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  3. Portugal 14 Nights 15 Days Group 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
3 Nights Stay
Lisbon3 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
Lisbon Tram No. 28 Ride & Walking Tour
Morning
Lisbon Tram No. 28 Ride & Walking Tour
Noon to Evening
At leisure. Add Activity
Train ride to Lagos - Portugal
Lagos - Portugal
3 Nights Stay
Lagos - Portugal3 Nights
Day 07
Morning
Checkout of your hotel. Take your train from Lisbon to Lagos - Portugal. Check-in to your new hotel
Noon
At leisure. Add Activity
Portimo: Benagil Caves Speed Boat Tour with Sunset Option
Evening
Portimo: Benagil Caves Speed Boat Tour with Sunset Option
Day 08
Morning
At leisure. Add Activity
Portimo: Carvalho & Marinha Beach, Benagil Cave Boat Tour
Noon
Portimo: Carvalho & Marinha Beach, Benagil Cave Boat Tour
Algarve: Seven Hanging Valleys Walking Tour
Evening
Algarve: Seven Hanging Valleys Walking Tour
Day 09
Algarve: Benagil Cave Boat Tour and Algarseco Coastal Walk
Morning to Noon
Algarve: Benagil Cave Boat Tour and Algarseco Coastal Walk
From Portimo: Algar de Benagil and Sea Caves Boat Tour
Evening
From Portimo: Algar de Benagil and Sea Caves Boat Tour
Get transferred to Albufeira
Albufeira
3 Nights Stay
Albufeira3 Nights
Day 10
Morning
Checkout of your hotel and get transferred to Albufeira
Noon to Evening
At leisure. Add Activity
Day 11
Morning
At leisure. Add Activity
Albufeira: Tuk-tuk Sightseeing Tour
Noon
Albufeira: Tuk-tuk Sightseeing Tour
Vilamoura: Hop-On Hop-Off Eco Car Tour
Evening
Vilamoura: Hop-On Hop-Off Eco Car Tour
Day 12
From Faro: Benagil Cave and Seven Hanging Valleys Trail Tour
Morning to Noon
From Faro: Benagil Cave and Seven Hanging Valleys Trail Tour
Albufeira: Secret Caves & Beaches Kayak Tour with Swim Stop
Evening
Albufeira: Secret Caves & Beaches Kayak Tour with Swim Stop
Fly to Porto
Porto
2 Nights Stay
Porto2 Nights
Day 13
Full Day
Checkout of your hotel. Board your flight to Porto. Check-in to your new hotel in Porto
Day 14
Porto: Guided Tour by Tuk-Tuk & Optional Douro River Cruise
Morning
Porto: Guided Tour by Tuk-Tuk & Optional Douro River Cruise
Porto: Douro River Boat Cruise with Port Wine Tasting
Noon
Porto: Douro River Boat Cruise with Port Wine Tasting
Porto: 2-Hour Shared Tuk-Tuk Tour
Evening
Porto: 2-Hour Shared Tuk-Tuk Tour
Day 15
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
₹186,531/ 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 14 Nights Group Winter Escape Itinerary

Embark on a journey through Portugal that offers a beautifully diverse experience across remarkable landscapes, rich traditions, and vibrant culture. This 14-night winter escape invites you to explore the breathtaking archipelago of Madeira, the historical streets of Lisbon, and the stunning beaches of the Algarve. As you weave through Portugal’s best destinations, you'll not only discover the country but also create memories that you'll cherish for a lifetime.

Highlights of the Destination

  • Marvel at the stunning cliffs and pebbly beaches of Madeira, known for its warm climate and gorgeous landscapes.
  • Experience Lisbon, where every street has a story, with highlights like the majestic São Jorge Castle and vibrant Bairro Alto.
  • Bask in the sun at the breathtaking beaches of Lagos and Albufeira, where the golden sands meet the Atlantic waves.
  • Indulge in Porto, the city famous for its delicious port wine and charming medieval architecture.

Travel Tips for Portugal

  • Make the most of local public transport, as it’s efficient and a great way to mingle with locals.
  • Don’t miss trying the regional delicacies like Pasteis de Nata and fresh seafood.
  • Learn a few Portuguese phrases; it shows respect and often leads to a warmer welcome.
  • Pack layers, as coastal weather can be unpredictable.

Conclusion

Your 14 nights in Portugal will be a symphony of flavors, sights, and sounds. Each stop offers something unique—whether it’s exploring the history in Lisbon or enjoying the sun on Algarve's beaches. This winter escape promises unforgettable adventures and insights into a country where tradition and modernity dance harmoniously together.

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 are the must-see attractions in Portugal?

Must-see attractions include the stunning cliffs of Cabo da Roca, the historic neighborhoods of Alfama in Lisbon, and the beautiful beaches of the Algarve.

How is the weather in Portugal during winter?

The weather is mild during winter, with temperatures ranging from 8°C to 16°C (46°F to 61°F), making it ideal for exploration.

Is it safe to travel in Portugal?

Yes, Portugal is considered one of the safest countries in Europe with low crime rates, making it a great destination for travelers.

What type of cuisine should I try in Portugal?

You should definitely try traditional dishes like Bacalhau à Brás, Caldo Verde, and the famous Pasteis de Nata.

Do I need a visa to visit Portugal?

Visa requirements depend on your nationality. EU citizens do not need a visa, while others may require it; ensure to check before your trip.

What is the best mode of transportation in Portugal?

The best way to explore Portugal is via a combination of public transportation, such as trains and buses, along with walking in cities.

Are there any language barriers in Portugal?

While Portuguese is the official language, many people in tourist areas speak English, though learning a few phrases can enhance your experience.
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