Two weeks in Portugal is an excellent amount of time to experience the country's luxurious side while hopping between a few distinct regions. If you're eager to delve into the city's cultural hotspots, focus on Lisbon, Porto, and Évora, or swap in the Alentejo and Comporta for an off-the-beaten-path adventure. The Algarve and Madeira are superb options for a slice of coastal splendor, while those curious about Spain's wonders can include Seville and Granada in their itinerary.

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.

Sip port wine along the banks of Porto's Douro River
Sip port wine along the banks of Porto's Douro River
Day Highlights Overnight
Day 1 Arrive in Lisbon, Free Time to Explore Lisbon
Day 2 Lisbon Walking & Tasting Tour, Dinner & Fado Performance Lisbon
Day 3 Exclusive Tuk-Tuk Tour of Belém, Portuguese Cooking Class Lisbon
Day 4 Day Trip to Sintra's Palaces & Parks, Dinner at Fifty Seconds Restaurant Lisbon
Day 5 Transfer to Porto via Óbidos & Nazaré Porto
Day 6 Gastronomy & Culture Tour, Port Cellar Tasting, The Yeatman Restaurant Porto
Day 7 Day Trip to the Douro Valley, Wine Tasting & River Cruise Porto
Day 8 Day Trip to Braga & Guimarães Porto
Day 9 Transfer to Serra da Estrela Nature Park, Free Time to Explore Serra da Estrela 
Day 10 Serra da Estrela Guided Hike & Picnic, Dinner at Puro Restaurante Serra da Estrela 
Day 11 Transfer to Évora via Marvão Évora
Day 12 Tour Historic Évora, Dinner at Divinus Évora
Day 13 Transfer to Cascais, Dinner at Fortaleza do Guincho Cascais
Day 14 Transfer to Lisbon, Depart  

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. 

Your 5-star accommodations include a waterfront Algarve resort (photo courtesy of Palmares Beach Resort)
Your 5-star accommodations include a waterfront Algarve resort (photo courtesy of Palmares Beach Resort)
Day Highlights Overnight
Day 1 Arrive in Lisbon, Dinner at Cervejaria Trindade Lisbon
Day 2 Lisbon E-Bike Tour, Dinner & Fado Performance Lisbon
Day 3 Belém's Age of Discovery Segway Tour, Free Time in Lisbon Lisbon
Day 4 Day Trip to Sintra: Palaces, Parks & Coastline Lisbon
Day 5 Transfer to Lagos & the Algarve, Dinner at Luca's Rooftop Restaurant Lagos
Day 6 Boat Trip to Benagil Cave, Discover the Algarve's Beaches Lagos
Day 7 Kayaking Tour to Ponta da Piedade, More Beach Time Lagos
Day 8 Transfer to Évora & the Alentejo, Dinner at Tábua do Naldo Évora
Day 9 Água de Prata Aqueduct Guided Hike, Free Time in Évora Évora
Day 10 Transfer to Porto via Coimbra, Dinner at Brasão Porto
Day 11 Porto Walking Tour & Bridge Climb, Douro River Cruise Porto
Day 12 Day Trip to the Douro Valley: Wine Tasting & River Cruise Porto
Day 13 Transfer to Cascais via Nazaré & Óbidos, Dinner at Baía do Peixe Cascais
Day 14 Transfer to Lisbon, Depart  

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

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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.

Views of the Serra da Estrela (photo courtesy of Casa de São Lourenço)
Views of the Serra da Estrela (photo courtesy of Casa de São Lourenço)
Day Highlights Overnight
Day 1 Arrive in Porto, Culinary & Cultural Highlights of Porto Tour Porto
Day 2 Porto Architecture Tour, Taylor's Port Tasting Porto
Day 3 Kayaking & Hiking in Peneda-Gerês National Park Porto
Day 4 Scenic Drive to the Douro Valley Wine Region Douro Valley
Day 5 Scenic Drive to Serra da Estrela Nature Geopark  Serra da Estrela
Day 6 4WD Tour of Serra da Estrela's Landscapes & Villages Serra da Estrela 
Day 7 Drive to Lisbon, Cooking Class or Dinner with a Michelin-Star Chef Lisbon
Day 8 Tour Lisbon with a Local, Evening of Fado Lisbon
Day 9 Sintra & Cascais Tour with Coastal Cruise Lisbon
Day 10 Fly to Madeira, Funchal Food & Cultural Tour Madeira
Day 11 4WD Tour of Madeira  Madeira
Day 12 Madeira Leisure Day, Sunset Catamaran Cruise  Madeira
Day 13 Guided Hike on the 25 Fontes Trail Madeira
Day 14 Fly to Lisbon, Depart  

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.

Venture deep into the Douro Valley to find a vineyard-set retreat (photo courtesy of Casa do Rio Wine Hotel)
Venture deep into the Douro Valley to find a vineyard-set retreat (photo courtesy of Casa do Rio Wine Hotel)
Day Highlights Overnight
Day 1 Arrive in Porto, Portuguese Cuisine Experience Porto
Day 2 Porto World Heritage Tour, Evening Wine Tasting Porto
Day 3 4WD Tour of Peneda-Gerês National Park Porto
Day 4 Scenic Drive to the Douro Valley Douro Valley
Day 5 Archaeology, Wine Tasting & Lunch in the Greater Côa Valley Douro Valley
Day 6 Traditional Portuguese Cooking Class Douro Valley
Day 7 Scenic Drive to the Alentejo Alentejo
Day 8 Alentejo Jeep Tour with Winery Visit Alentejo
Day 9 Hot-Air Balloon Over Évora, Dark Sky Reserve Stargazing Alentejo
Day 10 Drive to Comporta, Explore the Hotel & Beach Town Comporta
Day 11 Arrábida Marine Reserve Boat Trip Comporta
Day 12 Horseback Riding with Picnic Lunch Comporta
Day 13 Drive to Lisbon, Cooking Workshop or Michelin-Star Dinner Lisbon
Day 14 Depart Lisbon  

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. 

Tour UNESCO-listed cities, such as Lisbon
Tour UNESCO-listed cities, such as Lisbon
Day Highlights Overnight
Day 1 Arrive in Porto (Portugal), Explore the UNESCO City Porto
Day 2 Porto World Heritage Tour & Wine Tasting Porto
Day 3 Portuguese Cooking Class, Art Museum Visit Porto
Day 4 Train to Lisbon, Food & Cultural Tour Lisbon
Day 5 Explore Lisbon's Highlights Independently Lisbon
Day 6 Visit Sintra's Palaces, Castles & Forests Lisbon
Day 7 Transfer to the Alentejo, Explore the Hotel's Grounds Alentejo
Day 8 Alentejo Jeep Tour with Winery Visit Alentejo
Day 9 Transfer to Seville (Spain), Jamón Tour & Tasting Seville
Day 10 Seville Historical Tour, Gourmet Tapas & Wine Tasting Seville
Day 11 Andalusian Olive Oil Estate Tour, Michelin-Star Dinner at Abantal Seville
Day 12 Transfer to Granada, Alhambra & Generalife Gardens Tour Granada
Day 13 Explore Granada, Hammam Session & Flamenco Show Granada
Day 14 Train to Madrid, Depart   

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.


Map of 2 Weeks in Portugal - 5 Luxury Itinerary Ideas
Map of 2 Weeks in Portugal - 5 Luxury Itinerary Ideas