Portugal 2-Week Tours & Itineraries

Explore 9 trips designed by local kimkim specialists to get ideas for your trip to Portugal.
See our itineraries below or read our guide to the best 14-day trips in Portugal.
Plan your trip to Portugal
Chat with a local specialist who can help organize your trip.
Madeira Island's northern coast
Map of Explore Portugal: Porto, Lisbon, & Madeira Island - 14 Days
Explore Portugal: Porto, Lisbon, & Madeira Island - 14 Days

This epic Portugal tour highlights two cosmopolitan cities and a stunning mid-Atlantic island—part of an autonomous region—known for its tropical foliage and eternal spring-like weather. You'll kick off in Porto, home of centuries-old wine production and colorful architecture along the Douro River. Then fly to Madeira Island for secluded beaches and untouristed villages waiting to be discovered. Last but not least is Lisbon's friendly, up-and-coming capital—a striking city built on seven hills.

Sunset from the Cabo da Roca near Lisbon
Map of Ultimate Portugal Tour: Lisbon, Porto, The Algarve, Douro Valley, & More - 14 Days
Ultimate Portugal Tour: Lisbon, Porto, The Algarve, Douro Valley, & More - 14 Days

This itinerary includes Portugal's two biggest cities, a slew of historic villages, and some spectacular beaches for an epic adventure to remember. Start off in up-and-coming Lisbon to explore ancient ruins and trendy districts before making your way north to UNESCO-listed Porto (and its nearby wine region). You'll also get time in the university towns of Évora and Coimbra—each with their own medieval attractions and dining scenes—before kicking back for a few days in the Algarve.

The emerald landscape of São Miguel Island
Portugal: the Azores, Lisbon & Porto - 14 Days

Spend two-weeks taking in the best of Portugal's scenery, history, food, and wine. This trip plan begins with three days in the Azores on the gorgeous green isle of São Miguel; discover the charming city of Ponta Delgada, sample local delicacies, go whale watching, and admire the island on an amazing hike. You'll then head to Lisbon for two days of city life, followed by a string of beautiful towns and UNESCO World Heritage sites. End your stay with time in Porto and enjoy tasting flights of incredible Porto wine in the sweeping romance of the Douro Valley. 

Crashing waves in Porto, Portugal's second largest city
Map of Best of Portugal: Lisbon, Porto, Douro Valley, & More - 14 Days
Best of Portugal: Lisbon, Porto, Douro Valley, & More - 14 Days

This exciting two-week itinerary combines cosmopolitan cities, medieval architecture, and spectacular beaches for a Portuguese trip of a lifetime. After exploring Lisbon with a local guide, you'll stay in the fairytale village of Sintra and the surf town of Nazaré. Then work your way north to UNESCO-listed Porto and its nearby wine region before heading to the university town of Évora. End the trip in pure bliss with some beach time in the western Algarve.

Lisbon, Portugal
Map of Romantic Portugal: Lisbon, Porto, Évora, Douro Valley, Algarve - 14 Days
Romantic Portugal: Lisbon, Porto, Évora, Douro Valley, Algarve - 14 Days

Experience the beauty, depth, and romanticism of Portugal, in this 14-day road trip that will show you the variety of the Portuguese landscape, from the city to villages and beaches.  You'll experience the art and culture of Lisbon, see the fairytale village of Sintra, sip wine in Porto, and explore the wonders of Évora.

Sunset in Aveiro
Explore Portugal's Coast: Porto, Lisbon, The Algarve, & Peneda-Gerês National Park - 14 Days

Explore Portugal's epic coast and spend time discovering city centers, tiny towns, and picturesque beaches on this 14-day trip plan. You'll enjoy guided tours of Porto and Lisbon and will hike through the stunning landscapes in Peneda-Gerês National Park. With the Atlantic at your side, you'll discover beautiful towns like Viana do Castelo, Braga, and Aveiro (whose Venice-like canals are sure to charm you). Make the most of the coast with stops in gorgeous Lagos and surfing hotspots like Vila Nova de Milfontes and Sagres. 

Porto's colorful riverfront
Portugal Relaxed Self-Drive: Lisbon, Porto, Évora & Lagos - 14 Days

This two-week Portuguese odyssey combines cities, countryside, and coast for a road trip to remember. Savor traditional cuisine in Lisbon, lose yourself in the riverside neighborhoods of Porto, explore vineyards and cork forests around Évora, and soak up some sun on the golden beaches of Lagos. Along the way, a series of guided tours introduce you to the culture and customs of each city, while plenty of downtown means you can cut loose and choose your own adventure on day trips.

Bridge of S. Gonçalo in Amarante, Portugal
Portugal's Jewish Heritage - 14 Days

This trip takes you from north to south, discovering Portugal's Jewish heritage with city tours in Porto, Lisbon, Évora, and Tomar, plus a visit to Sintra with its National Palace of Pena and the Portuguese Riviera. Relax in the Douro Valley with a wine tasting and a river cruise, and then explore the monasteries of Batalha and Alcobaça, the castle in Amourol, and the synagogue and old Jewish quarter of Castelo de Vide. Other highlights include the community museum in Belmonte, the Amoreira Aqueduct in Elvas, and Amarante's iconic stone bridge.

Play on the beaches of the Algarve in Portugal
Map of Family Vacation to Spain & Portugal - 14 Days
Family Vacation to Spain & Portugal - 14 Days

This two-week family vacation combines Portugal's beaches, palaces, and flavors with Spain's flamenco, royalty, and parks. Start your trip in Portugal with highlights kids and adults love, including playing on the beach, sailing in the ocean, and spotting dolphins. Then, make your way to Spain, where unique cultural experiences await, including sites like Granada's Alhambra, Madrid's Plaza Mayor, and Seville's Royal Alcázar.

Other durations: 4 days · 5 days · 6 days · 7 days · 8 days · 9 days · 10 days · 11 days · 12 days · 13 days · 14 days · 15 days