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  3. Portugal 5 Nights 6 Days 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
₹72,151/ 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

Discover Portugal: A 5 Nights Winter Escape Itinerary

Why not escape to Portugal this winter? Nestled off the northwestern coast of Africa, Madeira offers stunning vistas and a warm, subtropical climate that's a far cry from the chill of winter elsewhere. In just 5 nights, experience the rich culture, vibrant nightlife, and breathtaking landscapes of both Madeira and Lisbon. Stand on the cliffs of Madeira, sip on the world-renowned wine, and delve into Lisbon's bustling streets.

Highlights of the Destination

  • Madeira’s Spectacular Coastlines - Explore the rugged cliffs and gorgeous pebbly beaches that define this volcanic haven.
  • Funchal's Botanical Gardens - Walk through lush gardens, where the unique flora is as striking as the views over the harbor.
  • Lisbon's Rich History - Marvel at the views from the iconic São Jorge Castle, a symbol of the city's storied past.
  • Nightlife Adventure - Take part in Lisbon’s largest pub crawl and immerse yourself in the local nightlife scene with fellow travelers.

Travel Tips for Portugal

  • Embrace the Local Cuisine - Don't miss out on trying the traditional Bacalhau (codfish) and pastéis de nata for dessert.
  • Wear Comfortable Shoes - Lisbon’s hills can be steep and challenging, so comfy shoes will help you explore without discomfort.
  • Learn a Few Portuguese Phrases - Basic greetings and polite expressions go a long way in enhancing your travel experience.
  • Use Public Transport - The metro in Lisbon is efficient and great for getting around without breaking the bank.

Conclusion

This 5 Nights Winter Escape to Portugal is not just a trip; it's an adventure filled with culture, breathtaking sights, and camaraderie. Whether you’re tasting Madeira wine, wandering through Lisbon’s charming neighborhoods, or enjoying the scenic views from a gondola lift over the Tagus River, each moment is a memory waiting to be made. Make this winter one to remember in the mesmerizing heart 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.
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 to visit Portugal for a winter escape is from December to February when the weather is mild and crowds are fewer.

What activities can I enjoy in Madeira?

In Madeira, you can enjoy hiking, visiting botanical gardens, tasting local wine, and experiencing thrilling water sports such as jet skiing.

Is public transport reliable in Lisbon?

Yes, Lisbon’s public transport system, including trams, buses, and the metro, is reliable and easy to navigate, making it convenient for tourists.

Do I need to book in advance for the pub crawl in Lisbon?

While you can often join a pub crawl spontaneously, it’s advisable to book in advance to secure your spot, especially during peak seasons.

What local dishes should I try while in Portugal?

While in Portugal, be sure to try Bacalhau à Brás, Caldo Verde soup, and the famous pastéis de nata for a sweet treat.

How do I get from Madeira to Lisbon?

The easiest way to get from Madeira to Lisbon is by taking a direct flight, which takes about 1.5 hours.

What is the typical weather like in Portugal during winter?

During winter, Portugal generally enjoys mild temperatures, with Lisbon averaging around 15°C (59°F) and Madeira being slightly warmer.
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