On this seven-day, self-guided tour from Kyiv to Odesa, you will explore the Ukrainian history and culture of both cities. Your trip coordinator will arrange apartments and guidebook materials in both locations. In Kyiv, the capital city, you can experience Independence Square and visit the many gold-domed cathedrals and monasteries. Next, in Odesa, you can kick back on the different beaches along the Black Sea, climb the iconic Potemkin Stairs, and go to the opera and ballet theater for a live performance. Make sure to indulge in plenty of Ukrainian fare along the way!

Highlights

  • Learn about the history of Kyiv at Independence Square 
  • Experience the bohemian vibe of Andriyivskyy Descent
  • Enjoy the Black Sea beaches around Odesa
  • Go shopping in the hidden Odesa Passage 

Brief Itinerary

Day Highlights Overnight
Day 1 Arrival in Kyiv Kyiv
Day 2 Self-Guided Tour of Kyiv Kyiv
Day 3 Explore Kyiv and Train to Odesa Overnight Train
Day 4 Arrival in Odesa Odesa
Day 5 Self-Guided Tour of Odesa  Odesa
Day 6 Last day in Odesa and Train to Kyiv Overnight Train
Day 7 Departure From Kyiv  

Detailed Itinerary

Day 1: Arrival in Kyiv

Independence Square
Independence Square

Welcome to Kyiv, the capital of Ukraine! When you arrive, a guide will take you to your hand-picked apartment, which will be your home for the next few days. Your accommodations will include a detailed guidebook that will help you map out your self-guided tour of the city.

There is a lot to explore in Kyiv, from historical sites to art galleries and the city’s beautiful waterways. Launch into the day over at Khreshchatyk, which was significant in World War II, and experienced widespread destruction, but has since been rebuilt. A lively area that is home to many street performers and musicians, the busy road closes on holidays and weekends for the enjoyment of spectators and visitors.

Here, you will find Independence Square, which hosts the Monument of Independence. Erected in 2001, the tribute honors the separation of Ukraine from Russia. You will also find the Friendship of the Nations monument nearby, which, conversely, celebrates the 1654 integration of the two countries.

Then, walk over to Andriyivskyy Descent. This is one of the oldest streets in the city. You will find charming history here, from the iconic architecture style to the unique color schemes. Long ago, this is where many musicians, sculptors, and artists lived. Today, it remains a bohemian hub with a variety of art galleries, salons, art cafés, and shops selling items from local craftsmen. Make a stop at the One Street Museum, too, where you will find one-of-a-kind wares, including paintings, photos, and furniture representative of Kyiv’s decorated history.

For dinner, make sure to taste the local flavors, which range from Ukrainian cuisine to American, Georgian, Asian, and Mediterranean. Afterward, take some time to explore the famous nightlife scene of Kyiv. You can enjoy the array of dive bars and pubs, along with nightclub hot spots. You can drink and dance your way through Arena City, which is near the city center. Keep in mind that weather and dress code are factors that will impact your evening plans.

Day 2: Self-guided tour of Kyiv

National Opera of Ukraine
National Opera of Ukraine

Good Morning! Today, you will explore all the historical sites of Kyiv. A breakdown of the most notable sites includes:

  • Kyiv-Pechersk Lavra: Perched on top of the grassy hills of the Dnipro River, this iconic cluster of golden-domed churches attracts tourists and Orthodox pilgrims, alike.
  • Maydan Nezalezhnosti: This pro-independence square has seen significant historical events, including protests in the 1990s, the Orange Revolution in 2004, and the Euromaidan Revolution in 2013-2014. In times of peace, you can enjoy the festiveness of the locals, popular weekend concerts, and the nightly fountain show.
  • St. Sophia’s Cathedral: Kyiv’s oldest church, the interiors of St. Sophia’s are filled with original mosaics and murals and is influenced by the 18th-century baroque style. Climb the bell tower for a bird’s-eye view, and a panoramic look of Kyiv below.
  • St. Michaels Golden-Domed Monastery: You can learn all about this golden-domed monastery’s decorated history, including its rebuild in 2001, at the museum located in the bell tower.

In the evening, you can enjoy a nice dinner and then go to a show. Popular genres of entertainment in Kyiv are ballet and opera, which are commonly fused together. Visit the National Opera of Ukraine for an affordable evening outing to experience an unforgettable local performance.   

Day 3: Explore Kyiv and train to Odesa

Dnieper River
Boat tour along the Dnieper River

On your final day in Kyiv, take a cruise along the beautiful Dnieper River. You can expect music to fuel your float, which is all part of the cultural experience. You will sail under famous bridges, like the Parkovy Pedestrian Bridge, the Metro Bridge, and the Patron Bridge. You can also expect great views of the Soviet-era Motherland Monument and the city skyline.

After you disembark, you can stroll through the colorful parks scattered throughout Kyiv. Feofaniya Park is historical and well-groomed, with peaceful pond views, while Holosiivsky Park is the ideal place for a quiet picnic. You can also browse the fantastic landscapes of Mariinsky Park, which is a popular tourist spot or take a trip to Taras Shevchenko Park, where you can visit the National University of Kyiv and see the students walking to and from class.

Then, take an afternoon break for lunch, coffee, and a sweet treat at one of the many cafés around town. Some options to consider are Wolkonsky, Honey, and Very Well Café.

Then, it will be time to make your way to the train station, where you will commute to the second leg of your trip to Odesa.

Day 4: Arrival in Odesa

Potemkin Stairs
Potemkin Stairs

Upon your arrival at the airport or train station in Odesa, a chaperone will meet you and drive you to your centrally located apartment. Once you are checked in, you will find a detailed guidebook, just like in Kyiv, that will help you plan your stay. 

The port city is located on the Black Sea in the southern region of Ukraine. Odesa is a town rich in history, arts, and culture, and you will get to experience everything while you are here. On your first day, you can visit:

  • Potemkin Stairs: Also known as the Potemkin Steps, this is a giant stairway, and is considered a formal entryway to the city. This is a great way to launch your sightseeing. There are 192 steps in total, an elevation of nearly 90 feet, and a distance just shy of 1 mile.
  • Primorsky Boulevard: Located next to Istanbul Park, you can walk up and down the streets to admire mansions and museums overlooking the nearby harbor, along with several monuments to teach you about the local history.
  • Privoz Market: This famed market is the largest food market in Odesa! Take the time to explore the different vendors and food offerings while you are here.
  • Derybasivska Street: Named for one of the town’s founders, the Neapolitan José de Ribas, you can find street artists performing here, plenty of shops to browse in, and many cafés and restaurant terraces to visit for lunch.
  • Odesa Passage: Part of a large development that includes a hotel on its top three floors, this hidden shopping passage is laced with statues, like Mercury and Fortuna, and you can visit the many boutiques and souvenir shops along the way.

If you are interested in more sightseeing adventures, you can also bookmark the following destinations:

  • Monument to the Founders of Odesa
  • Transfiguration Cathedral
  • Archaeological Museum
  • Vorontsov Palace
  • Museum of Western and Eastern Art
  • Shevchenko Park

Day 5: Self-guided tour of Odesa 

Black Sea Beaches
Visit the many beaches along the Black Sea

After a full day of sightseeing in Odesa, on your second day, enjoy the beach! Make your way down to the Black Sea, where you can relax and take in the rays, be active in the water, or explore the restaurants and shops surrounding. The top beaches to consider include:

  • Arkadia: This is the most affluent of the beaches in Odesa. Enjoy your time in the sun here, where you will also be able to enjoy a meal outside by the water and visit the surrounding shops.
  • Otrada: This beach can be accessed by cable cars, and you can walk the many small beaches contained within. Here, you will find beaches with bars and wait staff service, along with kid-friendly play zones. Visitors like to enjoy jet skiing and windsurfing, too. 
  • Lanzheron: This spot is popular thanks to its central location. You can ride watersides, take a ride on a speedboat and indulge in other watersports.
  • Delphin: This beach is stationed south of Lanzheron and Otrada. You will find great sand quality here, a clean beach, and exceptional service. This location is great for a summer day outdoors or a romantic evening with your partner.

Wind down from your beach day with a nice meal. Known for great food, there are many different genres of fare to taste in Odesa—try Sophie’s Café or Alexandrovskyi.

After dinner, you can visit the Odessa National Academic Theater of Opera and Ballet. Although you can take a daytime tour of the building, it is highly recommended you revisit in the evening, so you can attend a local opera or ballet performance live!

Day 6: Last day in Odesa and train to Kyiv

Odesa Cafe
Enjoy a final breakfast or brunch at an outdoor café

On your last morning in Odesa, enjoy a nice breakfast or brunch before you depart. Since late breakfast is common in Odesa, you can take your time in choosing between some of the following options:

  • Kompot: Where you can indulge in traditional Ukrainian fare
  • Jardin: Where you can dine in a laid-back garden setting
  • Dacha: Another traditional Ukrainian option with six prix-fixe breakfast menus
  • Berndazzi: Which hosts a Mediterranean-style courtyard and a local menu

Following breakfast or brunch, you will make your way to the train station. You can bid farewell to Odesa knowing you have fully enjoyed the town, from its history to the gorgeous Black Sea beaches.

Day 7: Departure from Kyiv

Kyiv Train Station
Take the train back to Kyiv

Once you arrive on your train from Odesa to Kyiv, you will prepare for your final departure home with memories of Ukraine to treasure forever!