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  3. Portugal 5 Nights 6 Days Luxury Winter Escape 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
Morning to Noon
At leisure. Add Activity
Funchal: Jet Ski Circuit
Evening
Funchal: Jet Ski Circuit
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
₹79,102/ 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

Experience Luxury in Portugal: 5 Nights 6 Days Winter Getaway

Immerse yourself in the breathtaking allure of Portugal on this exquisite 5 Nights 6 Days luxury winter escape. Explore vibrant cities, indulge in local flavors, and unwind in luxurious accommodations. Whether you’re traversing the hilly streets of Lisbon or luxuriating in the subtropical paradise of Madeira, each day presents a new adventure waiting to be unveiled. Picture yourself sipping a glass of fine Madeira wine while taking in panoramic views or discovering the vibrant nightlife filled with live music and laughter.

Highlights of the Destination

  • Wander through the enchanting streets of Lisbon, with its pastel-colored buildings and historic castles, which hold stories of centuries gone by.
  • Explore Madeira’s stunning natural landscapes, including dramatic cliffs and lush gardens that welcome the warm sea breeze.
  • Indulge in luxury stays at elegant hotels like Village Cabo Girao and Lisbon Arsenal Suites, where comfort meets style.
  • Experience local culture with unique activities from jet skiing in Funchal to a lively pub crawl in Lisbon—fun is guaranteed!

Travel Tips for Portugal

  • Engage with locals to discover hidden gems and authentic dining experiences away from tourist hotspots.
  • Take advantage of the efficient public transport; trams in Lisbon are both fun and a scenic way to navigate the city.
  • Always carry some cash; not all small vendors accept credit cards.
  • Reserve a few days for spontaneous adventures; sometimes the best memories come from unplanned explorations.

Conclusion

This 5 Nights 6 Days luxury winter escape to Portugal is not just a trip; it’s an unforgettable journey filled with exquisite sights, delectable tastes, and rich history. From the vibrant nightlife of Lisbon to the tranquil beauty of Madeira, every moment is crafted for your enjoyment. Pack your bags for an enchanting getaway where luxury and adventure await at every corner!

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 is the best time to visit Portugal for a winter escape?

The best time for a winter escape in Portugal is from November to February, offering milder weather and fewer tourists.

What activities can I do in Lisbon during my visit?

In Lisbon, you can enjoy a variety of activities including visiting historical landmarks, exploring neighborhoods like Alfama, and experiencing the vibrant nightlife.

Is Madeira suitable for a luxury vacation?

Absolutely. Madeira offers stunning landscapes, luxury accommodations, and high-end dining experiences perfect for a luxurious getaway.

How can I travel between Lisbon and Madeira?

You can travel between Lisbon and Madeira by taking a direct flight, which takes about 1.5 hours.

What should I pack for a winter trip to Portugal?

Pack layers, as winter temperatures can vary. Don’t forget comfortable walking shoes for exploring and a light jacket for cooler evenings.

Are there specific local dishes I should try?

Definitely! Be sure to try traditional dishes like Bacalhau à Brás, Pastel de Nata, and local wines for an authentic taste of Portuguese cuisine.

What are some popular landmarks to visit in Madeira?

In Madeira, visit the stunning Cabo Girao viewpoint, the beautiful Botanical Gardens in Funchal, and the unique traditional houses in Santana.
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