This morning, we’ll go to the Bet Yaakov Synagogue and explore the rejuvenated Skopje downtown area where Ottoman past and modern times blend harmoniously. Skopje boasts the Kale Fortress, the renowned Old Bazaar and Stone Bridge, the Double Hamam, the Clock Tower and more. We will visit the new Holocaust Memorial Center, which opened its doors in 2011, and learn about the tragic fate of North Macedonia’s Jews. From Skopje we depart for Ohrid, Macedonia’s most scenic gem – a UNESCO World Heritage site. Unique Resort and Spa Hotel. [100 miles]

• Breakfast
• Unique Resort and Spa Hotel
• 100 miles

Located on the spectacular lake Ohrid, the eponymous town is one of Europe’s oldest settlements and an important cultural, religious, and educational Slavonic center. Its archeological riches, Byzantine churches, monasteries, and medieval structures are organically situated amid exceptional natural beauty. Your city tour starts with a leisurely boat ride along the lake for a panoramic view of the city. Ohrid’s landmarks include the Saint Sofia Church, the St. Jovan Kaneo medieval basilica, the 3rd century BCE ancient theater, Samuil’s Fortress, and the historic pedestrian street. Ohrid is also world-famous for its unique jewelry, made of the scales of the plashitsa fish. Free time in the afternoon to enjoy this city-on-a-lake and discover some of its breathtaking photographic opportunities. Unique Resort and Spa Hotel.

• Breakfast
• Unique Resort and Spa Hotel.

Today we head for Bitola (Monastir), site of Macedonia’s oldest Jewish cemetery, dating back to 1497. We’ll walk through the historic Jewish quarter and stroll down the city’s lively promenade. After lunch in town, we continue our journey into Greece and visit Vergina (Aigai) – one of the country’s most spectacular archaeological sites! We’ll explore the Royal Tombs of the ancient Macedonian kings, including the tomb of Philip II. From Vergina we continue on to beautiful Thessaloniki (Salonika). Greece’s second largest city and port has a long and rich history. Of specific interest to us is the arrival of some 20, 000 Jews from Spain at the end of the 15th century, inaugurating a period of vibrant religious and cultural Sephardic activity. Hotel MonAsty, Autograph Collection by Marriott 5*. [180 miles]

• Breakfast
• Hotel MonAsty, Autograph Collection by Marriott 5*
• 180 miles

We have a busy day to explore – by bus and on foot – much of what Jewish Thessaloniki has to offer. Salonika’s thriving Sephardic culture, at its creative peak in the 16th century, earned the city the monikers “Madre de Israel” (“Mother in Israel”) and “Jerusalem of the Balkans.” By the early 1920s, the majority of the population was Jewish, and roughly 50,000 Jews lived here when the Germans arrived in 1941. We’ll visit Salonika’s two synagogues – Monastirioton (1920s) and Yad Lazikaron (1984) – the Jewish community center, and the Jewish museum, located in a historic building. We’ll also explore the Upper City and its lavish Jewish villas, the new monument commemorating the destroyed Jewish cemetery, and we will end our tour at the Byzantine Walls, from where you can enjoy fabulous views of the bay. Hotel MonAsty, Autograph Collection by Marriott 5*. [10 miles]

• Breakfast
• Hotel MonAsty, Autograph Collection by Marriott
• 10 miles

You have a leisurely day to attend Shabbat services if you’d like and to take in on your own much more of what vibrant Salonika has to offer. You can take a morning walk along the seafront and visit the White Tower, stroll along the newly reconstructed port, or savor local life at the city’s famous flower and food markets – Modiano and Kapani are two of the best. The Ladadika and Valaoritou districts house some of the city’s best taverns, restaurants, and cafes. You can visit one of Salonica’s museums, the Roman Forum, the 8th century Hagia Sophia (modeled after the one in Istanbul), or the 5th century Hagios Demetrios Church – both UNESCO World Heritage sites. And you can use some of your free time to relax in our hotel’s pool, spa, sauna, and steam baths. We will all get together in the evening and go out to dinner. Hotel MonAsty, Autograph Collection by Marriott 5*.

• Breakfast
• Hotel MonAsty, Autograph Collection by Marriott

Today we head north and reenter Bulgaria through the Kulata checkpoint. Our road through the Bulgarian southwest offers particularly scenic views along the Struma river and the Pirin mountains. The region around the town of Melnik is the location of some of Bulgaria’s most pristine and picturesque vineyards, which is why it is colloquially called Bulgaria’s Tuscany. We will explore the historic town of Melnik and learn about its centuries-old winemaking tradition. We’ll also visit one of Bulgaria’s leading boutique wineries and sample some excellent indigenous wine varietals. We will remain in the region for a memorable overnight stay at a particularly luxurious wine estate, equally well known for its unique local cuisine. Zornitza Family Estate Relais & Châteaux. [85 miles]

• Breakfast
• Zornitza Family Estate Relais & Châteaux
• 85 miles

Our morning drive will take us through the Kresna Gorge, and we’ll pass by the southwestern towns of Sandanski and Blagoevgrad, home to the only American university in the region. Our main destination today is the Rila Monastery, the nation’s greatest religious symbol and a UNESCO site. Perched in the heart of Bulgaria’s tallest mountain, the monastery was founded in the 10th century and has been an influential spiritual and cultural hub over the centuries. (King Boris III was buried here in 1943.) After lunch – mountain trout is the local specialty – we’ll pass by the town of Dupnitsa, an important tobacco center and the historic home to a sizeable Jewish community. Next on our route is the town of Samokov. The mountain town was an important Jewish center and home to the Arieh dynasty – a rich and influential Jewish family. Our final destination is Plovdiv, Bulgaria’s second-largest city. After we check into our centrally located hotel, you’ll have time to explore Plovdiv’s vibrant promenade, which offers some irresistible gelato. Hotel Residence City Garden 5*. [210 miles]

• Breakfast
• Hotel Residence City Garden
• 210 miles

Bulgaria’s oldest city combines layers of its Thracian, Roman, Byzantine, Ottoman, and Bulgarian Revival past. As we walk the cobbled streets of the Old Town, we’ll see some of the most impressive examples of opulent nineteenth century vernacular architecture, a second-century Roman theater and stadium, and a 14th century mosque. Plovdiv’s promenade has lovely cafes and restaurants and is a popular destination for afternoon and evening walks. We’ll also learn about Plovdiv’s vibrant Jewish community, walk through the historic Jewish neighborhood, and visit the city’s lovely synagogue – the only other active one in Bulgaria. Plovdiv is also home to a spectacular Roman archaeological complex – the newly excavated 4th-century CE Bishop’s Basilica. Hotel Residence City Garden 5*. [10 miles]

• Breakfast
• Hotel Residence City Garden
• 10 miles

Our morning will start with a visit of the nearby 11th century Bachkovo monastery, nestled in the scenic Rhodope Mountains. Buried in the main church are two of the country’s Orthodox bishops who were instrumental in defending Bulgarian Jews during the Holocaust. The marketplace outside of the monastery offers many homemade Bulgarian jams, mountain honey, and some particularly unique traditional spices and herbs. From Bachkovo we head west towards Sofia. Afternoon exploration of parts of the city center. Grand Hotel Sofia 5*. [125 miles]

• Breakfast
• Grand Hotel Sofia
• 125 miles

Sofia’s center affords the unique opportunity to walk down a real “yellow brick road,” paved in 1907 with Austrо-Hungarian cobblestone. Important landmarks include the imposing Alexander Nevski Cathedral, the Russian Church, the National Theater and city garden, parliament, the Royal Palace, the fourth-century Roman Rotunda and newly excavated Roman ruins, and the 1950s socialist administrative complex. In addition to the Synagogue, we’ll also visit the city’s Jewish memorials and admire traditional Sephardi handiwork by the women of “Manos Bendichas” (Blessed Hands). You’ll have free time in the afternoon to explore parts of the capital you did not get to see or to get a few last-minute gifts for friends back home. We’ll end the day with a particularly delicious farewell dinner. Grand Hotel Sofia 5*.

• Breakfast, dinner
• Grand Hotel Sofia

Free time and departure.

• Breakfast