Bloopers! Enjoying a merry jaunt through the cobblestone streets of Sintra

Planning a road trip through Portugal? In this article, I’ll share the juicy details about a once-in-a-lifetime vacation I designed for my parents, a few friends and myself. I spent hours doing this research so you don’t have to!

What inspired our trip?

I love few things more than designing adventures. I enjoy this activity so much, in fact, that my trip planning often becomes borderline obsessive. I stay up way too late looking at hotels, check on flight prices first thing in the morning or spend hours investigating tiny towns that could provide an off-the-beaten-track experience.

Thus, when my parents expressed interest in a road trip through Portugal, I eagerly volunteered to design the itinerary. Within a couple of weeks (I’m fast like that!), I’d created a January road trip that took us down the country’s coast, stopping in both large cities and rural villages. With a focus on wine, music, seafood and hiking parts of the renowned Fishermen’s Trail, it was a lovely mash up of the incredible things Portugal has to offer.

The route for our road trip in Portugal
Our route in January 2020

I share this itinerary with you so that you can steal it.

Benefit from my obsession! Escape the cold weather and go have your own road trip through Portugal this coming winter! Then, compliment my awesome planning skills in the comment section below.

You must stop in Porto on your road trip through Portugal
Porto, Portugal old town ribeira aerial promenade view with colorful houses, Douro river and boats, banner panoramic view

Porto (4 nights)

We kicked off our road trip through Portugal in Porto, flying into the city’s international airport after a layover in Madrid.

Why we visited: We’d heard Porto is a beautiful city, a cultural hub and an easy staring point to explore the Duoro Valley – a UNESCO World Heritage Center that is famous for its wines.

What to do:

  1. Attend a show at Fado na Baixa: The best way I can describe fado music is as a lovechild of opera and blues. The performers at Fado na Baixa are excellent, and the show shares more about the history of this Portuguese tradition.
  2. Enjoy an AirBnB photo experience: I absolutely love AirBnB photoshoots for a number of reasons: you get beautiful pictures from your vacation, the photographers almost always end up playing a secondary role as tour guide and they’re affordable. I enjoyed a wonderful photoshoot in Porto with a lovely Brazilian couple who were very knowledgeable about the city. 
  3. Book a wine tour in the Douro Valley: Not only will you taste some of the best port of your life (not to mention some tasty red and white wines), you’ll do it in a breathtaking gorgeous location. The vineyards adorn the (extremely) steep hills of the Duoro Valley, which descends into the Duoro River down below.
  4. Take a peek inside The Majestic Café: It’s gorgeous from the outside and lovely from the inside, but you can skip the ridiculously expense cup of coffee. It’s not worth it.
  5. See the library: Livraria Lello has been called the most beautiful bookstore in the world. Make sure to get a voucherand then go early to avoid as much as the crowd as possible. The line to get in can be truly ridiculous. 
  6. Jaunt around town: There are so many amazing things to see. You can use this outline as a guide (IG influencers always seem to know the best spots!), or just wander around and see what you discover. We did plenty of wandering and loved the spontaneity of it!
A fun moment in Porto during our road trip through Portugal.
My dad explains the finer points of life to a Porto cat. It was a truly enlightening conversation.

Where to stay in Porto: While there are plenty of great hotels in Porto, we opted for a two-bedroom Airbnb in the city center. You can check it out here, as well as check out the photos below.

Pros about this Airbnb:

  • The location: You can’t beat it! This Airbnb let you walk to all the major sites and lovely restaurants.
  • The views from the top floor are absolutely gorgeous. While you sip your morning coffee you can look out over the city’s red-tile rooves.
  • The details: The decoration in this space is just plain charming.

Cons about this Airbnb:

  • Stairs make it a challenging location for older folks: This Airbnb has three levels. After you come in through the entryway, you walk up a very steep staircase to the first floor where the bedrooms are located. Then, you walk up another steep set of stairs to the combined kitchen and living room. While this didn’t bother me, it wasn’t ideal for my parents who are in their 70s.
  • Street noise: From the master bedroom, you can hear street noise. It kept my dad up, but my mom slept right through it. If you’re a sound sleeper, it shouldn’t be a problem. I heard nothing from the second bedroom.

Overall recommendation: 

  • Book it!

Photos from our jaunts around Porto

Lisbon (2 nights)

A three-hour drive south from Porto is Lisbon – the country’s capital. This was the next stop on our road trip through Portugal.

Why we visited: We were interested to see the sights in Portugal’s largest city. Plus, we’d heard there was a wonderful seafood restaurant…

Where to stay in Lisbon: We stayed at the Intercontinental Lisbon. Centrally located and with very spacious and comfortable rooms, this is a great option. 

What to do:

  • Eat at Ramiro: This three-story seafood restaurant serves up some fantastic dishes — including giant prawns that are the size of small lobsters.
Food was a focal point of our road trip through Portugal.
Behold the giant prawn
  • Take a day trip to Sintra: We loved our adventure to Sintra through AirBnB experiences. It’s a location full of fascinating history. 
  • Enjoy another photoshoot: Seriously. Adriana is going to take good care of you. Not only does she take amazing pictures in some of Lisbon’s coolest areas (see below), but she’ll also give you some killer restaurant recommendations. 
  • Wander: After getting the lay of the land with Adriana, see the city casually by foot. There are many amazing statues that you’ll stumble across as you’re meandering through neighborhoods. 

Vila Nova de Milfontes (1 night)

To make sure we had an afternoon in Vila Nova de Milfontes, we left Lisbon around 1 p.m., arriving at our destination by 3 p.m. The two-hour drive took us past rolling hills, plenty of cork trees (Portugal is known as a leading producer of cork) and storks nesting along the highway.

Why we visited: With so many small towns along the route, I chose this one because I really liked the hotel I found through, several blogs mentioned its lovely and easy hikes along the coast, and it is home to Tasca do Celso — a restaurant where reviews included phrases such as “best meal of my life.”

Where to stay in Vila Nova de Milfontes: Guarda Rios! This is the epitome of simple lodging with tons of character. The rooms are basic, quaint and clean. In the common area, there is a gorgeous wood burning fireplace that guests are welcome to use. To make it all the more welcoming, the host sets out homemade breads, cakes, jams and local wines for guests.

One of our favorite hotels on our road trip through Portugal.
Photo from

What to do:

  • Cliff walks: A few minutes up the road from the hotel, you’ll find a dirt path that goes alone the coast. You can stay up on top of the cliffs or go down to the beach. Take some time to work up an apatite, since dinner is going to be awesome.
  • Enjoy a meal at Tasca do Celso: This place oozes character. From the dark wood accents to the lovely fireplace, plan for a long, relaxed meal. 
We had a fabulous meal at Tasca do Celso during our road trip through Portugal.
Photo credit: Tasca do Celso

Carrapateira (1 night)

One of the incredible hikes we took on our road trip through Portugal.
Me, my mom and my dad on a hike near Carrapateira

Because Carrapateira is just one hour and 15 minutes south of Vila Nova de Milfontes, we had a leisurely morning before hopping back in the car.

Why we visited: As I researched the best hikes along the Portuguese coast, I came across one called the Praia da Bordeira Loop. While it was highly rated, it didn’t particularly stand out from the others. Luckily, I followed my gut feeling that this spot would be good.

Where to stay in Carrapateira: Hotel Monte Da Vilarinha

Just when you think you’re lost is when you finally stumble onto this hotel. The property is in a secluded, peaceful part of the Portuguese countryside. 

Photo 1: Credit to, Photo 2 and 3: I took these photos on the property

What to do:

  • Praia da Bordeira Loop: See the pictures below. Enough said.
  • Eat at a local bar: In the winter, many of the local restaurants are closed or have extremely limited hours. After our hike, we stopped to eat at the only place that was open — a local bar that was lit by fluorescent light and full of fishermen. The bartender there had prepared a vegetable puree soup from scratch and it was so delicious that I ordered two bowls. We had a great time hanging out in one of the town’s local haunts where villagers were playing darts and talking about their day.
  • Relax: Read or journal on your private veranda at the hotel

Vilamoura (2 nights)

The Seven Hanging Valleys Trail was one of our favorite hikes on our road trip through Portugal.
My mom on the Seven Hanging Valleys trail, not far from Vilamoura

On our way to Vilamoura, we stopped in Sangres to see the southernmost tip of Europe. It was a lovely place to stretch our legs and, even with this detour, the total driving time that day wasn’t more than 90 minutes. 

Why we visited Vilamoura: To be completely honest, the resort town of Vilamoura only made our list because my dad loves golf. Nevertheless, it turned out to be a fantastic experience, thanks to the incredible spa at our hotel and convenient access to the Seven Hanging Valleys Trail. This was the last stop on our road trip through Portugal, and it made for the ideal balance of outdoor adventure and relaxation.

Where to stay: Hilton Vilamoura FTW! Guests receive free entrance to the spa. That alone is worth the price of the room.

What to do:

  • Seven Hanging Valleys Trail: This will go down in history as one of the top 10 hikes of my life. Read more about the trail here.
  • Spend a day at the 7 Seven Spa: After you’ve hiked, it’s time to be pampered! The spa is home to an indoor thermal pool, Turkish baths, saunas, an experience shower, and a zen garden. You can also book yourself a massage or another service.
The Seven Spa was a great place to end our road trip through Portugal.
You, too, can wear a stylish swim cap and have this much fun at the spa

This is a road trip I could do many times over. With minimal driving time, great food, plenty of opportunities to meet local people and beautiful scenery, it’s a win all around. 

Please do let me know if you try it out! 

About me: I am a coach, best-selling author and dance-obsessed world traveler. When I’m not working with my clients, you can find me making tamales, planning my next trip, lindy hopping or binge watching Madame Secretary. Learn more about me here.

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