2 Weeks in Portugal - 5 Luxury Itinerary Ideas

Itinerary #1: Luxury Portugal Flavors & Culture Tour

Ideal for those who relish luxury and seek a comprehensive introduction to Portugal, this two-week highlights itinerary showcases Lisbon, Porto, Serra da Estrela, and Évora. Throughout, unwind at 5-star accommodations, dine at Michelin-starred restaurants, and enlist the help of local experts for unique and immersive experiences. Other highlights include an exclusive Portuguese cooking class, vineyard tours, a guided hike, and a stay in a historic town once favored as a royal retreat.

Welcome to Portugal! Your luxurious trip begins in Lisbon, where you'll check into the 5-star One Palácio da Anunciada and spend the afternoon exploring independently. Then, over the following three days, tick off numerous immersive experiences, including a walking tour, tuk-tuk excursion, cooking class, and a day trip to Sintra's whimsical palaces. A private transfer to Porto is next on your agenda, and while here, you'll visit a wine cellar and dine at the Michelin-starred The Yeatman Restaurant. Porto also serves as your gateway to the Douro Valley and the historic cities of Guimarães and Braga.

Just over the halfway point of your luxury-infused adventure, swap the city for the serene landscapes of Serra da Estrela. Using the lavish Casa de São Lourenço Burel Panorama Hotel as your base, you can indulge in spa treatments between spectacular hikes and dinner at the decadent São Lourenço restaurant. Afterward, continue to the laid-back city of Évora, where you'll tour its Roman ruins and dine at the upmarket Convento do Espinheiro. Then, as your adventure nears its end, spend a night in the historic royal retreat of Cascais before returning to Lisbon for your departure. Learn more

Itinerary #2: Luxury Adventure in Portugal: Lisbon, Lagos, Évora, Porto & Cascais

Enjoy immersive stays in colorful cities and lively beach towns on this luxury adventure in Portugal that includes the Algarve. Perfect for travelers seeking unique ways to experience the country's highlights, you'll e-bike through Lisbon, boat and kayak along the Algarve coast, hike alongside Évora's ancient aqueducts, and climb Porto's magnificent Arrábida Bridge. In between, delight in lavish stays at 5-star hotels, including The One Palácio da Anunciada, Palmares Beach House, and M'ar de Ar Aqueduto. 

Spend the first four days of your luxury trip in Lisbon, Portugal's hip and historic capital. While here, you'll find ample time to embark on active and culturally focused excursions, such as an e-bike adventure, fado performance, and segway tour. A side trip to the enchanting Sintra and the fairy-tale-like Pena Palace is also included, followed by a private transfer to the sun-kissed Algarve coast. Your destination is Lagos, and between lavish nights at the 5-star Palmares Beach House, your days are filled with beach excursions, coastal boat and kayak adventures, and dinners featuring fresh local seafood.

Next on your itinerary is a transfer to Évora, where you'll check into a 16th-century palace turned luxury hotel and enjoy an evening of gourmet dining at Tábua do Naldo. You'll also enlist the help of a local guide to discover the marvels of Évora's Água de Prata Aqueduct before continuing north to Porto. Here, you'll delve into the city and region's delights, first on a private walking tour, followed by a thrilling Arrábida Bridge climb and a day trip into the Douro Valley. Lastly, return to Lisbon, but only after stopping for a relaxing overnight in a former seafront fortress in Cascais. Learn more

Itinerary #3: Luxury Portugal Escape: Porto, Douro Valley, Serra da Estrela, Lisbon & Madeira

Discover Portugal's allure on this luxury escape across the mainland and the lush island of Madeira, tailored for travelers desiring an elevated experience. Immerse yourself in the luxury of the Douro Valley with wine tastings, venture on guided treks through Peneda-Gerês National Park and Serra da Estrela, and master Portuguese culinary arts in an exclusive cooking class. Then, conclude your journey with four days in Madeira, where thrilling 4WD explorations and a serene sunset catamaran cruise await.

Your journey begins in Porto, and with the lavish The Yeatman Hotel as your base, you'll delight in leisurely mornings and fill your days with luxury-touched adventures. Local guides will ensure you sample the best food and wine in the city, and a side excursion to Peneda-Gerês National Park promises a fulfilling day of hiking and kayaking. Then, on the morning of Day 4, set off in your rental car to Douro Valley for an indulgent afternoon of pampering and dining. Your journey next leads you to the scenic Serra da Estrela Nature Geopark for a quick but immersive stay, complete with a private 4WD tour. 

Midway through your adventure, you'll continue to Lisbon and kick off your stay with an exclusive Portuguese cooking class. While here, you'll also attend a fado performance and spend a day exploring Sintra and Cascais alongside a guide. However, a real treat has been saved for last, and after a 2.5-hour flight, you'll find yourself on the volcanic island of Madeira. Your base is the elegant Reid's Palace in Funchal, and during your stay, you'll get a well-rounded introduction to the island during a private 4WD tour, a sunset catamaran cruise, and a guided hike on the famous 25 Fontes Trail. Learn more

Itinerary #4: Off-the-Beaten-Path Luxury in Portugal: Porto, Douro Valley, Alentejo, Comporta & Lisbon

Take the path less traveled and discover Portugal's finest hidden gems on this luxury journey. Ideal for those seeking a perfect blend of upscale travel and immersive experiences, you'll collect a rental car in Porto and travel south to Alentejo before making your way back up to Lisbon. Along the way, a few of your carefully selected excursions include two nights spent tucked among the Douro Valley's enchanting vineyards, a hot-air balloon ride over Évora, and a memorable horseback ride along the Atlantic coast.

Your two-week adventure begins in the beloved city of Porto, where you'll venture beyond the tourist path to family-run eateries and join an expert sommelier for a private wine-tasting experience. Continue the off-the-beaten-path theme the following day on a 4WD tour of Peneda-Gerês National Park before collecting your rental car and driving to Douro Valley. Here, you'll check into the boutique Casa do Rio Wine Hotel and dedicate three days to indulging in the region's divine flavors. Highlights include a picnic lunch at Quinta da Vinea, a visit to Côa Valley Archaeological Park, and a chef-led cooking class. 

Next, drive into the Alentejo region, famed for its picturesque vineyards and olive groves. Check into the stylish São Lourenço do Barrocal and take in the region's beauty from all angles, first during a private Jeep safari, followed by a hot-air balloon ride and an Alqueva Dark Sky Reserve stargazing experience. By now, the coast is sure to be calling, so you'll continue to the quaint beach village of Comporta and fill your time here with a sail along the Arrábida Marine Reserve and a horseback riding tour. Lastly, continue to Lisbon and celebrate the end of your adventure with an evening of fine dining. Learn more

Itinerary #5: Luxury Journey Through Portugal & Spain: Culture, Countryside & Gastronomy

This multicountry itinerary is perfect for travelers who are eager to discover the highlights of Portugal and Spain while keeping luxury top of mind. In Portugal, you'll sip wine with an expert sommelier, embark on a guided tour through Sintra's storied forests, and happen upon rural vineyards during a private Jeep safari. Then, spend the second leg of your trip in Spain, where you'll join a private tapas experience, meander through a historic olive oil estate, and tour Granada's Alhambra. 

Upon arriving in Porto, delve into Portugal's luxurious side while settling into your room at The Yeatman Hotel. Then, over the following few days, expert guides will lead you through the city's architectural marvels, teach you Portuguese culinary skills, and reveal intriguing insights at the Museum of Contemporary Art. A train journey to Lisbon is next on your agenda, where you'll join a food and culture tour, explore independently, and embark on a side trip to Sintra. Afterward, continue to the Alentejo region, where you'll relax at a chic hotel and discover rural vineyards during a private Jeep safari. 

On Day 9, it's time to bid farewell to Portugal and transfer over the border to Seville, Spain. Delve straight into luxury while checking into Hotel Alfonso XIII, and take advantage of a restful evening, as the following days are dedicated to exploring the city's highlights alongside a guide and touring a historic olive oil estate. Next, continue east to Granada for a bucket-list-worthy visit to the Alhambra. In Granada, you'll also find plenty of time to relax at your accommodation, the 5-star Parador de Granada, and attend a flamenco show in a cave before wrapping up your trip with a train ride to Madrid. Learn more

More Great 2-Week Portugal Itineraries

Looking for more inspiration for your trip to Portugal? Check out these other two-week Portugal itineraries, with outdoor adventures, cultural trips, and best-of tours to hit the highlights.