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.

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!

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.

– 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.

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?).