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  1. Home
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  3. Portugal 5 Nights 6 Days Family 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
₹77,048/ 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 with a 5 Nights Family Winter Escape Itinerary

Join us on a vibrant journey through Portugal, where winter transforms this stunning land into a wonderland of unique experiences. Over five enchanting nights, your family will explore the stunning landscapes of Madeira and the vibrant streets of Lisbon, creating unforgettable memories that will last a lifetime. From lush gardens to bustling markets, Portugal offers a perfect blend of leisure and cultural exploration, tailored for families seeking both adventure and relaxation.

Highlights of the Destination

  • Experience the captivating beauty of Madeira, known for its rugged cliffs and stunning vistas.
  • Revel in the historical charm of Lisbon, with its colorful architecture and rich past.
  • Enjoy thrilling activities like a jet ski circuit and a full-day Eastern Madeira tour with rum tasting.
  • Dive into Lisbon's vibrant nightlife with a fun pub crawl, perfect for older teens and adults.

Travel Tips for Portugal

  • Check local weather conditions—Madeira is subtropical, while Lisbon can be cooler in winter months.
  • Use public transport or tuk-tuks to navigate Lisbon's hilly terrain effortlessly.
  • Familiarize yourself with local customs, such as greeting with a simple 'Olá.'
  • Try local treats—don't miss the famous Pastéis de Belém in Lisbon and the Madeira wine.

Conclusion

As your family embarks on this 5 Nights journey through Portugal, you'll uncover not just breathtaking landscapes and rich history, but also the warmth of its people. Each moment will draw your family closer together, right from the high cliffs of Madeira to the colorful streets of Lisbon. This itinerary promises a delightful blend of leisure and adventure, making it the perfect escape this winter.

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?

The best time to visit Portugal is during spring (March to May) and fall (September to October) when the weather is pleasant.

Is Portugal family-friendly?

Yes, Portugal is very family-friendly with numerous attractions and activities suitable for all ages.

What are some popular activities for kids in Lisbon?

Popular activities for kids in Lisbon include visiting the Oceanarium, riding the tram 28, and exploring the Lisboa Story Centre.

Do I need to know Portuguese to visit Portugal?

While knowing Portuguese can be helpful, many locals speak English, especially in tourist areas.

What local dishes should I try while in Portugal?

Don't miss trying Bacalhau à Brás, Pastéis de Nata, and grilled sardines for an authentic Portuguese experience.

Is Madeira safe for children?

Yes, Madeira is considered very safe for families with children, boasting low crime rates and friendly locals.

How do I get around in Lisbon?

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