We’ve been talking about Portugal quite a bit in our updates and now it’s finally time to dig into what our itinerary for the trip looks like.

How Things Started

At first, we were thinking of heading down south to either Mexico or Colombia. Figured with the 2 hour time change, warm weather, and low cost of living it would be a good starting spot to travelling with kids.

Then as we were doing some research, an email came through with $575 CAD round trip direct flights from Calgary to Amsterdam.  We jumped on it.

Ok, that was a bit rash.

Our thoughts were:

  • We both love Europe.  This will be my 9th trip over there and I could easily live there someday.
  • Starting things off in Europe is *likely* going to go smoother with two kids in tow.

We know while the costs to get there are low (given flights these days) we will likely be spending more overall as the cost of living is higher in Europe.

But where to go?

I’ve been to Amsterdam and while it is lovely it’s not where we want to be for a few months over the winter as it’s cold there too.  So then we had to figure out where to go from Amsterdam.

We narrowed it down to the following locations:

  • Portugal
  • Turkey
  • The Balkans

I’ve been to Turkey and also loved it there and felt like there’s so much more to explore.  But there is a bit of unrest and instability going on (in comparison to the other areas we were considering). And of course, with the recent earthquake boy are we thankful to not be there at this time. The Balkans are *very high* up on my list but we thought it may be too off the beaten path with kids.  So, Portugal it is!

Once we decided on Portugal our itinerary changed oh I don’t know, 42 times.  Originally we were trying to find a place to park for a month with 2 weeks of travel on each end but then we’d tweak it slightly. And then adjust again, and again, and again.

The Final Itinerary

Finally, after weeks of digging around, we settled on our itinerary and here it is!

  • Amsterdam
  • Lisbon
  • Madeira Island
  • Lagos
  • Lisbon
  • Peniche
  • Porto (Arcozelo)
  • Lisbon
  • Amsterdam

We will have a car rental for all locations except Amsterdam and Lisbon and will be using public transit in those two cities.  We will be staying in hotels while in these two locations and Airbnbs everywhere else.

Amsterdam: (1 night)

We will be spending 1 night on both ends of the trip in Amsterdam mainly as hang out and rest days.  Our hotel (paid via IHG credit card points) is near a few shops/restaurants that we can walk around and stretch our legs.

Lisbon: (4 nights)

We will be starting things off in Lisbon via a 3 hour direct flight from Amsterdam, again staying at an IHG hotel paid with points.  Overall, we will be staying in Lisbon for 12 nights spilt up between three 4 night stays (mainly because of IHG’s 4th night free point system).  Since we won’t have our own kitchen to cook in, we ensured our hotel comes with free breakfast and we are also close to Pingo Doce (Portuguese grocery chain) to pick up some easy-to-prep items.

To start things off, we always try to see if the place we are visiting has a free walking tour and Lisbon does so that will likely be the first thing we do.

Other places to check out during our overall 12 nights in Lisbon include:

  • Alfama neighbourhood and take Tram 28 up to Estrella Cathedral
  • Belem – Torre (tower), Padrao dos Descobrimentos (Monument of the Discoveries), Jeronimos Monastery, and the original pasteis de nata
  • Chiado neighbourhood – Time Out Market
  • Parque Eduardo VII and Estufa Fria (greenhouse)
  • Oceaniaro – largest aquarium in Europe
  • Praca do Comercio and Rua Augusta side street
  • Funicular/lifts: Ascensor da Gloria, Bairro Alta, or Ascensor da Bica
  • Pink Street

Madeira Island: (12 nights)

I think we are both really looking forward to this part of our trip as Madeira looks very tropical and Hawaii-esque.  We were trying to decide between the Azores and Madeira and choose Madiera because it seems like it has more kid-friendly type hikes (levadas) and walks for us to go on.

We’re excited to check out the natural swimming pools, check out many of the levada trails, and drive through stunning scenery.  It also sounds like the town we’re staying in (Santana) has some great little restaurants to check out. And then of course, the jagged rock formations and beaches.

Lagos: (14 nights)

After doing some digging, I’m quite excited to explore the southern part of Portugal and the Algarve region.  Most people say this is the sleepy part of Portugal (which is just fine with us) but the beaches and rock formations look unreal.  There definitely seems like there are plenty of beaches and things to see in Lagos let alone some of the other nearby towns.  Our Airbnb has a pool on sight so while most locals will think we are crazy, I’m sure we will be in the (unheated) water often during our 2 weeks here.

Some places to check out:

  • Praia de Marinha
  • Salema beach (dinosaur footprints)
  • Meia Praia
  • Farol da Ponta da Piedade Lagos
  • Beach Estudantes
  • Forte da Ponta da Bandeira
  • Praia do Barranco do Martinho
  • Ponta da Piedade
  • Praia do Camilo
  • Praia de Donna Ana
  • Praia dos Mos
  • Algar Seco in Carvoeiro

Lisbon: (4 nights)

We then start to work our way north with a stop back in Lisbon for 4 more nights.  We will see what we were able to accomplish during our first round of Lisbon being jetlagged and go from there.

On the way from Lisbon to Peniche, we plan to stop in Sintra for the day.

Peniche: (8 nights)

While Peniche doesn’t seem to be on any tourist radar, we were able to find an Airbnb here for 1/3 of the cost of anywhere else along the Silver Coast, so Peniche it is! I’m actually excited to be calling Peniche our home as it looks like it a central spot for the Silver Coast region and there are some great little restaurants and bakeries in town.

Places to check out from Peniche:

  • Obidos
  • Caldas de Rainha
  • Foz do Arelho
  • Sao Martinho do Porto
  • Nazare

Porto (Arcozelo): (10 nights)

We’re staying just outside Porto in a town called Arcozelo.  Reason being, we found an Airbnb with a nicer and larger setup than anything in Porto proper for a lower cost and only a 10 minute drive into the city.  Originally we were planning on Aviero as our most northern location but after some digging it sounds like it’s quite sleepy there this time of year.

Things to do in Porto:

  • Again, a free walking tour is in order
  • La Ribeira river walk
  • Bolhao market
  • Take a tram ride
  • Teleferio da Gaia cable car
  • Funicular doa Guindais
  • Jardins do Palacio de Cristal
  • Day trips to Aviero, Braga, and Guimaraes

Lisbon: (4 nights)

On the way back to Lisbon from Porto we plan to stop at Coimbra on the way down.

We likely will be exhausted at this point and I imagine us winding down and going to strolls along the streets, checking out our favourite places one last time, and checking out the aquarium.

We’re also looking into getting dentist appointments for teeth cleanings while in Portugal so if that does end up happening I’ll report back with more info about our experience with medical tourism.

Amsterdam: (1 night)

We then hop back on a plane to bring us back to Amsterdam for a night before heading back to Calgary.

There you have it!  I honestly have done very little planning (for my standards at least) for this trip.  I liked how when we spent 5 weeks on Vancouver Island last year we came up with a list of things to do but not really much info for each place which added a bit more spontaneity to the trip which I surprisingly enjoyed. We shall see if I wish I did more planning once all is said and done.

For those who have been to Portugal before, any suggestions of places to check out, off the beaten ideas we haven’t thought of yet, meals/restaurants to try? For those who have Portugal on their radar, hope this itinerary helps with you future travel plans!

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16 thoughts on “Our Itinerary: Two Months in Portugal”

  1. I haven’t even read the whole post yet and I’m so excited for you! And will be following and tracking closely as this is my dream! Except the kids are early 20s. And I haven’t convinced them to come with us. Yet. Have to run out now but will savour reading this and planning right along with you! PS. I’m the one who camped for the night in Cochrane on our way through AB in our new to us rv, checking out your cool town. 😀

    1. Ah awesome, hi Tracy Cochrane RV Camper! 😆

      I think you’re on to something waiting to take the kids until their early 20s. I’m sure they will appreciate it more at that age – if you can convince them to join ya!

  2. Love it! The plan you’ve made by mapping out the big stuff and leaving room for spontaneity in each location is exactly how we like to travel with our son (now 9). I think it’s the best approach with kids and there are so many things you’ll find that you never could have googled in advance. I also like how it mirrors your approach to finances (control the big stuff, stay flexible with the small stuff)
    What’s your planned cost for the full trip? Asking as someone starting to rough out 12 months traveling in a couple years. Or maybe that’s a future post…
    You’re going to have an amazing time, can’t wait for the updates!

    1. I like how you aligned our travel strategy with our financial strategy – I haven’t thought of it in that light, thanks for bringing that up Robert!

      Future post indeed will dig into the costs, stay tuned!

  3. So excited for you all !
    We were thinking of Portugal for September this year but ended up booking for Madrid and Malaga. I will definitely be following your posts and look forward to hearing about everything. I’m sure it will help me decide on Portugal for next time !

  4. Hi Court and Nic. This post made me excited for you guys and also for myself. I’ll pay close attention to how you plan things and hopefully use it to plan our European tour next year. It’s way too far ahead but just thinking about it makes my head spin already. I have to remind myself it’s gonna be fun. But first things first. Plan, plan, plan. And save. Don’t rob the savings for travel fund.

    This gave me an idea that there are direct flights from Calgary to Amsterdam. I’ll check the other countries and how much will it cost us. I’m just wondering why you guys decided to go back to Amsterdam on your way back to Calgary. Wouldn’t it be possible to catch a flight from Portugal or other close European country back to Calgary?

    And also what travel insurance did you guys choose if you have one? I used World Nomads before the lockdown and looking for other options.

    Thanks for all the details and upcoming updates. Enjoy your trip and the sunny weather (or is it also winter in Amsterdam and Portugal this time of the year?).

    1. H! So sorry for the delay getting back to you! Definitely play around with Google and different airline websites to see what sort of flight routes you can find from your origin destination. Piecing the two flights together Calgary to Amsterdam and Amsterdam to Portugal ended up being more cost effective than booking a more standard flight Calgary to Lisbon (and same thing for the return) as we were able to use a low cost European carrier + the sale price from WestJet for that same direct AMS-YYC route for the longer transatlantic flight. So it was two low cost flights priced together for a total of $753 CAD round trip per person Vs a more normal flight purchase of 1 single booking from Calgary to Lisbon would have been closer to $1,000 CAD round trip per person. Hope that makes sense!

      We ended up using TuGo for our travel insurance. It was considerably lower cost vs World Nomads for the same coverage. I’d definitely recommend checking out that travel insurance search engine link in the post as it saved us a few hundred dollars.

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  7. Hi there! I’ve visited Portugal three times, about 2-3 weeks each. Here are a few thoughts:

    – Madeira is lovely, but 12 nights may be somewhat too long, and cut too much into your mainland time. A week should be ample to hike the levadas 🙂
    – The Algarve isn’t sleepy at all! It’s the primary tourist region, and attracts hordes of Brits, Germans, and others in the high season. Tons of condo and resort developments, and a lot of ex-pats … that being said, it is very seasonal, and many places are shut this time of year.
    – Evora, Coimbra, and the Douro Valley upriver from Porto are absolute musts, as is Vila Nova de Gaia across the estuary from Porto – the port wine cellars are amazing.
    – 12 nights in Lisbon, like Madeira, may short you on some of the lovely towns nearby; Cascais is just a 30-40 minute commuter train away, and it’s a delight, complete with a 19th century carousel. Sintra is just plain gorgeous.

    Evora is incredible – a beautifully preserved medieval town with its 14th-century walls, shops and houses tucked into the arches of its ancient aqueduct, a charnel chapel made of bones and skulls …

    Coimbra also has stunning medieval architecture – particularly the cathedral and the university – talk about dreaming spires and shadowed colonnades!

    The Douro Valley train is a must-do; we took the train up and a kitschy but delightful boat ride back. Gorgeous scenery, terraced vineyards that date back to Roman times, & just all-round lovely.

    The food is amazing. Look for the pratos do dias – daily specials – in the holes in the walls where the locals are.

    Have fun! My partner and I are going for a month in late September – catching the last of the beach bars in the Algarve! – and October.

    1. Hey Joanne thanks for all of this! Sorry for the delay getting back to you!

      Madeira ended up being our highlight and if we could go back, we would lengthen this portion and shorten everything else except the 12 nights in Lisbon portion of the itinerary.

      Algarve definitely gave us a touristy/expat vibe and we could only imagine the hustle and bustle in the summer. Glad we were there when all the boat tour kiosks were closed! Not our personal cup of tea but can see why so many expats head over there.

      Agreed that Sintra was super cool! We didn’t get to stop in Evora but passed through Coimbra and did some driving on the outskirts of Porto. It really is some cool landscape throughout the country and our long days driving through the countryside were some of our highlights.

      Your suggestions sound great for someone heading to Portugal without young kids haha but when traveling with littles in tow we had to adjust our pre-kid-travel expectations and cater a lot of the activities to their interests.

      Hope you enjoy your upcoming visit!

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  10. Mark C - Toronto

    Hi Court,
    Thanks for sharing your itinerary. It’s giving me some ideas for possible future Portugal travel, which I have not seen yet. I like the detail on your approach to planning and decision-making. I am reading this after the fact, but better late than never.

    1. Thanks Mark! I must admit there was much less planning for this trip than for previous trips we have been on but it all worked out! Looking back, I would have spent more time in Madeira and Lisbon and less time in the southern part.

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