Choosing between a few European destinations? Portugal should be high on your list. It would be almost impossible to over exaggerate the sheer, breathtaking beauty of this often overlooked little nation. From its port wine to its rolling hills and rugged cliffs, this is one destination that has to be seen to be believed.
When to Go
Ah, the age-old question. We planned our trip for the end of March, and we didn’t have a single regret. The general consensus amongst our Portuguese hosts was that the best time to visit is between March and May, or September to October. By booking during this time, you’ll avoid the tourist crowds while still enjoying pleasantly warm weather.
Where to Start
To start your journey, we’re going to send you to Lisbon—but you’re not going to spend any time there (yet). This is the cheapest airport in the country to fly into, and it also offers the most budget-friendly car rentals. You’ll find that most major US airports offer direct flights into Lisbon for pretty reasonable prices. We paid $490 out of New York City.
Days 1-2: Sintra
Congratulations! You’ve made it to Portugal, and you’re jetlagged as heck. You haven’t slept properly, it’s around 4 AM on your home clock, and you’re pretty sure that whiff you keep smelling is you. Too bad. Grab an espresso beverage, splash some water on your face, and head over to the car rental desk. You’ve booked your car in advance (we hope), so all you need to do is show your license and your passport to the rental guy—and you’ll be good to go.
Okay, now you’re on the road (yay!) And we’re sending you into the magically ethereal wonderland that is the municipality of Sintra. Alas, you’re first in for a terrifying two hours of driving. It’s okay, though. You’re so tired that you won’t remember any of it tomorrow.
So What’s the Deal with Sintra?
Sintra is a picturesque UNESCO world heritage center about a 2-hour drive outside of Lisbon. Nestled in the foothills of the Sintra mountains, it’s home to the Sintra National palace, the commonly dubbed “fairy forests,” and spectacular cliff top hiking.
Where to Stay in Sintra
We chose this loft situated in the Sintra mountains by the Penedo village. At $70/night, it was an amazing deal from a budgetary perspective…But it offered many perks above and beyond the pricing. We’re talking sweeping views of Sintra, a pool in the backyard, and a cultured host with a penchant for bringing us fresh oranges for breakfast.
What to Do in Sintra
Trust us, this is going to be your favorite stop (aside from the jet lag). Here’s your agenda:
- Hike from Praia da Ursa to Cabo de Roca: This spectacular coastal walk will take you from one of Sintra’s most beautiful beaches to the famous lighthouse on the rock. The cliffs can get blustery, so bring a jacket.
- Try a goose barnacle at Adraga Restaurant: Portuguese hospitality is a force to be reckoned with, and you’ll find some of the best of it at this little coastal restaurant. Eat some fresh seafood and drink some Portuguese wine, and (if you’re brave enough) try a nibble of a goose barnacle (a Portuguese delicacy)
- Potter around the town of Sintra: Take an hour or two to walk around the town center of Sintra, taking in the quaint old buildings and the delicious smells. Stop in one of the many coffee bars for a Galão, try a shot of Ginja (a kind of signature cherry liquor, and grab a bite to eat at one of the many street food stands. There are souvenir stores galore here, as well — so this is also your chance to pick up a cork purse for mom.
- Hike up to the Moorish Castle and the Pena Palace: From the town center, you can walk up the hill through the beautiful Pena park to access the castle and the palace. There’s also a driving route to both, but the walk is an experience in itself.
- Visit the Quinta Regaleira: This is where the famous well you’ll see in a lot of Sintra pictures is located. But don’t go just for the well—it’s not even the most impressive part. This historic estate is a wonderland in and of itself!
Day 3: Portimão
You’re going to leave Sintra with a heavy heart, possibly after an intense Googling spree of the price of properties in the area. But fear not, because you’re on your way to the resort-lovers center of Portugal: Portimão in the Algarve region (a little under a 3-hour drive from Sintra).
So What’s the Deal with Portimão?
We’ll explain Portimão to you the way our host in Sintra explained it to us: “There’s Portugal,” she said—sweeping one hand as though to encompass its vastness and beauty within one small gesture. “And then, there’s the Algarve.” With her other hand, she swept away the first—dismissive and disgusted.
Why the horror? The Algarve is one of Portugal’s best-known and most-visited regions. It’s where the tourist hoards will head in the summer, and it’s where all the cultural charm of Portugal is replaced by British pubs, rampant graffiti, and towering concrete sky rises. For all that, we can’t bring ourselves to regret our trip to the Algarve (although we’re glad we didn’t plan an extended stay there) —and you’ll see why we’ve kept it on your itinerary shortly.
Where to Stay in Portimão
We stayed at this Portimão Airbnb on the first line of Praia da Rocha with panoramic balcony views of the ocean and boardwalk. It was ultramodern and clean, and it had LAUNDRY. We paid $87 for the night and had everything we needed—there’s even a pool attached are the complex, should the weather be nice enough for you to use it.
What to Do in Portimão
Portimão is a classic “relax on the beach” stop, so this is your opportunity to have a little downtime. Breathe in the ocean air, putter up and down the boardwalk, and be a tourist for a bit. Next, you’re going to:
- Hike the cliffs: This walk is perhaps the number one reason why we can’t bring ourselves to take Portimão off your itinerary. Starting at Praia do Vau beach, there’s a cliff top trail that will take you all the way to the neighboring town of Alvor. And wow, just wow. You’ll come across secret beaches, majestic rock formations, and flower-laden glades.
- Visit the Fort of Santa Catarina: This medieval fort sits above Praia da Rocha beach at the mouth of the estuary of the Arade River. From here, you can also walk down the causeway to the lighthouse of Praia da Rocha (this isn’t much of a lighthouse as lighthouses go, but you’ll get splendid views from the end of the causeway)
- Stop by the Portimao Market: Here you’ll find fresh fruit, fish, vegetables, and plenty of locals who know the area well.
- Grab a drink on the boardwalk: You won’t find much in the way of authentic Portuguese food and drink on the boardwalk, but the drink prices are low and the vibe is lively.
Day 4: Évora
You’re going to get up early on your last day in Portimão, because Évora is your next stop and you’re going to want to make the most of it. You’re looking at about a little over a 2hr drive today, but it’s a nice easy one. Think open roads and scenic views.
So What’s the Deal with Évora?
Évora is the capital of Portugal’s south-central Alentejo region, and it’s packed with history worth seeing (not to mention oodles of quaint Portuguese charm). Here you’ll find narrow, cobblestone streets, Roman ruins, whitewashed buildings, and classic Azulejos tile.
What to do in Évora
- Walk around the town center: You’re going to enjoy the simple act of wandering around the narrow streets of Évora. There are coffee shops and bakeries galore, and you’ll have the pleasant feeling that you stepped back in time to a simpler world.
- Check out the Roman ruins: This won’t take you long, as the ruins are located quite centrally, but they’re well-worth seeing. Once an active temple, there’s not much left of this 1st century structure aside from the signature stone columns—but you’ll still find yourself gaping up at it in awe
- Visit the Capela dos Ossos: This 16th-century chapel is filled with the bones and skulls of the monks who once walked its halls. It’s an eerie feeling stepping inside, and yet an oddly peaceful one.
- Stop by the Cathedral of Évora: From the top of this spectacular Roman Catholic Cathedral, you’ll get panoramic views of Évora.
- Go gift shopping: Évora’s high street is lined with all the cute little gift shops you could possibly desire. From Portuguese cork to tiled souvenirs, you’ll find everything you need to severely overstuff your carry-on bag.
- See Almendres Cromlech: This Neolithic-era stone circle is located About a 30 minute drive outside of Évora. But if pre-history interests you, you won’t want to miss it.
Days 5-6: Porto
Up and at ’em, you’ve got a 3 1/2 hour drive ahead of you, but it will be well worth it when you get to your destination.
So What’s the Deal with Porto?
Porto is a merchant city of wonders, and it’s home to some of Portugal’s most famous wineries. As the second-largest city in Portugal, it’s a real change of pace from quiet little Évora. You’ll have a great time here, we promise.
What to do in Porto
What isn’t there to do? You could spend a full week in Porto alone. Since you don’t have that much time, be prepared to walk your feet off.
- Walk around the Medieval streets: When you are visiting a city with the sheer size and vibrancy of Porto, you don’t want to pin yourself down to a tight agenda of seeing certain popular sights. The best approach is to head towards the town center, and spiral out from there. Stop in the churches, read the signs, climb the steps. This is how you see the things that other tourists don’t see.
- Visit the Riverfront: Towering old merchant houses line the Porto riverfront, and you’ll definitely want to spend some time here drinking in the old-world feel.
- Do a port wine tour & tasting: We chose Ramos Pinto for our tour and tasting experience. At €12 per person, it was a great deal—especially considering all we got out of it. The tour of the winery itself was really interesting, and we learned a lot about the history of Porto and the port wine industry. Once the tour was over, we were treated to a tasting of five port wines.
- Grab a Francesinha: The Francesinha is Porto’s signature sandwich. This unique creation is traditionally made with four meats (ham, linguiça, sausage, and steak), then covered with melted cheese and a hot, thick tomato beer sauce.
- Visit the Livraria Lello: This spectacular bookstore was frequented by JK Rowling when she taught English in Porto, so if you’re a Potter fan…take a potter around!
Your last day: Lisbon
We know, you’re not ready for this trip to be over. But at least you still have a world-famous stop left to make: The capital city of Lisbon. To get there, you’ll be looking at around a 3-hour drive. Plan on returning your rental car before exploring the city—you won’t need it, and you won’t find parking (Trust us. We tried. All we can say for our efforts is that they greatly amused the locals).
So What’s the Deal with Lisbon?
Lisbon never sleeps. It’s packed with street entertainment, art, culture, vibrancy, and eclectic personality. And if you’re a foodie, you’ll be in heaven here. Given all that Lisbon has to offer, you’re a bit short on time. Put your sneakers on for this one, and knock back a few shots of espresso.
Where to Stay in Lisbon
We weren’t expecting a lot from our Lisbon Airbnb. It was dirt cheap, and we only chose it for budgetary reasons. But in actuality, it was a pleasant surprise. The decor was very unique and “Lisbonish,” but what really set it apart was the efforts of our host. He was determined to ensure that we knew everything about Lisbon before setting out to explore, and he gave us tons of helpful advice (not to mention maps and brochures).
What to do in Lisbon
- Check out the street art and entertainment: Start exploring on foot to catch the street entertainment, grab a quick lunch from a street stall, and admire the so-called “graffiti.”
- Take the hop-on hop-off tram: This will take you to all the major city sites for a very budget-friendly price, and you’ll be able to get on and off as you please. Normally we’d recommend seeing everything via your own two feet, but you’re really short on time.
- Visit the São Jorge Castle at sunset: It’s a steep walk up to the São Jorge Castle, But the panoramic views are worth the climb. If you visit just before closing time, you can catch the sunset from the castle walls. The small castle restaurant will start serving hot chocolate and mulled wine, and the locals will show up with blankets in hand to send off the day in style.
- Experience the nightlife: You’re flying out in the morning, so don’t experience the nightlife ‘too’ much, but head out for a couple of drinks and enjoy the music that seems to echo from every corner of Lisbon when the sun goes down.
Time’s up! We hope you have as much fun road-tripping Portugal as we did. Questions? Let us know! We’re always happy to chat.
*Note: There are no affiliate links in this post. We just genuinely recommend the accommodations mentioned above.