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  1. Home
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  3. Portugal 4 Nights 5 Days Luxury Road Trip Route Itinerary
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Itinerary
Madeira
2 Nights Stay
Madeira2 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
Fly to Lisbon
Lisbon
2 Nights Stay
Lisbon2 Nights
Day 03
Morning
Checkout of your hotel. Board your flight to Lisbon. Check-in to your new hotel in Lisbon
Noon
At leisure. Add Activity
Lisbon: Pub Crawl with Open Bar (Premium Upgrade Available)
Evening
Lisbon: Pub Crawl with Open Bar (Premium Upgrade Available)
Day 04
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 05
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
₹87,772/ 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

Ultimate Luxury Road Trip: 4 Nights in Beautiful Portugal

Embark on an unforgettable journey through Portugal with our exclusive 4 Nights 5 Days Luxury Road Trip itinerary, where each destination offers a unique flavor of the nation's rich culture and breathtaking landscapes. First, we'll whisk you away to the stunning island of Madeira, known for its striking cliffs, serene beaches, and subtropical climate. After a luxurious stay, we’ll take you to Lisbon, the capital, where history breathes life into every alley. Picture yourself against the striking backdrop of São Jorge Castle or savoring exquisite regional dishes in Alfama—the heart of old Lisbon.

Highlights of the Destination

  • Discover Madeira's jaw-dropping cliffs and lush, volcanic landscapes.
  • Taste the renowned Madeira wine and indulge in fresh seafood.
  • Roam Lisbon's vibrant neighborhoods, rich in history and charm.
  • Engage in nightlife adventures, including an exciting pub crawl in Bairro Alto.

Travel Tips for Portugal

  • Always try the local cuisine; don’t miss out on Bacalhau à Brás.
  • Public transport is efficient in Lisbon; a metro card can save you time.
  • Book tours or activities in advance, especially during peak season.
  • Respect local customs, especially when visiting religious sites.

Conclusion

Whether you find yourself enjoying a cabriolet ride along the dramatic coastline of Madeira or soaking up the vibrant atmosphere of Lisbon, this luxurious road trip is poised to create lasting memories. Let Portugal's beauty, history, and culture sweep you off your feet as you explore this magnificent country in style.

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?

Must-see attractions in Madeira include the stunning Ponta de São Lourenço, the serene Monte Palace Gardens, and breathtaking viewpoints like Pico do Arieiro.

What is the best time to visit Portugal?

The best time to visit Portugal is from May to September, when the weather is warm and perfect for exploring.

Is this itinerary suitable for families?

Yes, this itinerary can be adapted to suit families, offering activities that appeal to both adults and children.

How do I get around in Lisbon?

Lisbon has an excellent public transport system including trams, buses, and metro which makes getting around easy.

Are there any local customs I should be aware of?

Yes, it's important to greet people with a handshake and to be respectful when visiting churches by dressing modestly.

What should I pack for a trip to Portugal?

Pack lightweight clothing for warm weather, comfortable shoes for walking, and a light jacket for cooler evenings.

Can I book guided tours in advance?

Absolutely! It's highly recommended to book guided tours ahead of time to secure your spot and avoid long queues.
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