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Planning a Trip To Italy and Greece: Tips & Ideas

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There’s no doubt that Italy and Greece are two of the most iconic countries to visit in Europe but planning a trip to Italy and Greece might sound a bit overwhelming to some. If that’s you, we’re here to help.

In this comprehensive guide, you’ll find all the practical information you need to plan the perfect trip to Italy and Greece, alongside suggestions on which destinations to visit during your Italy and Greece vacation. What’s more, we’re recommending some of the best Italy and Greece itineraries according to your travel style. Keep reading and, soon, planning a trip to Italy and Greece will seem like a breeze.

A Guide To Planning a Trip To Italy and Greece

Best Time To Visit Italy and Greece

Both Italy and Greece are spectacular all year round. That said, when planning a trip to Italy and Greece, you should consider several factors, such as the weather and the places you’ll be adding to your Italy and Greece itinerary, but most importantly, your own expectations.

For instance, are you traveling to Italy and Greece mainly for sightseeing in the major cities or are you mostly interested in a relaxing beach vacation? Whatever the reason behind your desire to visit Italy and Greece though, here are a few tips to help you decide on the best time to visit Italy and Greece. Both countries share similar weather throughout the year, and are typically a little warmer in the south than north, saving us some time!

July & August – Perfect For Beach Trips or Make Savings in The Cities

Italy and Greece have very similar weather conditions. July and August are particularly hot. If you’re used to the heat and are spending your time by the sea, this might be perfect. In the cities, it can be too warm for comfortable sightseeing in the middle of the day.

You might have heard that it’s best to avoid Europe in summer because Europeans take their summer vacations then. Bear in mind that most Europeans are heading just for the beaches (or mountains) and avoiding the cities, so hotel rates are often lower in places like Athens, Rome, and Florence than in the shoulder-season months of May, June, September, and October.

September – The New Peak Month

Across Italy and Greece, September might just be the perfect month in terms of weather. It’s warm but not too hot and the days are still relatively long. But the Goldilocks month comes at a price. September has always been the month that sees more Americans visiting Europe than any other. Over 20% of our trips start in September in fact.

Hoteliers have cottoned on this. Therefore, what might be traditionally thought of as summer destinations, like the Amalfi Coast, or Greece’s big-name islands, are more expensive than in July or August, when more price-conscious Europeans make up the majority of the guests. The cities are busy with locals, freshly returned from their own summer holidays, conferences and events are back in full swing, while seaside hotspots and popular areas like Tuscany are full of your countrymen.

Shoulder Season – The Best Time For Almost Anywhere in Italy & Greece

Based on our own experience, the best months to visit Italy and Greece are April, May, and October. During these months, the temperatures are mild and you can enjoy the outdoors to your heart’s content. Regardless of what the outdoors means to you. It could be sightseeing in grand open-air archaeological sites, hiking, or just sipping a glass of wine in marvelous squares and quaint narrow streets.

For a beach holiday though, aim for late June or early October if you can’t handle the cold sea temperatures. In June, you’ll enjoy the longest days of the year, great for packing a lot in, even if that means a lot of time in the water.

Go All in on Culture in Winter – True Off-Season Bargains

Winter can be a great time to travel if you’re not planning a trip to Italy and Greece for a beach vacation. Although the smaller towns and islands might feel a bit lonely in the winter, with several hotels and restaurants closed until the high season, in the cities, winter might just be the perfect time to have the main sites almost to yourselves and experience the local lifestyle in the best possible way. Sicily is a delight in winter, with the proviso that the purely tourist town of Taormina will be in hibernation mode, but still worthy of a day trip.

This is a close up of Rome's skyline with snow on the rooftops.
Visiting Rome in winter can be a very good idea

How Many Days Each in Italy and Greece?

Although you can explore the basics of Italy and Greece in 10 days, we’d say that you should aim for a minimum of two weeks if you want to enjoy an immersive experience in these two diverse countries. If you have more time to spare, that’s even better. Three or even four weeks would allow you enough time not only to check out the main sites and visit the best cities, towns, and villages in Italy and Greece but also to delve into the distinct cultures of these magnificent countries.

Now, if you’re wondering how to split your time between Italy and Greece during your 2-week trip, we’d recommend setting aside equal amounts of days for each country.

This is a panoramic shot of the Meteora rocks at sunset.
Spending much time in Italy and Greece means you can add more lesser-known destinations to your itinerary, like Meteora in Greece

Which Country To Start Your Journey From

With international flights to main airports in both Greece and Italy, it doesn’t make much of a difference which of the two countries you visit first. Both Italy and Greece are abundant in historic sites but are also ideal for laid-back moments with your loved ones. Therefore, your time between sightseeing and relaxing is probably going to be balanced in either country.

The best way to determine which country to enter first when planning a trip to Italy and Greece is to check the international flights available and choose those that are better suited to your Greece and Italy itinerary.

This is a panoramic view of Athens with Lycabettus Hill in the background.
Athens is a great place to kick off your Greece and Italy trip

Feel Like One Country Might Be Enough?

There’s no shame in deciding that you might be taking on too much in visiting these two magnificent countries in one trip and focusing on just one. Our travel advisors will be able to craft an itinerary with plenty of variety, even in just one country. And if you’re visiting Greece because you want to see some Ancient Greek temples, well southern Italy has those too, in Paestum, not far from Naples and the Amalfi Coast, and scattered around Sicily.

How To Travel Between Italy and Greece

You can get from Italy to Greece by plane or ferry. The latter though, involves very long journey times that would only make sense if you were on a multi-month trip across Europe. Therefore, flying is the best way to get from Italy to Greece and vice versa. Several airlines – both low-cost and full-service ones – operate direct flights from Italy to Greece, connecting not only the capitals and main cities but also lesser-known cities and island destinations.

This image shows the wing of a plane as it flies over Venice, a city you must include in your itinerary when planning a trip to Italy and Greece.
Flying over a beautiful place like Venice is a unique experience in its own right

Best Way To Travel Within Each Country

Italy is renowned for its modern, efficient, and fast trains. With a railway network covering the entire country, Italy is one of the best countries in Europe to explore by train. On the other hand, Greece is not for train lovers.

Yet, with its so many islands, Greece boasts some of the best, cleanest, and safest ferries in Europe. Getting on board a ferry should be your go-to way to discover the Greek Islands. However, for your mainland Greece escapades, you’d be better off renting a car or – if driving isn’t the best option for you – booking car transfers with a private driver.

This image shows two people standing at the half open ferry door as the ferry approaches Parikia Port in Paros.
Arriving in the port of Paros by ferry

Unique Accommodations in Italy and Greece

Both Italy and Greece have been welcoming guests from all over the world for many decades. The tourist infrastructure and hospitality facilities in both countries are second to none. Therefore, when planning a trip to Italy and Greece, get ready to experience some of the finest accommodations you’ve been to during your travels. From high-end 5-star hotels to stylish boutique properties to fully serviced apartments, Greece and Italy can cater to the needs of all types of travelers.

Some destinations within these two countries also offer unique stays that can significantly enhance your overall travel experience and this is why you should make sure you add some of these special accommodation types to your Greece and Italy itinerary.

Some examples would be a farm stay in a centuries-old estate tucked away in the rolling hills of Tuscany, a room with a view of the Grand Canal set in a glorious palazzo in Venice, or one that opens to the magnificent Trevi Fountain in Rome, an atmospheric sojourn in a lakeside mansion on Lake Como or a luxury cave hotel with many tales to tell in Matera or Santorini, or a couple of nights within the walls of Monemvasia in the Peloponnese, a medieval castle town that never ceased to be inhabited throughout the centuries.

These are only a few of the most striking examples of the one-of-a-kind accommodations you can find in Italy and Greece but they’re not the only ones. Both countries offer countless opportunities for a stay to remember.

This image shows whitewashed stairs and a small pool in Santorini. The iconic Skaros Rock is in the background.
There are several cave hotels with private pools in Santorini

What To Eat and Drink in Italy and Greece

It’s no secret that both Italy and Greece are culinary gems. Italian and Greek cuisines have transcended the boundaries of their respective countries and can be found everywhere in the world. Yet, nothing beats sampling authentic Italian and Greek food in their birthplace.

Eat Italy’s Regions

In Italy, you can eat your weight in pizza, pasta, and gelato, but Italian cuisine doesn’t stop there. Italian restaurants outside of Italy tend to serve up the greatest hits of Italian cuisine. But there’s so much more to uncover. Make sure you taste the regional dishes of the destinations you’re visiting to discover not only the gastronomy but also the culture and traditions that forged these local cuisines.

In Northern Italy, the typical dishes are usually meat-heavy, but the closer to the south you get, the fresh vegetables, a focus on locally sourced and seasonal ingredients, and simple yet hearty recipes work together to put real masterpieces on your plate.

Discover The Breadth of Greek Cuisine

And then there’s Greece. Blessed with sunshine all year long, the Greek land renders top-quality fruit, vegetables, and of course, the most delicious olives and extra virgin olive oil, Greece’s liquid gold. You should definitely try the quintessentially Greek souvlaki but don’t forget that Greek cuisine is very diverse and has a lot more to offer.

From vegetable stews in rich tomato sauce to superb seafood dishes to the omnipresent feta-filled Greek salad, Greece is a paradise for foodies and travelers who are aware that the best way to get to know a destination is through its tastes.

This is a close up of big brown Kalamata Olives topped with oregano.
Greece’s scrumptious Kalamata olives

Paradises For Wine-Lovers

Wine lovers will be equally – if not more – satisfied in Italy and Greece. Both Italian and Greek wines are spectacular, made from indigenous grape varieties. One of the best things to do in Italy and Greece is to plan tours of varied wineries where you can sample local wines and discover the differences between the wine-making methods of these two countries, but also the similarities shared by two peoples that have always been neighbors throughout their history.

Two Takes on a Cup of Joe

Coffee enthusiasts are in for a treat, too. From hastily sipping an espresso standing at a bar in Italy among loud locals to taking your time to lazily enjoy a Greek coffee under the bright Mediterranean sun in Greece, the coffee culture in Italy and Greece can never go unnoticed.

This image shows a hand holding a glass of red wine amid vineyards with the rolling hills of Tuscany in the background.
Tuscany is one of the best places to go wine-tasting

Best Destinations To Include in Your Italy and Greece Trip

With so many amazing destinations to choose from, deciding on which places to add to your Italy and Greece itinerary is no easy task. However, we’ve come to the rescue again. In this section, we’ve included some of the best places to visit in both countries, depending on how familiar you are with Italy and Greece.

Italy and Greece Basics

If it’s your first time in Italy and Greece, it makes sense to start with the basics and maybe sprinkle your itinerary with some of the more laid-back destinations if you have enough time.

Rome and Venice

When in Italy, you simply can’t skip Rome and Venice and they are by far the most-visited locations in the country. Yes, they’re both quite busy and often overcrowded but for a reason. In Rome, history is tangible at every turn. Sites like the Colosseum, Roman Forum, and Palatine Hill narrate the Italian capital’s ancient history in the most eloquent way. Yet, there’s more to the Eternal City than its ancient past.

From marveling at the wonders of the Vatican City, such as the Sistine Chapel and St. Peter’s Basilica, to snapping the perfect shots at the most emblematic locations like the Spanish Steps and Piazza Navona, Rome is sure to seduce you in a heartbeat but maybe not as instantaneously as Venice. The gorgeous City of Canals will have you pinch yourselves to make sure you’re not dreaming as you walk past the iconic cafés lining Piazza San Marco or indulge in a mesmerizing gondola ride.

This image shows a canal in Venice lined by gorgeous buildings.
Nobody can resist the allure of Venice

Florence and Tuscany

Another must-see destination in Italy is Florence, a city that feels like an open-air museum with its abundance of art and grandiose architecture. From joining a guided tour along the corridors of the famed Uffizi Gallery to strolling through Piazza della Signoria with its impressive copy of the Statue of David, Florence is a treasure trove of masterpieces that will amaze all art enthusiasts.

But Florence shouldn’t be your only stop in Tuscany. A journey through the region’s celebrated hills, past towns and villages that seem as though they have sprung out of the pages of a storybook, like Siena, Lucca, or San Gimignano, will grace your eyes with beauty.

A Bit More of Italy

In the south, the Amalfi Coast awaits to fill your days with sunshine, lemon scents, and scenic drives. If you have more time to spare during your first trip to Italy and Greece, there are several other destinations in Italy to check out, such as Milan, Naples, the colorful Cinque Terre, or the lush Italian Riviera.

This is a panoramic view of Florence in the blue hour.
Florence in the blue hour is a dream


Moving on to Greece, more magic awaits. In Athens, you’ll be immersed in the fascinating history of one of the world’s oldest cities as you wander around the sacred ancient ruins of the Acropolis and so many other sun-kissed archaeological sites. But after you’re done with the historic sites, Athens awaits to enchant you with its unparalleled culinary scene and offer you the gift of jasmine-scented nights sipping wine in the company of locals.

The Cyclades Islands

From there, your journey continues to Mykonos and Santorini, the most popular Greek Islands. In Mykonos, try to resist the sirens that call you to spend the wildest party nights before you continue to the Aegean Sea’s ultimate enchantress. Few places can claim the uniqueness and beauty of Santorini, an island born of a volcanic eruption that was responsible for a stunning landscape that was meant to become instantly recognizable to people from all corners of the world.

For an island-hopping adventure to remember, don’t stick to the most famous Greek Islands, though. The nearby islands of Naxos and Paros offer a glimpse into real island life and countless opportunities for the most relaxing moments of your Europe trip.

This image shows Little Venice in Mykonos with its characterisitic white houses with colorful wooden balconies built on the edge of the sea.
The iconic Little Venice in Mykonos

Lesser-Known Italy and Greece

If you’ve been to Italy and Greece before, you must have covered the basics already. That’s great news because now you can delve into lesser-known Italy and Greece, where pure magic awaits.

Italy’s Strong Second String

In Italy, you can start with the somewhat less popular destinations, such as Romeo and Juliet’s Verona, the ancient cave town of Matera, or the spectacular islands of Sicily and Sardinia, before you move on to the country’s actual off-the-beaten-path parts.

Bologna, the beating red heart of Emilia Romagna, is a foodie’s dream. In the south, the rugged region of Puglia awaits to take you on unforgettable strolls through ancient olive groves, whitewashed villages that resemble the Greek Islands, and long sandy beaches with crystal clear turquoise waters.

Farther south, the unspoiled Aeolian Islands seem to dwell only in a romantic author’s imagination while, in the north, the Dolomites promise the most rewarding hiking and landscape photography sessions amid a scenery of unfathomable natural beauty.

This is a panoramic view of the quaint harbor of Marina Corta in Lipari.
The serenity of Lipari in the Aeolian Islands

Greece: Beyond Athens and The Cyclades

In Greece, the mystical complex of the Meteora monasteries built atop dramatic gigantic rocks, and the nearby city of Ioannina, dominated by a tranquil lake that has defined the locals’ lives for centuries on end, are among the country’s best-kept secrets. The now-not-so-secret co-capital of Thessaloniki in the north still retains its authentic character and it’s one of the top culinary destinations in Greece. Corfu is the ideal place to add some island time to a northern Greece itinerary.

In the south, no words can describe the alluring Peloponnese, a peninsula of wonders that abounds in vibrant cities, like Kalamata, traditional villages, natural treasures, and beautiful beaches. No second – or third – trip to Greece and Italy would be complete without a stay in Crete, the largest of all Greek Islands, a blessed land that renders delicious local products, a unique destination steeped in history, Greek culture, and long-standing traditions.

This is a panoramic drone shot of the seaside village of Limeni in the Peloponnese, a Greek region you should consider when planning a trip to Italy and Greece.
The Peloponnese has no shortage of scenic villages like Limeni

Suggested Itineraries For Italy and Greece

At JayWay Travel, we’ve crafted more Italy and Greece itineraries than we can count during the last couple of decades. In this section, we’re presenting you a super small selection of some of our most popular Greece and Italy itineraries. These are not set in stone, though. They’re only there to trigger your imagination and get you started on dreaming of your very own Greece and Italy journey.

Italian & Greek Showstoppers

Ideal for first-time visitors, this Italy and Greece itinerary shows you around the very best these two countries have to offer, with stops in Rome, Florence, Venice, Santorini, and Athens.

Italy and Greece For Foodies

As we’ve already mentioned, Italy and Greece boast two of the most delicious cuisines worldwide. This carefully crafted itinerary is for those wishing to embark on a gastronomic trip through Italy and Greece, featuring destinations, such as Rome, Bologna, Crete, and Athens.

The Ultimate Italy and Greece Honeymoon

There are no better places to create cherished memories with your favorite person in the world than Italy and Greece. Spending a honeymoon in these two countries is the dream of many and, although the sky’s the limit when deciding which places to add to your honeymoon itinerary, our suggestion would include Rome, Positano, Naples, Mykonos, Santorini, and Athens.

This is a panoramic view of Positano at sunset.
Positano provides the perfect setting for a memorable honeymoon

Learn a Little of The Language

Wherever you travel, it always helps to learn a few phrases in the local language. We’ve made that easy for you with a couple of short language videos filmed by our locals.

Learn the Basics: Italian
Learn the Basics: Greek Language

Planning a Trip To Italy and Greece With JayWay

These suggested itineraries are only a tiny sample of the countless amazing destination combinations and themed routes our expert staff can come up with for you. This is because, here at JayWay, we know Italy and Greece quite well.

Our knowledgeable travel advisors and trip planners will help you choose the most remarkable accommodations in Italy and Greece, ensure the most memorable activities, food tours, day trips, and experiences are added to your itinerary, and take care of all the time-consuming and often stressful logistics, such as booking train and airline tickets within Europe or arranging private car transfers, for you.

Like Traveling With a Local Friend

The final touch? Our exceptional staff on the ground in both countries are all eager to show you their beautiful countries through their eyes. Therefore, if you’re currently planning a trip to Italy and Greece, why not leave all the logistics to us and skip to the good part instead? After all, the best way to see Italy and Greece is, of course, with JayWay!

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