Portugal in 2 Weeks: 5 Recommended 14-day Itineraries to Portugal

Check out our 2-week Portugal itinerary ideas below. Each itinerary is meticulously curated to ensure you make the most of a 2-week trip to Portugal and beyond.

From Portugal’s deepest southern basin in the Algarve to its central-south landscapes in Alentejo, enjoy the freedom of driving through Portugal’s coastal siblings. Without rushing from A to B, you really get a sense of each destination: cue the traditional towns and villages, gastronomic delights, history, culture, and loads of enthralling day trips. Explore the centuries-old architecture in Faro and Silves (the ancient Moorish capital of the Algarve), discover castles in Beja, skeleton-covered churches in Évora and Moura’s olive groves and vineyards. Beach-hop through Tavira and Olhão, ending back on the Algarve’s craggy-cliff coast. See more 2-week tours in Portugal.

Venture on a 14-day odyssey through the Azores, often dubbed "the Hawaii of Europe.” Begin your exploration on São Miguel, the largest volcanic island, where you'll be captivated by the stunning landscapes, from the majestic Sete Cidades caldera to the intricate artistry of traditional basket weaving. Immerse yourself in the vibrant culture of Terceira, witness the volcanic vitality of Faial, and ferry to Pico for wine tasting and insights into the island's whaling heritage. Indulge in unique experiences like swimming with the dolphins, soaking in hotsprings adjacent to the Atlantic Ocean or tasting Cozido das Furnas, a stew unique to the town of Furnas. Your journey culminates in Lisbon with a memorable farewell dinner.

It’s all sun, sea and sights in Portugal’s most treasured islands, kicking off with a perfect introduction in the cobbled streets of the country’s capital city. Designed for those with an appreciation for slow-paced travel, explore some of the most magical sites—the kinds splashed across social media feeds. Uncover Sintra’s fairytale stairwell. Fly over to the volcanic-rich Azores, falling into the ebb and flow of its insane natural wonders! Explore national parks, tea plantations, craters, thermal lakes and waterfalls. Dazzling with exotic gardens, lively markets, cultural riches, and of course, wineries and vineyards, Madeira’s charm is undeniable. 

You can create your own 14-day personalized trip to Portugal with our local travel experts.

Come join us on this two-week Portugal journey, where you’ll explore the vibrant capital of Lisbon, the dramatic landscapes of the Azores, and the picturesque beauty of Madeira. Your adventure begins with a seamless blend of traditional and modern experiences in Lisbon, including savory Portuguese cuisine and captivating Fado music. Continue to the Azorean island of St. Michael, where natural wonders and unique local culinary traditions await you. Delight in the lush landscapes of Terra Nostra Botanical Park and the intriguing geological formations of Sete Cidades. Next, discover Madeira, renowned as the "Pearl of the Atlantic," with its captivating city of Funchal, colorful markets, and delightful wine tasting opportunities. Enjoy leisurely days filled with personal discoveries, whether wandering historic streets, lounging in volcanic pools, or soaking in the breathtaking cliffside views. Conclude your memorable tour with a classic farewell dinner in Lisbon, leaving with cherished memories of Portugal's rich culture and stunning scenery.

This 14-day Portugal itinerary will take you across the Azorean Islands, beginning with the charming island capital of Ponta Delgada on Sao Miguel. The journey offers a blend of scenic hikes, cultural explorations, and unique experiences. Discover the striking volcanic landscapes of Sete Cidades and Furnas, where thermal pools and botanical gardens promise relaxation. Enjoy opportunities for whale watching and uncover the fascinating history tied to the region’s volcanic activity. As you journey to Sao Jorge, Pico, and Faial, delve into the rich maritime culture and admire dramatic coastlines, all while indulging in local culinary delights, including a traditional Cozido cooked in volcanic soil and wine tasting at a renowned vineyard. Each island presents a new opportunity to explore captivating landscapes, from the serene valleys of Sao Jorge to the vibrant heritage of Faial. This itinerary ensures an enriching mix of nature, adventure, and cultural insights, culminating in a journey that captures the enchanting Azores archipelago in all its glory.

A 2-week Portugal itinerary plan promises an enriching experience. Whether you savor the historic charm of Lisbon, the scenic wonders of the Douro Valley, or the coastal allure of the Algarve, our two-week packages ensure a perfect balance of adventure and tranquility. Opt for a customized trip to Portugal for an even more bespoke travel encounter, crafting unforgettable memories in this enchanting European destination.

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