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Thessaloniki - Plovdiv - Sofia: Chauffeured Collection

7 to 10+ Nights from $1,845*
* Sample price: priced within the past 7 days for a 2/1/2026 arrival, departing Washington WAS (All Airports)(DC), US. Choose departure city, cabin and dates.

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This 7 night sample itinerary includes:

  • Flight into and out of Thessaloniki
  • Hotel for 2 nights in Thessaloniki
  • Transfer from Hotel in Thessaloniki to Hotel in Plovdiv via Ancient City of Philippi
  • Hotel for 2 nights in Plovdiv
  • Transfer from Hotel in Plovdiv to Hotel in Sofia
  • Hotel for 2 nights in Sofia
  • Transfer from Hotel in Sofia to Hotel in Thessaloniki via Rila Monastery
  • Hotel for 1 night in Thessaloniki

This route is an essential exploration of Bulgaria's Culture Ring plus Greece. Journey in comfort from Thessaloniki (important Bizantine port since antiquity; major centre of culture and trade), to the core of Bulgaria and back. This exclusive Return Arc includes two UNESCO anchors: the Roman and Apostolic site of the Ancient City of Philippi, and the magnificent, frescoed Rila Monastery. Spend time in the historic bulgarian cities of Plovdiv (one of Europe's oldest cities, showcasing layers of Thracian, Roman, and Ottoman history) and Sofia (capital city, roman ruins meet modern life and stunning religious architecture) with all logistics handled by your private chauffeur until your final arrival back in Thessaloniki.

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Flexible Itinerary

  • Thessaloniki

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  • Plovdiv

    about
  • Sofia

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  • Thessaloniki

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Greece
Bulgaria

Customer Reviews

Trip Summary

  • Thessaloniki
    Thessaloniki

    Thessaloniki (also known as Salonica) offers the cosmopolitan culture and energy of a big city with the friendly ambience and charm of a smaller town. It's a wonderful destination to experience the real Greece without the crowds and congestion of Athens. This beautiful city has an impressive multi ethnic heritage, influenced by the diverse civilizations that have left their mark, including the Romans, Venetians, and Ottoman Turks. Visitors are awed by the ancient ruins, Byzantine churches, and the world-class archaeology museum, one of the best in Greece.

    Visit and discover the Ano Poli (The Upper town or Old Town), Ladadika District, Archaeological Museum, Museum of Byzantine Culture, Roman Rotunda (Saint George's Church), the markets, the White Tower: Relic of the Byzantine-Era Ramparts, Church of Saint Demetrius, Arch of Galerius, and so much more.

  • Plovdiv
    Plovdiv

    Plovdiv is one of the oldest cities in Bulgaria. Founded on seven hills around 4000 BCE, Plovdiv was originally a Thracian settlement. No fewer than twelve different ethnic groups conquered Plovdiv over the centuries, and the various groups' influences can be seen in such areas as the Old Town, with its Bulgarian Renaissance architecture; and the Roman City, centered on the Ancient Theatre of Philippopolis, which is still in use today. The city's beautiful history and culture are on display everywhere you turn, and once you're there, you will see why the European Union named Plovdiv a European Capital of Culture for 2019.

    Discover and explore the Ancient Theatre of Philippopolis, Plovdiv Roman Stadium, Plovdiv Old Town, Plovdiv Regional Ethnographic Museum, Nebet Tepe, Alyosha Monument, Dzhumaya Mosque, Singing Fountains, Balabanov's House, Garden of Tsar Simeon, Hills of Plovdiv, and so much more.

  • Sofia
    Sofia

    One of the oldest capital cities in Europe, Sofia dates back to the 8th century BCE. Its landmarks reflect more than 2,000 years of history, including Greek, Roman, Ottoman and Soviet occupations. Sofia houses numerous museums, notably the National Historical Museum which has a vast collection of more than 650,000 historical items. Sofia is one of the hippest cities in Bulgaria, boasting a lively nightlife scene with many different nightclubs, live venues, pubs, mehani (Bulgarian traditional taverns), and restaurants. The city also offers large green spaces and manicured gardens, and the ski slopes and hiking trails of mighty Mount Vitosha are just a short bus ride away.

    Visit and discover the Alexander Nevsky Cathedral, Boyana Church, National Historical Museum, Banya Bashi Mosque, Church of St. George, Vitosha Boulevard, Mount Vitosha, National Palace of Culture, St. Sophia Church, St. Nedelya Church, National Art Gallery, Central Sofia Market Hall, Cherni Vrah, Sofia Synagogue, Church of St. Petka of the Saddlers, Museum of Socialist Art, and so much more.

  • Thessaloniki
    Thessaloniki

    Thessaloniki (also known as Salonica) offers the cosmopolitan culture and energy of a big city with the friendly ambience and charm of a smaller town. It's a wonderful destination to experience the real Greece without the crowds and congestion of Athens. This beautiful city has an impressive multi ethnic heritage, influenced by the diverse civilizations that have left their mark, including the Romans, Venetians, and Ottoman Turks. Visitors are awed by the ancient ruins, Byzantine churches, and the world-class archaeology museum, one of the best in Greece.

    Visit and discover the Ano Poli (The Upper town or Old Town), Ladadika District, Archaeological Museum, Museum of Byzantine Culture, Roman Rotunda (Saint George's Church), the markets, the White Tower: Relic of the Byzantine-Era Ramparts, Church of Saint Demetrius, Arch of Galerius, and so much more.

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