Getting Between Stops
Lisbon to Porto is easiest by train. The Alfa Pendular reaches Porto Campanhã in about three hours, with regular departures. Book seats in advance in summer, though fares are reasonable even close to the date.
For the Douro, the train is the romantic way in. Regional trains from São Bento follow the river for the last hour to Régua and Pinhão. Once in the valley, quintas sit on steep, narrow roads and taxis are scarce, so either rent a car in Porto or arrange a private driver through your hotel for tasting days. Portugal's blood alcohol limit is lower than in most US states.
For the flight home, Porto Airport is about 1.5 to 2 hours from the Douro. It has a nonstop from Newark and seasonal service from Boston. Lisbon has many more US flights and is about three hours from Porto by train, so allow a night in Lisbon if your flight leaves from there.
Where to Stay
In Lisbon, your neighborhood shapes the trip. Alfama is the oldest quarter, with fado at night. Memmo Alfama has a small pool terrace over the rooftops. Chiado and Príncipe Real are more polished, with the best restaurant density. The Bairro Alto Hotel sits on the square at the edge of Chiado. Avoid the Bairro Alto nightlife streets unless you enjoy noise until 2 a.m.
In Porto, Pestana Vintage Porto sits on the Ribeira quay. The Yeatman in Gaia is a wine hotel with a serious cellar and every room facing the river. The Infante Sagres in the Baixa is a long-standing classic.
In the Douro, sleep at a wine estate. Six Senses Douro Valley has a large spa. The Vintage House sits on the riverbank in Pinhão. Quinta do Vallado near Régua and Quinta da Pacheca, with suites built into giant wine barrels, let you eat at the estate.
When to Go
May, June and September to early October are the best months for this route. Days are warm, evenings are pleasant for outdoor dinners and the Douro's pools are open. Late September is the Douro harvest, when estates fill with pickers and some invite guests to tread grapes in stone lagars in the evening. Book harvest dates months ahead.
July and August are hot in the Douro Valley, which sits inland in a deep river canyon. Lisbon is busy too. They still work if you plan for pool afternoons and early morning walks.
Winter is cheaper and quiet, but Porto is rainy and many Douro estates scale back their services. Porto around June 23 hosts the Festa de São João, an all-night street party with sardines and fireworks over the river, which is great fun but means higher hotel prices that week.
What It Costs
Portugal remains one of the better-value honeymoon countries in Western Europe. As an approximate guide, good boutique hotels in Lisbon and Porto run about $250 to $450 a night for two, with the Bairro Alto Hotel and The Yeatman starting roughly in the $400s. In the Douro, simple quintas cost less, while Six Senses Douro Valley starts around $700 a night.
Trains between the cities are inexpensive. Port lodge tours and tastings are modestly priced, with private tastings of old tawnies costing more.
Spend on the Douro. A river-view room, a private driver for one tasting day and a sunset boat trip from Pinhão add the most to the trip. Lisbon and Porto are cities where cheap seafood lunches and miradouro wine kiosks are some of the best meals you will have.
Tips for the Two of You
Both cities are steep. Pack comfortable shoes with grip for each of you and use cheap ride-hail cars for the climbs at night. The historic trams and funiculars are fun once but slow. Pickpockets work the crowded ones, especially Lisbon's tram 28.
Lisbon and Porto are relaxed about dress. Churches expect covered shoulders for both of you, so carry a light layer. The Douro is casual, though smarter estate restaurants appreciate a step up at dinner.
The route works for different tastes. One partner might spend a morning at a museum such as the Gulbenkian in Lisbon while the other surfs or swims near Cascais. In the Douro, one of you can join a vineyard walk while the other books a spa treatment. Reserve fado in Alfama and the best Douro estates ahead in high season.
Make It Shorter or Longer
With a week, spend two nights in Lisbon, two in Porto and three in the Douro, or skip Lisbon and fly straight into Porto on the Newark nonstop.
With two weeks, add a beach. The Algarve is about 2.5 to 3 hours south of Lisbon by car. Four nights on its cliffs and coves make a relaxing finale. Or fly from Porto or Lisbon to Madeira, under two hours, for levada walks and lava pools.
Couples who love palaces can add two nights in Sintra before Lisbon, sleeping among the gardens to see Pena Palace at opening time. Those who want more countryside could add two nights in the Alentejo, about 1.5 hours east of Lisbon, for wine estates, cork oaks and some of the darkest night skies in Europe.