2 Weeks in Portugal - 5 Unique Itinerary Ideas

Itinerary #1: Ultimate Portugal Tour - Lisbon, Porto and Algarve

The name of this trip plan says it all: this is the ultimate itinerary, particularly for first-time visitors. You'll see Porto and Lisbon, tiny villages, UNESCO World Heritage Sites, and unbelievable beaches, paired with off-the-beaten-path gems.

Lisbon serves as your home base for the first part of your trip: tour the city’s highlights with a guide and taste your way through Lisbon’s flavors on an epic epicurean tour of the town. After visiting a smattering of villages and UNESCO Heritage Sites like Pena Palace in Sintra, you’ll spend some time in Coimbra, a storied university town you’ll discover with the help of a local expert. 

From there, it’s off to Porto, your jumping-off point for excursions to gorgeous Guimarães and the wine region of the Douro Valley. Keep the rural vibe going in the Alentejo Region — visit rustic wineries and olive groves, and lose yourself in the medieval charm of Évora. End your trip in total bliss in Lagos, the gateway to Portugal’s best beaches. At the end of your fourteen days, you’ll return to Lisbon for your departure. Learn more

Itinerary #2: Food, Wine, & Island Living

Looking to blend some tropical romance with well-rounded city experiences? Check out this trip plan which includes time in Lisbon, Porto and their surroundings punctuated by a jaunt to the gorgeous subtropical island of Madeira. 

Bookend your trip with time on land in Portugal’s two biggest cities. Tour Porto through a gastronomic lens on a culinary tour that culminates with a tasting flight of some Port wines. The next day, travel through town with the help of a private guide. Then it’s off for three days in the Douro Valley, considered by many to be the most beautiful wine region in all of Europe. Tour wineries, learn about Port wine and olive oil production and relax on the scenic banks of the Douro River. 

On day six, you’ll fly to the tiny island of Madeira, situated in the mid-Atlantic, just northwest of Africa. Your home base for the next few days is the capital city of Funchal, from which you can explore the volcanic island’s villages, beaches, and exotic mountains.

Transition from island vibes to city life as you spend the remainder of your trip based out of Lisbon. Get to know the city on your own and on a guided half-day tour, and balance your stay in the capital with a gorgeous day trip to a trio of romantic towns, as well as time to explore nearby medieval villages, beaches, and national parks. Learn more

Itinerary #3: Nature & Culture in Portugal

Calderas, lakes, caves, and whale watching await on the Green Island of São Miguel in the Azores; get swept away by dramatic landscapes, then head ashore to tour Porto and Lisbon, as well as tiny towns in this fun trip plan. 

Begin your adventure in the Azores on the gorgeous island of São Miguel; you’ll spend the next few nights based in Ponta Delgada, the region’s capital. Explore the town and its 16th-century treasures, dive deeper into local history and heritage with a guided food and cultural tour, then hit the high seas for an epic day of whale watching followed by a hike of the island, its lakes, and calderas. 

Bid farewell to island life on day four when you land in Lisbon, Portugal’s up-and-coming capital. Explore the town first with a guide, then at your own leisure, before heading off for a day of castles, gardens, and seaside charm in the towns of Sintra, Cascais, and Estoril. Sink into rural serenity with two days in Évora and the rolling hills of the Alentejo region, then discovered a collection of storied villages close to the historic university town of Coimbra. Wrap up your trip in and around Porto: taste local food, go wine tasting in the gorgeous Douro Valley, and enjoy a phenomenal picnic view after an epic hike in the verdant Peneda-Gerês National Park. Learn more

Itinerary #4: Explore the Iberian Peninsula - Spain & Portugal

Interested in exploring the Iberian Peninsula? This trip plan combines Lisbon and Porto with a delicious exploration of Madrid and Barcelona. Hit the beach, sample the shared yet distinctive palate of Iberian cuisines, and lose yourself in art exhibits and on cobblestone streets. 

Spend the first half of your trip in Lisbon and Porto, where private guides will help you dive deep into the flavors and history of Portugal. You’ll soon discover that it’s not just heritage sites, museums, and architecture that tell the story of Portugal and Spain, but it’s the food that does a lot of the talking. That said, take advantage of tasting tours, street food, and wine tasting flights. Eat up!

In addition to exploring cities, you’ll also visit romantic enclaves like Sintra, home to the butter-yellow Pena Palace, whose structure, gardens, and view seem straight out of a fairytale. Learn about Coimbra, a historic town full of rich lore, with a guide who’ll also take you through the town’s famed university. After eating and touring your way through Porto, spend one last day in Portugal wine tasting in the spectacular Douro Valley, home to Port wine, the gorgeous Douro River, and lush green landscapes. 

On day seven, it’s off to Madrid and its world-class art center, El Prado; thankfully you’ll make the most of your time in the museum with the help of a private guide, then unwind with a night of tapas around town. Hop over to Toledo for a fun day trip, then let the blend of medieval drama, Gothic architecture and Gaudi's imagination take hold with two electric days in Barcelona. From there, head north along the Mediterranean coast to the Costa Brava for some hiking, beach time, and great snorkeling. Learn more

Itinerary #5: Best of Portugal's Coast

Hit the road for two weeks of off-the-beaten-path discovery along Portugal’s coastline You’ll visit fairytale towns, medieval centers, and wine country on this comprehensive trip plan perfect for the traveler who likes to set their own pace. 

The fun begins with two days in Porto, which you’ll discover with some expert help; enjoy a private tour of the city’s sights as well as a fun excursion about town tasting its flavors and learning its stories. You’ll spend the next four days on the road visiting towns and heritage sights far from the typical traveler’s itineraries.

On the road between Porto and Lisbon, you’ll stop through gorgeous enclaves like Viana do Castelo, crowned with the white Santa Luzia church high up on a hill. You’ll also hit quaint towns like Aveiro (Portugal’s take on canal-filled Venice), the labyrinthine Óbidos, and can splash around the base of a spectacular waterfall deep in a national park. 

Get to know Lisbon’s history and musical traditions, then unplug and unwind in the rural tranquility of the Alentejo region: go wine tasting, stroll idyllic trails, and find your favorite fortified town. The water awaits you for the rest of your trip; the iconic Algarve will treat you to phenomenal beaches and dramatic cliffs, but chill surfing communities like Sagres and Vila Nova de Milfontes are sure to help you sink into major beach vibes. Learn more

More Great 14-Day Portugal Itineraries

Looking for more inspiration for your Portugal trip? Check out these other 14-day Portugal itineraries, ranging from active, to cultural, to luxury, or family-friendly trips.

Or, describe your ideal trip and we will connect you with a local specialist to make it happen.