You’ll begin the day with an immersive walking tour of the Bulgarian capital, from Roman ruins and fourth-century churches to impressive works of modern architecture. Investigate an imposing monument to the Soviet Army, and learn about Sofia’s numerous communist heritage sites and the precarious status they find themselves in today. This afternoon you’ll visit the Museum of Socialist Art to explore some of the statues and monuments salvaged from scrapyards around the country. Walking back to the city center (weather permitting), you’ll stroll through Sofia’s "Borisova Gradina" park, taking in sights including the Russian Embassy and Hotel Moskva, the Astronomical Observatory, and the Fraternal Barrow: a Socialist-realist memorial complex that watches solemnly over the park. This evening you’ll head to a unique retro socialist-themed restaurant for dinner and drinks.

Your day starts at the Banner of Peace memorial complex, where you’ll ring the ornamental bells that hang from this unique musical monument. The bells were each donated by different nations, and you’ll spot a few from places that no longer exist, including the USSR, Yugoslavia, and the GDR (East Germany). Driving into the foothills of the Balkan Mountains, you’ll stop at the town of Koprivshtitsa to learn about a local revolutionary hero and to sample a regional culinary specialty. In the afternoon, at the highest elevation on your trip, you’ll find the Arch of Liberty, a massive monument situated at an altitude of 1,520 meters (4,986 feet) in the Beklemeto Pass. Later you’ll reach Troyan, a town famed for its fine wines and brandy. After settling in at your luxurious hotel here, you’ll meet a Bulgarian sommelier for a curated wine and dinner pairing.

Stopping at a couple of interesting monuments along the way, you’ll drive to Bulgaria’s medieval capital: Veliko Turnovo. Veliko Turnovo is easily one of the most beautiful cities anywhere in the Balkans. Here, you’ll learn about the resilience of the Bulgarian Orthodox faith as we explore the Preobrazhenski Monastery. The monastery, established in the 11th century, is still standing in spite of both religious persecution and dramatic landslides. After a tasty lunch, you’ll have a guided exploration of the Old Town area with its flea markets, craft workshops, and the historic Tsarevets Fortress. Enjoy dinner this evening with a panoramic view over the river valley and some relaxation time at your hotel in the Old Town.

After breakfast, you’ll drive to Shumen and visit the Monument to the Founders of the Bulgarian State. Prepare to be blown away by the sheer size and intensity of this unique, cubist memorial complex, which sits on a plateau overlooking the city. For lunch, you’ll drop in at the local cultural center for a traditional Armenian feast. (You’ll learn how this region is home to a sizable Armenian community.) Afterward, aiming for the Black Sea, you’ll head east to Varna and visit the imposing Monument to the Bulgarian-Soviet Friendship. After checking into your hotel for the night, you’ll take a walk down to the beach and finish the day with cocktails and a seafood dinner at the waterfront.

This morning is yours to sleep in, wander, or relax. Feel free to explore the city, visit the Retro Museum, see the Roman baths, visit the Varna Museum of Archaeology and see the oldest gold jewelry in the world, or simply unwind on the beach. You’ll also be provided with a map, detailing some of Varna’s architectural highlights. In the late morning, you’ll hit the road again, traveling south along the Black Sea coast. After a lunch by the sea, you’ll stop at the Burgas Aviation Museum for a hands-on investigation with some of the retired craft of the Bulgarian Air Force. Arriving in the sleepy port city of Burgas, you’ll be welcomed to your seafront hotel before freshening up and heading out for a group dinner.

Today is an action-packed day! Your first stop will be to see the Monument to the Bulgarian-Soviet Friendship, a concrete obelisk situated on a hilltop near the city of Yambol. From there you’ll travel to Dimitrovgrad, a planned socialist city famous for its Stalinist-classical architecture and colorful mosaic art, where you’ll also have lunch. Ascending the mountain in the afternoon, you’ll visit the Buzludzha Memorial House: a remarkable concrete structure designed in the shape of a flying saucer, once a lavish memorial museum subsequently abandoned for decades. You’ll discuss the complex history of the monument, its years of decline, and also its potential for future preservation. At the end of a day packed with striking sights, treat yourself to a steakhouse dinner and a well-earned drink in Stara Zagora.

Today you’ll start at the impressive "Defenders of Stara Zagora" memorial complex, which commemorates the sacrifice of the Russian and Bulgarian soldiers who fought here during one of the bloodiest battles of the 1877-1878 Russo-Turkish War. You continue your journey, making your way to Plovdiv, one of the oldest cities in Europe with a history dating back 5,000 years. You’ll have a guided tour followed by some free time for exploring the city on your own, seeing everything from Roman ruins to contemporary street art. Reconvene with the group for dinner at a local restaurant in the Old Town.

Departing Plovdiv, you’ll stop to investigate the Fraternal Barrow memorial complex: an unusual Brutalist structure that commemorates the local soldiers lost in Bulgaria’s wars for independence. You might even recognize this monument from its features in a couple of recent movies. Continuing to Perushtitsa, on the edge of the Rhodope Mountains that separate Bulgaria from Greece, you’ll see the Monument to the Three Generations: a church-like structure in red and white stone, very different to the concrete monuments you’ll have seen elsewhere, which overlooks the plains. After that you’ll head towards Sofia, stopping en route at a museum of socialist cars. Check into your hotel and then share a final farewell dinner in the capital.

This morning, you’ll bid your farewells and begin your journey home. One last breakfast at the hotel is included, and a transfer to the airport is included and will be arranged according to your departing flight. Until the next adventure!