Two Weeks in Portugal

Plotting an escape to Portugal? From north to south, starting in Porto and ending in the Algarve, we’ve charted a course that makes the most of the country’s abundant charms. Take these tips and plan a trip for early fall or late spring—pleasanter temps and fewer crowds pair well with Port wine.


Days 1-5: Porto and Douro Valley

Bring your appetite, the north is lauded as the country’s most food-forward region—not to mention the place for Port wine. Where river meets ocean, Porto is Portugal’s Venice, brimming with vibrant photo ops. From there, head inland and explore the Douro Valley.


  • Stroll Cais da Ribeira, Porto’s riverside promenade, for some of the best views of the iconic Dom Luis I Bridge
  • Ride down the Douro River aboard a traditional wooden ravelo boat
  • Peruse the shelves at Livraria Lello, one of the most beautiful bookstores in the world, which is said to have inspired elements of Harry Potter
  • Visit family-owned Port wine producer Quinta de Marrocos and request a tour with the owner, Cesar


Six Sense Douro Valley Dinner View

In Porto, check-in at The Yeatman for two nights and revel in their decanter-shaped pool and 25,000-bottle wine cellar. On the third day, make your way inland. Overlooking both vineyards and the Douro River, the Six Senses Douro Valley (pictured above) has a stunning 10-room spa and offers easy access to the region’s wineries.

Days 6-10: Cascais, Sintra and Lisbon

Only 20 minutes away from each other, Lisbon, Cascais and Sintra are must-see. Cascais makes an excellent home base—the seaside town is heavy on history and just minutes from Lisbon. From here, the day trips are nearly endless, as it’s only a 2.5 hour drive to the Algarve and around 3 hours to Porto.


  • Trek out to Boca do Inferno (Hell’s Mouth) in Cascais where the Atlantic’s unceasing waves have carved out a dramatic rock arch
  • Day trip from Cascais to Sintra to see Pena Palace, a vibrant 19th-century Romanticist structure encircled by verdant forest
  • Experience traditional folk music unique to Lisbon at a Fado House in Alfama or Bairro Alto
  • Devour a signature pastry at the legendary Pastéis de Belém—they’ve been making sweets since 1837


Farol Farol Design Hotel Guest Room with Water View

Soak up the Cascais seaside with three nights at the Farol Design Hotel (pictured). Portuguese fashion designers decorated 10 of the stylish property’s 33 rooms. Then head to Lisbon for two nights in the heart of the city at Tivoli Avenida Liberdade Lisboa, or on the waterfront with views of the Targus River at Altis Belém Hotel & Spa.

Days 11-14: Algarve

The Algarve is beloved by tourists, thanks to its holiday trifecta of beaches, golf courses and relaxing vibe. Stay in Lagos or Villamoura, and if possible, rent a car and explore the beach towns west to east— point to point, it’s only a 1.5 hour drive.


  • Hit the picturesque beaches of Ponta da Piedade where rugged rock pillars meet turquoise waters
  • Scope out the waves in Sagres—the western tip serves up some of the best surf conditions
  • Tee off at a golf course in Quinta do Lago
  • Spend an afternoon weaving through Old Town Lagos


Vila Joya Pool and Beach

Anantara Vilamoura Algarve is just minutes away from the trendy Vilamoura Marina, which offers a vast array of shopping, dining and nightlife choices. In Lagos, Vila Joya (pictured) offers a more traditional vibe with its Moorish architecture and Azulejos tiles.