Seven Days in Portugal: A Long-Read Itinerary
LISBON • SINTRA • ÉVORA • PORTO • DOURO VALLEY • OCTOBER 2025
7-day route
A scenic road trip from Lisbon up to Porto, including Sintra's castles and Douro Valley vineyards.
Lisbon — city of seven hills
"Arrive in Lisbon, drop your bags, and ride the classic Tram 28 up to the high historic district of Alfama for golden hour views."
Check into a boutique riad-style guest house in Alfama
Ride the legendary Tram 28 through narrow historic streets
Watch the sunset from Miradouro da Senhora do Monte
Memmo Alfama Hotel
A pristine white boutique hotel set directly inside Alfama, with a gorgeous red-tiled rooftop pool overlooking the Tagus.
Taberna do Sal Grosso
Stunning small-plate traditional taverna serving delicious petiscos and local red wines.
Lisbon -> Sintra
"Take a quick morning train to Sintra, a fairy-tale mountain kingdom of romantic castles, pristine forests, and misty gardens."
Board a direct train from Rossio station to Sintra
Tour the surreal Pena Palace with its bright yellow walls
Wander the mysterious initiation wells of Quinta da Regaleira
Tivoli Palácio de Seteais
An 18th-century palace hotel with ornate frescoes, lush formal gardens, and majestic valley views.
Cafe Saudade
A historic tearoom serving freshly baked scones, local travesseiro pastries, and herbal infusions.
Sintra -> Porto
"Board a northbound train to Porto. Spend the afternoon walking across the iconic Dom Luís I Bridge and exploring Ribeira."
Take a scenic train north to Campanhã station
Walk the high deck of Dom Luís I Bridge over the Douro river
Explore the colorful riverfront medieval houses of Ribeira
The Yeatman Hotel
A luxury wine hotel in Vila Nova de Gaia with a decanter-shaped pool overlooking the Porto historic core.
Cantinho do Avillez
Creative modern twists on classic Portuguese cooking in a bright and lively bistro setting.
Porto -> Douro Valley
"Take a historic steam train or drive up the winding Douro River valley, the oldest demarcated wine region in the world, for terrace vineyard tastings."
Take the highly scenic train from São Bento to Pinhão
Tour a traditional terraced vineyard estate (Quinta)
Enjoy a sunset boat cruise on a traditional rabelo boat
Six Senses Douro Valley
A beautifully restored 19th-century manor house set on a hill overlooking the Douro River, featuring a world-class wellness spa.
DOC Restaurant by Rui Paula
Exceptional modern fine dining floating right on the Douro river waters, featuring masterfully prepared regional delicacies.
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