Getting Between Stops
Do not rent a car until you leave Lisbon. Parking in the city is scarce and the old streets are narrow. Pick one up on the morning of day four, either at the airport or a city rental office.
Évora is about 1.5 hours east of Lisbon by highway, with Monsaraz roughly another hour beyond. From the Alentejo estates to the central Algarve is about two and a half to three hours on quiet roads. Watch for electronic tolls on Portuguese highways and get a rental with a transponder, especially for the A22 along the Algarve coast.
On the Algarve, a car is close to essential, since the best beaches, villages and viewpoints are spread out and buses are infrequent. In July and August, beach parking fills by mid-morning, so arrive early or choose a hotel within walking distance of a good beach.
Where to Stay
In Lisbon, the Bairro Alto Hotel sits on the square at the edge of Chiado with a rooftop terrace. Memmo Alfama has a small pool terrace over the rooftops, while Torel Palace occupies a pair of mansions with a pool and garden view.
In the Alentejo, São Lourenço do Barrocal is a restored farming estate near Monsaraz with a vineyard and a large pool among the oaks. L'And Vineyards and Torre de Palma Wine Hotel are other strong estate choices. Herdade da Malhadinha Nova in the south is a family wine estate with a well-regarded restaurant.
On the Algarve, the central coast between Portimão and Albufeira suits most honeymooners. Bela Vista Hotel & Spa in Portimão and Vila Vita Parc near Porches are the polished options. For quiet and space, look east to Tavira's old town and the Ria Formosa, or west toward Sagres, where the landscape is wilder.
When to Go
June and September are the sweet spots. The Algarve water is warm, the days are long and the beaches are busy but not packed. September often has the warmest sea temperatures of the year. Late May works well if you are happier walking than swimming.
The Alentejo is very hot in July and August, with afternoons that call for a pool and a siesta. Spring brings green fields and wildflowers, while autumn brings the grape harvest and November is when many cellars open the new amphora wines.
July and August are peak season on the Algarve, with European families, higher prices and crowded beaches. The route still works then if you book early and plan beach time for morning and late afternoon. Winter is mild but the sea is cold, so this itinerary is best from late spring to early fall.
What It Costs
As an approximate guide, good boutique hotels in Lisbon run about $250 to $450 a night for two, with the Bairro Alto Hotel starting in the $400s. Alentejo wine estates such as São Lourenço do Barrocal start around $400 a night. On the Algarve, Bela Vista Hotel & Spa starts around $350 a night, rising sharply in July and August, while village guesthouses cost much less.
Add a rental car for about eight days, fuel and electronic tolls. Food is good value throughout, especially seafood lunches on the coast and estate dinners in the Alentejo.
Spend on the experiences that make this route special: the Tagus sunset sail, a stargazing session in the Alqueva reserve and a boat trip along the Algarve cliffs. These cost far less than an extra night at a resort and are what most couples remember.
Tips for the Two of You
The Algarve's south-facing coast is calm in summer, but the western beaches near Sagres face the open Atlantic. Swim only where there are lifeguards and flags. On the clifftop trails, stay well back from the edges, which can crumble.
Pack sun protection, hats and water shoes for rocky coves. Lisbon is steep, so bring comfortable shoes with grip for both of you.
Agree on driving before the trip. Portugal's blood alcohol limit is lower than in most US states. Alentejo estates make it tempting to linger over wine at lunch. Most hotels can arrange a driver for a tasting day.
This route gives each of you space. One partner can play golf or surf on the Algarve while the other takes a spa treatment or a boat trip, then meet for a sunset drink. In the Alentejo, bikes and horses are often available at the estates.
Make It Shorter or Longer
With nine days, keep Lisbon at three nights, cut the Alentejo to two and spend four on the Algarve. With a week, skip the Alentejo and drive straight from Lisbon to the Algarve in about 2.5 to 3 hours.
With two weeks, add Comporta, the Alentejo's barefoot-glamorous coast, for two nights of dunes, pine forest and rice fields between the inland estate and the Algarve. Or start with two nights in Sintra, sleeping among the palaces before Lisbon.
Another option is to fly from Lisbon or Faro to Madeira for three or four nights of levada walks and lava pools before heading home. Couples who love wine could also add two nights in the Douro Valley, about three hours north of Lisbon by train to Porto and then a scenic regional line upriver.