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  1. Home
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  3. Portugal 5 Nights 6 Days Road Trip Route Itinerary
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Itinerary
Madeira
3 Nights Stay
Madeira3 Nights
Day 01
Morning
Arrive in Madeira airport. Get transferred to your hotel.
Noon to Evening
At leisure. Add Activity
Day 02
Madeira: East Coast Cabriolet Road Trip
Full Day
Madeira: East Coast Cabriolet Road Trip
Day 03
Eastern Madeira: Full-Day Tour with Rum Tasting
Full Day
Eastern Madeira: Full-Day Tour with Rum Tasting
Fly to Lisbon
Lisbon
2 Nights Stay
Lisbon2 Nights
Day 04
Morning to Noon
At leisure. Add Activity
Evening
Checkout of your hotel. Board your flight to Lisbon. Check-in to your new hotel in Lisbon
Day 05
Lisbon: Nations Park Gondola Lift Cable Car Round Trip
Morning
Lisbon: Nations Park Gondola Lift Cable Car Round Trip
Noon
At leisure. Add Activity
Lisbon: Tuk Tuk with hotel pick up and the best of old city
Evening
Lisbon: Tuk Tuk with hotel pick up and the best of old city
Day 06
Morning
At leisure. Add Activity
Noon to Evening
Take your flight back home. Hope you end up with a lot of memories and a few souvenirs too.
Add trip details
₹103,753/ person
Excluding Applicable Taxes
Your route
city
We went for a trip to Portugal .. had a good experience with pick your trail. The support group was helpful and quite prompt. Some minor mishaps were there related to our visa.. but most of it was great. Hotel bookings were excellent. They were very helpful in planning the destination and suggested some changes for the good. Igni, srivatsan, loni all were very enthusiastic in responding to any of our queries! Overall good experience.Madhura Kelkar, Trip to Portugal

Your Ultimate Portugal 5 Nights Road Trip Itinerary

Embark on an exhilarating 5-night road trip through Portugal, where adventure meets culture in a breathtaking landscape. This itinerary will lead you from the rugged cliffs of Madeira to the vibrant streets of Lisbon, ensuring every moment is packed with unforgettable experiences.

Highlights of the Destination

  • Experience the stunning natural beauty of Madeira's rugged coastline.
  • Explore Lisbon's rich history, from São Jorge Castle to the colorful buildings of the Alfama district.
  • Indulge in local culinary delights, from traditional Pastéis de Nata to fresh seafood.
  • Discover hidden gems like the picturesque village of Santana that showcases traditional madeiran architecture.

Travel Tips for Portugal

  • Renting a car is essential for exploring off-the-beaten-path destinations in Madeira and beyond.
  • Visit during spring or autumn to enjoy milder temperatures and fewer tourists.
  • Don’t miss the local markets; they offer unique products and authentic experiences.
  • Learn a few basic Portuguese phrases; locals appreciate the effort and it enhances your experience.

Conclusion

This road trip itinerary promises you a blend of stunning vistas, rich histories, and immersive local experiences. Whether you're hiking the trails of Madeira or wandering the iconic streets of Lisbon, you're bound to create lasting memories. Prepare for a journey that delights all the senses as you uncover the many treasures Portugal has to offer.

See what’s included in this tripCost your itinerary to see the hotels, flights, and activities included in your trip
Inclusion card
4.7
From 8250 reviews
Verified Reviews
Photos from Travellers
Pickyourtrail's Original Reviews
Madhura Kelkar-Profile
Madhura Kelkar
Reviewed on :01 Mar 2018
We went for a trip to Portugal .. had a good experience with pick your trail. The support group was helpful and quite prompt. Some minor mishaps were there related to our visa.. but most of it was great. Hotel bookings were excellent. They were very helpful in planning the destination and suggested some changes for the good. Igni, srivatsan, loni all were very enthusiastic in responding to any of our queries! Overall good experience.
Madhura Kelkar-Profile
Madhura Kelkar
Reviewed on :01 Mar 2018
We went for a trip to Portugal .. had a good experience with pick your trail. The support group was helpful and quite prompt. Some minor mishaps were there related to our visa.. but most of it was great. Hotel bookings were excellent. They were very helpful in planning the destination and suggested some changes for the good. Igni, srivatsan, loni all were very enthusiastic in responding to any of our queries! Overall good experience.
harshal holkar-Profile
Harshal Holkar
Reviewed on :19 Feb 2026
Overall we had great experience with pickyourtrail! Right from bookings, itinerary and transfers everything went smoothly. Thank you team pickyourtrail!
harshal holkar-Profile
Harshal Holkar
Reviewed on :19 Feb 2026
Overall we had great experience with pickyourtrail! Right from bookings, itinerary and transfers everything went smoothly. Thank you team pickyourtrail!
Nandini suresh-Profile
Nandini Suresh
Reviewed on :19 Feb 2026
We had booked our honeymoon trip via pick your trail. The trip was super smooth. Everything was very well organized and we are super satisfied. Special appreciation to fahim and jagatheeshpathy for helping us with the arrangement of trip and always helping us with the queries
Nandini suresh-Profile
Nandini Suresh
Reviewed on :19 Feb 2026
We had booked our honeymoon trip via pick your trail. The trip was super smooth. Everything was very well organized and we are super satisfied. Special appreciation to fahim and jagatheeshpathy for helping us with the arrangement of trip and always helping us with the queries
Santhosh Kumar-Profile
Santhosh Kumar
Reviewed on :18 Feb 2026
We recently completed a 7-day trip booked for thailand through PickYourTrail, and overall it was a great experience. The itinerary was well planned, hotels were comfortable, and airport transfers were smooth. Their support team was responsive whenever we had questions. The trip was mostly hassle-free and enjoyable. A few activities felt a little rushed, but overall everything was managed professionally. I would definitely recommend PickYourTrail for a well-organized and stress-free vacation.
Santhosh Kumar-Profile
Santhosh Kumar
Reviewed on :18 Feb 2026
We recently completed a 7-day trip booked for thailand through PickYourTrail, and overall it was a great experience. The itinerary was well planned, hotels were comfortable, and airport transfers were smooth. Their support team was responsive whenever we had questions. The trip was mostly hassle-free and enjoyable. A few activities felt a little rushed, but overall everything was managed professionally. I would definitely recommend PickYourTrail for a well-organized and stress-free vacation.
Toolika Pandey-Profile
Toolika Pandey
Reviewed on :18 Feb 2026
It was great experience booking through pick your trail. They provided package at very reasonable rate as compared to other travel sources and the experience was good. We booked honeymoon package and they guided us everything regarding booking and the country that we travelled. Thanks a lot PYT!!!
Toolika Pandey-Profile
Toolika Pandey
Reviewed on :18 Feb 2026
It was great experience booking through pick your trail. They provided package at very reasonable rate as compared to other travel sources and the experience was good. We booked honeymoon package and they guided us everything regarding booking and the country that we travelled. Thanks a lot PYT!!!
niwash deen-Profile
Niwash Deen
Reviewed on :18 Feb 2026
It was an wonderful experience for my family. Right from the start they guided me very well shabreen in phase 2 and Abinaya in phase 3. We enjoyed a lot, Thank you Pick Your Trail for your perfect itinerary and support.
niwash deen-Profile
Niwash Deen
Reviewed on :18 Feb 2026
It was an wonderful experience for my family. Right from the start they guided me very well shabreen in phase 2 and Abinaya in phase 3. We enjoyed a lot, Thank you Pick Your Trail for your perfect itinerary and support.
4.7
From 8250 reviews
Verified Reviews

Frequently Asked Questions

What are the must-see attractions in Madeira?

Top attractions include Pico do Arieiro, Funchal's botanic gardens, and the stunning cliffs at Ponta de São Lourenço.

How do I get around during the road trip?

Renting a car is the best option, allowing you to explore at your own pace and reach remote areas.

What is the best time to visit Portugal?

Late spring (April to June) and early autumn (September to October) offer pleasant weather and fewer crowds.

Is Lisbon easy to navigate?

Yes, Lisbon's public transport system, including trams, buses, and metro, makes it easy to explore.

What local dishes should I try in Portugal?

Be sure to sample Bacalhau à Brás, Pastéis de Nata, and fresh seafood like grilled sardines.

Are there any cultural customs to be aware of?

Respect for traditions is important; when dining, wait to start until the host begins and try to learn a few local phrases.

What activities are recommended in Lisbon at night?

Experience the vibrant nightlife through a pub crawl or dinner in Bairro Alto, known for its lively atmosphere.
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