As we drove into the city, the sun flickered through the birch forests and directly into my eyes, demanding a realization that the final leg of my journey east was a westward turn to Kiev – the birthplace of Slavic civilization that spans the green banks of the vast and historic Dnepr river. My driver pointed upstream when the field of dark water had come into view, pronouncing the expanse nyep that ended in a soft purr.

Modern Kiev rises high above the river's steepest edge, cloaked in an ancient chestnut forest that continues to mix the old and new, the natural and manmade. We crossed the river in the shadow of the gargantuan Motherland statue – a titanium goddess with sword and shield, standing in defiant testimony against the Nazi invaders. And yet beneath her hollow glare, I could spot the sparkle of gold domes, like stars, atop Kiev's one hundred churches, hinting at brighter hopes amid darker times.

It was Prince Vladimir, a royal descendant of Vikings, who sanctified this land and fused together his civilization with Christian Orthodoxy. Over a millennium ago, the converted ruler watched from the bank as the entire population of Kiev was marched into the Dnepr and the waters blessed by Byzantine priests – remembered as the baptism of Kievan Rus. The centuries have seen empires rise and collapse since this forced ritual on these shores, but today's Ukrainians feel their river is no less sacred than any Nile or Ganges.

Indeed, Russian Orthodoxy's holy of holies boasts the boldest and brightest of Kiev's gold-topped towers, delivering a concentrated energy to those who wander the Dnepr's banks. Walking among the ensemble of white and green churches within Kiev's Caves Monastery, I found myself in the company of solemn monks, their cassocks brushing against the cobblestones in rhythm, fingers pushing through prayer beads. In spite of all the magnificence above ground – the towering baroque bell tower, incredibly detailed mosaics, the ornate icons with gold inlay – it was only underground that my mind could comprehend the meaning of one thousand years. The caves were first settled in 1051 by St. Anthony of Lyubech – a travelling monk from Greece's Mt. Athos who expanded the natural caverns into an elaborate system of tunnels, cells and subterranean chapels to accommodate a vibrant and growing monastic community hidden away from the rest of the world. As my eyes grew accustomed to my handheld candlelight, I spotted the patches of early frescoes along the walls and breathed in the honey-scented incense. The polyphonic chanting of priests and visiting pilgrims granted a marked stillness among the entombed bodies of Orthodoxy's most beloved saints, including St. Anthony himself, as well as Nestor, the scholastic monk who chronicled Kiev's history prior to the onslaught of the Golden Horde in the 13 th century. Squinting through the shadows, I could make out the saint's black mummified hands curled into the holy signs portrayed in icons, as well as the holy relics – skulls locked away on gilded shelves.

Grateful for the sun, I emerged from the winding tunnels and caught a glimpse of the river below – a path of water that once carried Viking traders of the north all the way to the Black Sea and the riches of Byzantium. My voyage would follow this same route down through Ukraine's heartland, meandering through both primitive landscapes and industrial glories to the dark waves of the Black Sea – once the destination of ancient Greek ships.

An effigy of Prince Vladimir's hillside effigy, cross in hand, gazed downriver in farewell as we floated south and past Kiev's forested islands and into the heart of Ukraine. At 1,400 miles, the Dnepr is the second longest river in Europe, after the Danube. The complex system of Soviet dams created some reservoirs so wide, I felt suspended on a sea of glass. But sailing closer to these uneven banks grants the viewer a guileless backstage view of the country.

The morning swimmers came down to the water with the sun and returned everyday without fail – even in winter, I was told, when they cut holes in the ice for a quick and rather cold dip. We passed legions of devoted fishermen, probing the riverbed with nets and poles, pulling fish from the water with ease. Barefoot children waved with both hands before splashing backwards, and then chased our ship from the bank, laughing. Cities disappeared into miniature wooden villages with tin-roof churches and the landscape opened up into those same picturesque sunflower fields that I had seen on my dinner tray.

Ukraine's exotic flare relies on the simplest elements: the grassy steppe stretching unbroken into the distance, the clear summer sky, drooping willows that trail silver ripples in the water, and the calmest twilight. For centuries, this was a no man's land – an open expanse of prairie outside the empires of the day, subject to occasional raids from the south. Only the most adventurous farmer chose to homestead these unprotected acres, and only out of necessity did these farmers evolve into an organised band of independent warriors. Dubbed “Cossacks” by their Turkish invaders, these “free men” fought only to protect their plots of land – the open spaces of wheat, potatoes and flowers, now dotted with linden trees and earnest farms.

Descendants of the freemen still inhabit the island farms and fishing communities marking the delta – a place where the Dnepr surrenders vaguely to the sea in a series of sandbars, islets and estuaries – all now protected nature reserves. A cacophony of seabirds, their swooping aerial displays, and the rich salt in the air announced the approching sea long before we met the open water.

It was Catherine the Great who chased the Turks from these northern shores and christened the Black Sea coastline a “New Russia”, an expanded empire that would extend the glory of St. Petersburg into the physical realm of ancient Greece. In the course of battles, allied Ukrainian Cossacks lay siege to the Turkish fortress Eni-Dunya and freed the infamous slave port in 1789. A mighty city was planned in its place, and a dramatic Greek-sounding name bestowed: Odessa.

The heroic port delivers its best view from the sea, as I first saw it – in the morning light, rising above a misty beach as a cluster of pastel palaces and shipping cranes. We disembarked at the bottom of the legendary Potemkin Stairs, 192 granite steps rising up to the city from the pier. I ascended slowly, remembering vaguely the episode of Sergei Eisenstein's epic film, the Battleship Potemkin, when an unattended baby carriage bounces down these very steps amid the flying bullets and charging soldiers. Nearly one hundred years ago, Tsarist troops really did stand at the top of this descent and fire upon a workers' uprising in the port, with thousands jumping into the sea to escape. A legacy of under-appreciated labour movements detracted little from the sunny vista at the top of the stairs, nor does it seem to affect the jovial mood in the city.

Declared a free port from its very beginning, “Odessites” descend from an eclectic band of freed slaves, liberal Marxists, Bulgarians, Greeks, Albanians, Jews, Cossacks, and a continued flow of the nomadically-inclined. Good conversation is key to the mixing – I couldn't help noticing that every park bench in the city had been forcibly relocated to directly face other benches at knees-length: obviously custom-built for true tête-à-tête . I became lost in observation, listening to an organ grinder (complete with dancing monkey) and watching the gesticulation and laughter all around. An elegantly-dressed woman (draped in faux leopard skin) suddenly dove into my thoughts, explaining the scene in dramatic tones “We in Odessa, you see – we love jokes!” They must, for Madame insisted I return for Odessa Day, on April 1 st .

Odessa owes its grand aesthetic to the guidance of an aristocratic Frenchman, the Duke de Richelieu, who, when made governor of the city, cut trade duties and set aside one fifth of the port's income in order to “make the city beautiful.” The regal Opera House, the exquisitely unique Philharmonic Hall, and a belle époque shopping arcade – passazh – are all proof of the Duke's success, as are the well-pruned trees and the civil pride manifest by Odessa's inhabitants today.

That same dignity and independent streak were flaunted in the Crimean port of Sevastopol – a modern city-state so steeped in past glories that the Tsarist tri-colour flag still flew above its many alabaster, neo-classical buildings. It was among these intricate natural harbours and hidden coves that 19 th century St. Petersburg found a warm water refuge for its growing navy, and Russia's greatest rail lines still meet there terminus at Sevastopol harbour, now a two to three day train journey from the forgotten northern capitals.

I sauntered down Sevastopol's impressive Nakhimov Boulevard, a descending cobblestone thoroughfare, now lined by polished churches and luxurious window displays. Just a few years ago, my foreigner's presence in this town was utterly forbidden – the home of the Black Sea Fleet has literally been kept a well-guarded secret, and most Ukrainians and Russians have still never seen these giant ships, nor felt the Mediterranean-like breeze that warms the streets. I am inclined to believe the former secrecy had nothing to do with naval security and everything to do with limiting such a dazzling spot to the privileged few. Sun, sea and larger-than-life government subsidies marked Sevastopol as the posh side of the Soviet Union – a delicate mood that still lingers in the aftermath: my taxi driver that morning informed me that he ballroom dances very well, thank you, as should “any respectable seafaring man.”

Such seafaring men were legion, and my gaze over the blue bay was consistently interrupted as I dodged the formations of uniformed sailors, marching in step and frowning in mock seriousness. Their youthful anticipation for the sea was contagious. At night, these same soldiers filled the pubs with gusto, as did their counterparts exactly one hundred and fifty years ago, during the great Crimean War of 1854. The famed Malakhov Mound offered the best view of the city today, and a stunning panorama detailed the yearlong battle for Sevastopol. To the south, I made out the flowered meadows over Balaclava's enclosed harbour – wholly serene, but still the “valley of death” immortalised by Tennyson in his poem “The Charge of the Light Brigade”.