Lisbon is one of those cities that ruins you for everywhere else, in the best possible way. Seven hills, 300 days of sunshine a year, the world's oldest trams rattling through the Alfama, and pastéis de nata so good you'll order a second before you've finished the first. Within two hours of the city you've got fairy-tale palaces in Sintra, cork forests and medieval villages in the Alentejo, and the terracotta rooftops of Porto. Whether you want a leisurely week of wine and history, an active adventure through wild landscapes, or something in between Lisbon is the perfect place to start.

Our tours starting in Lisbon are designed for travelers who want structure and value without sacrificing flexibility. These packages typically include flights, hotels, and transfers. Many extend beyond Lisbon into the wider Iberian Peninsula or deeper into Portugal itself, so they also include intercity transportation. Some included guided tours and day trips to help you make the most of your time.

Departure Airports

Most of our Lisbon tours are built around departures from Toronto and Montreal, where  direct flights are more readily available. If you are departing from other Canadian gateways and want help finding the best route, give us a call.

Popular Itineraries

Lisbon is a wonderful starting point because it connects naturally to so much, both within Portugal and across the Iberian Peninsula.

Lisbon & Sintra: The essential introduction. Lisbon for its neighbourhoods, its food, its beautiful chaos, and Sintra for palaces and pine-forested hills just 40 minutes away by train. This is a great fit for first-timers who want to get a real feel for Portugal without rushing.

Lisbon & the Alentejo: A wonderful contrast to the city, the Alentejo is cork oaks, medieval walled towns like Évora, excellent wine, and arguably the best food in Portugal. Slower, quieter, and deeply rewarding. A great choice if you've already done Lisbon and want to go deeper.

Sunny Portugal: A broader sweep of the country, covering Lisbon, the coast, and the countryside. Great for travelers who want a taste of everything and aren't yet sure which part of Portugal they'll fall in love with yet, (spoiler: it'll probably be all of it).

Lisbon, Madrid & Barcelona: The big Iberian adventure. Three capital cities, each with a completely different vibe. A lot of ground to cover, but the rail and flight connections make it very doable. This one tends to convert people into Iberian regulars.

Cities of Light, Lisbon & Madrid: A more focused two-city pairing, ideal if you want to spend meaningful time in each place. Lisbon and Madrid complement each other nicely: both walkable, both underrated, and both extremely easy to love.

Pearls of the Iberian Peninsula: A fuller tour that includes smaller towns and hidden gems alongside the main cities. Great for travelers who've already seen the highlights and want to go a little off the beaten path.

Where You May Stay

• Lisbon: One of Europe's most livable and loveable cities. It's hilly, colourful, and full of character, with a historic centre and winding streets that open suddenly onto sweeping views over the Tagus. The food scene is excellent. It's also a remarkably easy city to get around, whether you're hopping on the metro, catching a vintage tram, or simply walking from one neighbourhood to the next. 
• Sintra: Just 40 minutes from Lisbon by train, Sintrais a small, forested hill town dotted with extravagant palaces and crumbling Moorish castles. The most famous landmarks, including the candy-coloured Pena Palace perched dramatically above the treeline and the mysterious Quinta da Regaleira with its spiral initiation well, are genuinely worth the hype.  If your tour includes a night or two in Sintra, lean into it. Staying overnight once the day-trippers have gone home is a completely different experience, quieter, and more magical.
• Évora: Évora is a wonderful place to spend a night or two. It's a small, walled UNESCO city with Roman ruins, a medieval cathedral, and some of the best restaurants in Portugal. Staying here rather than day-tripping from Lisbon makes a real difference. The pace slows right down, the evenings are lovely, and you get the city largely to yourself once the day visitors head home.
• Cascais: A relaxed coastal town about 40 minutes west of Lisbon by train, Cascais is a great option if you want easy access to the city without staying in the middle of it. It has its own charming old town, good beaches, excellent seafood restaurants along the waterfront, and an unhurried feeling of being on the coast. Particularly worth considering if you're travelling in summer and want to be near the water.
• Porto: Porto is compact, moody, and built around the steep banks of the Douro River. The old city centre, a UNESCO World Heritage Site, is a tangle of narrow streets lined with crumbling azulejo-tiled facades, ornate baroque churches, and one of the most beautiful bookshops in the world. The riverside Ribeira district is the place to eat well and linger over a glass of wine, with Vila Nova de Gaia and its historic port wine lodges sitting just across the water.
• Douro Valley: If your tour ventures into the Douro, you're in for something special. This is one of the most beautiful wine regions in the world, with terraced vineyards dropping steeply down to the river and quintas offering tastings and overnight stays. It's best explored slowly, ideally with a river cruise component or at least a full day on the water. The region is at its most dramatic in autumn during harvest, but it's honestly stunning in any season.

Portuguese weather

Portugal is one of the sunniest countries in Europe, and Lisbon in particular has a genuinely excellent climate for most of the year, however there are a few things worth knowing before you book:

Spring (March through May) is arguably the best time to visit. Temperatures are warm but not hot, the hills are green, the flowers are out, and the crowds haven't arrived yet. A very strong choice.

Summer (June through August) is hot and busy, particularly July and August. Lisbon can reach 35°C or above, and popular spots like Sintra get very crowded. That said, the evenings are beautiful and the beach access is hard to beat.

Autumn (September and October) is another sweet spot, warm, less crowded than peak summer, and a great time to explore the Alentejo wine regions at harvest.

Winter (November through February) is mild by European standards. Lisbon rarely drops below 10°C, and winter can be a perfectly pleasant time to visit if you don't mind some rain and the shorter days. Flights and hotels offer better value, and the city feels calmer and more authentic without the rush of tourists.

If you're combining Lisbon with the Algarve coast and beach time is a priority, plan for June through September. For a city and culture-focused trip, April, May, or October are hard to beat.

Not sure which tour to book?

That's exactly what our agents are here for. They know Portugal, with many agents having traveled there themselves, and can help you figure out whether you want to go deep into one area or cover more ground across the Peninsula. Whether you're planning a romantic first trip, a solo adventure, a food-and-wine escape, or a multi-country Iberian journey, we'll help you find the package that fits. Give us a call at 1-800-665-4981 and let's figure it out together.