Highlights of Greece and Italy for 2020-2021

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Beautiful windmill villa in Oia, Santorini, Greece
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Total Trip:

15 Days
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Countries Visited:

Greece, Italy, Vatican City
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Places Visited:

Naples, Sorrento, Bay of Naples, Isle of Capri, Pompeii, Mount Vesuvius, Teatro di San Carlo, Rome, Vatican City, Athens, Nauplia, Epidaurus, Mycenae, Santorini,

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Departure Dates:

Dates are flexible and customizable for private departures.
Footsteps on cobbles, aromas of coffee, back street pizzerias, and whitewashed villages are the charms that seal your experience across Italy and Greece. This highlights tour brings many of the iconic sights including Rome, Athens, Capri and Mycenae, your handcrafted selection of destinations will evoke the small pleasures that make these countries so unique while Sorrento, Naples, Nauplia and Santorini all provide their distinctive atmospheres and pleasures. 

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Customizable Itinerary

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Day 1

Naples to Sorrento – Sweeping Water Views and Medieval Cobbles

Land in Naples and travel along the coast as Sorrento awaits, a town of colorful houses perched on the cliffs above the Mediterranean. Admire the sweeping water views from your hotel and go for a stroll through the old cobbled center. At any hour of the day, you can smell the aroma of strong espresso, but when the lanes open, you will also find a bustling piazza with cafes lining the square and all of the smells intensified. For easing into a vacation, there is nowhere quite like Sorrento. So relax, take your time and enjoy your first impressions of Italy, be inspired by the architecture, and keep gasping at the town’s location on the cliffs.

What's Included:

included

Transfer

included

Accommodation

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Day 2

Sorrento – Exploring the Bay of Naples and Isle of Capri

Rugged and rounded rocks dominate Capri, an island that has been wowing visitors since the time of the Roman Republic. Sail across the Bay of Naples, passing shards of rock that stand like nature’s sentinels. Stop in the island’s caves and grottoes, stroll through the small village, and then ride on the funicular to Capri’s upper town, where you continue to celebrate the allure of old-world Italy. There are gardens to discover, pizzerias on the piazza, and so many Italian treasures on an island of vast natural splendor. The wind carries you back to Sorrento, and a second evening in the old town is yours to enjoy to be immersed in a classically Italian atmosphere.

What's Included:

included

Accommodation

included

Tour

included

Breakfast

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Day 3

Pompeii to Naples – Legendary Ruins, Mount Vesuvius and a Modern Masterpiece

Traveling back to Naples you can stop at Pompeii, a legendary ruined city that has been excavated from the ashes of Mount Vesuvius. Villas and temples line broad streets, their columns stretching out towards the mighty volcano peering down. Take a closer look at Vesuvius and its history, and then continue the journey north to Naples, a city that’s become an unexpected masterpiece of Italian travel. Naples is more than the birthplace of pizza, as it is also a city of inspiring art and architecture and a place of wonderfully local experiences. The guide will provide an orientation, gathering your bearings for some self-guided exploration in the late afternoon and evening. Take a walk around, and you will find Naples to be a very local city, where you can live and breathe an Italy mostly untouched by tourism.

What's Included:

included

Accommodation

included

Tour

included

Transfer

included

Breakfast

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Day 4

Naples – Art and Architecture of a Surprising Italian Masterpiece

Stand on Piazza del Plebiscito and admire the building and see how their grandeur stretches out towards the broad boulevards. Stand within the sanctuary of the royal palace, and then go walking into staterooms where great works of art fill entire walls, and it is amazing the attention to detail. Also on a guided tour of Naples, you can explore the old theater, Teatro di San Carlo where gold glistens and the extravagance of a past age is everywhere to see. Keep walking through Naples, your guide taking you into the back streets where the smell of cafes and pizzerias keeps you entertained. Move into the afternoon, and there is a choice of art galleries to explore, each telling a tale of an art world that is just as impressive as the one in Rome and Florence.

What's Included:

included

Accommodation

included

Tour

included

Breakfast

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Day 5

Rome – First Footsteps in the Eternal City

Take the fast train to Rome and take your first steps into the city of legend with your hotel located in the old heart of empire and civilization. This first day in the Eternal City is at your leisure for a chance for you to explore without a map. Almost everywhere you turn, there is a new impression, the modern and antiquated juxtaposed on streets that grab all your senses. Sometimes it appears that you are lost, turning corners onto streets that all look the same. But then you make one more turn, and a towering monument comes into view, perhaps Trajan’s Column or the Colosseum. And then you realize what it means to be in a city with over 2,000 years of history.

What's Included:

included

Accommodation

included

Tour

included

Breakfast

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Day 6

Rome – Highlights of Rome

Trajan’s Column rises like a legend from antiquity. Piazza Venezia has such elegance and spreads enchantment everywhere you look. The Arch of Constantine and Arch of Titus bring details etched all over the facades. Move next to the Temple of Venus, columns suggestive of what used to stand there before going onwards to the Colosseum and you can almost hear the atmosphere of yesteryear, chatter and footsteps echoing around walls that have stood for so long. With your engaging local guide, the Eternal City really comes alive with so many whispers sneaking out from the walls, each with their own accompanying story. Today’s tour celebrates the famous icons of Rome, bringing you eye to eye with monuments that have defined the world.

What's Included:

included

Accommodation

included

Tour

included

Breakfast

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Day 7

Rome – Vatican City Exploration

Walk a little further through Rome, and you enter a new state, the Vatican City opening up in all its pomp and excess. Stand beneath the Sistine Chapel ceiling and look up at Michelangelo’s masterpiece, and then stroll through the Vatican Museums to connect the dots of art history with so many statues and canvases from around the Christian world. It is best to go early, just as the doors open, so you can view the art before the midday crowds start blunting the experience. Enjoy your lunch on a square that looks up at the Pope’s residence, and then return to the back streets for a free afternoon in Rome.

What's Included:

included

Accommodation

included

Tour

included

Breakfast

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Day 8

Athens to Nauplia – On the Seaside in Greece

Fly across the Mediterranean to find that Greece has a fragrance entirely different to Italy. Touch down in Athens and travel to your small resort town on the seaside, Nauplia your base for the next two nights. Along the way, you can stop to admire the Corinth Canal, where the color of blue is quite remarkable. Stretching along the hillsides, Nauplia looks a little like Sorrento at first glance. But as you walk around and drink at the cafes, you will find the town to be distinctively Greek. Smells, sounds, the subtle feelings that exist down each street are very different in the sultry Mediterranean air.

What's Included:

included

Accommodation

included

Tour

included

Transfer

included

Breakfast

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Day 9

Nauplia – Discovering Epidaurus and Mycenae

Take a short morning walk along the harbor, the soft sound of lapping water accompanying you past grand yachts. Nauplia dates to the Middle Ages, but today you can go further back in time in Epidaurus nearby, a spellbinding old city with an amphitheater that is on a phenomenal scale like no other in Greece has been so expertly preserved. Mycenae maintains the feeling of times past, thick slabs of stone lining walkways and creating archways, imposing ruins showing the splendor of the Mycenaean civilization. That is 3,400 years ago now, but on an archaeological tour, you can still explore the artistic expression of a people that left a lasting legacy on the world. Of course, it is a UNESCO World Heritage Site, as such a majestic citadel could not be anything but.

What's Included:

included

Accommodation

included

Tour

included

Transfer

included

Breakfast

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Day 10 - 11

Athens – Breathing in the Antiquated History

It will be a short drive back to Athens, and your local guide will narrate the journey through a bustling old capital. Artisanal plates spill out from small stores as traders shout down the narrow, cobbled lanes. The Acropolis looks down, glimpsed when you come to a crossroads in the oldest part of the city. As you walk, you will pass great odes to the past with the Olympic Stadium, Syntagma Square, and the Arch of Hadrian, and then move upwards to the Temple of Zeus. On your first day in Athens, you will stay beneath the Acropolis where the streets come alive with everyday life. You will be walking the lanes of history, and in some ways they are untouched, but in another way, they juxtapose modern vibrancy with an antiquated setting.

The next day, you will travel higher and up the hill to the ancient Acropolis, the birthplace of democracy as we know it. Marvel at the Parthenon, with so many columns built upon rugged stone. When the sun shines through during early morning hours, it is easy to see why people would think this is a site for godly purpose. Stand before the Temple of Athena Nike and see the megalithic columns, and then the most sacred of all ancient Greek temples, Erechtheion. Your afternoon and evening both days in the city are free, so you can explore sides to Athens that most interest you, your guide able to provide plenty of recommendations. Two days is enough in Athens as the bustle and traffic can become challenging, but in two days, it will feel like you have covered a thousand years of history and memories.

What's Included:

included

Accommodation

included

Tour

included

Transfer

included

Breakfast

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Day 12

Santorini – Blue and White Beauty

The Mediterranean glistens all kinds of blue as you take the ferry to Santorini, an island that is every bit as beautiful as the photos. Famous for the white and blue facades of Fira and Oia, Santorini is one of those places everyone should see. You feel privileged to be in such a pristine and preserved place, the white and blue houses standing on cliffs high above the water. Your hotel is in Fira, a town that looks like a postcard everywhere you turn. Nothing is planned for today, so you can take a walk along the steep streets, take your photos over the Mediterranean, sit at the cafes along the water, and feel the warm breeze through your air as you enjoy your welcome to the finest Greek island of all.

What's Included:

included

Accommodation

included

Tour

included

Transfer

included

Breakfast

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Day 13 - 14

Santorini – Exploring and Relaxing on the Volcanic Isle

Spend the last couple of days exploring to find that there is more to the volcanic isle than just the blue domes and the white walls. Prehistoric settlements can be seen at the Akrotiri Excavations, suggestive of a time before the ancient Greeks. Ride the funicular up Profitis Ilias Mountains for panoramic views that greet you when disembarking at the summit. Eat lunch in the quaint village of Pyrgos and find fresh seafood and local delicacies on the menu, accompanied by some Greek wine tasting. Then head off along cliff-lined shores and spend the afternoon at a beach of black volcanic sand. Back in Oia, the evening can go any which way you like with so many cute restaurants and lookout points in a compact, pedestrianized town.

The next day is mostly left free for more time to spend on the beach or along the harbor watching the world go by. As afternoon spills into the evening, you will board a catamaran and start sailing towards the sunset. Cruise beneath the cliffs and perhaps choose to go for a late swim in the Mediterranean. Wine and dinner are served on board, and you will probably be traveling on the power of the wind, sailing back into Oia as the stars start to shine. The cruise epitomizes Santorini’s travel experience, a chance to explore but most importantly, a time to relax in the most glorious of settings.

What's Included:

included

Accommodation

included

Tour

included

Breakfast

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Day 15

Santorini to Athens – Departure

To depart from Greece, you will fly from Santorini to Athens to meet your international departure, but only after one last leisurely morning

What's Included:

included

Transfer

included

Breakfast

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Trip Highlights

  • Immerse yourself in the Eternal City of Rome and discover its antiquated brilliance
  • Stand upon the Acropolis in Athens and wander leisurely past all the ancient wonders
  • Relax on the island of Santorini, where blue and white facades backdrop your quiet days on the coast
  • Start your trip on the Italian cliffs of Sorrento, a calm yet vibrant place to ease into the vacation
  • Discover the surreal and surprising beauty of Naples, a city that will prove a great contrast to visiting Rome and Sorrento
  • Find yourself on the seaside in Greece with a two-night stay in Nauplia
  • Compare legendary ruins from different eras, like the Roman city of Pompeii and the ancient Greek sites of Epidaurus and Mycenae
  • Contrast the Italian landscapes including Mount Vesuvius, the Isle of Capri, Profitis Ilias Mountain, and Santorini’s black-sand beaches
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Detailed Description

There are parts of Italy and Greece you cannot miss. The Colosseum in Rome, the Sistine Chapel, the Athens Acropolis and the amphitheater at Epidaurus are all essential. However, these two countries have more than just storied histories and attractions. There is the feeling of Italy that you can savor on the cobbled streets, sense it in villages standing on cliffs, and explore it in destinations full of local quirks. Fly across the Mediterranean to Greece, and there is a contrasting feeling to find. In places like Santorini and Nauplia, you can discover a true impression of Greece, so full of mystery and magic, different from the temples of Zeus and Athena.

Your handcrafted tour of highlights will be centered upon the diversity of its destinations, with one week spent in Italy and one week spent in Greece. Fly to Naples to begin and spend your first couple of nights on the cliffs with Sorrento as your base and the Isle of Capri your excursion for the next day. Then get to know Naples, a city of endless masterpieces and local flavor, rough around the edges but delightful to discover. Finish your Italian leg in Rome with private tours through the Eternal City and Vatican City, world-famous highlights complemented by the tones and hues of modern day. You will see that the Italian experience is just as much about a quiet espresso on a piazza, as standing in the Colosseum. 

Fly from Rome to Athens and travel to the coast, starting your Greek experience with nights spent on the sea in Nauplia. Spend your day amid ancient history in Epidaurus and Mycenae, and then spend a couple of nights in Athens, your hotel in the shadow of the mighty Acropolis. With an expert as your guide, you can admire odes to antiquity and see what remains of the vast old empire. From the Greek capital, it is a quiet ferry ride along the Mediterranean to the island of Santorini, that place of postcard blue and white fame. Relax on the black beaches, take your time in the villages, and soak up the soothing atmosphere of this summertime retreat. Contrasts are everywhere, and as you fly home, you might make the comparisons, Santorini versus Athens, Santorini versus Sorrento, the highlights of Italy and Greece that will linger in your memory for a long time.

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Starting Price

$3925 per person (excluding international flights)

This trip is customizable for your private travel.
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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.

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