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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.
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 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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