Alentejo is Portugal’s vast golden heartland—where cork oaks shade rolling plains and whitewashed villages glow under epic skies. The Romans called Évora “Liberalitas Julia,” leaving temples and tesserae; medieval kings crowned it with convents, cloisters, and the famed Chapel of Bones. Out west, dunes and rice paddies give way to the Atlantic, where Comporta trades city buzz for barefoot elegance.

Expect a delicious pace: slow lunches of black pork and migas, talha wines born in clay amphorae, and sunsets that stretch forever. History runs deep—older than Rome—at stone circles like Almendres, among Europe’s most impressive megalithic sites. The coast adds contrast: empty beaches, sleek storks on pier posts, and dolphins riding bow waves near the Arrábida cliffs.

Practical notes: summers are hot inland; plan early starts and siestas. Renting a car offers the most freedom, though buses and ferries connect key spots. Book popular restaurants and experiences ahead, especially on weekends and in July–September.

Évora

Évora, a UNESCO World Heritage city, is a compact “open-air museum.” You’ll wander from the Roman Temple and cathedral (Sé) to cobbled lanes shaded by the Água de Prata aqueduct’s arches. The Chapel of Bones, lined with skulls and femurs, is macabre and unforgettable—built by monks to remind citizens of life’s brevity.

Top sights include the Roman Temple, the cathedral roof walk, the University’s azulejo-clad halls, and the public market for cheeses and acorn-fed pork. Food is a highlight: think bread-thickened stews, coriander-scented soups, and Alentejo DOC wines.

• Where to stay (Évora): Browse stays on Hotels.com or character homes via VRBO. Look near the historic center for easy walking.
• Getting there: Fly into Lisbon, then take a direct train or bus to Évora. Compare options on Omio (flights), Omio (trains), or Omio (buses). Trains from Lisbon Oriente take ~1h30–1h45 (from ~€10–€18); buses are ~1h45 (from ~€8–€16).

Comporta

On Alentejo’s Atlantic edge, Comporta is a chic barefoot hideout of rice fields, pine forest, and endless sand. Days drift by between Praia do Carvalhal and Pego, with stylish beach shacks, surf lessons, and dreamy golden-hour walks on near-empty strands.

Beyond the beach, wander the stilted fishermen’s pier at Carrasqueira, watch storks nesting on chimneys, and snack on seafood rice. Evenings swing from rustic petiscos to refined farm-to-table dining under the stars.

• Where to stay (Comporta): Check boutique hotels on Hotels.com or private villas on VRBO. For a design-forward splurge, book Sublime Comporta. Budget-friendly near the dunes: Alojamento Local Verde e Mar. Heading farther south on the Alentejo Coast? Consider Zmar Eco Experience.
• Getting there from Évora: Driving is fastest at ~1h45 via Alcácer do Sal. Without a car, plan ~2.5–3.5 hours using bus connections—compare on Omio (buses).

Day 1: Arrival in Lisbon → Évora’s Roman bones and golden hour

Afternoon: Arrive in Lisbon and continue to Évora by train or bus (1h30–1h45). Check in, then take a gentle orientation walk: Roman Temple, Largo da Porta de Moura, and the aqueduct’s arcades hiding tiny houses beneath. Coffee and convent sweets at Pastelaria Conventual Pão de Rala—try sericaia with Elvas plums.

Evening: Dinner at Café Alentejo for classic migas with black pork or cod açorda. For a deeper dive into regional flavors, book Taberna Típica Quarta-Feira (set-menu, convivial, very local—reserve). Nightcap at Enoteca Cartuxa for a taste of the region’s wines.

Day 2: UNESCO Évora, Chapel of Bones, and megalithic Alentejo

Morning: Join a guided city stroll to decode Évora’s layers and skip lines at key spots like the Chapel of Bones.

Évora Walking Tour: Small Group Tour with Chapel of Bones Tickets

Refuel at Pastelaria Violeta near Praça do Giraldo, then lunch at Dom Joaquim (creamy prawn açorda, partridge pie) or Fialho for refined Alentejo staples.

Afternoon: Head out with an archaeologist to the Almendres Cromlech and Menhir—one of Europe’s largest stone circles, older than Stonehenge. Learn about Neolithic astronomy amid cork and holm oaks.

Half Day Megaliths Cromlech Tour from Evora by Archaeologists

Evening: Reserve Degust’AR for contemporary takes on Alentejo produce in a vaulted palace setting. If you want a tiny, locals-favorite counter with petiscos and conversation, try Botequim da Mouraria (arrive early—only a handful of stools).

Day 3: Morning transfer to Comporta, dunes, and rice fields

Morning: Depart Évora for Comporta (drive ~1h45; bus connections ~2.5–3.5h via Setúbal—check Omio (buses)). Optional stop in Alcácer do Sal for castle views over the Sado River. Check in, then lunch at Dona Bia on the EN261 (razor-clam rice or fried cuttlefish).

Afternoon: Beach time at Praia do Carvalhal or Pego—wide, clean, perfect for a first dip. Stroll the Cais Palafítico da Carrasqueira, a photogenic stilted pier where storks nest on electric poles and fishermen mend nets among the marshes.

Evening: Sunset on Pego’s dunes, then dinner at SAL (grilled dourada or seafood rice) or Cavalariça in the village (creative plates inside an old stable, farm-to-table vibe). Nightcap with a glass of Arinto at Gomes – Casa de Vinhos & Petiscos.

Day 4: Dolphins and cliffs of Arrábida, seafood in Sesimbra

Morning: Drive ~1h20–1h40 to Sesimbra (or via Troia–Setúbal ferry and coastal road) for a wildlife-rich cruise along the Arrábida coastline. Bottlenose dolphins are frequently seen off the headlands; the scenery is stunning even without cetaceans.

Sesimbra: Arrábida Dolphin and Whale Watching tour with biologist

Afternoon: Lunch on Sesimbra’s waterfront—Casa Mateus for grilled sardines, or O Velho e o Mar for arroz de marisco. If time allows, swing by Setúbal’s Mercado do Livramento to eye today’s catch and local cheeses before returning to Comporta.

Evening: Dinner at Sem Porta (Sublime Comporta’s signature restaurant) where garden produce and regional fish anchor the menu. For something simple, hit Sublime Comporta Beach Club for a barefoot meal with the surf as soundtrack.

Day 5: Bikes, horses, and a lazy last swim

Morning: Grab a coffee and light breakfast bowl at Be Comporta, then pedal quiet lanes through rice fields. Prefer hooves to wheels? Book a beach ride with Cavalos na Areia—an iconic Comporta experience—best in the cool morning light.

Afternoon: Final hours on the sand at Carvalhal, or a long lunch at Gomes – Casa de Vinhos & Petiscos (pica-pau, octopus salad, local cheeses) paired with a crisp white from the Sado peninsula. Pick up woven baskets and linens from the village boutiques for thoughtful souvenirs.

Evening: Early dinner before your departure window: choose SAL for one last grilled fish or return to Cavalariça for a celebratory tasting of small plates. If you’re ferrying to Setúbal afterward, check schedules on Omio (ferries); for onward buses or trains, see Omio (buses) and Omio (trains).

Logistics at a glance

• Best time: May–June and September–October for warm seas and milder inland temps.
• Car vs. public transport: Car hire offers flexibility for beaches and rural megaliths; expect ~€30–€60/day. Buses/trains cover main routes; build in extra time for connections.
• Dining tips: Book dinners in peak season; many beach restaurants serve lunch late (2–4 pm). Try sericaia for dessert and talha wines for a uniquely Alentejo taste.

In five days, you’ll taste Alentejo’s full spectrum: Évora’s stone-on-stone history, prehistoric circles hidden in cork forests, and the ocean’s hush along Comporta’s sands. It’s a trip stitched together by simple pleasures—good bread, good wine, and big skies you’ll dream about long after you’ve gone.