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Retracing The Footsteps of Roman Emperors

10 Days / 9 Nights

Rome, Thessaloniki, Istanbul

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

First Time in Rome

Included in your vacation package price.

You'll be introduced to the layout and history of Rome today. Riding in a golf cart through the picturesque cobbled streets of the historical center of Rome flanked by beautifully built aristocratic palazzi, your eyes will be enchanted by the white marble churches and they will feast on the famous variety of colors that make Rome unique. This tour is designed to get you oriented in the city and the main sights in the great center of Rome without duplicating the city's signature attractions such as the Colosseum and Roman Forum and the Vatican.

Rome By Golf Cart Private Tour

Rome By Golf Cart Private Tour

Included in your vacation package price.

Making our way by golf cart through the picturesque cobbled streets of the historical center of Rome flanked by beautifully built aristocratic palazzi, our eyes will be enchanted by the white travertino marble churches and they will feast on the famous variety of colours that make Rome unique. This tour is designed to get you oriented in the city and the main sights in the great center of Rome.

On this tour you'll learn all about Villa Borghese, Piazza di Spagna and the Spanish Steps, the Pantheon, Piazza Farnese and Piazza Navona as well as getting a little outside the obvious and crossing over the Tiber to the Trastevere neighborhood.


Activity Level : Easy
Duration : 3 Hours

Rome Private Bike Tour

Rome Private Bike Tour

Included in your vacation package price.

This three-hour bike tour is a great way to see Rome and get a little exercise while you're at it. So much of the city is accessible on two wheels, and you'll be able to cover much more ground than if you were walking. Your guide is insightful and entertaining and will tell you all about the places you'll see, which include the most famous monuments in the city.


Activity Level : Moderate
Duration : 3 hours

Day 3

Day 3 - Your Second Full Day in Rome

VIP Colosseum Underground, Roman Forum & Palatine Hill Group Tour

Boldly go to Ancient Rome

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

You'll have the chance of going where very few tourists have gone before, on a small group tour that features VIP access to the closed-off areas of the Colosseum so you can get a unique perspective on this most iconic of Ancient Roman sites. You'll visit the Colosseum underground, walk on the arena floor and admire the views from the third tier. Aside from these limited-access areas you'll also be touring the main parts of the Colosseum (with the plebeians!) along with the Roman Forum and Palatine hill, all with an expert guide.


Activity Level : Moderate
Duration : 3.45 hours

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

Tivoli Villas & Gardens Private Tour
Light6 hours
(FOR PRIVATE GROUP) Full Day Rome Colosseum and Walking Tour with Lunch Included
Light7 hours
4 Day Private Gourmet Tour - Guide and Driver
Light4 Days
Colosseum and Roman Forum Private Tour
Light3 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

The Nymph of the Thermaic Gulf

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!

Thessaloniki City and Museum Private Walking Tour

Thessaloniki City and Museum Private Walking 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

Thessaloniki Evening Private Tour

Thessaloniki Evening Private Tour

Included in your vacation package price.

Discover vibrant neighborhoods of Thessaloniki, including their lifestyles and culture. Visit a mix of modern and local venues and enjoy interesting stories shared by your local host. Learn how to make a cocktail with local ingredients, and taste unique, specially selected drinks and bites. This experience is perfect for relaxation after a busy day and for those who like exploring the city in the evening.


Activity Level : Light
Duration : 4 hours

Day 6

Day 6 - Your Second Full Day in Thessaloniki

Thessaloniki City and Archaeological-Byzantine Museum 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.

We also offer the following excursions in Thessaloniki

Byzantine Walks - Meteora Monasteries Private Tour
Light9 hours
Into St.Paul's Footsteps: Amphipoli, Philippi and Kavala Private Tour
Light8 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 6-hour 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. End the tour among locals in one of the world's most famous markets, the colorful and historic Grand Bazaar.


Activity Level : Moderate
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. One of the best ways to get to know Istanbul is through the city's unique tastes during a full-day private tour that will take your tastebuds on an unparalleled culinary trip. From the mesmerizing scents of spices to the sweet aromas of butter and sugar, follow your guide on a quest to uncover the city's secrets through the most authentic tastes. 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.

Tastes of Istanbul Private Tour

Tastes of Istanbul Private Tour

Suggested activities for an additional cost, depending on your choice

From kebabs to baklava to Turkish delight, Turkish food is famous all over the globe. Yet, there is so much more to Turkish food than just these staple delicacies. During this thorough food tour of Istanbul, your knowledgeable guide will take you off the beaten track to sample the real tastes of Istanbul and experience delicious Turkish specialties, many of which you probably never knew existed.


Activity Level : Moderate
Duration : 6-7 hours

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

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
Moderate8 Hours
Bazaars and Inns of Ottoman Empire Half Day Private Tour
Light4 hours 30 minutes
Bosphorus Tour with 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
Rome By Golf Cart Private Tour
Rome Private Bike Tour
Rome Ciampino Airport Transfer
Rome - Thessaloniki Flight (Non-Refundable)

Thessaloniki

3 Nights Accommodation
Breakfast (hotels only)
Thessaloniki Airport Transfer
Thessaloniki City and Museum Private Walking Tour
Thessaloniki Evening Private Tour
Thessaloniki Airport Transfer
Thessaloniki - Istanbul Flight (Non-Refundable)

Istanbul

3 Nights Accommodation
Breakfast (hotels only)
Istanbul Airport Transfer
Highlights of Istanbul - Old City Walk Private Tour
Istanbul Airport 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.

Glowing Reviews from Our Guests

5 / 5
Average of our Guest's Ratings of vacation packages including these destinations
Review by Maya & Jack
Maya & Jack
California

JayWay Travel did a great job of helping to create a custom trip with introducing me and my son to places that fit our interest, all the coordination of travel and places to stay along with the local tours was amazing and saved me so much work and stress...I could not have done this on my own.

JayWay Travel did a great job of helping to create a custom trip with introducing me and my son to places that fit our interest, all the coordination of travel and places to stay along with the local tours was amazing and saved me so much work and stress...I could not have done this on my own.

Year : 2022
Visited : Italy, Greece
Itinerary : Rome, Athens, Delphi, Meteora, Thessaloniki, Athens
Rating :
5 / 5
Year : 2022
Visited : Italy, Greece
Itinerary : Rome, Athens, Delphi, Meteora, Thessaloniki, Athens
Rating :
5 / 5
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