18 days in Portugal Itinerary
Created using Inspirock Portugal route maker
Start: Montreal
Fly
1
Lisbon
— 5 nights
Drive
2
Lagos
— 2 nights
Drive
3
Sintra
— 2 nights
Fly
4
Porto
— 2 nights
Fly
5
Funchal, Madeira
— 5 nights
Fly
End: Montreal
Tue, May 2 - Fri, May 19
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Lisbon — 5 nights

City of Seven Hills
Lisbon is known for sightseeing, historic sites, and zoos & aquariums. Your trip includes some of its best attractions: contemplate in the serene atmosphere at Mosteiro dos Jeronimos, wander the streets of Alfama, get the lay of the land with Walking tours, and don't miss a visit to Belém Tower.
For where to stay, traveler tips, reviews, and tourist information, you can read our Lisbon tour planning website.
Montreal, Canada to Lisbon is an approximately 10.5-hour flight. The time zone changes from Eastern Standard Time (EST) to Western European Standard Time (WET), which is usually a 5 hour difference. Traveling from Montreal in May, expect nights in Lisbon to be about the same, around 15°C, while days are somewhat warmer, around 28°C. Finish up your sightseeing early on the 7th (Sun) so you can go by car to Lagos.
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For where to stay, traveler tips, reviews, and tourist information, you can read our Lisbon tour planning website.
Montreal, Canada to Lisbon is an approximately 10.5-hour flight. The time zone changes from Eastern Standard Time (EST) to Western European Standard Time (WET), which is usually a 5 hour difference. Traveling from Montreal in May, expect nights in Lisbon to be about the same, around 15°C, while days are somewhat warmer, around 28°C. Finish up your sightseeing early on the 7th (Sun) so you can go by car to Lagos.
Find places to stay May 2 — 7:
Highlights from your trip
Lagos — 2 nights

Jewel of the Algarve
On the 8th (Mon), stop by A Guilda, stroll through Praia Da Rocha, then paddle through the water with a kayaking and canoeing tour, and finally explore the striking landscape at Ponta da Piedade. Here are some ideas for day two: enjoy the sand and surf at Praia da Falesia, visit Centro Historico de Albufeira, and then find something for the whole family at Zoomarine Algarve.
To see reviews, traveler tips, where to stay, and tourist information, refer to the Lagos day trip planning tool.
Getting from Lisbon to Lagos by car takes about 3 hours. Other options: take a bus; or take a train. In May in Lagos, expect temperatures between 28°C during the day and 18°C at night. Wrap up your sightseeing on the 9th (Tue) to allow time to drive to Sintra.
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To see reviews, traveler tips, where to stay, and tourist information, refer to the Lagos day trip planning tool.
Getting from Lisbon to Lagos by car takes about 3 hours. Other options: take a bus; or take a train. In May in Lagos, expect temperatures between 28°C during the day and 18°C at night. Wrap up your sightseeing on the 9th (Tue) to allow time to drive to Sintra.
Side Trips
Find places to stay May 7 — 9:
Highlights from your trip
Sintra — 2 nights

Start off your visit on the 10th (Wed): explore the historical opulence of Quinta da Regaleira, then admire the landmark architecture of Sintra National Palace, then admire the striking features of Park and National Palace of Pena, and finally appreciate the history behind Pelourinho de Sintra. Get ready for a full day of sightseeing on the next day: step into the grandiose world of Castelo dos Mouros, then stop by The Sintra Gift, and then make a trip to Cabo da Roca.
To see reviews, where to stay, traveler tips, and other tourist information, read our Sintra day trip planning tool.
Traveling by car from Lagos to Sintra takes 3.5 hours. Alternatively, you can do a combination of bus and train; or take a train. In May, plan for daily highs up to 28°C, and evening lows to 15°C. Finish up your sightseeing early on the 11th (Thu) so you can catch the flight to Porto.
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To see reviews, where to stay, traveler tips, and other tourist information, read our Sintra day trip planning tool.
Traveling by car from Lagos to Sintra takes 3.5 hours. Alternatively, you can do a combination of bus and train; or take a train. In May, plan for daily highs up to 28°C, and evening lows to 15°C. Finish up your sightseeing early on the 11th (Thu) so you can catch the flight to Porto.
Side Trip
Find places to stay May 9 — 11:
Highlights from your trip
Porto — 2 nights

Unvanquished City
Kick off your visit on the 12th (Fri): test your team's savvy at popular escape rooms, take in panoramic vistas at Torre dos Clerigos, take in the spiritual surroundings of Porto Cathedral (Se Catedral), then get into the urban bustle at Palacio da Bolsa, then take in the views from Ponte de Dom Luis I, and finally stroll through Ribeira do Porto. Here are some ideas for day two: indulge your senses at some of the top wineries in the area.
For other places to visit, where to stay, photos, and tourist information, use the Porto trip maker.
Fly from Sintra to Porto in 2.5 hours. Alternatively, you can drive; or take a train. Traveling from Sintra in May, you will find days in Porto are a bit cooler (23°C), and nights are about the same (13°C). Finish your sightseeing early on the 13th (Sat) so you can fly to Funchal.
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For other places to visit, where to stay, photos, and tourist information, use the Porto trip maker.
Fly from Sintra to Porto in 2.5 hours. Alternatively, you can drive; or take a train. Traveling from Sintra in May, you will find days in Porto are a bit cooler (23°C), and nights are about the same (13°C). Finish your sightseeing early on the 13th (Sat) so you can fly to Funchal.
Find places to stay May 11 — 13:
Highlights from your trip
Funchal, Madeira — 5 nights
Spend the 17th (Wed) spotting exotic species with a safari tour. The adventure continues: see Off-Road Tours, admire the natural beauty at Botanická zahrada Madeira, do sightseeing your way with Madeira Sidecar Tours, and view the masterpieces at Lillie Ceramics.
Plan my trip to Funchal with suggested itineraries provided by Inspirock.
Fly from Porto to Funchal in 3.5 hours. Plan for somewhat warmer nights when traveling from Porto in May since evenings lows in Funchal dip to 19°C. Cap off your sightseeing on the 18th (Thu) early enough to catch the flight back home.
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Plan my trip to Funchal with suggested itineraries provided by Inspirock.
Fly from Porto to Funchal in 3.5 hours. Plan for somewhat warmer nights when traveling from Porto in May since evenings lows in Funchal dip to 19°C. Cap off your sightseeing on the 18th (Thu) early enough to catch the flight back home.
Side Trips
Find places to stay May 13 — 18:
Highlights from your trip
Portugal travel guide
Small in size but rich in history, culture, and natural beauty, Portugal features contrasting landscapes that include long beaches, lush vineyards, verdant valleys, and rolling hills dotted with tiny settlements where old traditions still prevail. The country's serene interior, often overlooked by foreigners, remains largely unspoiled by mass tourism and offers visitors a chance to discover this less-trodden part of Europe at their own pace. Ripe for leisurely adventures on foot or by bicycle, Portugal's fertile countryside boasts well-preserved medieval castles and outstanding wineries, producing some of the world's finest ports. The country's cities offer a lively culinary scene known for its many award-winning restaurants, topping the itineraries of foodies from around the globe.