8:30 AM — Departure from Beirut Your private English-speaking driver collects you from your Beirut hotel and heads east on the Damascus highway, climbing through the Lebanese mountains before the Bekaa Valley opens dramatically below — a vast fertile plain stretching between the Lebanon and Anti-Lebanon mountain ranges, one of the most historically significant valleys in the entire Middle East.

Arrive at one of the most underrated and most historically significant archaeological sites in Lebanon — the Umayyad city of Anjar, the only surviving example of an Umayyad palatial city in the entire Levant. Built in the early 8th century by Caliph Walid I — the same ruler who commissioned the Umayyad Mosque in Damascus and the Al-Aqsa Mosque in Jerusalem — Anjar was occupied for only a few decades before being abandoned following a political upheaval, leaving its streets, buildings, and monuments remarkably intact. Walking through Anjar today is like walking through a snapshot of 8th-century Islamic urban planning — colonnaded streets dividing the city into four quarters, a grand palace with over 40 towers, a mosque, bathhouses, and hundreds of decorated arches still standing. Your driver brings the extraordinary and little-known story of this UNESCO city to life.

Before the temples, stop at the ancient Roman quarry to see the Stone of the Pregnant Woman — a single limestone block measuring 21 metres long and weighing an estimated 1,000 tonnes, still lying exactly where it was cut 2,000 years ago. One of the heaviest objects ever worked by human hands in the ancient world — and the perfect prologue to the temple complex ahead.

Enter the greatest Roman temple complex on earth. The Temple of Jupiter was built on Trilithon stones each weighing over 800 tonnes — the largest dressed stones in human history. The Temple of Bacchus, larger than the Parthenon and almost entirely intact, is the best-preserved Roman temple in the world. The elegant circular Temple of Venus completes a complex that has stood for two thousand years at the crossroads of civilisations — Phoenician, Greek, Roman, Byzantine, Arab. Your driver brings the full extraordinary story to life.

End the day at Chateau Ksara — Lebanon's oldest winery, founded by Jesuit monks in 1857 and now the country's largest wine producer. The highlight is the Roman cave cellar system stretching 2 kilometres beneath the winery — ancient tunnels where wine ages at a naturally constant temperature year-round. After a morning walking through Umayyad and Roman ruins above ground, descending into Roman caves beneath a winery creates a remarkable final chapter to a day defined by ancient civilisations. The tasting showcases Ksara's iconic Cabernet-Syrah blends, crisp Blanc de Blancs, and beloved Sunset Rosé.

Return to Beirut — approx. 5:00–6:00 PM Scenic drive back through the Bekaa Valley and over the Lebanese mountains with drop-off at your Beirut hotel — completing a full day through three of the Bekaa's greatest civilisations: Umayyad, Roman, and the ancient art of Lebanese winemaking.