14 Day Itinerary in Italy and Greece

You’re going to miss something on your first go round. Even with 14 days to play with, you are still going to have to pick and choose your adventure and something you really want to see may have to get cut. That’s how much there is to see when your goal is to see the best of Greece and Italy in one trip.

It’s understandable. Both countries are ancient with civilizations that date back thousands of years. Of course you have to see the Colosseum when in Rome and who goes to Greece without Crete? But there are also the incredible views of the monasteries in Meteora, the oracle in Delphi, or Olympia in Peloponnese where the Olympics were born.

So how do you create the ultimate Italy and Greece itinerary given those challenges? You provide choices – lots and lots of choices! In our ultimate Italy and Greece itinerary, you will visit Athens and tour the Greek Islands over seven days BUT you can also go northeast or southwest from Athens to tour some of the world’s most famous ruins.

In Italy, you will have your choice of partying it up along the western coast from beach resort to beach resort or taking in Holy sites and historical ruins in the north. Choose your adventure and map your own quest through two amazing countries – Italy and Greece – following the ultimate Italy and Greece itinerary.

The Best Time to Travel to Italy and Greece

Picking the right time to come to Italy and Greece depends on whether it is more important for you to have less crowds or better weather. The summer months from June through September are when the temps are the nicest and thus, the cities are a lot more crowded. But if you get there at the beginning or end of the season, then you’re more likely to have good weather and fewer tourists to contend with.

Italy is a little different. The weather is nicer in the spring than in the summer in Italy. June is actually the end of the high season. Your other alternative is from September to August. Temperatures are mild and there are lot less people clogging up the streets and hotels. Not to mention the prices go down at the end of the season too – and you’ll want to pocket as much as you can on this trip; getting around can be a bitch!

Pre-Travel Information

Make sure that you have a current passport and photo ID. You will need both when you arrive in Athens since you’ll have to go through customs and immigration before you can enter the country. Beware; you might be waiting for hours in line to get your bags and to be processed so make sure to leave time in your check-in schedule for long delays.

How to get to Italy and Greece

Getting to Greece and Italy is the easy part. There are flights to Athens daily but from the U.S., but you can only fly there from Philly or New York. Otherwise, you’ll have to fly to Europe and then connect to a flight to Italy or Greece. A lot of itineraries go from Rome to Athens. We’re going to do it in reverse.

Tour the ancient ruins of Greece or bask in the Mediterranean along the shores as you hop from island to island. When the first week is over, you will travel north to Italy where you will speed rail it to some of the most exciting and fascinating places in the world!

How to Get Around in Italy and Greece

Getting Around Greece

Since this itinerary is going to take you to Athens, Greece first, you’re going to get a crash course in ferry riding. You shouldn’t fly all the way to Greece without visiting the Greek Islands where there are literally thousands of little isles to explore – well not on this trip. You only have a week in Greece and a few days in the isles so here’s what you need to know:

• You have to book flights and hotels at least six months in advance because they fill up pretty darn fast. You could fly into one of 25 different airports on the different islands but only if you are flying in from Britain or another European country.
• Ferries come in both speedy versions and slow sauntering sightseeing versions. Both are your means of transportation to, from, and around the islands. If you have to connect to a train or flight inland, you have to pay close attention to which one you choose keeping in mind that fast boats book up quickly.
• Buying ferry tickets too far ahead of time is a waste of time in Greece. You can view ferry schedules online but the schedules change on a whim during tourist season. Some may be delayed by hours – you could even find your return ferry to the mainland cancelled and you’ll end up marooned on the island for the night.
• It is first come first served for seating on ferries so get to the docks an hour before you’re supposed to depart to get a good seat.
• Once you’re on the mainland, buses are the best ground transportation unless you rent a car. Plus the buses stick to the schedule.
• Unlike most parts of Europe, train travel is not as top notch. They don’t go everywhere, there are no high speed rails and you would miss some important sites if you were depending on getting there on a bullet train.

Getting Around Italy

You’ll be relieved to find that getting around Italy is much easier than Greece. Of course, it too has its own island chains but we won’t be visiting Sicily or Sardinia on this trip – maybe next year. There are lots of choices on this trip ticket. Greece and Italy or so close, you could ferry your way from mainland Greece to Italy to continue the itinerary or hop on a small airline carrier – the flights are super cheap and short.

Some like to rent cars in Italy, especially when traveling in groups so that you can sightsee and explore more on your own. If you are a bike rider, you could rent a motorbike to see Italy. Here, you can book your tickets in advance and be confident that they will leave on time.

For the train you have multiple high speed rails to choose from, including the fastest one, the Frecciarossa which tops out at 224 mph. The Frecciargento speeds around Italy at 155 mph and the Frecciabianca is the slowest, zooming along at 124 mph. In city, you can depend on your handy prepaid Rail Europe train pass or a Eurail pass to jump on and off local city trains or just buy them at the point of sale like you would here in the states.

Where to stay in Italy and Greece

Over the two weeks that you’ll be traveling in Greece and Italy, you’ll be staying at some of the finest hotels in the world.

• Athens – Starting with your first night in Athens, you’ll post up in the King George Hotel in Syntagma Square. Its accommodations are très magnifique and the location is unbeatable – shopping, ruins, and sightseeing as soon as you step out of the hotel.
• Mykonos – In Mykonos, you’re going to stay in one of the premiere villa and suites hotels at the Myconian Villa Collection. The views are spectacular and there is an infinity pool on-site that looks out onto the sea and a fancy Greek restaurant downstairs for your pleasure.
• Santorini – On your last couple of days touring the Greek Islands, you will visit Santorini and stay at the immaculate Tsitouras Collection right on the shores of the Mediterranean. With fantastical views all around you, this last stop on the Greek leg of your trip is going to make it hard to say goodbye.
• Amalfi Coast – Saying goodbye to Greece is made a little easier once you check-in to the Hotel Miramalfi on the Amalfi Coast in Italy. Famous people from around the world call this hotel home on their visits too, with its private beach and family operated on-site restaurant.
• Rome – When in Rome you are going to enjoy the 5-Star treatment you receive at the Rocco Forte Hotel de Russie. You’ll be close to all the action, walking distance from some of the most famous historical sites, all from your home base of luxury and pomp.
• Venice – Nearing the end of this extraordinary vacation, you will stay at the Bauer II Palazzo in Venice. There, in the center of town, you’ll say ciao to this amazing country after taking in some of the historic attractions while scarfing down some of Italy’s finest foods before heading back home.
• Florence – On your last night in Italy, you will land in Florence where you will spend a night in a palace that is over 500 years old! Don’t let its age scare you – the Palazzo Vecchietti is a completely refurbished luxury hotel and is ultra exclusive so book early – there are only 14 suites available!

Ultimate Italy and Greece Itinerary

Week 1 – Exploring Greece

The lack of good high speed rail in Greece makes trying to see it all in just one week virtually impossible. For history buffs who want to spend time visiting all of the many ruins and ancient places in Greece, it means hours out of your day traveling by bus or by car which leaves little time for relaxing. So what we’ve done is given you some options.

You have the main itinerary where we’ll spend two nights in Athens, a couple of days in Mykonos, and then spend the rest of our time hopping along the Greek Islands. But we’ll give you a few jumping off points while on the mainland that you can choose to check out before joining the island itinerary.

Day 1: Arrive in Athens

On day one after landing in Athens, you may want to relax for a moment, but there is not a moment to lose if you want to see all 3,000 years of history. Fortunately, where you’ll be staying puts you right in the heart of it all. View the Parthenon, the Acropolis, and the Temple of Zeus in one day. Here’s the jumping off point.

Day 2: Go North to Delphi or South to Peloponnese

Day two you have options. You can go north to see the second most famous ruins in Greece but you’ll have to drive north for about six and a half hours to Delphi (once thought to believe the center of the world in ancient Greece). Another three hours north from Delphi and you’ll see the monasteries of Meteora “suspended” thousands of feet in the air – a UNESCO site.

Drive east a little ways and you’ll hit Thessaloniki in Macedonia. See history from the Byzantine era, take a dip in a Turkish bath, and party at the many clubs there. Halkidiki is another northern site in Greece that if you have the time has some interesting history as well as a few hot beaches. From Thessaloniki, you can take a four hour drive east to check out the Vikos Gorge or hike through the deep forests in Zagori.

But if you want to stay on the beaten path, we recommend traveling for about two hours southwest of Athens to Peloponnese. There you’ll tour ancient places and temples including the ruins of Olympia – the site of the first Olympics!

Day 3: The Greek Islands

On day three we’ll leave the mainland and catch a ferry for a leisurely five hour ride to the Greek Islands. Here you’ll find a mix of lively touristy beach crowds to quiet holy ruins. There are tried and true islands that have been populated for thousands of years but there are also isolated, remote isles that have barely been touched by humans. You’ll have four days and three nights to explore!

Day 4: Santorini

You can’t go to the isles of Greece without stopping in Santorini. It’s fancy, full of life, and plenty to look at. Island tours abound here so that you don’t miss a thing.

Day 5: Crete

Legendary Crete and the ancient culture there are preserved nicely along with all of the modern trappings of today on this, the biggest of the islands. Take in the history and the sites while dining on classic Greek cuisine.

Day 6: Mykonos

You have your choice – party with loud beach crowds or sunbathe in peace and quiet. Mykonos offers both where the party is on all day and night.

Day 7: Depart the Greek Islands for the Amalfi Coast

Last day in Greece, find your nearest ferry station and book your ticket to Italy. It’s really that close and you will enjoy some spectacular views, cruising the Mediterranean on your way from Greece to Italy.

Week 2 – Discovering Italy

You’ll have to remember to make a bucket list of the places you didn’t get to see on this trip and make it for your next visit to Italy and Greece. In Italy, we hit the most exciting and important sites for you to see.

Day 8: Arrive on the Amalfi Coast

Also a UNESCO site, the Amalfi Coast is a must-see when you visit Italy. With miles and miles of shoreline, you are guaranteed to be taken in by the scenery. When you get off of the ferry, you could catch a train up the coast, but driving gives you such awesome views, you may want to rent a car for the day. You’ll spend day one relaxing and eating your way to the hotel.

Day 9:  Capri and Sorrento

Along the Amalfi Coast, you’ll find plenty of little trattorias and villages to visit. We recommend making Capri and Sorrento two of those stops. Feast your eyes on Mt. Vesuvius from the cliffs of Sorrento and walk along the shores of Capri. Explore the ruins of Pompeii and walk the “Path of the Gods” all along the Amalfi Coast.

Day 10: Venice

Venice is literally on water. Instead of buses, you’ll take boats around this fascinating city. You can hire a boat to take you around or just float along the many waterways in a gondola while being serenaded. Don’t forget to go see the Colosseum while you’re here!

Day 11: Rome

Catholic sites are among the many religious relics to see but there is also a strong mythical heritage that belongs to the gods in Rome. Visit the Pantheon, the Vatican, and the Roman Senate all in the same city. Plus, fill your gut to the brim with so much Italian food you could burst!

Day 12: Florence

Just a hop, skip, and a jump north, you’ll arrive in Florence where you’ll be enchanted by the Renaissance era art and culture. In a blend of new and old, you will find fantastic shopping for modern day fare in Florence also. Here’s a small jumping off point.

The Dolomites are a geological marvel and a must-see attraction. But you will have to travel several hours east of Florence to check them out. We recommend taking high speed rail there for a magical day trip while in Florence.

Day 13: Cinque Terre

On your way back from The Dolomites you could stop in Cinque Terre for the night. We recommend it regardless. It’s an easy two hour drive north from Florence along the coast where you can start to unwind in the easygoing town of Cinque Terre before heading back to Florence for the night.

Day 14: Tuscany, Italy

To further unwind, we recommend stopping in to Tuscany before you depart from Florence for home. It’s so close you can walk to Tuscany from Florence! Why make this stop? It’s a great place to have your last great Italian meal before you leave and it is so calm and peaceful, it will put you in the perfect frame of mind before heading back to your real life!