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5-DAY ITINERARY · PORTUGAL

5 days in Lisbon & Sintra

📅 5 days · 4 nights💵 ≈ US$1,865 per person with flights✈️ Priced for December 2026💑 Couples🗓 Best: Mar–Jun, Sep–Dec
💵 About US$1,865 per person with flights from Toronto (US$3,730 for 2 adults)

Priced for travel in December 2026. Prices change with dates: peak holidays cost more, quieter months less. Pick your own dates with “Customise this trip” and the planner shows prices for them.

Experience the vibrant culture, rich history, and delicious cuisine of Lisbon over a 5-day getaway. Explore iconic neighborhoods, indulge in local delicacies, and take a scenic day trip to the fairy-tale town of Sintra.

DAY 1Fly to Portugal
17:45🚆

Travel to the airport in Toronto

Taxi, ride-share or transit · arrive 3 hours before the flight · cost depends on where you live

21:30✈️

Flight from Toronto to Lisbon

Overnight flight · lands the next day at 10:40

See flights ↗
≈ US$635 pp
DAY 2Arrive & Alfama≈ US$418 pp
11:25🚆

Pre-booked private transfer

About 30 min from the airport

Book ↗
US$16 pp
11:55🛏

Check-in at Hotel Lisboa Plaza (3 nights)

3 nights in Lisbon · ~US$205 per night · Arriving before check-in time: leave your bags and explore · Baixa

See hotels ↗
US$307 pp
12:55📍

Jerónimos Monastery

A UNESCO World Heritage Site with stunning architecture.

Book ↗
US$14 pp
14:30🍽

Lunch at Time Out Market

Enjoy a variety of local dishes in a vibrant market atmosphere.

US$28 pp
16:00📍

São Jorge Castle

Explore the historic castle with panoramic views of Lisbon.

Book ↗
US$11 pp
18:30🍽

Dinner at Ramiro

Famous for its seafood, especially the garlic shrimp.

US$42 pp
DAY 3Exploring Belém and Alfama≈ US$74 pp
08:00🍽

Breakfast at Hotel Lisboa Plaza

At your hotel, or a café nearby

09:15📍

Alfama District

Wander through the charming, narrow streets of this historic neighborhood.

Free
11:00📍

Belém Tower

Visit this iconic UNESCO World Heritage site by the river.

Book ↗
US$7 pp
12:30🍽

Lunch at O Prego da Peixaria

Enjoy delicious seafood sandwiches and fresh ingredients.

US$21 pp
14:00📍

MAAT - Museum of Art, Architecture and Technology

Explore modern art and architecture in a stunning riverside setting.

Book ↗
US$11 pp
18:30🍽

Dinner at A Cevicheria

Savor Peruvian-inspired dishes in a trendy setting.

US$35 pp
20:30📍

Miradouro de Santa Catarina

Enjoy stunning views of the sunset over the Tagus River.

Free
DAY 4Day trip to Sintra≈ US$92 pp
08:00🍽

Breakfast at Hotel Lisboa Plaza

At your hotel, or a café nearby

09:15📍

Quinta da Regaleira

Explore the enchanting gardens and initiatic wells.

Book ↗
US$11 pp
11:00📍

Pena Palace

Visit this colorful Romanticist castle with stunning views.

Book ↗
US$18 pp
13:00🍽

Lunch at Tascantiga

Enjoy traditional Portuguese tapas in a cozy setting.

US$21 pp
14:30📍

Sintra National Palace

Discover the historical royal residence with unique architecture.

Book ↗
US$14 pp
16:00📍

Cabo da Roca

Visit the westernmost point of mainland Europe for breathtaking views.

Free
18:30🍽

Dinner at Cantinho Gourmet

Savor local dishes with a modern twist in a charming atmosphere.

US$28 pp
DAY 5Back home≈ US$11 pp
08:00🍽

Breakfast at Hotel Lisboa Plaza

At your hotel, or a café nearby

08:50⭐

Check-out from Hotel Lisboa Plaza

Check out

Free
09:05🚆

Taxi to Lisbon Airport

Arrive 3 hours before the flight

Book ↗
US$11 pp
12:30✈️

Flight from Lisbon to Toronto

Flight home

See flights ↗
≈ US$635 pp
🚆

Travel home from the airport

Taxi, ride-share or transit · cost depends on where you live

Prices are estimates per person, checked November 2026, for 2 travellers sharing, shown in US$. Times are a guide: check opening hours before you go. Booking links go to our travel partners; we may earn a small commission at no extra cost to you. Planned with the Nanajee AI trip planner and reviewed by Nanajee Travels.

Questions about this trip

How much does a 5-day trip to Lisbon cost?

About US$1,865 per person (US$3,730 for 2 adults) for this 5-day plan travelling in December 2026, including return flights from Toronto (about US$1,270) and 4 nights in a mid-range hotel, sharing a room. Without flights it is about US$595 per person. These are estimates checked in November 2026; prices change with dates, and peak holidays cost more.

What is the best time to visit Lisbon?

March to June and September to October are warm and sunny; winter is mild and quiet, with lower hotel prices.

How many days do you need in Lisbon?

5 days (including travel days) covers the highlights: Arrive & Alfama; Exploring Belém and Alfama; Day trip to Sintra. For a slower pace or more day trips, add a day or two with “Customise this trip”.

Can I change this itinerary?

Yes. Press “Customise this trip” and the free Nanajee planner opens with this trip filled in. Change the length, dates, budget, who is coming or your home city, and you get a new day-by-day plan with costs in about a minute.

How do you get around Lisbon?

This plan uses taxi and domestic flight to get between places; local transport costs about US$26 per person for the whole trip. Each journey is shown on the day it happens, with its time and cost.

Where should you stay in Lisbon?

This plan uses Hotel Lisboa Plaza (Hotel Lisboa Plaza, Lisbon) (or similar), 3 nights in total, chosen to be close to the places you visit. Hotels cost about US$307 per person for the trip, sharing a room. You can pick a different hotel or area with “Customise this trip”.

Can I do this trip with kids?

Yes, with a few changes. This plan is written for 2 adults. Press “Customise this trip”, choose “We have kids” and add their ages: the planner adjusts the pace, the stops and the costs for your family.