The Best Way to Plan a Trip to Italy and Greece

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The Best Way to Plan a Trip to Italy and Greece
From the wine to the architecture, indulge in Italy and Greece's most stunning views in this guide to planning a trip of a lifetime between both countries! From multi-city trips to dos and don'ts, find out everything you need in this ultimate guide to trip planning!
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Why choose between Italy and Greece when you can have both? With so many sights to see and activities to do, creating the best itinerary can be a challenge. Here are some of the best ways to plan a trip to these beautiful destinations. 

Italy and Greece have a comprehensive mix of eclectic heritage, vibrant culture, and lively locals. These Southern European countries should definitely be on your travel bucket list. You'll be on your way to falling in love with their beautiful landscapes, culinary delights, and warm hospitality!  

In this article, find out more about when to travel, where to stay, and other fascinating facts about Italy and Greece. Without further ado, let's dive into how you can prepare for your next big adventure!

Can You Do Italy and Greece on the Same Trip?

Yes, it's very possible to cover Italy and Greece in a single trip as they're close to each other. There are also many transportation options between the two countries. A common way to travel between Italy and Greece is by ferry. There are also many direct flights between the two countries. 

Before anything else, make sure you know exactly what you want to do and the cities you plan on visiting. Italy and Greece offer many activities, so you may miss out on the best adventures if you go without enough preparation and research.

Know your priorities so you can create the ideal itinerary. If you're traveling with others, ask your travel buddies what their preferences are as well. You can make use of travel planner apps for help in coming up with the best plan for your trip.

Map to italy and greece
Photo by Vemaps

What to Consider When Visiting Italy and Greece

Firstly, I'll break down the most important considerations when visiting Italy and Greece. Follow these tips to make your trip research and planning process smooth sailing all in one go! 

1. Plan the Perfect Time to Visit

Like any destination, there are peak and low seasons to visit Italy and Greece. Italy's peak season happens to be in the summer, around May to September. If you want to score the lowest prices for transport and accommodation, try to avoid these months!

If you're visiting Italy for the wine, you should travel in early spring or fall. These are the harvest seasons, which are fantastic for wine lovers. Still, you should research the exact months because harvest season changes from year to year.

On the other hand, there's no specific best time to visit Greece. However, if you want to avoid the cold weather, it's best to visit Greece from April to June. September through October is also a good option, but temperatures may drop to around 16°C.

Before traveling in the winter, you need to know that many venues, hotels, and hostels in Greece will be closed due to a lack of demand. If you want to visit Greece between late October and January, you should first check for suitable accommodation options.

2. Choosing the Right Cities For your Trip

It's hard to say which are the best cities in Italy and Greece since each has irreplaceable characteristics. However, to make planning your trip itinerary easier, here are some of the best destinations to visit in both countries.


Some of the world's greatest painters and artists lived in Florence. The birthplace of the Renaissance, this city boasts elegant architecture and world-renowned museums.

A unique feature of Florence are the hole-in-the-wall cafes that serve paninis, pizzas, and many other Italian delicacies. If you're a fan of all things vintage, you'll also like the fascinating thrift shops that dot the city.


It's just a short drive to Tuscany from Florence, where you can enjoy the calm and quiet of Italian hills and villages. Some Tuscany lodgings also provide farm-to-table dining and natural wines unique to the region.


Rome is definitely a must-visit city. Getting to Rome from Tuscany is easy as you only need to take a 1.5-hour express train ride. Once you arrive in Rome, you'll be hard-pressed not to fall in love with the delicious food and iconic landmarks.

It's impossible to see everything that Rome has to offer in a single day. Be sure to set aside at least two or three days to immerse yourself in Italy's capital. Don't miss out on seeing the Vatican and the Colosseum for the ultimate Rome experience!

Woman standing near colosseum in Rome
Photo by L A L A S Z A on Unsplash


Moving on to Greece, Santorini is the best place to start your next adventure. You can find everything here, from beaches to high-end shopping malls. Santorini also boasts some of the world's most beautiful sunsets that will leave you in awe.


Mykonos is the next place to be if you want to experience a more modern side of Greece. Filled with cave hotels and beach clubs, Mykonos is the perfect place for party-goers to let loose on vacation. 


From Mykonos, you can take a direct ferry ride to Athens, where you can experience a bit of everything that Greece has to offer. From city sightseeing to nightlife entertainment, you'll never run out of things to do in Athens!

Tourists love visiting the Acropolis and the Temple of Poseidon. You should also visit the nearby stores, restaurants, and pubs. Many offer traditional Greek cuisine made with fresh ingredients from local farmers, so you can get an authentic taste of Athens.

Woman with yellow dress next to a white and blue building
Photo by Jialin Hu on Unsplash

3. Consider the Dos and Don'ts in Italy and Greece

Whatever your background, it's critical to remember that Italy and Greece each have distinct cultures and traditions. Each region will have its own set of dos and don'ts, but here are the most crucial things to remember throughout your vacation.

Be Open to Sincere Hospitality

If you meet someone on your journey who invites you to have dinner at their home, be open to accepting their offer. 

People in Italy and Greece enjoy welcoming newcomers into their homes and learning about various cultures. Feel free to share some intriguing anecdotes about your life or history! This could also be a wonderful opportunity for you to learn more about the local culture. 

Kick Back and Relax

Italians and Greeks are known for taking their time in life. Even the Italians have a concept they call "dolce far niente," which roughly translates to "the joy of doing nothing." While you're here, learn to forget about your worries! Enjoy your pasta and have a digestivo while you blend in with the locals. 

Mind Your Clothing

Who doesn't love wearing denim shorts and a tank top to enjoy the summer sky on vacation? But going to the wrong places with the wrong outfit can make the locals frown, especially when visiting churches and cathedrals. When in Italy and Greece, make sure you dress appropriately for the occasion.

Woman walking on seaside while holding a woven bag
Photo by Tamara Bellis on Unsplash

Should You Visit Italy or Greece First?

Italy and Greece share many similarities yet offer entirely different vacation experiences. Italy has a classic elegance, while Greece enjoys a more laid-back island atmosphere. Hence, your first choice of destination depends on the type of travel experience you want.

If you're a lover of museums and galleries, start planning a trip to Italy first on your itinerary. Cities like Rome, Florence, and Milan boast fascinating museums that feature centuries-old masterpieces. If you prefer beach and island hopping, you should spend most of your trip in Greece.

Alternatively, if you want to spend the same length of time in each country, you could base your decision on your flight paths. For example, if you're coming from the United States, it makes more sense to begin your vacation in Rome and end it in Athens.

How Many Days Do You Need in Italy and Greece?

You can take as much time as you'd like in Italy and Greece. If you want to fully experience both countries, I recommend you set aside two weeks for the trip. This allows you to visit two main cities within every country and spend one or two nights in each without feeling rushed.

It's a good idea to spend no fewer than 10 days on your trip. A 10-day itinerary for Italy and Greece should allow you to visit around three cities. Of course, this also depends on the places you want to see and the activities you want to do. 

However, if you don't have more time to spare for the trip, it's best to prioritize Rome, Florence, Mykonos, and Santorini on your itinerary.

Colorful houses near the see with boats
Photo by Martino Grua on Unsplash

Explore Southern Europe With Pilot!

Italy and Greece are both beautiful destinations with so much to offer. Whether you're planning a fun holiday with friends or a romantic honeymoon, this guide has hopefully prepared you for an amazing trip. Start planning your travels to Italy and Greece with Pilot!

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Charmian Lo Blogs
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Charmian Lo
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