5 Unforgettable Weeks in Portugal: A Love Letter to a Beautiful Country
By DeeAnn Gray, Travel & Cruise ConsultantUpdated October 2026 · 6 min read
Quick takeaways
- DeeAnn spent five weeks travelling Portugal from Lisbon to the Algarve, and found it beautiful, welcoming and surprisingly affordable.
- Lisbon highlights: Alfama’s winding streets, sunsets from the miradouros, Bairro Alto and daily pastéis de nata.
- Don’t miss medieval Óbidos, the giant waves of Nazaré, Pena Palace in Sintra and historic Évora.
- In the Algarve, compare the dramatic cliffs of Lagos with the calm beaches of Tavira.
If you’ve ever thought about traveling to Portugal—do it. After spending five glorious weeks exploring this charming, sun-drenched country, I can wholeheartedly say: I am in love. From the winding cobblestone streets of Lisbon to the golden cliffs of the Algarve, every moment was a dream come true.
Portugal welcomed us with open arms, and as a travel consultant, I couldn’t wait to soak up every experience, every flavor, every view—and bring all of it back to inspire your own adventures in Portugal.
Lisbon: the city of light and soul
Our journey began in Lisbon, and what a perfect place to start in Portugal. With its colorful facades, historic trams, and stunning river views, Lisbon effortlessly blends old-world charm with modern energy. We wandered through Alfama’s maze-like streets, caught sunsets from Miradouros, and soaked in the lively atmosphere of Bairro Alto.
The food scene was fantastic—fresh seafood, warm pastries, and of course, daily doses of pastéis de nata. We found the city incredibly affordable and easy to explore.
Óbidos and Nazaré: hidden gems with heart
From Lisbon, we ventured north to Óbidos, a storybook town encircled by medieval walls. Walking along the ramparts felt like stepping back in time. Óbidos, in Portugal, boasts whitewashed houses splashed with vibrant flowers that are picture-perfect.
In nearby Nazaré, we were lucky enough to witness the powerful Atlantic waves the town is famous for. It’s a place where the ocean roars, and you can feel the raw beauty of nature in every salty gust of wind. The beach town vibe, fresh seafood, and laid-back energy made it a highlight of the trip.
Advisor tipVisiting Nazaré in the winter months gives you the best chance to see the famous giant Atlantic waves.
Pena Palace: a fairytale in the clouds
No trip to Portugal is complete without a visit to Sintra, and the Pena Palace was absolutely magical. Perched high above the town, this colorful palace looks like something out of a dream. The combination of Romanticist architecture and lush forest surroundings made it one of the most enchanting stops in Portugal.
Évora: timeless charm in the Alentejo
Évora was a beautiful change of pace—quiet, historic, and rich with culture. Roman ruins, charming squares, and peaceful walks through centuries-old streets made for a soulful experience in Portugal. The slower pace and authentic feel of this region left a lasting impression on us.
The Algarve: coastal bliss
Then, we made our way south to the Algarve, where we fell head over heels for Portugal all over again. From the dramatic cliffs of Lagos to the calm beaches of Tavira, every coastal town offered something unique in Portugal. We swam in crystal-clear waters, explored sea caves, and dined by the ocean under the stars.
The Algarve stole our hearts—sunny days, delicious food, and an easygoing vibe that made us feel completely at peace.
Planning your own Portugal trip
Feeling inspired? Here’s what we tell clients who are starting to plan a trip to Portugal.
- Best time to go: spring (April to June) and fall (September and October) bring warm weather and fewer crowds. July and August are hot and busy, especially in the Algarve.
- Flights from Canada: you can fly nonstop to Lisbon from Toronto and Montréal, with Porto as another easy gateway.
- Getting around: trains make Sintra an easy day trip from Lisbon (about 40 minutes), and also connect Lisbon with Évora and the Algarve. For Óbidos, Nazaré and hopping between Algarve beach towns, a rental car gives you the most freedom.
- How long to stay: even 10 days to two weeks lets you see Lisbon, Sintra and the Algarve. With more time, follow DeeAnn’s lead and add Óbidos, Nazaré and Évora.
- Entry for Canadians: Portugal is part of Europe’s Schengen area, so Canadians don’t need a visa for short visits. Check the latest entry requirements before you go, as the EU is rolling out new digital border checks.
A sample two-week route
- Lisbon (4 nights): Alfama, Bairro Alto, the miradouros and a day trip to Sintra and Pena Palace.
- Óbidos and Nazaré (2 nights): walk the medieval walls, then watch the Atlantic waves.
- Évora (2 nights): Roman ruins, quiet squares and Alentejo food and wine.
- The Algarve (5 nights): split your time between the cliffs and sea caves of Lagos and the calm beaches of Tavira.
Advisor tipPena Palace uses timed-entry tickets and gets very busy, so book ahead and go early in the day. If you have extra time, add Porto and the Douro Valley wine region in the north.
Portugal, you have my heart
After five incredible weeks, one thing is certain: Portugal is a place we’ll return to again and again. It’s beautiful, welcoming, and surprisingly affordable—perfect for every kind of traveler. Whether you’re seeking culture, history, relaxation, or adventure, Portugal delivers it all with grace and warmth.
If Portugal is calling your name, I’d love to help you plan the trip of a lifetime. Let’s turn your dreams into itineraries—and make your own love story with Portugal.
Because life is short… take the trip.
Is Portugal calling your name? DeeAnn would love to help you plan the trip of a lifetime. Explore more European getaways.
FAQs
How long should I spend in Portugal?
DeeAnn spent five weeks and loved every minute, but even a week or two lets you see Lisbon, Sintra and the Algarve.
Is Portugal affordable?
DeeAnn found Portugal surprisingly affordable, especially Lisbon, which was also easy to explore.
What is the best day trip from Lisbon?
Sintra and its colourful Pena Palace is a must, and Óbidos and Nazaré make a great trip north of the city.
Where should I stay in the Algarve?
Lagos is known for its dramatic cliffs and sea caves, while Tavira has calmer beaches and a more relaxed pace.
When is the best time to visit Portugal?
Spring (April to June) and fall (September and October) offer warm weather and fewer crowds. Summer is hot and busy, and winter is the best time to see Nazaré’s giant waves.
Do Canadians need a visa for Portugal?
No, Canadians don’t need a visa for short tourist visits to Portugal. Check the latest entry requirements before you travel, as the EU is introducing new digital border checks.
