Tale of Two Empires: Italy & Greece Historical Tour

A 16 day trip to Greece & Italy 
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From the Pantheon to the Parthenon, Florence to Venice to Olympia, this is a journey to the heart of empire and civilization. You will explore places that changed the world, including the oldest Greek ruins and medieval Tuscany. Immerse yourself in the atmosphere of cities that live and breathe history. Lose yourself in archaeological sites and the redolent wonder of ruins. These are the countries of legend, and this two-week journey will take you far back in time.

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General Information

Venice Grand Canal in Italy.
View of an orthodox cathedral in Thessaloniki, Greece
Detailed Itinerary

Places Visited 

Rome, Colosseum, Pantheon, Vatican City, Vatican Museums, Piazza Navona, Trastevere, Pisa, Leaning Tower of Pisa, Florence, Florence Cathedral, Uffizi Gallery, Palazzo Vecchio, Tuscany, Venice, Murano, Burano, Torcello, Doge’s Palace, Saint Mark’s Basilica, Piazza San Marco, Athens, Acropolis, Parthenon, Acropolis Museum, Agora, Plaka, National Archaeological Museum, Olympia, Mani Penisula, Monemvasia, Peloponnese, Mystras, Sparta, Nafplio, Mycenae, Epidaurus

Departure Dates 

Please inquire for a custom quote. The price is customized based on final accommodation choices, travel dates, and other custom preferences.

Detailed Itinerary 

Day 1: Rome – Soaking Up the History

Your first footsteps in Rome will feel special. The Colosseum’s archways glow in the afternoon light, and the Pantheon is mere footsteps from your hotel. Everywhere you look there will be a place of legend. Rome is also a lived-in city that doesn’t stay frozen in the past. Locals hang out on the piazzas, people walk past with gelato ice creams, and the new juxtaposes with the old. You’ll be greeted at the airport and transferred to a very central hotel. The guide provides a brief orientation, and you have the evening free to walk around ancient Rome to enjoy your first impression of the place where so much started.

What’s Included: airport transfer, accommodation

Day 2: Rome – Highlights of Ancient Rome

Today your footsteps will echo off the marble as you explore the Colosseum, the great memoir to Roman entertainment. Then, the same steps fall silent in the Pantheon, a place that feels sanctified as it whispers of the past. There are other iconic remnants to Ancient Rome nearby that tell another tale from two millennia ago. There are also newer attractions in Rome as well, like the Spanish Steps and Trevi Fountain. Spend the day taking all this in while a local historian guide helps to separate fact from fiction. The day will take you beyond the postcards to reveal the atmosphere of these places from history.

What’s Included: accommodation, tour, breakfast

Day 3: Rome – Exploring the Vatican and Ostia Antica

This morning, while you stand before St. Peter’s Basilica you will certainly be awed. It seems like there are a hundred columns all around you as St. Peter’s Square is perhaps the most impressive of all Italian piazzas. When you travel into the Vatican Museums, you will feel the mystery of Catholic art with so much left unspoken in vivid frescoes and sculptures. From Raphael’s Rooms to the Sistine Chapel, you can easily imagine a medieval time. This afternoon, you will picture a far older history in Ostia Antica, a place of ruined columns and crumbling city streets. This was once a rival to Rome, and you’ll spend time imagining what it would have been like to live here 2000 years ago.

What’s Included: accommodation, tour, breakfast

Day 4: Florence – Past the Tower to the Domes

Today, a tower leans in a square that beckons to you, and a city in Tuscany opens its arms. In Pisa, the history is so much more than a single postcard image. It will be a stop on your journey to Florence, a city that feels a million miles from Rome. In the 15th and 16th centuries, Florence was the heart of the artistic world. The locals are very proud of the history, and you’ll find a city that’s been polished up to venerate past glories. Arrive in the afternoon and take a tour of the key sights, from the square where Michelangelo’s David originally stood to the inspiring churches of the High Renaissance.

What’s Included: accommodation, tour, breakfast

Day 5: Florence – Renaissance Art and Architecture

The day will begin with a relaxed morning as you sip a cappuccino on an al fresco terrace while listening to the bells chime. Florence is a city best explored through a lens of food or art. Explore a private gallery, where some of the early Renaissance works take pride in the city. Discover the legendary sculptures and paintings as you learn how they influenced the world. View the city through the eyes of the architects, seeing how early ideas morphed into what Florence is today. Then, rest and relax on a piazza while you watch the city roll past you.

What’s Included: accommodation, tour, breakfast

Day 6: Venice – History of Venice Gondola Tour

The high-speed train to Venice will be a good time to relax and reflect on what you’ve experienced so far. When you arrive in the City of Canals, you’ll be transported back into the early Middle Ages. During this time, the Venetian Republic was the most powerful place on the planet. So much of old Venice remains and it is best discovered in a time-honored fashion, with a gondola ride down the canals. Cruise past glamorous townhouses and beneath iconic bridges. Listen to stories as you drift past a palace. Feel what it was like to travel here a thousand years ago. In the end, you’ll embrace the romance that emanates from this corner of the world. While there are snippets of Rome and Florence across the world, there remains nothing like Venice.

What’s Included: accommodation, tour, breakfast

Day 7: Venice – Sailing to Venetian Islands

Wake up in the heart of Venice for another relaxed day. You can begin your morning by exploring on foot. Stop in an old-world coffee house, descend into the dungeons of Doge’s Palace, and walk across 1200-year-old bridges. This afternoon, you will sail beyond the central canals on a small boat that takes you to the islands of Murano, Burano, and Torcello. Dine on the water’s edge, learn about glass blowing, sail back to Venice, and watch the colorful houses come into sharp focus. Spend the evening amid history as Venice is a city where almost everything comes from the Middle Ages. Walk across a piazza to appreciate the grandeur of the city that was once at the center of the known world.

What’s Included: accommodation, tour, breakfast

Day 8: Athens – Welcome to Ancient Greece

When you fly direct to Athens, the atmosphere will change completely. You sense it in the people you meet, the food you eat, and the places you go. Aromas and sounds have changed, but the history is even older than Italy. Meet with a guide over lunch for an informal introduction to what has happened in this city over the last 3000 years. Tomorrow you’ll visit the historical sights, but today you’ll walk the streets and see how Athens has evolved over the centuries. With a guide on hand, you will discover how the ancient civilization has shaped today, notably on the cobbled streets of Plaka around your hotel. The guide will provide many recommendations for dinner, and there’s always a tantalizing contrast in flavors after your time in Italy.

What’s Included: accommodation, tour, breakfast

Day 9: Athens – Atop the Acropolis and Amid the Ancient Agora

The next day, you’ll stand atop the Acropolis and look down on the city. A breeze ruffles past your ears as the columns rise to attention. The Athenian temples are in a remarkably good state at 2500 years old with detail etched into the sun-scorched rock. You’ll explore the highlights of one of the world’s oldest cities, including the Golden Age temples and the enigmatic Parthenon. The Acropolis Museum is contemporary from the outside but packed with treasures within, which helps to complete a picture of early Greek civilization. It will take four to five hours to see it all, and there’s a lot of walking. Then, relax at a family-run taverna this evening, and enjoy a very Greek ambiance.

What’s Included: accommodation, tour, breakfast

Day 10: Olympia – 2700 Years Of History Come Alice

Travel across Greece to enter the mountains where the road twists rapidly as it reaches Olympia. The remains of temples stand amid the lush temperate forest. Columns line walkways through the ancient city. While the architectural style is similar to Athens, the experience is completely different. Olympia is frozen in time, a vast archaeological site compared to a lived-in city. Take a walk through the temples and athletic venues with a local guide. Find places of solitude as you wander on rock that was laid 2,700 years ago. Then, spend the night in the mountains at a boutique retreat that’s as hidden from the world as Olympia has become.

What’s Included: accommodation, tour, breakfast

Day 11: Mani Peninsula – Unique Villages and Tower Houses on the Coast

Travel forward in time on today’s drive that takes you south to the Mani Peninsula, where traditional villages hang high over the water and pyrgospita illustrate their age. These unique tower houses are suggestive of a time of clan wars, which took place long after Ancient Greece has disintegrated. Eat with the locals in a village tavern, go off the beaten path to places few tourists visit, and discover how history dominates the everyday on the Mani Peninsula. Once again you’ll remark at how distinctive the experience can be, as well as how relaxing it can be to be so immersed in history. Today you don’t go looking for sites. They are everywhere and the villagers invite you with open arms.

What’s Included: accommodation, tour, breakfast

Day 12: Monemvasia – A Dramatic Medieval Town on the Aegean

Follow the Aegean coastline, and a giant rock will guide you. It rises dramatically from the turquoise of the sea and provides a compass point for the next two days. This rock is an island, and behind the vertical cliff there’s a medieval walled town. Isolated by nature and untouched by time, Monemvasia breathes the confluence of historical eras. Byzantine remains juxtapose with grand Ottoman architecture. Venetian history pops up in the Upper Town. There’s a romance to the streets and a cozy sense of escaping the world. When you arrive in Monenvasia, the guide will give you a tour of the key sights as they help you piece together all the influences. The rest of the day will be free for you to swim in the Aegean, hike up the rock, or enjoying a cooking demonstration.

What’s Included: accommodation, tour, breakfast

Day 13: Nafplio – Byzantine Churches, Legendary Sparta and Fortress Nafplio

Just like yesterday, there will be a confluence of narratives and histories as you travel into Peloponnese, the historic south of Greece. Mystras is almost haunting with a fortress in an evocative state of disrepair. Early Byzantine churches are located nearby, mysterious and magical as they provide a link to centuries as yet unexplored on this historical tour. There’s not much left of Sparta but there’s no doubting the legend, and it’s always fun to hear stories from a local guide. Then, your day ends in Nafplio, another fortress-topped town that overlooks the water. Greek wine and ouzo tastings provide an insight into local culture as the taverns continue your affair with local delicacies.

What’s Included: accommodation, tour, breakfast

Day 14: Nafplio – The Mysteries of Mycenae

The story of Mycenae will be the oldest legend on your tour. Enter through the Lion Gate and admire the cyclopean walls, while you wonder how all this was built a millennia before the Parthenon took shape. Discover the domes of the tholos-styled tomb and use Mycenae to explore the foundations of Ancient Greece. In the afternoon, travel back to Nafplio. Wander the atmospheric alleyways, take a boat to a castle island in the harbor, or hike up to the fortress for superb late-afternoon views.

What’s Included: accommodation, tour, breakfast

Day 15: Epidaurus to Athens – The Famous Healing Center and Theater; Back to Athens

Today you’ll visit the earliest of the healing centers, Epidaurus, a place to learn about the roots of medicine and theater. Stand in the enormous theater, continue to admire the columns, and take a late lunch with views over the ruins. It’s not too far back to Athens from here and you return to Plaka, where the family-run taverns are a good place to celebrate what you’ve experienced in both Italy and Greece.

What’s Included: accommodation, tour, breakfast

Day 16: Athens – Departure

With a full morning in Athens, you will end this historical tour at the National Archaeological Museum. Here there are marble masterpieces, golden legends, and bronze snippets, taken from all across Greece and beyond. It’s impossible to explore all of Ancient Greece in just nine days, but this museum will help piece together parts of the jigsaw you didn’t get to see. Late check-out has been arranged so you can return to the hotel and freshen up before a private airport transfer and your outbound flight.

What’s Included: airport transfer, tour, breakfast


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.