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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.
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 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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