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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.
meghraj singh-Profile
Meghraj Singh
Reviewed on :11 Mar 2026
It was a nice facilities and coordination
meghraj singh-Profile
Meghraj Singh
Reviewed on :11 Mar 2026
It was a nice facilities and coordination
Prakash Peksi-Profile
Prakash Peksi
Reviewed on :11 Mar 2026
Well managed and seem less of execution
Prakash Peksi-Profile
Prakash Peksi
Reviewed on :11 Mar 2026
Well managed and seem less of execution
Soumya Devi-Profile
Soumya Devi
Reviewed on :10 Mar 2026
Had wonderful and stress-free experience with pick your trail.
Soumya Devi-Profile
Soumya Devi
Reviewed on :10 Mar 2026
Had wonderful and stress-free experience with pick your trail.
Mehul Gandhi-Profile
Mehul Gandhi
Reviewed on :10 Mar 2026
I had my Maldives booking done from pickyourtrail app and believe me that I had a very good experience. Their representatives were in constant touch and very ready to solve my queries immediately. Highly recommend
Mehul Gandhi-Profile
Mehul Gandhi
Reviewed on :10 Mar 2026
I had my Maldives booking done from pickyourtrail app and believe me that I had a very good experience. Their representatives were in constant touch and very ready to solve my queries immediately. Highly recommend
Aditya Arun-Profile
Aditya Arun
Reviewed on :09 Mar 2026
8.5 We liked : 1. Well organised trip with absolute no stress during Travel. 2. Time to Time pickup and drop, additionally drivers were pretty good and of welcoming nature. 3. Food and service were really tasty in both the Hotels. 4. All pre-visit information and requested modifications were delivered amazingly. Improvement : 1. hotel room details (backside room, no good view from window, and missing gallery) 2. Swimming pool not present in IBIS hotel. (Same missing view/gallery) 3. Better cruise experience expected, food was bland and no open-upper deck. (We saw a few cruises there with an open upper deck) Improvements are just suggestions and not complaints.
Aditya Arun-Profile
Aditya Arun
Reviewed on :09 Mar 2026
8.5 We liked : 1. Well organised trip with absolute no stress during Travel. 2. Time to Time pickup and drop, additionally drivers were pretty good and of welcoming nature. 3. Food and service were really tasty in both the Hotels. 4. All pre-visit information and requested modifications were delivered amazingly. Improvement : 1. hotel room details (backside room, no good view from window, and missing gallery) 2. Swimming pool not present in IBIS hotel. (Same missing view/gallery) 3. Better cruise experience expected, food was bland and no open-upper deck. (We saw a few cruises there with an open upper deck) Improvements are just suggestions and not complaints.
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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