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  3. Portugal 4 Nights 5 Days Luxury 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
₹61,067/ 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

Embark on a Luxury 4 Nights 5 Days Winter Escape to Portugal

Imagine yourself surrounded by stunning landscapes and vibrant cultures. Portugal, a jewel of the Iberian Peninsula, invites you to revel in its rich heritage and natural beauty during a luxurious 4 nights, 5 days winter escape. From the sun-kissed hills of Lisbon to the rugged coastlines of Madeira, this itinerary promises an unforgettable getaway.

Highlights of the Destination

  • Lisbon’s Historic Neighborhoods: Wander through Bairro Alto’s vibrant streets, lined with bars and restaurants, and take in splendid views from Miradouro de Santa Catarina.
  • Unique Nightlife Experience: Join one of Lisbon’s legendary pub crawls to immerse yourself in its lively nightlife. Meet fellow travelers, share stories, and taste local drinks.
  • Luxurious Stay in Madeira: Relax at the 5-star Quinta do Estreito Vintage House, where comfort meets stunning views, perfect for unwinding after a day of exploration.
  • Adventure on the Water: Experience the thrill of a jet ski ride in the azure waters near Funchal, perfect for making lasting memories with friends or family.

Travel Tips for Portugal

  • Local Cuisine: Don’t miss out on tasting iconic Portuguese dishes such as Bacalhau à Brás or the delicious Pastéis de Nata. Each bite tells a story!
  • Public Transport: Utilize the efficient public transport systems in Lisbon for easy access to attractions. Trams and metros ensure you see it all.
  • Language: While many locals speak English, picking up a few Portuguese phrases could enhance your experience and show appreciation for the culture.
  • Dress Code: Portugal is casual, but smart-casual attire is encouraged for dining. Avoid beachwear in restaurants to ensure a pleasant dining experience.

Conclusion

A luxurious 4 nights, 5 days winter escape in Portugal encompasses everything from adventure to relaxation. As you bask in the warm Portuguese sun and explore the coastlines and cityscapes, you'll feel a deep connection to this enchanting land. Each day will unfold new adventures, heartfelt connections, and cherished memories. Don’t just dream about it; experience the magic of Portugal for yourself.

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 should I pack for my winter escape in Portugal?

Pack layers for varying temperatures, comfortable walking shoes, and a light rain jacket as winter can be unpredictable in Portugal.

Is it easy to get around Lisbon and Madeira?

Yes, both cities have accessible public transportation systems, and taxis and rideshares are readily available for convenience.

What is the best time to visit Portugal?

Winter offers a unique charm but spring and autumn provide mild weather and fewer tourists, ideal for exploring.

Are locals in Portugal friendly to tourists?

Absolutely! Portuguese people are known for their hospitality and warmth, often eager to share their culture with visitors.

What are some must-try foods in Portugal?

Don’t miss the chance to try Bacalhau à Brás, Caldo Verde, and the famous Pastéis de Nata for a true taste of Portuguese cuisine.

Can I see any cultural events during my trip?

Yes! Depending on your travel dates, you may catch local festivals, artistic performances, or traditional music events, especially in the Algarve and Lisbon.

Is drinking water safe in Portugal?

Yes, tap water is generally safe to drink, but many locals also recommend bottled water, especially in rural areas.
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