South of Sines, the coastal roads narrow, and neither local maps nor GPS systems seemed to include all of the possible routes, so my solution was simply to keep the ocean on my right. Halfway down the coast, I stopped in Vila Nova de Milfontes, a beachfront town with a jumble of streets that surround a tiny harbor. Milfontes has only about 4,000 residents, but it gets busy in the summer with city folk who prefer its low-key simplicity. The seascapes from the 16th-century Castelo de Milfontes are spectacular; the fact that there are just seven rooms means guests have to book way in advance.

About 20 miles further south is Zambujeira do Mar, a fishing village on the southern edge of the Alentejo. By law, hotels within this part of the preserve can only be housed in existing single-story farms. When I arrived at the Herdade do Touril de Baixo, I was greeted by the smell of freshly baked orange cake. The 11-room hotel and cattle ranch has a saltwater pool and a few suites scattered in white-and-blue outbuildings. The Falcao family has been farming this rugged land for generations; tin and wooden animal statues--sheep, chickens, pigs, cows--peek out from every corner of the hotel.

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After a dip in the pool, I ordered a glass of wine at the outdoor bar and started chatting with a couple from Los Angeles, John Knight and Michelle Saylor. As we watched the sunset and compared restaurant recommendations, we were unable to name another destination with the Alentejo's rich history, unspoiled nature, and easygoing charm. Every resort town that any of us suggested was quickly qualified with "30 years ago" and "before the crowds discovered it." Then John paused and said, "I've seen a lot of places, but the Alentejo is one where I find myself saying, 'I might stay here.'"

Taking their advice, I made a dinner reservation at Café Central, a restaurant 15 minutes away in Brejão. "It's all about the rice," Michelle said, warning me that their lunch for two had been more like dinner for six. After polishing off a cheese plate and an octopus salad, I also managed to finish a stockpot of herb-infused rice and giant prawns.

I walked off some of my supper with a leisurely stroll along the cove in Zambujeira do Mar, past outdoor cafés packed with people lingering over coffee and liqueur. As the church bells chimed 1 a.m., I paused before walking into the Speram'entrando bar (the name translates as "Come in and wait for me"), which had yet to fill up. Like the best of the Alentejo, its moment was about to arrive.

Lodging

• Pousada D. João IV Convento das Chagas, Vila Viçosa, 011-351/268-980-742, pousadas.pt, from $220
• Castelo de Milfontes Vila Nova de Milfontes, 011-351/283-998-231, from $200
• Herdade do Touril de Baixo Zambujeira do Mar, 011-351/283-950-080, touril.pt, from $102

Food

• Tasquinha d'Oliveira Rua Cândida dos Reis 45-A, Évora, 011-351/266-744-841, petiscos from $7
• Trinca Espinhas Sines, 011-351/269-636-379, entrées from $24
• Café Central Brejão, 011-351/282-947-419, rice dish from $34

Activities

• Herdade do Esporão Apartado 31, Reguengos de Monsaraz, 011-351/266-509-280, esporao.com, tour and tasting $5
• Alentejotrails Mourão, 011-351/963-446-904, alentejotrails.com, tours from $10

Shopping

• Sempre Noiva Rua Alexandre Herculano 33, Arraiolos, 011-351/266-490-040
• Mizette Rua dos Celeiros, Monsaraz, 011-351/266-557-159, blankets from $60

Nightlife

• Speram'entrando Rua das Flores 9, Zambujeira do Mar

Across the Alentejo
Most towns in the Alentejo are less than three hours from Lisbon by car. Take A12 south over the Vasco da Gama Bridge and follow the signs to A2 if you're heading south to Sines, or A6 to Évora. Regional maps are available in the tourism offices of virtually every town in the Alentejo. In February, a compact car with manual transmission costs less than $300 per week with basic insurance; an automatic is $575 per week (888/223-5555, autoeurope.com).