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  1. Home
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  3. Portugal 5 Nights 6 Days Luxury 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
₹110,704/ 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

Portugal 5 Nights Luxury Road Trip Itinerary

Prepare for an unforgettable escape as you journey through the stunning landscapes of Portugal on this 5-night luxury road trip. From the vibrant streets of Lisbon to the enchanting echoes of Madeira, every mile reveals spectacular views and treasured experiences that will stay with you long after your trip ends.

Highlights of the Destination

  • Experience the bustling charm and history of Lisbon.
  • Soak in breathtaking views from Pico do Arieiro in Madeira.
  • Discover traditional Madeiran culture in quaint villages like Santana.
  • Indulge in world-famous Portuguese wines and delectable local dishes.

Travel Tips for Portugal

  • Always try a pastéis de nata, a scrumptious custard tart, in Lisbon.
  • Book tours in advance during the peak seasons to ensure availability.
  • Learn a few basic Portuguese phrases – locals truly appreciate the effort!
  • Dress in layers; Portugal's coastal climate can change quickly.

Conclusion

Whether you’re a first-time visitor or returning to reclaim lost memories, this 5-night luxury road trip offers a rich tapestry of experiences that make Portugal irresistibly captivating. From the vibrant heart of Lisbon to the relaxed vibe of Madeira, every stop is a new adventure waiting to be unwrapped. So buckle up and get ready to create lasting memories on the roads of Portugal.

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 best places to visit in Portugal on a road trip?

Top spots include Lisbon, Madeira, Sintra, Estoril, and Porto, each offering unique attractions and experiences.

How long does it take to drive from Lisbon to Madeira?

Driving from Lisbon to Madeira requires a ferry or a short flight, as Madeira is an island located off the coast.

What is the best time to visit Portugal?

The best time to visit is during spring (March to May) or fall (September to October) when the weather is pleasant and crowds are fewer.

Are there luxury accommodations available in Portugal?

Yes, Portugal offers a variety of luxury hotels and resorts, particularly in Lisbon and Madeira.

What kind of activities can I do in Madeira?

In Madeira, you can enjoy hiking, wine tasting, visiting botanical gardens, and exploring scenic viewpoints.

Is driving in Portugal easy?

Yes, driving is generally easy with well-maintained roads and clear signage. Just be mindful of local driving regulations.

Do I need to rent a car for this itinerary?

Renting a car is highly recommended for flexibility and to fully explore both Lisbon and Madeira.
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