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Retracing The Footsteps of Roman Emperors

10 Days / 9 Nights

Rome, Thessaloniki, Istanbul

from$3,525 per person

Travel and LeisureFodorsUSA TodayNew York TimesNational GeographicWashington PostVogue
For history enthusiasts, this is the ultimate itinerary across three fascinating cities that used to be seats of the almighty Roman Empire. Start your adventure in Rome, the city where it all began, and admire the stunning remnants of the Roman Empire that are scattered across the city. Continue your quest in Thessaloniki, the second-largest city in Greece and one of the Roman Empire's most significant centers. End your trip in the fairest of them all, the lovely Istanbul where the New Rome was established. Formerly known as Constantinople, Istanbul was the longest-serving seat of the Roman Empire and one of the most important cities in recorded history.

One of our team members in the region will be available to you leading up to and during your trip to answer any questions and arrange local services. You will receive access to your Guest Page, which includes all the necessary information on the best these destinations have to offer, including things to see and do and other inside tips from restaurant recommendations to tipping advice. Upon arrival, we will provide you with a local SIM card with data that you can use to reach your local JayWay contact (who you will meet in person) throughout your trip. In all of our destinations, we offer a wide selection of memorable 3-5 star accommodation options, including boutique hotels and charming B&Bs. With our firsthand experience, we can ensure they are all clean, comfortable, and centrally located, with local ambiance.
Route for Rome, Thessaloniki, Istanbul tour

3 Nights in Rome

3 Nights in Rome

4 days in Rome
4 days in Rome

3 Nights in Rome

The capital of Italy is a vibrant, energetic and stylish city. While thoroughly modern in sensibility, Rome is also home to some of the world’s most important works of classic art and architecture. This city has been an epicenter for culture, politics and religion for more than 2,500 years. From the Spanish Steps to the Vatican, there are more than enough sights to keep even the most active tourists busy and even somewhere as popular as Rome you can find places just off the tourist trail and bustling with locals. But it’s also nice to slow down and enjoy Rome’s famous cafes and restaurants, which can be just as beguiling as the buildings. Lounge with an espresso on the Campo de Fiori and watch the changing light on the fountains and the facades. Visit the Vatican and explore some of the world’s most beautiful churches. Rome really comes alive at night, when restaurants and wine bars bring a renewed vitality to the city. You’ll also have opportunities for day trips to local vineyards, olive groves, and other places producing regional delicacies. No matter what your interests, or what kind of holiday you’re looking for, Rome will be an enjoyable destination.

The capital of Italy is a vibrant, energetic and stylish city. While thoroughly modern in sensibility, Rome is also home to some of the world’s most important works of classic art and architecture. This city has been an epicenter for culture, politics and religion for more than 2,500 years. From the Spanish Steps to the Vatican, there are more than enough sights to keep even the most active tourists busy and even somewhere as popular as Rome you can find places just off the tourist trail and bustling with locals. But it’s also nice to slow down and enjoy Rome’s famous cafes and restaurants, which can be just as beguiling as the buildings. Lounge with an espresso on the Campo de Fiori and watch the changing light on the fountains and the facades. Visit the Vatican and explore some of the world’s most beautiful churches. Rome really comes alive at night, when restaurants and wine bars bring a renewed vitality to the city. You’ll also have opportunities for day trips to local vineyards, olive groves, and other places producing regional delicacies. No matter what your interests, or what kind of holiday you’re looking for, Rome will be an enjoyable destination.

Day 1

Day 1 - Arrival in Rome

After you land at Rome's Fiumicino airport you will be met in the arrivals hall by a driver holding a sign with your name on. The journey to your accommodation in the center of Rome should take around an hour.

Day 2

Day 2 - Your First Full Day in Rome

Golf Cart Around Rome Private Tour

Golf Cart Around Rome Private Tour

Included in your vacation package price.

The Private Rome Golf Cart Tour sounds like an incredible way to explore the Eternal City! It offers a unique and comfortable way to experience Rome's iconic sites while learning about its fascinating history. Riding in an eco-friendly golf cart not only allows for convenience but also minimizes the physical strain of touring the city on foot. With a knowledgeable guide at the helm, travelers can make the most of their time by efficiently navigating through Rome's streets while uncovering hidden gems and significant landmarks. The personalized nature of a private tour ensures that visitors can pause for photos, take in the sights, or even enjoy a quick refreshment break, enhancing the overall experience. This blend of culture, history, and fun promises an engaging and enriching adventure through one of the world's most captivating cities!


Activity Level : Easy
Duration : 3 hours

Day 3

Day 3 - Your Second Full Day in Rome

Gladiator's Gate Special Access Colosseum Group Tour

Boldly Go to Ancient Rome

Please ask your travel advisor for the cost to add this to your package

No trip to Rome is complete without a journey into the city's ancient past. From the secrets of the Colosseum to the wonders of the Roman Forum to the hidden treasures of the Palatine Hill, the essence of Ancient Rome awaits to fascinate you.


Activity Level : Moderate
Duration : 3 hours 15 minutes

Day 4

Day 4 - Traveling to Thessaloniki by Airplane

To get from Rome to Thessaloniki, the best option is to take a flight on a low-cost airline. On your day of departure, a driver will pick you up at your accommodation and bring you to the airport for your flight.

Suggested Flight: Departure: Arrival: Please note that the flight included in your package is non-refundable. If you prefer more flexibility, we can check the flexible fares for you and let you know about the price difference. Moreover, the price of the flight is subject to change until we receive your deposit.

We also offer the following excursions in Rome

Colosseum and Roman Forum Private Tour
Light3 hours
Cooking Class in the Jewish District Group Tour
Easy2.5 hours
Crypts, Bones and Catacombs - Rome Group Walking Tour
Light3 hours
E-bike Along the Appian Way Private Tour
Moderate3 hours

3 Nights in Thessaloniki

3 Nights in Thessaloniki

4 days in Thessaloniki
4 days in Thessaloniki

3 Nights in Thessaloniki

Thessaloniki, Greece’s second largest city, offers urban sophistication and cultural diversity. With its ancient roots, Thessaloniki, also known as Saloniki and Salonica, offers a delightful amalgam of historical, culinary, and cultural activities. Due to its prime location, this city has had many rulers, from the Venetians to the Saracens to the Ottomans. For centuries, Thessaloniki was Byzantium's second largest and wealthiest city, after Constantinople, and it even served as a "co-capital" at times. Thessaloniki was a haven for Sephardic Jews fleeing Spanish persecution, a group that for a time formed most of the city's population, and which is still visible in the city's diverse architecture, music, and cuisine. While compact in size, Thessaloniki is home to 15 UNESCO-listed monuments. The expansive harbor is its heart and soul, offering magnificent views of Thermaikos Bay. This urban waterfront is the center of many of Thessaloniki’s happenings, as well as the location of its iconic landmarks, such as the White Tower and the Monument of Alexander the Great. Its former warehouses now house the Museum of Contemporary Art, the Thessaloniki Museum of Photography, and the Thessaloniki Cinema Museum.

Thessaloniki, Greece’s second largest city, offers urban sophistication and cultural diversity. With its ancient roots, Thessaloniki, also known as Saloniki and Salonica, offers a delightful amalgam of historical, culinary, and cultural activities. Due to its prime location, this city has had many rulers, from the Venetians to the Saracens to the Ottomans. For centuries, Thessaloniki was Byzantium's second largest and wealthiest city, after Constantinople, and it even served as a "co-capital" at times. Thessaloniki was a haven for Sephardic Jews fleeing Spanish persecution, a group that for a time formed most of the city's population, and which is still visible in the city's diverse architecture, music, and cuisine. While compact in size, Thessaloniki is home to 15 UNESCO-listed monuments. The expansive harbor is its heart and soul, offering magnificent views of Thermaikos Bay. This urban waterfront is the center of many of Thessaloniki’s happenings, as well as the location of its iconic landmarks, such as the White Tower and the Monument of Alexander the Great. Its former warehouses now house the Museum of Contemporary Art, the Thessaloniki Museum of Photography, and the Thessaloniki Cinema Museum.

Day 4

Day 4 - Arrival in Thessaloniki

Welcome to Northern Greece! A driver will be waiting for you in the arrivals hall to take you to your accommodation in Thessaloniki.

Day 5

Day 5 - Your First Full Day in Thessaloniki

Thessaloniki Walking Half Day Private Tour

Thessaloniki Walking Half Day Private Tour

Included in your vacation package price.

Cosmopolitan Thessaloniki has been a crossroad of Greek, Jewish, Turkish, and Slavic cultures for millennia (indeed, in the late 19th century, it was even the only European city where Jews were in the majority). Let a local guide show you around, and help you discover why the city was a treasure fought over countless times, as you take in the White Tower, Galerius Arch, Rotunda monument, Old Town, and city walls, where you can take in a memorable view of the city!


Activity Level : Light
Duration : 4 hours

Laladika, Nightlife Central

Suggestion to explore on your own

Laladika is the nightlife hotspot of Thessaloniki, attracting locals, students, and tourists every night. Following the most popular shopping street of Thessaloniki, Tsimiski Avenue, a five-minute walk from Aristotle’s Square, the district of Laladika is a beautiful area home to colorful neoclassical buildings full of bars, restaurants, traditional taverns and clubs, mixing the traditional and new.

Laladika, Nightlife Central

Day 6

Day 6 - Your Second Full Day in Thessaloniki

Thessaloniki City Full Day Private Tour

Museums Aplenty

Please ask your travel advisor for the cost to add this to your package

Greece's second largest city, Thessaloniki is stuffed with cultural and artistic institutions. The Archaeological Museum has a wide collection of findings from the Archaic period through the Classical and Hellenistic periods to the Roman era. The War Museum houses more than 10,000 artifacts from various wars, especially from the 20th century, including the Balkan Wars, WWI, WWII (and the civil war that followed) and the Greek War of Independence. The White Tower Museum is devoted to the city's history, while the award-winning Museum of Byzantine Culture focuses on life during and following the Byzantine era. As the Ottoman Empire broke up, Macedonia, and Thessaloniki itself, was a prize coveted by many, and the Folklore and Ethnological Museum of Macedonia and the Museum for the Macedonian Struggle (not to be confused with its identically named counterpart in Skopje) cast light on why even the word "Macedonia" is a politically loaded word to this day.


Activity Level : Light
Duration : 8 hours

Day 7

Day 7 - Traveling to Istanbul by Airplane

To get from Thessaloniki to Istanbul, the best option is to book a flight on a low-cost airline. On your day of departure, a driver will pick you up at your accommodation and bring you to the airport for your flight. Suggested Flight: Departure: Arrival: Please note that the flight included in your package is non-refundable. If you prefer more flexibility, we can check the flexible fares for you and let you know about the price difference. Moreover, the price of the flights is subject to change until we receive your deposit.

Istanbul by Air
We also offer the following excursions in Thessaloniki

Byzantine Walks - Meteora Monasteries Private Tour
Light11 hours
Into St.Paul's Footsteps: Amfipoli, Filippi and Kavala Private Tour
Light10 hours
Macedonian Tresures: Pella, Edessa, and Vergina Private Tour
Light8 hours
Meteora Day Trip from Thessaloniki by Train
Moderate12 hours

3 Nights in Istanbul

3 Nights in Istanbul

4 days in Istanbul
4 days in Istanbul

3 Nights in Istanbul

Istanbul is a sprawling city of 15+ million people that contains two continents and a wealth of history. From the Byzantines to the Ottoman Empire to the modern Turkish Republic, Istanbul has seen the churn of history throughout the centuries, and the remains of all these eras live alongside the ever-changing face of contemporary Turkey. The Hagia Sophia, formerly a Byzantine church, an Ottoman mosque, and a Republic-era museum, before reverting recently to a mosque, is Istanbul’s most significant site, located in the heart of Sultanahmet. The hip districts of Beyoglu, Besiktas, and Kadikoy overflow with restaurants and cafes, and the central boulevard Istiklal Caddesi serves as the main artery for shopping, food, and nightlife in this buzzing city.

Istanbul is a sprawling city of 15+ million people that contains two continents and a wealth of history. From the Byzantines to the Ottoman Empire to the modern Turkish Republic, Istanbul has seen the churn of history throughout the centuries, and the remains of all these eras live alongside the ever-changing face of contemporary Turkey. The Hagia Sophia, formerly a Byzantine church, an Ottoman mosque, and a Republic-era museum, before reverting recently to a mosque, is Istanbul’s most significant site, located in the heart of Sultanahmet. The hip districts of Beyoglu, Besiktas, and Kadikoy overflow with restaurants and cafes, and the central boulevard Istiklal Caddesi serves as the main artery for shopping, food, and nightlife in this buzzing city.

Day 7

Day 7 - Arrival in Istanbul

After your flight arrives at Istanbul Airport, a driver will meet you at the airport to bring you to your accommodation. The drive from the airport lasts around 50 minutes.

Day 8

Day 8 - Your First Full Day in Istanbul

Highlights of Istanbul Full-Day Private Walking Tour

The Best of Istanbul in a Day

Included in your vacation package price.

Today, you are about to delve into the rich history of a city like no other, a city that sits at the crossroads of East and West, the enchanting Istanbul. During this full-day tour, you will visit top-rated attractions, such as the Topkapi Palace and Hagia Sophia. Moreover, you will marvel at breathtaking views of the city from some of the best viewpoints in Istanbul. You will end the tour among locals in one of the world's most famous markets, the colorful and historic Grand Bazaar.


Activity Level : Strenuous
Duration : 7 hours

Day 9

Day 9 - Your Second Full Day in Istanbul

Tasting Istanbul

Suggested activities for an additional cost, depending on your choice

At the crossroads of East and West, Istanbul is one of the most fascinating and diverse cities. With influences from the many different people that co-existed within the Ottoman Empire for centuries on end, Turkish food is equally diverse. Apart from world-renowned savory and sweet specialties, such as kebabs or baklava, Turkish cuisine features countless other delicious dishes. Alternatively, join a small-group cooking class to learn how to prepare some staple Turkish specialties and bring your new skills back home with you, keeping Istanbul in your heart forever in the most delicious way.

Istanbul Small Group Cooking Class

Istanbul Small Group Cooking Class

Suggested activities for an additional cost, depending on your choice

It’s time to roll up your sleeves and tie on a cooking apron. During this 3-hour cooking class, you will learn how to prepare five delicious authentic Turkish recipes and then enjoy them for lunch or dinner in a traditional restaurant with a glass or two of local wine. This is undoubtedly one of the most fulfilling cultural experiences you can enjoy in Istanbul.


Activity Level : Easy
Duration : 3 hours

Sweet Tooth of Istanbul Private Walking Tour

Sweet Tooth of Istanbul Private Walking Tour

Suggested activities for an additional cost, depending on your choice

Explore Istanbul's diverse culinary scene on a tour spanning its various districts, even venturing to the Asian side. Delight in authentic local flavors, particularly the rich variety of desserts. Led by an experienced guide, absorb the city's history, culture, and gastronomy as you stroll through its vibrant streets. Immerse yourself in the city's flavors, stories, and sights on this enriching excursion.


Activity Level : Strenuous
Duration : 6 hours

Day 10

Day 10 - Departure Day

A driver will pick you up at your Istanbul accommodation and drop you off at the airport for your departing flight. The journey to the airport takes around 50 minutes.

We also offer the following excursions in Istanbul

Backstreets of Istanbul Private Walking Tour
Strenuous8 Hours
Bazaars and Inns of Ottoman Empire Half Day Private Tour
Strenuous4 hours
Bosphorus Tour on a Private Yacht
Light2 hours
Cumalikizik and Bursa Private Full Day Tour
Moderate11 hours 30 minutes

What's Included

Here are all the services provided as part of your complete vacation package. See what every JayWay trip includes.
Please let us know if you'd like to upgrade any transfers or add any additional tours or excursions to your itinerary.

Rome

3 Nights Accommodation
Breakfast (hotels only)
Rome Fiumicino Airport Transfer
Golf Cart Around Rome Private Tour
Rome Ciampino Airport Transfer
Rome - Thessaloniki Flight

Thessaloniki

3 Nights Accommodation
Breakfast (hotels only)
Thessaloniki Airport Transfer
Thessaloniki Walking Half Day Private Tour
Thessaloniki Airport Transfer
Thessaloniki - Istanbul Flight (Non-Refundable)

Istanbul

3 Nights Accommodation
Breakfast (hotels only)
Istanbul Airport (IST) Private Transfer
Highlights of Istanbul Full-Day Private Walking Tour
Istanbul Airport (IST) Private Transfer

package excludes:


  • Flights to and from Europe.
  • Tips for Tour Guides, Drivers and Local Reps.
  • Meals (other than breakfast if included in room rate and meals listed as included in food tours and excursions, unless explicitly stated otherwise).
  • Parking fees for your Rental Car (if you are booking one with us) unless otherwise indicated. Some hotels provide free parking facilities.
  • Travel Insurance. See the insurance link on our website
Benefits of Traveling with JayWay

A JayWay vacation is more than the sum of its parts. Our team work tirelessly to ensure your experience is memorable for all the right reasons. Your trip is personalized to maximize your enjoyment. You're taken care of every step of the way.

A Travel Advisor who speaks your language

We will make sure that all your requirements and interests are taken into account in preparing your itinerary.

A totally tailored itinerary for your vacation

Your trip is customized for you by  an experienced trip planner and an expert on the region.

A choice of hand-picked hotels and excursions

We've personally inspected and tested all the hotels and local tour providers we work with to ensure quality.

Detailed pre-trip preparation to make the most of every day

Your Europe-based Tour Manager will be in touch by email and phone a month before you arrive to finalize timings.

On-trip Concierge Service to smooth out any bumps in the road

Your tour manager is at your service throughout your journey. We'll provide a local SIM so you can stay connected.

Personalized Guest Page to make sure you're not missing out

Packed with detailed information and recommendations curated by locals on the best things to do, see and eat.
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