Portugal truly has it all. Wine that'll make you reconsider your drinking habits (in the best way), beaches carved into dramatic cliffs, rivers winding through ancient valleys, narrow cobblestone streets that were definitely not designed for modern cars, and yes, that famous yellow tram. I traveled from the sun-soaked Algarve in the south all the way north to the terraced vineyards of the Douro Valley and the vibrant streets of Porto, with plenty of stops in Lisbon and charming villages along the way.
This is my 10-day itinerary that actually worked – no rushing, no FOMO, just the right balance of sightseeing and soaking it all in. And if you want help booking this luxury trip for less? Reach out to me.
Getting There: The Flights ✈️
My family flew to Lisbon using points and miles, but here's where it got interesting: we were coming from four different cities, arriving and departing on different days, and arriving and departing on different flights to and from different destinations. Chaos, right?
Actually, it was both complex and simple at the same time. Simple because we were essentially four solo travelers with some flexibility, which makes award bookings much easier to piece together. Complex because keeping track of everyone's itinerary required a detailed spreadsheet and possibly too much coffee.
Want the full breakdown? You can read about exactly how I used points and miles for these flights here.
Days 1-3: Lisbon ☕
Lisbon hits different. Europe's second-oldest capital somehow manages to feel both ancient and alive, with its hilltop neighborhoods cascading down to the Tagus River. The tile-covered alleys of Alfama will have you stopping every five steps for photos, while the contemporary buzz keeps things fresh.
My top picks:
🚶♀️ Start with a FREE walking tour – I do this in every city I visit. You'll get the history, the layout, and those crucial local tips about where to actually eat (not the tourist traps).
🚋 Tram 28 – Hop on and let it rattle you through the historic districts. Pay on board, around €2.50. Yes, it's packed with tourists, but there's a reason for that.
⚓ Maritime Museum – Give yourself 2-3 hours here. Portugal's seafaring history is wild, and this place tells it well.
🏛️ Carmo Convent – The roofless ruins are hauntingly beautiful.
📚 Baixa district – Wander through and pop into Livraria Bertrand, the world's oldest bookstore. It still smells like old paper and possibilities.
🌅 Sunset viewpoints – Miradouro da Graça and Miradouro Senhora do Monte are where you want to be when the light turns golden.
🍴 Mercado da Ribeira – Food stalls galore when you need a quick bite.
The Pastéis de Nata situation 🥐
Look, you're going to eat approximately 47 of these custard tarts. Here's where to find the best ones:
- Manteigaria
- Fábrica de Nata
- Pastelaria Santo António
- Pastéis de Belém (the original from 1837 – yes, there will be a line)
Days 3-5: Sintra & Douro Valley 🏰🍷
Sintra is basically a fairy tale that wandered into Portugal and decided to stay. Castles everywhere you look.
Pro tip: Do NOT drive into the town center. Just don't. Park outside and walk in, or take the train from Lisbon as a day trip. If you must drive, grab a parking meter spot (download the parking app so you can add time remotely) and hoof it from there.
There are dozens of castles here. Take a FREE walking tour to see most from the outside, then pick your favorite 2-3 to explore inside. Pena Palace is the famous colorful one on the hill – you'll need to bus up from town to reach it.
🍰 Must-try: Stop at Periquita (on the corner in town center) for local pastries that'll ruin your diet plans.
Douro Valley 🌄
This is where Portugal gets serious about wine and scenery. Most people day-trip from Porto, but I'm begging you – stay overnight. The valley at sunset, with a glass of wine in hand? That's the moment you'll remember.
🏡 Where to stay: Book a vineyard like Quinta da Portela. We spent two nights here, and our host brought breakfast baskets to our villa each morning – fresh pastries, yogurt, eggs, coffee, homemade jams. After a private wine tasting on the terrace overlooking the vines, I never wanted to leave.
🍷 Wine tastings: We did two, both around €20 per person:
- D'Origem – Started with an olive oil factory tour, ended with wine tasting on a deck with valley views that'll make your Instagram followers jealous
- Second vineyard (closer to our quinta) – More commercial vibes but held in an atmospheric wine cellar at a gorgeous table
Also available: hiking, biking, and boat tours on the Douro River.
Days 5-7: Porto 🌉
Porto just works. The history, the architecture stacked on hillsides, the entire culture built around Port wine – it's got everything.
🚶 FREE walking tour alert – I love Guruwalk but there are lots of tours available. They focus on the old historic center, which is where Porto's soul lives. After the tour, head downhill to where the magic really happens.
The Riverfront 💙
Seven bridges span the Douro here, with water taxis zipping underneath. The views are absolutely breathtaking – you can walk for hours along the promenade, ducking into shops, grabbing petiscos (Portuguese tapas), and watching street performers.
🍷 Port cellars – All located across the river in Vila Nova de Gaia (thanks to old tax laws). Dozens to choose from, but we loved Ferreira, one of the oldest producers. The cave and cellar tour is fascinating, ending in a proper tasting room where we sampled ruby, white, and tawny ports. Tours run about €20 per person.
🏛️ Palácio da Bolsa – Get tickets (around €11) if you can. Even if you've seen your share of palaces, this one will drop your jaw. Trust me on this.
Days 8-10: Algarve 🏖️
Portugal's southern coast delivers on natural beauty, dramatic cliffs, and that perfect beach vacation energy.
Base yourself in Lagos so you're not packing and unpacking every day.
🚣 Benagil Caves – Absolutely unmissable. Choose between a boat tour or kayaking (heads up: the ocean can get choppy). The view from the water looking back at those golden cliffs is stunning. Plus, you'll hit a secret beach and explore a hidden tunnel.
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