
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

14 Day Trip IdeaFrom $3,700
Highlights of Portugal in Two Weeks: Lisbon to Porto

13 Day Trip IdeaFrom $9,800
13-Day Classic Portugal Tour: Lisbon, Castles, Wine Country & More

14 Day Trip IdeaFrom $3,700
Portugal Wine Tour: Lisbon, Evora, Douro Valley, Porto

14 Day Trip IdeaFrom $3,700
Romantic Two-Week Getaway to Portugal & Azores

14 Day Trip IdeaFrom $6,000
Portugal Adventure Vacation for Families with Teens

14 Day Trip IdeaFrom $3,700
Seven Island Portugal Escape: Azores and Madeira Vacation
How Zicasso Works
Here's how we create life-enriching, luxury travel experiences
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.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.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.

14 Day Trip IdeaFrom $3,700
Stepping into Portugal ’s Storied Past: Two Week Historical Tour

14 Day Trip IdeaFrom $3,700
Portugal for the Seasoned Traveler: 14-Day Vacation

12 Day Trip IdeaFrom $4,700
Ultimate Portugal Food and Wine Tour

14 Day Trip IdeaFrom $3,700
Best of Azores: Magical Atlantic Island Tour

14 Day Trip IdeaFrom $3,700
Leisurely Portugal Tour for Seniors: Lisbon, Porto and Madeira
Reviews of Zicasso's Two Week Portugal Itineraries
Based on 415 verified traveler reviews.
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Our travel agent made this an extraordinary, unforgettable, and wonderful trip for our family! The events and tours she arranged were exactly what we were looking for. The tour and transportation companies she contracted were on time, flexible, knowledgeable, and provided outstanding value for the cost.
Our agent provided an incredible, complete package at a cost much less than competitors. We highly recommend our agent and her team to anyone looking for a memorable trip to Lisbon and/or the Azores.
-Glen
Five Stars!
Loved all the service and tour guides.
Most enjoyable was the Azores. Doing the trip again I would focus more time on the Azores. Lisbon is nice but a whole different world. Thanks for a great trip.
-Tony
5 Stars.
The guides made this trip most enjoyable. They shared their knowledge willingly and always with a smile.
The only thing I would do differently is make the trip longer.
-Mary
My star rating is 5. We had a wonderful trip without a concern over logistics thanks to this travel company. With 9 of us, it was a challenge to get the itinerary we all wanted but our agent did a great job. I was also impressed by the low cost, given all that we did, and the quality of the hotels and tours. I will absolutely recommend and in fact, plan to write a review on TripAdvisor.
The highlight was seeing my grandmother’s house in Santa Luzia on our free day in Pico. I enjoyed the Azores more than the mainland. Every one of our tour guides was excellent. I especially liked the coffee plantation in Sao Jorge, the volcano museum on Faial, and the whaling museum on Pico. Ponta Delgado was a great place to stay. I didn’t much like Madalena though with two ferry trips on the itinerary it was the best option.
What I would change, in retrospect, is less time in Lisbon, perhaps substituting a fifth island. The crowds were a problem in Lisbon and we found it a little frustrating to be pressed for time at each destination. Maybe offer Sintra or Cascais but not both, and pick two of the Batalha/Nazare/Obidos options. It’s a shame to not see it all, but also a shame to have only 45 minutes in a place like Nazare.-Susan
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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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