Small Groups: Never more than 10-16 travelers—guaranteed!
For more than a millennium, the fertile land that is now the Ukraine has been a subject of desire – from the Golden Horde to the Soviets, whose mantle they cast off just over twenty years ago. In the new century, the gems of the Ukraine have regained their luster, from culture-rich Kiev to Chekhov’s beloved seaside town of Yalta, and onward to enduring Sevastopol, which stood bravely in the face of World War II devastation. In a journey of discovery spanning the agricultural hub of Kherson and majestic Odessa, you’ll experience the blend of history and natural beauty that define the region.
You’ll crown your discoveries with a three-night stay in Moldova, an inland kingdom with thousands of years of history, whose riverside capital, Chisinau, greets you with the warm welcome of the region’s friendly people. You’ll sample Moldova’s famed wines and learn about its culture-within-a-culture in a visit to the history-steeped (and hotly disputed) territory of Transnistria.
Depart from the U.S. on your flight to Kiev, Ukraine.
Arrive today. We will be met at the airport by an OAT representative and assisted to our hotel. There, we meet our expert resident Trip Leader, who will guide our discoveries throughout our trip. We will also be introduced to our fellow travelers—including those arriving from the Moscow pre-trip extension.
Our Trip Leader will lead a brief orientation walk to familiarize us with the area around our hotel before our small group gets acquainted over dinner together tonight.
Following breakfast, we set out to discover the flavor of Kiev on an included city tour. For a city that is nearly a millennium old, Kiev is surprisingly youthful as well. The large student population and the many young professionals who have flocked here in recent years give Kiev the feeling of a city on the verge of becoming a world-class destination for visitors.
Among our destinations is the St. Sophia Cathedral, a UNESCO World Heritage Site. When construction of St. Sophia was begun in 1037, it was intended to replace the first church built in Kiev. Designed to be both functional and symbolic, the cathedral features a vast central cupola and twelve surrounding cupolas mirroring Christ and his twelve apostles. Part of a larger complex, the grounds of St. Sophia Cathedral include two churches, a bell tower, a school, and monastic buildings. The monks’ cells were built out of wood in 1633, but destroyed by fire 64 years later and subsequently rebuilt in stone in a distinct Ukrainian Baroque style. When World War II rained great destruction down upon Kiev, the complex at St. Sophia was miraculously spared and is now an enriching museum. Be sure to note the ancient icons and frescoes, as well as old columns that retain the scribbling of people who visited the church centuries ago.
We’ll also enjoy an included tour of the Cave Monastery—a UNESCO World Heritage Site consisting of miles of maze-like underground tunnels where ancient crypts hold ecclesiastical treasures. Our tour will also bring us to thriving Khreschatyk Street—a wide boulevard lined with chestnut trees that is among the most famous and active streets in Kiev. Take in the street’s unique, historic architecture, which was painstakingly restored following World War II, and the array of shops, hotels, government offices, and performance halls that are located along this popular thoroughfare.
Following our visit, enjoy lunch on your own before free time to make your own discoveries in Kiev. You might choose to explore Independence Square—the city’s inspiring central square, which was renamed following Ukraine’s peaceful secession from the Soviet Union in 1991. Here you'll see statues dedicated to several influential figures in Ukrainian history.
This evening, enjoy a Welcome Dinner with your fellow travelers at a local restaurant.
No city can look forward without also remembering the past. Today, we’ll learn about the major landmark of recent history, Ukrainian Independence, in a lively discussion. It wasn’t until 1991 that Ukraine was able to wrest control of its fate from Soviet control, as we’ll hear today.
Then, we’ll travel to the Chernobyl Museum, where we’ll get a firsthand account of the catastrophic accident that occurred here from one of the survivors. It’s sure to be a memorable exchange.
After lunch together at a local restaurant, enjoy an afternoon of leisure to explore Kiev on your own, perhaps making a trip to the bustling Bessarabsky Market, located at the southern end of Vulitsya Kreshchatik, one of the busiest shopping streets in Kiev. Here you will find the locals shopping for fruits, meats, and caviar, and stocking up on kvas, a fermented bread-based beverage that is a favorite on picnics.
Or, join an optional excursion to Mamayeva Sloboda, an open-air museum of folk architecture and lifestyle. Located within a picturesque area of Kiev, the sprawling grounds of the museum—which feature wooden peasants’ homes, mills, and farms—reflect the styles of different Ukrainian villages and regions. You’ll see folk art, traditional household utensils, clothing, and tools from the 16th to 20th centuries used for crafts including weaving, pottery, and barrel making. The museum also includes a church that is still used for services.
After breakfast, we transfer to the airport for our flight to Simferopol, en route to Yalta. A Crimean city on the coast of the Black Sea, Yalta was originally an ancient Greek settlement. Assimilated into the Russian empire in the 18th century, it became an elite retreat for wealthy Russians, who prized Yalta for its warm climate, fertile vineyards, and picturesque coastline. Among those who spent time there are writers Anton Chekhov and Leo Tolstoy, as well as tsars Nicholas II and Alexander III. Under Lenin, Yalta became a recreational destination for working-class Russians.
In the years immediately following the fall of the Soviet Union, Yalta struggled. Freed from restrictive Soviet policies barring international travel, many vacationers chose to holiday in other cities. But the last few years have seen the city renewed, re-emerging as a destination for both Russian and foreign travelers.
We arrive in time for lunch at a local restaurant, followed by an orientation walk with our Trip Leader. Tonight, we'll enjoy dinner together at our hotel.
Today, it will be easy to see why so many Europeans over the centuries have considered Yalta the ideal escape, and why so many painters came here to capture the spell on canvas, as we take in the stunning views of mountains to one side and the vast sea to the other.
We begin with Alupka, a small village nestled in the shadow of the Ai-Petri mountain chain. The area's natural beauty inspired the Russian prince Mikhail Semyonovich Vorontsov to construct an elaborate summer palace here. We’ll visit this stunning residence, now a museum. It was here that Winston Churchill and his delegation from Great Britain resided during the Yalta Conference—and where important state functions are still held to this day.
Then, retuning towards Yalta, we'll enjoy an especially scenic drive complete with a photo stop at Swallow's Nest—an ornate, Neo-Gothic castle set high upon a cliff, and one of the most dramatic vistas in a landscape where drama is in no short supply.
After lunch on your own, drama is on the menu again when we visit Chekhov’s house. “The White Dacha” was Chekhov’s reward to himself after the success of The Seagull, and it is here that he wrote the plays Three Sisters and The Cherry Orchard, and the story, “The Lady with the Dog,” the latter based on a view from his front windows. Artistic luminaries like Rachmaninoff, Gorky, and Tolstoy all spent time here with Chekhov and his sister, who kept the home up until it became a museum in the 1920s.
We enjoy dinner together at a local restaurant this evening.
After breakfast, we bid farewell to Yalta with one last stop for an included tour of Tsar Nicholas II’s summer home, Livadia Palace. In addition to being a remarkable example of Neo-Renaissance architecture, this expansive structure was the site of the famous Yalta Conference in 1945, where Franklin D. Roosevelt, Winston Churchill, and Joseph Stalin met to determine the fate of war-ravaged Europe.
Then, we travel overland to Sevastopol, a city justifiably proud of its enduring spirit, having faced blistering war time sieges in successive centuries, only to emerge united and strong. We’ll enjoy lunch together here, then learn about the devastation of World War II, and gain insight into Ukraine's role in the war, during a moving visit with a group of Ukrainian veterans. We’ll learn about the 1942 Siege of Sevastopol in which the Germans—determined to have access to oil trade routes—not only surrounded the city but bombed it relentlessly for five days, killing all but 50 of the 1,000 Russian soldiers defending the site.
This evening, witness the reborn city—which completely reinvented itself in the decades after the massive destruction–during time on your own for dinner.
We’ll discover more about the first Siege of Sevastopol, from the Crimean War, when we visit the Sevastopol Panorama, a museum showcasing an expansive and realistic 360-degree painting depicting the city’s defense. This conflict was the setting of 1854's storied Charge of the Light Brigade, when British Cavalry forces attempted the attack immortalized in the famous poem by Alfred Lord Tennyson.
We'll also visit the site of an ancient Greek colony at Khersones. Nicknamed "the Pompeii of the Crimea," the site boasted a thriving democracy 2,500 years ago, and we'll see evidence here of not only Greek but Roman and Byzantine eras. Among the structures today are remnants of an amphitheater, a temple, defensive towers, and a basilica.
After lunch on your own, enjoy time at leisure in Sevastopol before we join together for dinner at a local restaurant.
After breakfast, we travel to nearby Bakhchisaray for an included tour of the remarkable Bakhchisaray Palace—a political and cultural epicenter for Crimean Tatars. You’ll view the fabled Fountain of Tears, built for a Crimean Khan in memory of his deceased wife, which inspired poet Alexander Pushkin to compose his most famous ode. Your tour also includes visits to the Harem building and the central mosque, with its imposing minarets.
After lunch together in Bakhchisaray, we'll return to our hotel in Sevastopol, where you can enjoy time to further explore this historic city on your own.
Or, join our optional tour to the Balaklava Valley & Submarine Pen. Located in Balaklava Bay, the museum site was once a Cold War-era top-secret naval outpost that housed nuclear weapons and outfitted, maintained, and repaired submarines. Subs were launched into the Black Sea through carefully camouflaged secret passageways, which, combined with the extraordinary natural features of the area, made them invisible to enemy satellites. Explore these former underground submarine facilities during this fascinating excursion.
Today we travel overland to Pochetnoye, a village located two miles from the city of Krasnoperekopsk. We’ll explore the village during a short walk, before getting a taste of Ukrainian hospitality during a Home-Hosted Lunch. As we enjoy traditional Ukrainian food in the homes of these agricultural families, we’ll learn how they run their farms.
Next, we’ll glimpse into the future of Ukraine by visiting a local kindergarten. Here, we’ll have a chance to interact with the children and their teachers to gain a unique insight into life in a Ukrainian village.
We’ll conclude our time in Pochetnoye by visiting a small community center for the village’s retired and low-income residents. The center was established by village authorities—without government support—with the goal of giving these locals a place to socialize, practice hobbies, and do crafts. However, the center also offers the services of physicians, tailors, barbers, and masseuses.
Bidding farewell to the Ukrainian village, we'll continue overland to Kherson, a port city located at the beginning of the Black Sea Delta. Long a thriving shipbuilding center, Kherson was founded in the late 18th century by Russian military leader Grigori Potemkin while serving under Catherine the Great.
Today, Kherson is known not only for its location along the Dnieper River, where men still cast their fishing lines from the promenade, but as the hub of agricultural learning. Though the city has four universities in distinct disciplines, the Agricultural University draws students from across Ukraine and throughout the region who are determined to preserve agrarian traditions.
Arriving this afternoon, we enjoy a brief orientation walk to get us acquainted with this historic setting before dinner together at a local restaurant.
This morning, we enjoy an included overview tour of Kherson, including a visit to St. Catherine's Church, where Potemkin is buried, and Suvorov, a pedestrian-only street popular with the local people. Then we visit Kherson State Agrarian University (when in session), where you’ll learn more about this region, its agriculture, and the lives of its younger inhabitants during a meeting with local students.
After a morning of discoveries, we travel overland for historic Odessa, stopping to enjoy lunch at a local restaurant on the way. The warm water port was a major hub of trade and one of the great cities of Imperial Russia. Greek in origin, ruled variously by Ottoman and Russian forces, Odessa became a nexus of revolutionaries in the Bolshevik uprising.
This afternoon, we'll explore Odessa during an orientation walk, perhaps visiting one of its many green parks. One of its largest is Shevchenko Park, where chess players spend hours in outdoor games. Here, you may stroll the wandering paths popular with walkers and joggers, and enjoy the array of trees, flowers, and shrubs that provide a lush welcome.
We enjoy dinner together at a local restaurant this evening.
Enjoy a tour showcasing highlights of this historic Black Sea port, including Primorsky Boulevard, Odessa’s popular pedestrian thoroughfare, which features expansive sea views and numerous statues and monuments. While exploring Primorsky Boulevard, you’ll see the city’s famous Potemkin Stairs. The steps were the brainchild of Italian architect Francesco Boffo, who also designed the impressive Governor’s Palace, and have been immortalized in one of the early classics of film, Battleship Potemkin.
After lunch at a local restaurant, spend the rest of the afternoon at leisure, with ample time to make your own discoveries in Odessa. Dinner is on your own this evening.
Discover a hidden side of Odessa this morning as we head underground, where an expansive series of tunnels stretch more than 2,000 miles. This morning, you’ll visit these catacombs, which have their origins as limestone mines. Once miners removed the limestone (which was used to construct houses in Odessa), smugglers widened the abandoned tunnels and transformed them into a network for surreptitiously transporting goods.
Then enjoy a tour focusing on the Jewish Heritage of Odessa. Until the first half of the 20th century, Odessa had the third-largest Jewish population in the world, behind New York and Warsaw. Consequently, the city was an intellectual hub, home to numerous prominent Jewish scholars, artists, writers, and photographers. After the Nazi occupation of Odessa, the city’s Jewish population rapidly declined, with many residents emigrating to Israel. Our journey begins with a visit to a local synagogue, followed by a moving stop at Ukraine's largest Jewish cemetery. We conclude our tour at the Odessa Jewish Museum. This carefully curated museum houses fascinating displays featuring historic documents, books, periodicals, musical instruments, art, religious garb, household items, and more.
Choose from the many local dining options this evening for dinner on your own.
Today, we travel overland to the independent country of Moldova, pausing for lunch en route to our destination, Chisinau.
Settled as far back as the paleolithic era, Moldova is a small country with a big spirit, a place where the heavy weight of the Soviet era never crushed local pride—still visible in the Patrea Mea (“my homeland”) signs all over its capital, Chisinau. The largest and most prosperous city in Moldova, Chisinau offers glimpses of the Soviet past, with massive building complexes, while proudly showing a contemporary face, with sleek glass and steel towers rising in the last decade. But its most dominant architectural feature are the massive “Gates of the City,” which are asymmetrical tiered building complexes that rise in height to peaks framing either side of main highway entering the town.
We arrive in Chisinau this afternoon, with ample time for an orientation walk in the vicinity of our hotel to acquaint us with our new neighborhood. Our hotel is located just off Stefan Mare, the city’s main street and hub of shopping, culture, nightlife, and government.
Today, we discover the history and culture of Chisinau on a guided tour of some of its highlights. We begin at Pushkin Park, where stands of trees, flower beds, stone pathways, and a fountain surround a statue of the Russian author Alexander Pushkin, who wrote The Prisoner of the Caucasus while living in the city. The massive Government House will make an impression before we visit two sobering sites: the World War II Memorial Park and the Monument to the Soldiers of the Afghan War. The Memorial Park includes an eternal flame to commemorate Chisinau’s soldiers who died fighting for the Soviets in World War II. The monument honoring soldiers who served in Afghanistan calls to mind an open-topped bell or a modernist air control tower with its sleek curves (which are illuminated in colored lights at night).
We'll round out our morning with a trip to the archaeological complex of Orheiul Vechi, or Old Orhei—one of Moldova's most fantastic sights. Here, we'll witness the complex's Cave Monastery. The monastery was carved into a limestone cliff in the 13th century by Orthodox monks, who indulged in its remote location and stunning views of the Raut River. We'll also visit the site's lovely hilltop church, which was built in 1905.
Late this morning, we visit Cricova Winery, the best known of all Moldova’s winemakers. With its labyrinth of underground tunnels and galleries running for miles with lanes boasting names like Cabernet Street and Pinot Noir Street, Cricova is a massive institution. But we’ll see it on an intimate scale, with an included tour, wine-tasting, and lunch here. Perhaps you’ll savor one of the many sparkling wine varieties for which Cricova is best known.
The balance of the afternoon is yours for discovery. You might follow the lanes of lake-studded Rose Valley Park, or visit the Botanica, the city’s largest park, near the Gates of the City.
Dinner is on your own this evening.
This morning, we set off for nearby Transnistria, a region which Moldova considers part of the country, but which considers itself a breakaway republic, with its own elected officials. Nestled between Ukraine and the Moldovan border, Transnistria follows the Dnieper River. The municipality forming the buffer zone between Transnistria and Moldova proper is Bender, which has been in existence since at least the 14th century, making it one of the oldest towns in the land – and one of the most contested, as it was a prime setting for the late 20th-century Transnistrian War, in which Moldova repelled Russian-backed independence forces to keep its grip on the region. We’ll learn more about the conflict, the human toll, and the recovery in a visit to the Bender War Museum this morning.
Before returning to Chisinau, we pause for lunch in Tiraspol, the capital of Transnistria, and enjoy a guided tour of the city.
Tonight, we toast our memories of Ukraine and Moldova in a Farewell Dinner together at a local restaurant.
Depart for U.S. or begin Bucharest extension