Pena National Palace, Portugal
28,000+ Verified Traveler Reviews

Two Week Portugal Itineraries

Your immersive journey to Portugal starts here. Discover colorful cities eager to display their beauty, small coastal towns blooming with cultural experiences, and immaculate countrysides in between. Be consumed by intoxicating energy as you travel through Portugal on a 2-week itinerary. With Zicasso, your ideal vacation will come to life.

Explore Our Trip Ideas

Let these itineraries inspire your personalized travel experience

View of the city and castle of Alfama São Jorge, Lisbon

14 Day Trip IdeaFrom $4,600

Highlights of Portugal in Two Weeks: Lisbon to Porto

Lisbon, Sintra, Ponta Delgada, Porto, Furnas +5 more
City of Porto in Portugal

13 Day Trip IdeaFrom $9,800

13-Day Classic Portugal Tour: Lisbon, Castles, Wine Country & More

Lisbon, Sintra, Alentejo, Évora, Crato +8 more
Alentejo is a legendary wine-growing region in Portugal

14 Day Trip IdeaFrom $4,600

Portugal Wine Tour: Lisbon, Evora, Douro Valley, Porto

Lisbon, Evora, Dao Region, Porto, Douro Valley
Stunning views of Lisbon's waterfront and Belém Tower.

14 Day Trip IdeaFrom $4,600

Romantic Two-Week Getaway to Portugal & Azores

Lisbon, Sintra, Chiado, Alfama, Bairro Alto +2 more
The central square of Nazare, Portugal.

14 Day Trip IdeaFrom $6,000

Portugal Adventure Vacation for Families with Teens

Batalha, Lisbon, Porto, Lamego, Belmonte +2 more
Lighthouse Ponta da Ferraria San Miguel, Azores

14 Day Trip IdeaFrom $4,600

Seven Island Portugal Escape: Azores and Madeira Vacation

Madeira, Azores, Funchal, Camara de Lobos, Cabo Girao +27 more

How Zicasso Works

Here's how we create life-enriching, luxury travel experiences

  1. 1.Share Your Travel Dreams

    Zicasso specializes in custom tours, vacations, and safaris tailored to your interests and preferences. From private African safaris to culinary experiences in Europe, submit a trip request to share your ideas and travel style.

  2. 2.Meet Your Travel Specialists

    To ensure a personalized experience, we'll carefully handpick and introduce you to two of our top travel specialists, each with unsurpassed destination knowledge and local insight aligned to your luxury travel dreams.

  3. 3.Design Your Perfect Journey

    Compare the expertise of two specialists with itineraries crafted exclusively for you. You can refine these further and choose your preferred proposal. Our unique process ensures a more creative, personalized, and expertly crafted trip.

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Colorful skyline of Porto in Portugal

14 Day Trip IdeaFrom $4,600

Stepping into Portugal’s Storied Past: Two Week Historical Tour

Lisbon, Sintra, Cascais, Obidos, Tomar +4 more
Cathedral in the ancient city of Evora in Portugal

14 Day Trip IdeaFrom $4,600

Portugal for the Seasoned Traveler: 14-Day Vacation

Porto, Aveiro, Tomar, Nazare, Ericeira +4 more
Mixed Portuguese traditional rustic tapas food

12 Day Trip IdeaFrom $4,700

Ultimate Portugal Food and Wine Tour

Porto, Douro Valley, Obidos, Lisbon, Trancoso +1 more
Sunny view of Angra do Heroismo, Terceira Island, Azores

14 Day Trip IdeaFrom $4,600

Best of Azores: Magical Atlantic Island Tour

Azores, Flores, Santa Cruz, Corvo, Faial +6 more
Jeronimos Monastery, Lisbon, Portugal

14 Day Trip IdeaFrom $4,600

Leisurely Portugal Tour for Seniors: Lisbon, Porto and Madeira

Lisbon, Belem, Baixa, Sintra, Porto +4 more
Abandoned Fortress and Lighthouse on Berlenga Grande Island, Berlenga Nature Reserve, Portugal

14 Day Trip IdeaFrom $4,600

Family-Friendly Vacation to Portugal: Lisbon to Porto

Lisbon, Porto

4.9

Reviews of Zicasso's Two Week Portugal Itineraries

Based on 383 verified traveler reviews.

Portugal Travel Review: Lisbon, Sintra, Nazare, Coimbra, Douro Valley, Azores, Porto, 16-Day Tour
"We thoroughly enjoyed our trip. Zicasso’s travel agency did a great job of arranging gorgeous hotels and top-notch tour guides."

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Portugal Family Travel Review: Lisbon, Sao Miguel, Sao Jorge, Faial, 12-Day Trip
"Our travel agent made this an extraordinary, unforgettable, and wonderful trip for our family!"

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Luxury Portugal Vacation Review, Evora to Douro Valley, Lisbon to Algarve, Cork Factory, Historical Sites, Waterfalls & Beaches
"Our drivers were safe, efficient and timely." 

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Luxury Portugal Travel Review: Golfing, Cork Forest, Wineries, Exploring Walled Cities, Tuk Tuk Tour, Castles
"If you are going to Portugal and you want a trip that is top-notch in every way, the travel company will exceed your expectations."

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Portugal Family Tour Review: Lisbon, Sintra, Evora, Porto, Algarve, Madeira, Douro Valley, Cooking Class, Tile-Painting Workshop, 13 Nights

The travel agent from Zicasso's tour company planned for my family of four the most spectacular and luxurious two-week trip around Portugal. We traveled to and enjoyed the highlights of Lisbon, the romantic architecture in Sintra, the incredible history of Évora, the beautiful coastline of the Algarve, the laid-back atmosphere and gorgeous scenery of Madeira, the beautiful, historical, bustling city of Porto, and the stunning scenery of the Douro Valley. 

The travel agent's suggestions and bookings were all perfectly aligned with what we envisioned and the accommodations booked were all beautifully appointed and family-oriented – five-star hotels that catered to the entire family, with indoor pools and kids greeted with backpacks and toys at the door, and nightly treats on pillows.

The tour guides booked were all very knowledgeable and kind. They were patient with my two- and four-year-olds, and taught us all so many new, amazing things.

Every day was a highlight, but I would say my girls really enjoyed the tile painting as well as the pastel de nata-making workshops.

My husband and I really enjoyed Évora and Sintra, and truly seeing the beauty and history of it all.

We absolutely fell in love with Portugal, the culture, and the food. My only regret is not having more time so we could’ve seen the Azores as well and stayed even longer. 

We so look forward to this travel agent planning us another perfect vacation in the near future!

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Portugal Luxury Anniversary Trip Review: Lisbon, Porto, Coimbra, Aveiro, Douro Valley, Sintra, Vineyards, Cruise, Fado, 10-Day Tour
"...everything went exactly as planned thanks to Filomena and all of her incredible planning and tour guides."

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