Pena National Palace, Portugal
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Two Week Portugal Itineraries

Ratings of Zicasso's Service
<p>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.</p>

Your immersive journey to Portugal starts here. Discover colorful cities eager...

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.

Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

Ratings of Zicasso's Service
View of the city and castle of Alfama São Jorge, Lisbon
Highlights of Portugal in Two Weeks: Lisbon to Porto

14 Day Custom Tour

Dynamic pricing from $3,635

Steeped in history and filled to the brim with beauty and charm, Portugal is a country that captures the heart and never lets go. On this 14-day luxury tour, you will see unforgettable sights with metropolitan flair, including Lisbon’s Alfama and Chiado districts and the primo spots in Porto. Then, be whisked away to the peaceful, sun-draped shores of the Azores. This unforgettable two-week adventure offers you the best of both worlds, pairing an idyllic island getaway with stunning city experiences. You will even enjoy a magical weekend getaway amid the fairytale turrets and stunning scenery of Sintra. Once this amazing and unforgettable experience culminates, you will be reminiscing about it for the rest of your life.

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The 25th April bridge in Lisbon, Portugal
13-Day Classic Portugal Tour: Lisbon, Castles, Wine Country & More

13 Day Custom Tour

Dynamic pricing from $7,795

Venture through a land filled with villages and towns divulging architectural and archeological secrets during this 13-day classical Portugal tour. Find the bustle of charming Lisbon, indulge in the relaxed ambiance of quaint villages created from cobblestones, and wander along the cobblestones of towns preserved from medieval times. Travel inland to discover gastronomical delights and embrace remote open landscapes while uncovering Portugal’s classic beauty.

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Alentejo is a legendary wine-growing region in Portugal
Portugal Wine Tour: Lisbon, Evora, Douro Valley, Porto

14 Day Custom Tour

Dynamic pricing from $3,635

Imagine luscious red wines as you sail down the Douro, an enological masterclass in a historical cellar, ports in Porto, and muscats in Setubal as you are immersed in the distinctive wine cultures of Portugal. Welcome to the ultimate Portugal wine tour with two weeks of experiential highlights as you travel across Lisbon, Evora, the Douro Valley, and Porto. You will connect old-world tradition with new-world styles and use your senses to understand a country that is, at last, getting the wide recognition it deserves.

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Stunning views of Lisbon's waterfront and Belém Tower.
Romantic Two-Week Getaway to Portugal & Azores

14 Day Custom Tour

Dynamic pricing from $3,635

When it comes to you and your significant other to choose a perfect destination for your ultimate romantic getaway, Portugal is the epitome of the ideal vacation. Steeped in history and filled to the brim with beauty and charm, Portugal is a country that captures the heart and never lets it go. The only problem you and your partner may have is choosing just where you will go and what you will want to see next, which is why we have created a 14-day luxury tour that is handcrafted to give you the best of both worlds, stunning city sights, and idyllic island vibes. From a whirlwind week based in Lisbon, soaking up metropolitan moments and culture, to a peaceful, seven-day escape to the serene and sun-dappled shores of the Azores islands, you will be wooed by Portugal’s vibrant nightlife and bustling energy. By the time your romantic getaway is finished, you will not want to return home.

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The central square of Nazare, Portugal.
Portugal Adventure Vacation for Families with Teens

14 Day Custom Tour

Dynamic pricing from $4,727

Teeming with cultural and historical highlights, this 14-day adventure in Portugal is a sensational experience for families with older children. On this customizable tour, you and your family will revel in the country’s exquisite culinary delights, witness staggering landscapes, and uncover the origins of Portugal’s spirited culture. Every step of the way will be immersive and exhilarating for your entire family to enjoy.

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Lighthouse Ponta da Ferraria San Miguel, Azores
Seven Island Portugal Escape: Azores and Madeira Vacation

14 Day Custom Tour

Dynamic pricing from $3,635

Madeira and the Azores are islands of volcanic wonder that abound with natural drama in the midst of the Atlantic Ocean. Escapist and expressive, the islands bring nature, history, culture, wildlife, lava trails and languid beaches all at once, and this luxury vacation tour visits the most inspiring seven islands.  Look forward to a private journey across spectacular landscapes and remote destinations for the very best of the Portuguese archipelagos.

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Benefits of Using Zicasso

Plan Your Trip with
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We connect you with the best boutique tour companies to plan your dream trip.
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Travel with a personalized itinerary and experiences designed for you.
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24/7 support and local assistance for every moment of your vacation.
Colorful skyline of Porto in Portugal
Stepping into Portugal’s Storied Past: Two Week Historical Tour

14 Day Custom Tour

Dynamic pricing from $3,635

This 2-week Portugal tour immerses you in the country’s cultural delights and storied past. While Portugal is not as widely known as Greece is for it’s history, Portugal is a country that is home to thousands of years of history and is often overlooked by travelers. Uncover the historical treasures of Obidos, follow in the footsteps of the Knights Templar, and attend an authentic fado performance.

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Cathedral in the ancient city of Evora in Portugal
Portugal for the Seasoned Traveler: 14-Day Vacation

14 Day Custom Tour

Dynamic pricing from $3,635

This luxurious, 2-week adventure has been specially curated and for the more mature and refined travelers. Whether you are perusing the best wines in Porto on a private estate tour or following in the footsteps of the Knights Templar in Tomar, you will sit in the lap of luxury throughout the entirety of this adventure. From the stunning beaches of Portugal’s captivating coastlines to cities like Lisbon and Porto that are filled with amazing architecture and historical wonders, Portugal presents itself as an ideal vacation destination regardless of your age or interests.

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Mixed Portuguese traditional rustic tapas food
Ultimate Portugal Food and Wine Tour

12 Day Custom Tour

Dynamic pricing from $3,739

Portugal’s culinary brilliance comes in many forms including vintage tasting in a port cellar, Michelin dining, and Europe’s first DOC wine region. Experience fishing village lunches, fragrant city markets, exquisite fine dining, and iconic food and wine pairings. Expertly handcrafted, this 12-day tour explores the very best of Portugal’s unique wine and cuisine, with stops including Porto, the Douro Valley, Alentejo, and Lisbon. Prepare for all your senses to be subtly aroused.

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Sunny view of Angra do Heroismo, Terceira Island, Azores
Best of Azores: Magical Atlantic Island Tour

14 Day Custom Tour

Dynamic pricing from $3,635

A forgotten archipelago in the Atlantic, where volcanoes soar and coastlines enchant. Welcome to the Azores. A land of waterfalls, lava tubes, vineyards, crater lakes, old whaling settlements, and superlative coastlines. Every island showcases unique landscapes, culture, cuisine, and attractions. This is the ultimate handcrafted voyage, exploring seven islands in two weeks: Flores, Corvo, Faial, Pico, Sao Jorge, Terceira, and Sao Miguel.

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Jeronimos Monastery, Lisbon, Portugal
Leisurely Portugal Tour for Seniors: Lisbon, Porto and Madeira

14 Day Custom Tour

Dynamic pricing from $3,635

Lisbon, Porto, and Madeira are three of Portugal’s iconic highlights and are combined on this leisurely two-week tour for seniors. Mixing free time with privately-guided tours, you explore the history and culture of two cities that love to surprise, as well as an island that blends intrigue with charm. Along the way, there are palaces, galleries, waterfalls, neighborhoods, dolphins, villages, coastlines, a Douro River cruise and a ceramics workshop, all while traveling at a very serene pace.

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Abandoned Fortress and Lighthouse on Berlenga Grande Island, Berlenga Nature Reserve, Portugal
Family-Friendly Vacation to Portugal: Lisbon to Porto

14 Day Custom Tour

Dynamic pricing from $3,635

Picturesque and welcoming, Portugal invites visitors to come and be swept away by its eclectic variety of stunning architecture, old-world charm, and historical treasures. From educational and informative tours of beloved, local gems to thrilling outdoor adventures, this 14-day luxury tour features an exciting adventure that is handcrafted to be family-friendly and fit to satisfy adventurers of all ages. From your bases of Lisbon and Porto, you will not only be able to avail yourselves of these two cities’ myriad of metropolitan offerings, but you will also visit some of the most jaw-dropping points of interest. You will not be simply standing around and listening to a tour guide; you will be soaring through the skies via helicopter, kayaking on dazzling waterways, sailing under the sun and even unleashing your inner Van Gogh on a fascinating Portuguese painting excursion.

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Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

We Work With the Best Portugal Travel Agents for 2 Week Itineraries

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Reviews of Zicasso's Referral Service

4.93 stars based on 1029 reviews.

Portugal Luxury Company Trip Review: Porto, Sintra, Douro...
"We could not have been more pleased with the trip Zicasso’s...

Reviewed By Mark K.

Portugal Trip Review: Lisbon, Porto, Douro Valley, Hiking,...
"I wouldn't change a thing that our agent and her crew planned!...

Reviewed By Andrea L.

Portugal Vacation Review: Madeira, Lisbon, Sintra, Cascais,...
"I cannot say enough good things about our travel company...

Reviewed By George M.

Portugal Tour Review: Porto, Lisbon, Algarve, Tomar, Obidos,...
"Thank you Filomena for the best trip."

Reviewed By Gayle L.

Portugal Luxury Tour Review: Lisbon, Porto, Algarve, Sintra,...
"We enjoyed our trip, even though the weather did not cooperate....

Reviewed By Nancy a.

Portugal Luxury Trip Review: Lisbon, Porto, Douro River...
"I would rate this as one of our best family vacations –...

Reviewed By George T.