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  3. Portugal 4 Nights 5 Days Winter Escape 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
Morning to Noon
At leisure. Add Activity
Funchal: Jet Ski Circuit
Evening
Funchal: Jet Ski Circuit
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
₹62,542/ 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 Winter Escape: 4 Nights 5 Days Itinerary

Embark on a mesmerizing journey through Portugal with our 4 Nights 5 Days Winter Escape itinerary. First up, the enchanting island of Madeira, where lush landscapes meet a subtropical climate and breathtaking views. Then, dive into Lisbon's vibrant culture, characterized by its historic architecture and lively atmosphere. This trip promises breathtaking adventures, and unforgettable memories, making it a perfect winter escape.

Highlights of the Destination

  • Madeira’s volcanic cliffs and stunning coastline offer unmatched beauty.
  • Experience the diverse nightlife of Lisbon through its iconic pubs and bars.
  • Enjoy local delicacies in unique gastronomic experiences throughout your journey.
  • Explore the UNESCO World Heritage sites in Lisbon, showcasing its rich history.

Travel Tips for Portugal

  • Pack layers as both Madeira and Lisbon can have varying temperatures in winter.
  • Make restaurant reservations ahead of time, especially for popular spots.
  • Familiarize yourself with local customs and basic Portuguese phrases for a more immersive experience.
  • Consider purchasing a Lisbon Card for free public transport and discounted museum entrance.

Conclusion

Your 4 Nights 5 Days Winter Escape to Portugal is not merely a trip; it’s a journey into a world steeped in rich heritage and vibrant culture. From the astonishing vistas of Madeira to the lively streets of Lisbon, every moment brims with charm and exhilaration. So pack your bags, immerse yourself in the local experiences, and let Portugal capture your heart.

See what’s included in this tripCost your itinerary to see the hotels, flights, and activities included in your trip
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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 should I pack for a winter trip to Portugal?

Pack layers for varying temperatures, comfortable walking shoes, and a raincoat for unexpected showers.

What are the must-try dishes in Lisbon?

Don't miss out on trying Pastel de Nata, Bacalhau à Brás, and Ginjinha, a local cherry liqueur.

Is public transportation reliable in Lisbon?

Yes, Lisbon has a reliable public transport system including trams, buses, and the metro, making it easy to navigate.

What are the best activities in Madeira?

Explore the levadas (irrigation channels) for hiking, savor Madeira wine, and enjoy stunning views from Cabo Girão.

How can I explore Lisbon's historical neighborhoods?

Consider taking a tuk-tuk tour or walking tour to learn about the city's history while enjoying its scenic streets.

What is the weather like in Madeira during winter?

Winters in Madeira are mild with temperatures averaging around 15-20°C (59-68°F), making it perfect for outdoor activities.

Are there any festivals in Portugal during winter?

Yes, note the local celebrations such as Christmas markets and New Year’s fireworks in Funchal, Madeira.
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