Portugal is the kind of place that’s so beautiful that it really doesn’t even need to deliver on anything else in order to be liked. Food. Wine. Culture. They could all be incredibly mediocre and Portugal would still be a compelling destination for its beauty alone. Except that they aren’t. At all.

The food, in fact, is outrageously good – I’m still dreaming of the swordfish carpaccio and duck confit we ate overlooking a cliff in the Douro Valley, and the literal cauldron of seafood we devoured in a cobblestoned alleyway restaurant in Évora . The wine is varied, delicious and from the source. Wherever you are in Portugal, you’re in a wine region, and it’s a good one. And the culture – ah, the culture. It’s laid back, informal and fun. Find yourself out in the Bairro Alto district of Lisbon on any given summer night, and you’re in a street party sipping caipirinhas out of tiny plastic cups feeling right at home. Add in the beauty – the rolling hills of vineyards, the palm trees and red roofs of Lisbon, the blue and white tiles on gorgeous, crumbling buildings – and Portugal is knocking it out of the park.

The only memories of Portugal I have that are less than fond have to do exclusively with getting there. And back. SATA Airlines (the airline of the Azores – also on the to-do list) really tested my thesis of “I can survive anything for six hours.” I am here to tell the story so I did survive, but it was less than comfortable. Fuel problems and a potential pit stop in the Azores that thankfully didn’t happen. No air-conditioning for the beginning of the flight. Late planes. The whole nine yards. If you have to fly SATA, if they are giving away actual flights, just consider yourself warned.

Once in Portugal, things are a cinch. You definitely don’t need a car in Lisbon, but our hotel did have parking which gave us the flexibility to do day trips on our own time. Outside of the city, you do want to have a car to be able to experience all that Portugal has to offer. The roads are well paved and well marked, and there are lots of scenic viewpoints along the way. We’d heard some frightening things about drivers in Portugal, but thankfully we found driving there to be very intuitive and easy. Just make sure you have one person who doesn’t want to guzzle wine!

I was so torn in putting together our two-week Portugal itinerary. There were so many things I wanted to see and just not enough time for it all. A few days in Lisbon was obvious. Porto and the Douro Valley were a definite given our family’s need to drink copious amounts of wine at vineyards while on vacation. For something different, we chose to end the trip in Évora, a medieval city in the center of the country. We skipped the Algarve, which is where most of Portugal’s tourists end up, so this itinerary is a little less on-the-beaten-path, but I assure you it’s well worth it. Get ready for seafood towers, castles, stunning vineyards, ancient ruins – they’re all here.

We saw Portugal as a family trip over two weeks. It included a jaunt into Galicia, Spain, which I’m not including here for obvious reasons.

Here was our itinerary (day trips are included within each base):
Lisbon (with day trips to Sintra, Mafra, Óbidos and Tomar)
Porto
Douro Valley
Évora

Lisbon

For a European capital city, Lisbon is an ideal size for spending a few days exploring. There is history in the air and a crumbling grandeur that reminds you that, while today Portugal is just a tiny country, it was once a great, seafaring power. The energy in this city is also totally electric. We visited during the summer in the middle of the World Cup and it was a constant party, especially in the Bairro Alto neighborhood. It’s lined with the quaintest bars and restaurants, and at night it comes alive with live music (get ready for a lot of cover bands) and cocktails being sold out of walk-by windows. And if nightlife is not your thing, Lisbon shines during the day as well, with castles, monasteries and compelling day trips galore.

Where We Stayed:
Heritage Avenida Liberdade. This boutique hotel is located in a townhouse on Lisbon’s main thoroughfare. It’s just a couple of minutes’ walk from the square where all the trams stop, and about 10 minutes to the water and equal distance (up a steep hill) to Chiado and Bairro Alto. Besides its convenient location, it has street parking available and some of the friendliest, most helpful staff I’ve ever encountered. The breakfast spread is top notch, as is the late afternoon wine and port break in the lobby. And the rooms, while not huge, are gorgeously decorated, with lots of attention paid to detail.

What We Ate:
Bistro 100 Maneiras. Tucked away on a side street in Chiado is this gorgeous and delicious spot. The vibe is upmarket but cozy and casual, with a varied menu containing some out-of-the-box and exciting options centering around what I’d call global Portuguese cuisine. The restaurant with the same name offers a tasting menu, but we chose to eat à la carte at the bistro, which worked for us. Choose this spot if you’re looking for a chic night out and have an adventurous palate!

Louro & Sal. We saw this teeny tiny restaurant on one of our first nights in Lisbon while we were getting acquainted with the bars of the Bairro Alto and vowed to come back for dinner. It was totally worth it. Louro & Sal is a little like eating at someone’s dining room table (there can’t be more than 25 seats in the place), and the staff is wonderfully friendly. The food is humble but elegant, and the seafood is particularly fabulous. We each ordered a different fish and no one could keep their forks to themselves.

Pastéis de Belém. You might think you’re above the tourist stuff, but at the end of the day there are just some things that are worth waiting in line for. Pastéis de Belém is one of them. If you’re venturing out to the Belém neighborhood (easily accessible by tram) to see the Jerónimos Monastery or the Belém Tower, you’ve got to make a pit stop at this renowned bakery. You’ll most certainly stand in a line that loops out the door and down the street, but it moves quickly and there’s good people watching. Your order once you get to the front of the line is as many pastéis de nata de nata custard tarts as you can feasibly carry with you or eat in one go.

What We Did:
Jerónimos Monastery. As previously mentioned, spending a half day in the Belém neighborhood is worth your while. Head out in the morning to see the absolutely magnificent Jerónimos Monastery. Founded in the 1500s, it’s an awe-inspiring sight to be seen, and you can stroll through it at your own pace. Portugal is chock full of monasteries but they’re so incredible that once you’ve seen one you have not seen them all. There will probably be a long line to get a ticket here, especially if you visit in the summer, but it’s worth it. Consider tacking on a visit to Belém Tower afterwards (we’d planned to but the line was just too long) before finding a cute spot to eat lunch outside. Don’t leave without buying pastries.

Tram 28. The city is connected by a network of trams, some new (like the one that goes to Belém), some utterly ancient, like Tram 28. Tram 28 will pick you up in the center of town (the ticket booths are well marked and staffed with humans who can answer your questions) and take you on a wild ride up the steep hills, hurtling you through the city with what feels like about 6 inches of space between the vehicle and the buildings on each side. While the tram is a great way to get up into the Alfama district without hiking up hills, it’s also an end in and of itself. Don’t miss this, and watch your purse!

São Jorge Castle. Another must-see historical sight, this Moorish castle stands at the top of the ancient Alfama district, overlooking the whole city of Lisbon and the Tagus River. The views are phenomenal (you’ll see across all the red roofs of the city) and the castle itself is impressive and well worth a visit.

Day trip to Sintra. If you go to Lisbon, you’ve got to visit Sintra, a town about 30 minutes away by car. Sitting on the edge of a forest, Sintra is packed with palaces and monasteries whose turrets rise out of the mist like a fairy tale. You can easily spend a full day here, and it’s very geared towards visitors which makes it easy to see the various buildings (there’s a bus that drives between sights, and different ticket combos depending on what you want to see.) We saw Pena Palace, with its kooky colorful exterior that looks like something out of an LSD dream (also make sure you see the grounds, they’re incredible), and the National Palace of Sintra, which impressed us with its distinctive domed chimneys and enormous kitchen (you can see where my priorities lie). We had lunch in between in a cute little alleyway to get out of the mid-day heat.

Day trip to Mafra. Never one to miss a chance to see over-the-top opulence, the Palacio de Mafra was on the top of my list of things to see as we left Lisbon for Porto. About 45 minutes away, Mafra is a great spot to spend an hour strolling through one of the most ridiculous palaces you may ever see. Particularly memorable are the sprawling library (more than 40,000 books with gold bindings) and the so-called antler room, in which every decoration and piece of furniture is made from antlers. It’s worth the trip for those rooms alone!

Day trip to Óbidos. About an hour north of Lisbon (and a good pit stop if you’re driving between Lisbon and Porto), Óbidos is a medieval gem of a town. While it’s not chock full of sights, it’s Instagrammable as all get-out and there’s plenty to keep you occupied for a few hours. Fully cobblestoned, the town’s buildings are all whitewashed and painted in accents of gorgeous royal blue and deep golden yellow. Vines with flowers grow over everything. And the entire little town is enclosed in medieval walls, with a perfect castle perched on a hill. Should you find yourself in Óbidos, you should stroll the alleys slowly and check out the number of curios for sale, take tons of pictures, walk along the walls taking in the views and give the castle a visit. We had a delicious lunch of pork and clams (a to-die-for classic Portuguese dish) at O Lidador, where we sat outside in an alley while the gracious staff charged my nearly dead Blackberry inside. I’ll always remember visiting Óbidos as the day I decided I needed to leave investment banking, as I sat taking a conference call in a nook in the castle walls while my family looked at me with pity and a little disgust.

Day trip to Tomar. We actually hit Tomar when we drove from the Douro Valley back down to Évora, so you can find any number of ways to fit it into your road trip. Tomar is home to the Convento de Cristo, a gorgeous former convent/monastery that was built in the 12th century as a headquarters for the Knights Templar. The views are beautiful, the architecture is decadent and the history is rich. This was one of my top must-sees in Portugal and it didn’t disappoint.

Porto

Portugal’s second city, Porto is like Lisbon’s rough-and tumble, slightly disheveled younger sibling. Situated on both sides of the Douro River, Porto is home to some fantastic food, plenty of port and Beaux Arts charm galore beneath the crumbling facades. While it’s a little less obvious and a little more gritty than Lisbon, there’s still plenty to do and see here. It’s a great place to spend two days or so, and an excellent jumping off point to elsewhere in the Douro Valley.

Where We Stayed:
Pestana  Vintage Porto Hotel. Right on the waterfront, Pestana Porto is a pleasant, modern hotel down a cobblestoned pedestrian road off the main drag in town. We were greeted after our long drive with white port and tonic cocktails in the lobby (which subsequently became one of my favorite summertime drinks). The rooms aren’t huge, and some could use some updating (the building is made of several townhouses converted into one) but the location is fabulous and so is the service. From the hotel, it’s an easy walk to the grand boulevards of the city center, or to the bridge across to the port cellars on the other side of the river. A number of adorable restaurants are also within easy walking distance.

What We Ate:
A Grade. One of my favorite meals of the trip was at A Grade, a teeny tiny mom-and-pop restaurant in a steep, looping alleyway serving traditional Portuguese fare. Reservations are a must as this place fills to the brim quickly and we saw many hungry and disappointed diners turned away. The octopus we ate here was out of this world and the roast kid was absolutely to die for. I’d wholeheartedly recommend this spot to anyone looking for the real-deal Portuguese food in a local spot.

Postigo do Carvão. We ended up here accidentally on our first night in the city after trying to get into A Grade without luck (we ended up making a reservation there for the following night). Postigo do Carvão, a very homey spot with green and white checkered tablecloths, enormous main courses and impressive seafood towers, was also bustling. We ordered a number of items, but the most memorable were a plate of the largest shrimp I’d ever seen and a bubbling cauldron of seafood that my parents shared. Very delicious and would certainly recommend, though a reservation would be wise as we did have to wait to get in.

What We Did:
Porto Cathedral. Sitting alongside the river is Porto’s imposing cathedral. It may not look like much from outside, but inside the 12th and 13th century church features a gorgeous cloister and some beautiful traditional tilework. It’s one of the oldest historical buildings in Porto and well worth popping into as you’re strolling across the bridge or out exploring the city’s beautiful boulevards and squares.

Vila de Gaia. Just across the river from Porto is Vila de Gaia, technically a city unto itself, and home to all the port cellars. This is basically Disneyland for port lovers, complete with a tourist office and maps. Of our group of 5, not all were port enthusiasts so we only hit one cellar, which was Cálem. They gave a great tour that explained how the port is made, which culminated in a tasting of several different vintages and types. I didn’t think I liked port much before visiting, but it’s grown on me since this education. You can’t visit Porto without the requisite port tasting.

Day trip to Guimaraes. There are a number of important towns north of Porto, including Guimaraes, which we visited on our way back from Spain to the Douro Valley, but it’s only a 45 minute drive from Porto. The medieval town center is a UNESCO World Heritage Site, and it’s home to a beautiful 14th century cathedral, a castle (Portugal is full of them) and a number of quaint shops. In particular, we found a lot of traditional pottery here and we each came home with bowls and platters with the distinctive brown, blue and white patterns of Portugal.

Douro Valley

Not far from the hustle and bustle of Porto is the stunning Douro Valley. Think patchworked rolling hills overlooking the beautiful Douro River below, and wineries speckled everywhere in between. The roads are switchbacks with gorgeous vistas, and the wines are delicious. If you are into wine – or even if you’re just into wellness and relaxing – the Douro Valley is an excellent place to base yourself for two days.

Where We Stayed:
Quinta do Vallado. This is truly one of my favorite places I’ve ever stayed in all my travels, Quinta do Vallado is a winery and hotel located on a hill overlooking the river. The hotel is made up of two buildings, one an 18th century manor house painted a bright terracotta, and the other a modern, slate-covered newer wing. We stayed in the Manor House, dressed with impeccable white linens and decorated with beautiful Portuguese accents. Around the lobby there are several rooms to relax in, and there is a stunning infinity pool on the property in an orange grove. A stay here includes a tour and tasting of the winery, and the wines are very good- I still have a Touriga Nacional from my visit that I’ve yet to drink and if you are into port, their 10 year tawny is spectacular. Also, be sure to book dinner here at least one night if you’re staying. Dinner is a coursed meal paired with the winery’s wines and takes place outdoors under the stars. Truly a memorable experience.

Where We Ate:
Quinta Nova. We stumbled upon Quinta Nova by accident as we were driving through the region looking for wineries to visit. It happened to be lunchtime, so instead of doing the tasting as we’d anticipated, we decided to go all-out and just have a coursed lunch with wine pairings. It was something I won’t soon forget, and not only because my mom accidentally took a video of us eating when she thought she was taking photos. The food and wine here were both outstanding (I can still taste the duck confit and swordfish carpaccio) and served on an elegant patio with magnificent river views. Highly recommend for a wine tasting, and if you come during a mealtime you would be missing out not to stay and eat.

What We Did:
Wine tasting. There are some fantastic (not to mention beautiful) wineries in the Douro Valley, and you could fill a day or two visiting them, easily. Most don’t require an appointment and will do the tasting for free, and driving in the region is spectacularly beautiful. The Douro Valley has some whites on offer but this is definitely red region – keep your eye out for Touriga Nacional, the native grape here. Before you set out, make sure you have a designated driver (these switchbacks are no joke) and a good plan about what’s open. The hotel you’re staying in can definitely help you plan this.

Évora

The last leg of our journey brought us to Évora, a charming ancient Roman city in Portugal’s central Alentejo region. This part of the country is hot and arid, the food is down home-country fare, heavy on the pork, and utterly delicious. Évora is an unexpected foodie town, and a great base for poking around, exploring Roman ruins, and tasting the wines in the area. It’s thick on charm and history and light on the tourists, making it an unexpected but wholly fulfilling stop on anyone’s Portugal itinerary.

Where We Stayed:
Hotel Albergaria do Calvário. This gorgeous hotel feels like a second home, in the best way possible. It’s a charming spot just on the edge of town within the Roman walls, and the proprietors are incredible people who will do whatever they can to make your stay in central Portugal a success. The common areas are eclectically decorated and comfy, perfect for sipping on wine and hanging out playing board games in the evening. There’s also an interior courtyard where you can avoid the midday blazing heat with snacks. The rooms are extremely comfortable, a little quirky and just gorgeous, and the breakfast is legendary. I’d highly recommend this spot.

What We Ate:
Restaurante 1/4 P’ràs 9. This is THE SPOT. Tucked in a cobblestoned alleyway just off the center of town, Restaurant ¼ to 9 is phenomenal and known for having the best seafood in town. We ate at an outside table in the alley on a perfect evening, and it felt like we were part of a community of people in the know. The service is charming and the food top-notch. We ordered several items, including a gigantic pot of seafood, all of which were fantastic. Strongly recommended.

BL Lounge. Situated right at the edge of town, this is a bright and cozy restaurant with a woman chef(!). We had a great meal here on our last night in Portugal. Definitely not a checkered tablecloth restaurant of yore, this is a hip spot serving Alentejo cuisine with a modern twist. Her chocolate cake is the stuff of legends and the wine list is impressive and extensive – what more could you ask for?

What We Did:
Roman temple. Just hanging out in the middle of the city is this extremely well preserved Roman temple with 12 Corinthin columns. You’ll come across this during your wanders through the city but it’s worth a visit and some photos, given that it’s known to be the most intact of its kind on the Iberian peninsula. You can also find the end of the old Roman aquaduct and follow it out of the city, if you’re so inclined.

Cathedral of Évora. Little Évora has a disproportionately magnificent cathedral. The interior is quite beautiful and features a 14th century cloister, and you can climb to the roof where there’s a glorious view of the plains and rolling hills of the Alentejo.

Chapel of Bones. This disconcerting chapel is literally filled with bones exhumed from the town’s graveyards back in the 16th century. I found it fascinating, but my mom was pretty disturbed. If you have a strong stomach this is a must-see attraction – it’s filled with about 5,000 bones covering every inch of the chapel.

Wine tasting. This hot, dry region of Portugal is home to yet more wines, namely reds. There are a number of wineries clustered in Alentejo that are open to visitors. We chose a tour and tasting of Esporão, whose wines we’d been drinking already throughout the trip. The tour was extremely informative, the tasting room was beautiful and we walked away with several wines and olive oils. We did not eat here but the restaurant also looked delicious.

Day trip to Monsaraz. There are a number of small picturesque towns east of Évora, and it was a struggle to choose which to visit. Monsaraz sounded particularly compelling in the guidebook so we decided to pay it a visit one morning near the end of our trip. Nestled just on Portugal’s border with Spain, Monsaraz is a town preserved in time, with whitewashed buildings, a preserved castle with walls, stalwart churches and little shops filled with beautiful handicrafts. We swore we were done shopping but walked away with a rug… We were here for lunch and initially wanted to check out Xarez, but it was closed and we ended up at Restaurante Lumbumba, which was fantastic- a small terrace with a great view, wonderful food (think slabs of pork and bread soup and local olives) and authentic ambience. Not many English speakers here but well worth a visit!