14 Day Portugal Tour Itinerary

Officially Licensed Guides

Over 23 years guiding US travelers

Small Private Tours

Explore Portugal your way

Our 14 day Portugal tour itinerary ensures that you will truly get to sample everything that makes Portugal such an attractive, inviting, and unique destination to visit.

Read through some of the itinerary ideas below, before getting in touch with our team to request your own personalized trip to Portugal and/or Spain!

Tour Highlights: 

What’s Included?

Certified To Keep You Safe

We are extremely proud that the Institute for Spanish Tourism has granted our team the “Safe Tourism Certified” seal of approval. In addition to the security and peace of mind this provides to our clients, we have extended our cancellation policy to entitle guests to a full refund if they are forced to cancel their tour anywhere up to 7 days before the start date. Find out more here.

14 Days Portugal Itinerary

Day 1: Beginning in Porto

Portugal tour. View of the Ribeira in Porto.
Porto, Portugal

Our expert private guide meets you at your hotel for an interactive, fun Porto half-day tour.

The historic city center of Porto is listed as a  UNESCO World Heritage Site. You’ll love discovering timeless traditions, lovely neoclassical facades, panoramic vistas over the Douro River, and cultural sites like the Porto Cathedral and the Batalha Square where you can see the 18th century Batalha Palace. 

How about a skip-the-line visit to Livraria Lello?  This is likely the most enchanting bookshop in Europe and it is linked to Harry Potter!

Later admire the 250 feet tall Clerigos Church Tower, a key Porto landmark or three-story-high fountain on Ribeira Square, and river views. For wine lovers, a tasting at the famous Porto Wine Cellars. Conclude the tour at a delicious local restaurant where we have reserved a table for you.

Day 2: Porto Douro Valley Excursion

Porto Douro Valley Wine Tour
Douro Valley Wine

Regua & Pinhao of the Douro Valley (with Lunch & Wine Tasting)

With a private driver-guide and comfortable Mercedes vehicle, head out to experience the beautiful and historic Douro Valley. The wine country, the Alto Douro Wine Region, is a World Heritage Site with over 200,000 hectares under vine producing growing quantities of highly-rated red wines (as well as the traditional Port wines).   

Don’t miss the historic pilgrimage town of Amarante where houses overhang the Tamega River. Enjoy the views as you continue through the picturesque hilly riversides and wine country’s unique terroir. Perhaps enjoy a walk along the Douro River in Regua and see the famous terraced Douro vineyards that cover the riverside hills. 

We love the blue-painted tiles at the Pinhao railway station. Of course, we can arrange private visits to top wineries that go beyond the mass market. This can include wine tastings of top local wines, and a tasty, traditional meal. Optionally enjoy unforgettable gourmet picnics, hot air ballooning, or a private yacht cruise as part of your unforgettable VIP day.  Conclude your day on arrival back to Porto. 

Alternative Douro Valley touring option:

Subject to availability, you may prefer to do a luxury trip into the scenic Douro Valley on the stylish Presidential Train.

This train was used by monarchs, nobles, and international dignitaries in times past.

Best of Spain & Portugal

“I urge everyone who values unforgettable vacations to contact Magical Spain and talk to Dan or Rachel.

Beyond the personalized planning and fine 24-7 tour support, we loved the quality and care of the licensed guides, the delicious tapas, the exotic ambiance of Seville and Granada, Madrid’s majesty and art, medieval Toledo, and meeting the olive oil estate owners, artist, chef & winemaker.”

R. Mathews, wife & friends (Northern Virginia)


Day 3: Porto To Lisbon Private Tour

Moliceiro boats at Aveiro, Portugal.
Moliceiro boats at Aveiro, Portugal
  • Private Tour & Transfer
  • Coimbra, Obidos or Aveiro options
  • Lisbon Fado show & dinner
  • You’ll depart Porto and be transferred in a private vehicle for an exciting day touring en route to Lisbon. Opt to visit Aveiro, Obidos or Coimbra.

 Aveiro is the “water city” of Portugal, Aveiro, and the fairy-tale castle at Santa Maria da Feira. Aveiro’s history is inextricably linked to the sea by fishing and salt-cured codfish production. The architecture is unique, a mix of Art Nouveau townhouses and traditional fishermen’s cottages.

Coimbra, the “Cambridge of Portugal ” with one of Europe’s oldest universities. It was here that many of the elite of Portugal’s former world empire started their rise to power. Tour the beautiful campus with our guide.

Or opt for Obidos, the Royal “wedding gift” town. Obidos is a whimsical white-washed medieval town, gifted by Portuguese kings to their brides. Obidos charms with flowered lanes, ramparts, and a fine medieval castle…  

Then on to cosmopolitan yet “old world” Lisbon with your driver to check in to your hotel. We remain fascinated by the eccentric blend of charming elements from the traditional streetcars that somehow never tire of climbing Lisbon’s seven hills, to the traditional, unique colors like the warm shades of orange, yellow, blue, and rusty red. Even in 2022, clothes are sometimes still hung out to dry from historic iron balconies. If electricity prices go higher here we may see more of this all over Europe! 

In Lisbon be sure to enjoy a Fado show & dinner with traditional style. We work with the best of the bunch!

Day 4: Lisbon: A Historic Walk Through the Past

skyline of alfama at lisbon, portugal at dawn
Lisbon, Portugal at dawn

Again with an official private guide, deluxe vehicle, and driver, enjoy a half-day Lisbon private tour. 

Possible highlights include the following: Discover the two Lisbon UNESCO World Heritage Sites: the Belem Tower on the Tagus River and the outstanding 16th-century Jeronimos Monastery. Don’t miss Rossio Square in Baixa city was devastated in 1755 and then upgraded.  If desired, learn more about the rise and fall of the powerful and wealthy 15th-16th century empire that included parts of Asia, Africa, and South America. Or visit the ancient Alfama district of Lisbon, see windows with flower boxes and the 12th century Lisbon Cathedral. 

Don’t miss the vistas from above commanding hilltops like that of St. George’s Castle, once a  Moorish fortress. We also suggest the amazing views from the Miradouro da Senhora do Monte. Later transfer back to your hotel.

Day 5: Sintra Excursion from Lisbon

Sintra castle in Portugal
Sintra, Portugal

See the Signature Sights in Style:

  • Estoril
  • Cascais
  • Cabo da Roca
  • Sintra with Pena Palace

Private excursion to Great Gatsby-like palaces of Sintra… like the Pena Palace built by the Royal family.  Later with your private driver & expert guide discover the Cabo da Roca National Park, the westernmost site of Continental Europe. Or enjoy a lovely alfresco seaside meal with panoramic views in Cascais or see Estoril. Don’t forget the famous pastries: Queijadas of Sintra and Travesseiros. Return to Lisbon.

Day 6: Lisbon Like An Insider

Portuguese traditional tapas food.
Exclusive Food Tour Class

Private touring of Lisbon, depending on your taste: Enjoy a private guided market visit and cooking with a chef, meeting artists or artisan crafts-makers. 

Our planners can arrange a private visit to the Ricardo do Espirito Santo Silva Foundation, dedicated to the preservation and reproduction of traditional Portuguese design and decorative art. Maybe with your guide explore the stylish Bairro Baixa, or Bairro Alto districts or a Royal historical monastery, or historic art… 

Next, channel great world explorers like Magellan, by doing the Tagus River by private boat. In the evening, feel the passion of soulful fado over dinner.

Day 7 & 8: Ancient Authentic Alentejo & Évora

Cloister of the Evora Cathedral, the largest cathedral in Portugal_
The Evora Cathedral, Portugal

Private transfer into the rustic beauty of the Alentejo region and a 2000-year-old Roman town. 

Évora is an authentic museum city with timeless traditions and old walls nearly untouched. Opt to visit postcard-pretty hilltop villages, discover famous Lusitano horses on a ranch, enjoy artisan cheeses, wines, or olive oils.

Discover Évora as an insider: From the authentic Roman Temple to the enigmatic medieval bone chapel, or a unique fortress cathedral that survived Moorish attacks with our guidance. 

Later perhaps a fine regional meal and tasting of regional cheeses & wines in a medieval cellar.

Or opt to hike in the Arrabida Mountains. We design your days your way. Despite all the ancient history, you can still enjoy a modern suite in a historic hotel property with ancient olive groves and a full-service spa if desired.

Screen Shot 2021-08-25 at 11.40.38

“Thanks for the great work during our Spanish Food and Wine Adventure…. you guys really know your stuff and are great guides & hosts! We’ll be back for northern Spain in the future!”

The Marshall Clan (Dallas, TX)


Day 9: Iberia’s Stonehenge & Lusitanos

Megaliths of Cromlech of Almendres, Alentejo, Portugal
Cromlech of Almendres, Alentejo, Portugal

Discover “Iberia’s Stonehenge” prehistoric Celtic stone circles and dolmens. 

Or for horse-lovers, experiences on a working horse ranch with thoroughbred Lusitano horses and quaint historic villages with hard-to-find artisan crafts. 

Or visit a traditional Portuguese wine and olive estate for a tour and traditional lunch. Citrus, olive oil, wine, cheese, and cork production are timeless crafts in Iberia since Roman times.

Day 10: Algarve Coast Adventure

Algarve Portugal

Be transferred south to the cherished Algarve Coast. Your driver will take you to your hotel and then off to your next activity if desired. 

We LOVE the sunny Algarve more than the famous coast of southern Spain’s Andalucia. In fact, the Algarve is a European favorite for the natural beauty, beaches, caves, cliffs, and variety of activities. 

Opt for hot air ballooning, historic village discovery, beach time, a private sailing or coastal hiking adventure.

Natural beauty, great food, scuba, surfing classes, mountain biking in the Monchique Mountains, private yacht or sailing charters, golfing, spas, golf, private, custom, luxury tours in Portugal, your way. A spa and/or fitness session is also an option.


“Outstanding, seamless planning with a very personalized itinerary executed perfectly…..

In Spain, we felt like VIPs as we met the winemakers in La Rioja and Ribera del Duero, the chefs, the village mayor  and flamenco dancer in Sevilla! The unique experiences and memories beat that of 4 or 5 cruises.  We will be back to do Andalucia or Portugal in a few years”

Scott & Kisha McCann (NYC)


Day 11: Algarve Active or Cultural Fun

Gate to the old town of Lagos, Portugal
Gate to the old town of Lagos, Portugal

Choose active Algarve outdoor fun or go cultural & historic exploring historic Tavira’s old town and medieval castle. 

Alternatively discover Lagos, Silves, or Cape Sagres. Savor fresh fish, the famous Piri-Piri, a tasty antioxidant-rich spice imported from Portugal’s colonial empire.

Don’t forget the savory cheeses, fine wines, and amazing Algarve sunsets.

Day 12 & 13: Algarve, Portugal


Again via private transfers from your hotel. The sun-kissed Algarve coast is powdery sandy coves, Mediterranean climate, ocean-front grottoes, medieval villages, castles, hiking, ballooning, surf classes, deep-sea fishing, or sailing with our captain and expert crew. Don’t miss the spicy grilled meats, and uber-fresh seafood.

Meet the owner of artisan salt pans (the Romans used them to create garum), now one of Europe’s top gourmet sea salts. Other options: dolphin watching, birding, surfing, scuba, winery tastings & meal, nature hikes, photography, or hitting the gym or spa in your hotel.

Day 14: Departure

Private transfer to Lisbon, Faro, or Seville to make your airport travel.

SideBar Tour Request

Meet our Founder & Iberian Tour Expert

Ola! I’m Dan O’Beirne, owner of Magical Spain and Portugal

Originally from America, I worked in the Health and Wellness sector until moving to Iberia over 20 years ago. Ever since then, I have made it my mission to combine classic American hospitality with the fascinating, beguiling, and simply beautiful landscapes, monuments, and cultures found across Spain and Portugal.

Step 1

Fill out the form with the destinations, wish-list, & personal preferences for your perfect trip. If you would like your tour planner to offer some inspiration, then we are happy to provide a suggested itinerary which we can then refine with you until you are 100% delighted with it.

Step 2

Soon after receiving your request, your personal tour planner will be in touch to begin planning your custom tour. You will then receive a tailor-made tour itinerary which can be revised an unlimited number of times to ensure total satisfaction and the perfect vacation.

Step 3

Your officially licensed private guide will meet you at the pre-arranged starting point of your tour. You can count on us for 24/7 in-country support and everything else necessary for a wonderful vacation and seamless tour experience. Welcome to Iberia!

Request Your Complimentary Custom Itinerary With Our Magical Experts

Fill in the form below with as much detail as you can and our tour planning experts will get in touch with you shortly to help you craft the perfect vacation to Portugal and/or Spain, tailored to you and your group! 

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