Two-Week Portugal Itinerary | Passport Magazine

Plotting an escape to Portugal? Sourced first-hand from the recent getaways of Passport contributor Jessica Wright of Bon Traveler and editor Joy Pecknold, we’ve crafted a 14-day itinerary that starts and ends in Lisbon, with stops in Évora, the Algarve and Comporta. Take these tips and plan a road trip for late spring or early fall—pleasanter temps and fewer crowds pair well with a refreshing Vinho Verde.

Seated where seven spectacular hillsides converge, the country’s capital and largest city is an enlivening medley of old and new. Beyond the big views Lisbon’s unique geography serves up, there are ancient sites to admire and Michelin-worthy meals to savor.


  • Book a walking tour to take in both the Belem Tower and Jeronimos Monastery.
  • Poke around LxFactory—the complex of shops, restaurants and maker studios is full of eye-candy and a great place to score unique souvenirs for friends and family.
  • Satisfy a bounty of cravings without needing a reso at the vast Time Out Market Lisboa.  
  • Devour a signature pastry at the legendary Pastéis de Belém, which has been making sweets since 1837. To skip the line, just pass by the left and ask for a seat.
  • Go for an aperitif at Toca da Reposa, a bar that makes most inventive cocktail places look pedestrian.
  • For spot-on traditional Portuguese, dine at Pica-Pau. Or opt for Senhor Uva for cool, casual vegetarian with impeccable wine pairings.


Portugal Itinerary - The Lumiares Hotel & Spa

In the iconic Bairro Alto neighborhood, The Lumiares Hotel & Spa provides a warm Lisboa welcome. Opposite a tram line, the location makes it easy to check-off that bucket-list item. The apartment-style rooms, whether it’s a studio or two-bedroom Penthouse, include fully equipped kitchens and living areas should guests want to give Portuguese hospitality a go themselves. Otherwise, leave it up to Chef Joao Silva up at the panoramic Lumi Rooftop Bar and Restaurant.

From Lisbon, it’s less than a 90-minute drive east to Évora, the Alentejo region’s charming capital. Surrounded by groves of cork and olive trees, the walled city has a rich and colorful history that includes Roman, Moorish, and Portuguese influences—and that’s earned it UNESCO World Heritage Site.


  • Take a historic sights-stroll. Stop into the Roman Temple of Évora, see the Chapel of the Bones, and climb the stairs to the rooftop within Cathedral of Evora.
  • Shop the local boutiques, such as Oxalá, O Cesto Artesanato, and Livraria Fonte de Letras, for olive oil, cork products and more.
  • Make a point of dining at Botequim da Mouraria, a restaurant with room for only eight where the owner himself serves you, and Dom Joaquim, a Michelin Guide pick that serves traditional and local dishes.
  • Drive out to the valley and go wine tasting. If you like the look, and taste, of L’AND Vineyards, you can also tack on a night’s stay.


Portugal Itinerary - Octant Évora

Octant Évora is an olive tree-dotted oasis just 15 minutes by car outside of Évora proper. The sustainably minded hotel offers a range of well-designed rooms and villas—some with private pools—to accommodate families or friend groups traveling together. There are also three shared pools, two outdoors, one indoors, as well as a spa with a sauna and Turkish bath. Guests can also get hands-on learning in the gardens and orchards.

From Évora, it takes about two hours of driving to reach the Algarve, Portugal’s southernmost coastal region beloved by tourists for its holiday trifecta of beaches, golf courses and relaxing vibe. Stay in Vilamoura, and explore the beach towns west to east—point to point, Sagres to Faro, it’s only a 90-minute drive.


  • Take a beach day. Hop on the free Anantara guest shuttle to Purobeach Vilamoura, or drive yourself west to Falésia Beach (or farther west to Marinha, pictured above) or east to Praia do Ancão Beach within the Ria Formosa Natural Park.
  • Stroll the Vilamoura Marina, then drink cocktails and dine on the patio at Salmora.
  • Book a boat tour to the Benagil Caves. Most operators anchor off-shore before heading back so you can jump in for a refreshing swim.
  • Plan a sunset dinner at Restaurante Rocha Baixinha, the beachside restaurant is a magical spot for feasting on fresh seafood while the sky goes from blue to ablaze.


Portugal Itinerary - Anantara Vilamoura Algarve Resort

The beauty of Anantara Vilamoura Algarve is there’s so much on the resort grounds that you only have to venture out when you absolutely want to. Here you’ve got pools, restaurants, shops, two adjacent golf courses, a spa and concierges to plan everything else you’d like to do.  You can even park your car rental for a while—a complimentary shuttle regularly whisks guests to  Vilamoura Marina for more shopping, dining and nightlife choices.

The straightest line between Vilamoura and Comporta is a two-hour drive along the A2. But if you really love beaches and don’t mind spending some more time in the car, take the longer, westernmost route—it’s the best way to get a greater sense of Portugal’s coastal bounty before digging your toes into Comporta’s sand and sea delights.


  • On the way, stop and check the surf conditions in Sagres. If you aren’t brave enough to hit the waves, opt to just walk across the wide, windy dunes of Bordeira.
  • Swim, soak up the rays and enjoy a long lunch at the Sublime Comporta Beach Club.
  • For a little retail therapy, check out Rice – Marta Mantero, Lavanda and Mercearia Gomes in Comporta town, or drive down to the up-and-coming village of Melides.
  • Go horseback riding at the nearby Cavalos na Areia. A 90-minute ride takes you along the beach for the ultimate movie-like moment.
  • Plan to a night to dine at Cavalariça. The renowned restaurant also has Lisbon and Évora locations, but this one is within a former horse stable.

Portugal Itinerary - Sublime Comporta

The name says it all—Sublime Comporta is sublime. The tucked-away property strikes a perfect balance between rustic and refined. Whether you stay in a unique Bio Pool Suite where aquatic plants naturally keep the water clean or a Villa Room with a traditional-style private pool, there’s no going wrong. For an extra special dining experience, book a dinner in the Food Circle where the chef prepares dinner right in front of you within a surrounding herb and vegetable garden.

It takes a little over an hour to return to Lisbon via Comporta. Drop off your car, check into a hotel for a night, and fill one last full day with a few more Portuguese sights and bites.


  • Now, let a local do the driving—a Hello Portugal guided tour will whisk you along the winding roads in a convertible MINI to see Pena Palace, Azenhas do Mar, Cabo da Roca and Cascais.
  • For your last supper, make it the Michelin-starred Belcanto. That is, if you reserved well in advance.
  • Before departing, tuck in a little last-minute luxury shopping at the shops along Avenida de Liberdade near the InterContinental.


Portugal Itinerary - InterContinental Lisbon

Towering above Eduardo VII Park in the heart of the city, InterContinental Lisbon makes a grand, final rest stop. Book a view room to really relish your last looks at the spectacular city that surrounds you. Before the 15-minute drive to the airport, swing into Akla, right next to the lobby, for one more bite of Portuguese cuisine.


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