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Italy & Greece Vacation Packages for 2022 & 2023

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Italy and Greece make for a marvellous Mediterranean vacation. These two countries with a long and intertwined history are home to some of history’s most important sites. A vacation combining Greece and Italy is like a greatest hits of Europe’s top sights.

Popular Itineraries for Italy & Greece Tours

Although every tour we build is unique, there are some popular routes and itineraries that we are asked for frequently. Our sample itineraries provide some ideas for you to consider as a basis for your own private tour combining time in both Italy and Greece. For each of these itineraries you can get a rough idea of the price using the Price Guide function. We cover many more destinations than those listed in these popular Greece & Italy itineraries. Our expert trip planners will work with you to incorporate any places in Italy and Greece you want to go.

Italy & Greece Vacation Reviews

4.9 / 5

Average of our Guest's Ratings of our Italy & Greece Vacation Packages
Based on 10 reviews

Our Italy & Croatia vacation packages provide a hassle-free way to see both these captivating countries. We take care of all the details. All you have to worry about is enjoying the one-of-a-kind experiences that will make this the vacation of a lifetime. Below you’ll find some recent testimonials from guests who have visited Italy and Greece with our help recently.

Review by Mary & Alex

Mary & Alex

Absolutely fantastic service. The modern way to use a travel agency.

Absolutely fantastic service. The modern way to use a travel agency.

Year : 2021
Visited : Italy
Itinerary : Rome, Positano, Rome
Rating :
5 / 5
Year : 2021
Visited : Italy
Itinerary : Rome, Positano, Rome
Rating :
5 / 5
Review by Maureen & Genrik

Maureen & Genrik

California

JayWay Travel takes away all the work and tension of travel while allowing you to research extensively and contribute ideas and suggestions about every aspect of the trip. Trust their instincts...they are all excellent.

JayWay Travel takes away all the work and tension of travel while allowing you to research extensively and contribute ideas and suggestions about every aspect of the trip. Trust their instincts...they are all excellent.

Year : 2021
Visited : Greece, Croatia, Slovenia, Italy
Itinerary : Athens, Naxos, Santorini, Athens, Dubrovnik, Hvar, Trogir, Plitvice, Rovinj, Ljubljana, Venice
Rating :
5 / 5
Year : 2021
Visited : Greece, Croatia, Slovenia, Italy
Itinerary : Athens, Naxos, Santorini, Athens, Dubrovnik, Hvar, Trogir, Plitvice, Rovinj, Ljubljana, Venice
Rating :
5 / 5
Review by Julia & Kirk

Julia & Kirk

Colorado

Love the friendly people you interact with either on the phone, or via email. The Guest Page is so easy to use with loads of great information. JayWay Travel makes it very easy to build a great completely customized vacation trip.

Love the friendly people you interact with either on the phone, or via email. The Guest Page is so easy to use with loads of great information. JayWay Travel makes it very easy to build a great completely customized vacation trip.

Year : 2019
Visited : Italy
Itinerary : Venice, Bologna, Milan, Levanto, Florence, Siena, Rome
Rating :
5 / 5
Year : 2019
Visited : Italy
Itinerary : Venice, Bologna, Milan, Levanto, Florence, Siena, Rome
Rating :
5 / 5

Italy & Greece: A Classic Duo

Two of the greatest civilizations the world has known, the Greek and Roman Empires, left their mark on Southern Europe for eternity. You’ll be treading in ancient footsteps on your Italy and Greece tour. More recent empires, kingdoms, republics and dynasties have contributed to the rich art and culture you’ll find in both countries.

Culinary Edens

Italian cuisine might have the edge when it comes to worldwide fame but Greece holds its own too. In both countries we’ve picked the best foodie experiences for you to try, from food tours to cooking classes, as well as olive oil and wine tastings. We’ll provide tips on the best places to eat in all your destinations too.

Just want to hit the highlights?

If you want to hit the main hotspots, you could start your trip in Rome, the eternal city, where you’ll be able to visit the Vatican Museums, the Sistine Chapel, and the sights of Ancient Rome. Add in Florence’s historical center where you can admire the signature Duomo, Michelangelo’s David at the Uffizi and stroll across the Ponte Vecchio. or Venice, the iconic floating city. Then jump on a quick flight to dream vacation destinations Santorini or Mykonos and then finish up in bustling Athens, site of one of the world’s oldest civilizations. If you’ve never been to either country, that’s definitely a good way to start.

Or dig deeper?

But that’s just the beginning of the story and our knowledge of both these countries goes much deeper than that. You could spend some of your trip discovering Crete, Greece’s largest island. Santorini’s beautiful, but the other Cyclades islands, Naxos and Paros, reward the more curious traveler. Buck the island-hopping trend and spend your time exploring mainland Greece. Meteora and Thessaloniki are of particular interest. If you’re on the trail of ancient Greek sites, then Sicily is a must, with Greek temples galore. Puglia can easily be combined with Greece thanks to either overnight ferries between Bari/Brindisi and Northern Greece or low-cost direct flights. Check out all the destinations we offer in Greece and Italy.

You’re in the best hands

Our Italy and Greece expert travel advisors and trip planners will work with you to create your dream vacation itinerary. You’ll stay at the very best hotels, apartments or villas. You choose how you want to spend your days, either enjoying day trips and city tours with our trusted partners or taking a day off to wander on your own. Before you arrive and during your trip our on-the-ground staff in both Greece and Italy are on hand by phone or email for any help you need. With staff in both countries, we’re perfectly placed to create the most memorable trip you’ve ever experienced.

Why Travel with JayWay?

Precious Time

Planning an amazing trip takes time. Our friendly travel advisors and experienced trip planners will listen to your needs and craft your personal dream itinerary. We will maximize your vacation time and enjoyment – we know the best way to get around and how to spend your hard-earned time off.

Peace of Mind

You’re in safe hands from the very beginning. Even before you arrive your dedicated tour manager in Europe will be in touch to help you prepare. When you arrive they’ll meet you and be available by phone, email and IM for the rest of your journey with us, for anything you need.

Memories Forever

Travel can create memories that last a lifetime. You’ll return home with indelible recollections of beautiful sunsets, magical vistas, fascinating stories, and meals so delicious you’ll want to fly back every time you think of them. This is why we do what we do.

Want to know a secret? Your next trip with us will be even better! Based on what we’ve learned from working together, your second, third and tenth trip will get better every time. We treat our dedicated and hard-working staff like family and that’s how they look after our guests. We keep expanding our family, and our map, with 30 countries and counting, because once you’ve traveled the JayWay, anything else just isn’t good enough.

Frequently Asked Questions about Travel to Greece & Italy

What is the best way to travel to Italy and Greece?

Most of our guests travel to Italy and Greece from the US by air, unless they are already traveling in a neighboring country.

Where should I start my tour of Greece and Italy?

Starting in either Rome or Athens makes sense. Buying an open jaw ticket is usally only a little more than a standard return and we’ll include any intra-European flights in your package. Our travel advisors will help you pick the best flights for your itinerary.

What are some must-see places in Italy and Greece?

It very much depends on your priorities. If you want to visit the most famous places then Rome, Florence, Venice, Athens and Santorini might be top of your list. If you’ve been to Italy before but not to Greece, we can arrange a trip combining lesser known destinations such as Bologna, Siena or Lucca with Greek destinations such as Athens, Mykonos and Santorini.

What do your Italy & Greece vacation packages include?

Our vacation packages are designed to make touring Italy & Greece effortless. From working with our travel advisors and expert trip planners to craft your ideal itinerary, to the moment you get on the plane to return home, we will take care of everything. Your custom tour package will include accommodation, transfers and transport, walking tours, day trips, and most importantly the support of our local staff in Europe. They’ll be in touch with you before your trip to finalize any details, and when you land we’ll give you a local phone or SIM so you can be in touch by phone, email or instant messsage. It’s like having a tour director, but still traveling “independently”.

How much does a private tour of Greece and Italy cost?

Our Italy and Greece vacation packages start from around $300 per person per day. The largest element is often accommodation, but private full day tours can increase the cost. All our sample itineraries have a price guide function to give you an idea of the cost for different levels of accommodation, month of travel and number of travelers.

Do your Greece & Italy tours have a set departure date?

No. As our tours are completely customized to you, you choose the dates, and destinations you want to visit.

When is the best time of year to visit Italy and Greece?

The best time of year for your trip will depend on what you want to do. Italy can be a great place to travel year round. Greece’s islands can be more seasonal with some almost shutting down in winter. If you want to swim then you should travel between mid May and mid October. If you are more interested in sightseeing and avoiding the hottest time of year then mid July and August could be too warm for you.

Which of Greece and Italy has the best beaches?

Both countries have some fabulous beaches. For the best Italian beaches you need to go beyond the most popular easily-reached locations like the Amalfi Coast and Cinque Terre and instead head to Sardinia, or Puglia’s western coast. In Greece, some of the most popular island destinations also have wonderful beaches, particularly Crete, Mykonos, Naxos, Paros, and Rhodes. While Santorini’s beaches are pleasant, they’re not its best feature.

Can I self-drive on an Italy & Greece trip?

We can arrange rental cars for all or part of the trip, but bear in mind that dropping off a rental in another country incurs high one-way fees. Your JayWay trip planner can arrange for separate rentals where needed so you can avoid unnecessary expenses and have the freedom to get around by car when you need. In Italy’s countryside in particular a car is useful. Should your trip be mostly city-based then trains and private transfers will be much more convenient. If the Greece portion of your trip concentrates on the islands, we advise against car rental.

What are some popular excursions and day trips on your Greece and Italy tours?

Among all the guided tours we offer in Rome, our most popular are culinary-based, whether food tours or cooking classes. Similarly in Athens food-based experiences are very popular, as well as tours of Ancient Athens, including the Acropolis and the Temple of Olympian Zeus. On the Greek islands, sailing trips are perennial favorites. Tours of the interior of an island provide a wonderful way to get to know the character of the place better.

Can I take a free day or two with no tours?

Absolutely. Our vacation packages are customized to your wishes. You don’t have to fill every day and we encourage leaving some time aside simply to appreciate the destinations you’re visiting. Getting lost in Venice’s narrow streets, with just the occasional glimpse of St Mark’s Campanile to guide you, is part of the fun!

Do you sell cruises that include Italy & Greece?

We don’t sell cruises of Greece and Italy. We believe you enjoy a far richer experience by spending as much time as possible on land, soaking up the culture and enjoying the local cuisine, while taking part in a more responsible type of travel.

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