Sintra is fantastically easy to navigate. Two tourist buses — #434 and #435 — complete circuits in either direction to the area’s most popular attractions so we were able to check off the following sites in one longish day:

    • Palácio Nacional da Pena — Pena Palace. This fascinating palace was built in the 19th century for Dom Fernando II, consort of Queen Maria II of Portugal. It’s a rather eccentric structure with an amalgam of quaint towers, vividly colored turrets in shades of yellow, red and purple, onion domes and oriental arches. 
    • Castelo dos Mouros — Moorish Castle. Built in the 9th century by the Moors, this castle ruin perches high above Sintra and snakes through the hilltops. After the Moors were chased out of Portugal during the Christian crusades, the castle fell into disrepair until it was partially restored by King Ferdinand II in the 19th century. Though it was a windy day, we thoroughly enjoyed exploring these ruins, probably because we had much of it to ourselves. 
    • Quinta de Regaleira. “The Palace of Monteiro the Millionaire,” this grandiose, mystical palace was built between 1904 and 1910 by Carvalho Monteiro. The entire property is somewhat of a treasure hunt, full of hidden caves, a spiraling well and secret passageways, and is believed to hide symbols related to alchemy, Masonry, the Knights Templar, and the Rosicrucians.

    Roadtripping from Lisbon to Porto: Óbidos, Nazaré & the Douro Valley

    We drove from Lisbon up to the Douro Valley in one day, including stops at Óbidos and Nazaré, the former being one of Europe’s sweetest villages and the later as Portugal’s surf capital. With more time, I would have liked to visit Coimbra and the Algarve, the southernmost province of Portugal, if only to indulge in the laidback charms of some out-of-the-way destinations.

    Óbidos was our mid-morning coffee stop. This medieval village is known as the “Wedding Present Town” because it was a gift from King Dinis in 1282 to Queen Isabel on their wedding day. Given our limited time here, the only thing to do was wander the picturesque lanes and get a bit lost with the hordes of other wandering tourists. Seriously, Óbidos is the stop along Portugal’s tourist path. I imagine that it’s an alluring destination with a huge cultural appeal once the masses depart for the day; however, we were not lucky enough to experience this side of Óbidos and instead had to swerve around various walking tours and ignorant tourists. We did take some time to walk along sections of the fortified walls, which offered excellent views of the rolling fertile countryside.

    Respite in Nazaré

    Further up the coast, Nazaré delighted us with its delicious seafood, expansive alabaster shores, roaring waves and utterly unscathed pedestrian center. Since it was the off season, many shops and restaurants were closed, as was the funicular to the old village perched on the cliff. Albeit, we could have climbed the imposing staircase to visit the old town; yet we chose to simply sit, enjoy the idyllic setting and relax by the ocean.

    Brian and I shared some type of seafood special, complete with potatoes, salad, octopus, scallops, and three types of fish: swordfish, cod and perch, plus a carafe (okay two carafes) of wine. This went down in the books as one of the best seafood experiences of our trip.

    Two-Day Douro Valley Roadtrip

    The Douro Valley is Portugal’s special grape-producing region and the ONLY place in the world that authentic port wine comes from. Yes, really! In fact, under the EU’s Protected Designation of Origin laws, only fortified wine made with grapes from the Douro wine region can be called port.  

    The Douro is know for its stunning scenery of steep, terraced vineyards, and one of the world’s most beautiful roads, the N222 highway, which showcases the region’s best vistas and most famous quintas (or wineries). Connecting the cities of Peso da Régua and Pinhão, this narrow, winding road hugs the Douro River, providing unforgettable views of the tiered vineyards carved into the face of mountains as far as the eye can see.

    We set off to explore the Douro armed with raincoats and appetites for all things port. Although it rained for the majority of the day, Mother Nature delivered a mystical scenery of low-hanging clouds, spotty sunshine and periodic rainbows. I can only imagine how lovely the landscape would be in clear weather! We borrowed a map from our hostess to select some quintas along the way, including Quinta do Panascal and Quinta da Pacheca, and we stopped in Pinhão for a few beers while waiting for a particularly intense rainstorm to pass.

    It turns out that neither one of us particularly likes port. It’s a bit strong (maybe bitter is the right word) for my palate.  Luckily, all of the quintas offered versions of both red and white wines with their variety of tastings. 

    Sipping Port in Porto … Because What Else Would You Do?

    Porto is Portugal’s second-largest city. Due to its vantage point along the Douro River, it was one of the most important ship building centers in the world during the “Age of Discoveries,” and a century later, it became one of the major ports for Europe’s wine trade. 

    The historic Ribeira, or UNESCO-listed waterfront, offered a lovely stroll. The old wood-framed buildings, once home to shopkeepers, tanners and ship builders, are now a hive of tourist shops, restaurants and hotels. Off of this main drag, we found the streets rather empty and enjoyed roaming the rustic side of the city that showcased architectural styles from medieval to baroque to Art Nouveau.

    On the opposite side of the river, reached by crossing the landmark Ponte Dom Luís I, are the lodges of Vila Nova de Gaia. As a visit to the wine cellars is a mandatory activity in Porto, we popped into a few … just in case we could convince ourselves that we actually did like the taste of port. Also, many of the cellars also offer chocolate and cheese tastings so how could we not partake?