3 Week Italy Itineraries

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How Zicasso WorksCustom Italy Tours

  1. Describe your dream 3 week Italy itinerary.

  2. We match you with up to 3 top travel specialists. They compete to plan your itinerary.

  3. Book the trip when you are satisfied.

From the Venetian lagoon and the Eternal City of Rome to the rolling Tuscan hills and the seaside villages of Sicily, your Italian escapade is best done through a customized tour. Discover iconic landmarks, unmatched food and wine, distinct local identities, and much more with a 3-week Italy itinerary from Zicasso. Inquire now to talk to the best local experts.

Sample Itineraries

Get inspired with our sample trips below. You can have any trip tailor made for your private travel. Any number of days.
Any departure date. Any experience you want.


3 Week Italy Itinerary at a Glance

Italy is known for its rich history, intriguing landmarks, and delicious food, and is the perfect destination for a 3-week vacation. From north to south, fascinating cities and a lively culture can be uncovered and enjoyed, and a vacation to this stunning country is sure to create many lifelong memories.


There are 20 different regions that make up Italy. Some are large and home to main cities while others are smaller and less populated. Some of the most well-known regions are Lombardy, Veneto, Tuscany, Umbria, Lazio, Campania, Calabria, and Sicily. Many of Italy’s top cities and attractions can be found in these regions: Milan in Lombardy, Venice in Veneto, Florence in Tuscany, Assisi in Umbria, Rome in Lazio, Naples in Campania, Reggio Calabria in Calabria, and Palermo in Sicily. Besides the many landmarks in these areas, each region also offers its own tasty cuisine, local customs, and dialect.


Italy has a Mediterranean climate, and the country can be enjoyed throughout the year. Spring and Fall months tend to be the nicest times, with comfortable temperatures in many cities. Summers are hot and dry while Winters are wet and colder in most of the country. The more north in the country you travel, the cooler the temperatures, while the more south you travel, the warmer the climate.


Italy is ranked as the 23rd most populated country in the world, and is home to over 60 million people. Rome is the most populated city, with over 2 million inhabitants. Milan and Naples round out the list of the top three populous cities.


Roman Catholicism is by far the main religion of Italy, and over 70% of Italians identify this as their faith. There are myriads of churches and Basilicas located all over the country, and the head of the Roman Catholic Church is located in Vatican City, just outside Rome.


The most common language you will hear during your 3-week vacation is Italian, and this is the national language of Italy. Many people in the main cities also speak English. In smaller towns and villages it is also common to hear local dialects spoken.


Italy’s currency, like many other European countries, is the Euro, and this is the most common form of payment. Major credit cards are also widely accepted in most areas.

Where to Visit in 3 Weeks

During a 3-week vacation, you can visit many of Italy’s cities and attractions. There is ample time to spend a few days in many spots, and enjoy a relaxed and easygoing trip. Three days in Milan, three days in Venice, four days in Florence, four days in Rome, three days in Naples, and 4 days on the delightful island of Sicily is a great way to break down your time. Milan is home to the famous La Scala Opera House and close to the gorgeous area of Lake Como. 

Venice is truly unique, and you can enjoy exploring its many winding canals and waterways, as well as St. Mark’s Square. Florence is the ideal city to immerse in the culture of the Renaissance, and you will find amazing museums, including the Uffizi Gallery. The capital city of Rome provides endless opportunities to discover historic landmarks, including the Colosseum and Pantheon. Naples is located along Italy’s beautiful coast, and during your time here you can visit Sorrento, Capri, and the impressive Mount Vesuvius volcano. Sicily is a short boat ride from the mainland, and has gorgeous cities to explore, including Palermo, Agrigento, and Taormina.

Best Time to Visit Italy

Italy is beautiful throughout the year, but the ideal time to visit in regards to weather is the late Spring, early Summer, and early Fall. During these months the weather is often very comfortable, in the 60s and 70s Fahrenheit in most locations. Cities and attractions also tend to be less crowded during these times. The Summer months of July and August are usually the most busy and warmest months of the year. An important note to consider is that many Italians go on vacation during the first half of August, so many places may be closed during that time.

Essential Experiences in Italy

Italy is filled with intriguing cities and unrivaled landmarks. Here are a few of the essential experiences you will not want to miss during your trip:

Explore the Fascinating La Scala Opera House

Milan’s legendary opera house has a lavish and grand main auditorium, and perhaps you can even see a live opera performance during your visit.

Discover the grander of the Florence Cathedral

Florence’s gorgeous Cathedral dates back centuries, and is known for its striking decor and architecture.

Wander the stunning galleries of Vatican City

Located just outside Rome, Vatican City is a must-see destination, and where you can view the magnificent Sistine Chapel.

Experience the opulence of St. Mark’s Square

Venice’s main square is the ideal place to immerse in the Venetian culture and tour the stunning St. Mark’s Basilica.

Bask in the seaside charms of Sorrento

Located close to Naples and along the beautiful coast, Sorrento is filled with idyllic views and wonderful shops and restaurants.

Travel Considerations


When considering the weather, May, the first half of June, September, and October are the best times to travel to Italy. Comfortable temperatures can be enjoyed in most places. The Summer months of July and August can get quite hot, in the 80s and 90s Fahrenheit, especially in southern regions of the country. Rain is a possibility at any time, but is more likely to occur in the months of April and November. Luckily, many attractions can still be visited even if the weather is not ideal, including museums and churches. Your Zicasso travel specialist can provide ideas and alternate options for any day the weather is a concern.


There are many transportation options available to you for your 3-week Italian vacation. Escorted tours, buses, trains, taxis, and rental cars are routinely utilized by tourists and visitors. Trains and buses are more likely to run between bigger cities. If you wish to visit more rural and remote villages, escorted tours may be a better option. Keep in mind that many rental cars are manual and not automatic, and navigating changing landscapes and traffic can get tricky. When traveling with Zicasso, you can rest assured all your transportation and logistic needs will be taken care of so you can enjoy every minute of your trip.


When preparing for a 3-week vacation, what to pack is often a question for many travelers. Since you are likely to be traveling between different cities and experience changing climates, we always suggest packing a variety of clothing, including shirts, pants, shorts (if traveling in Spring or Summer), and lightweight jackets.

Comfortable shoes are also essential. It is important to pack a jacket or shawl and a pair of long shorts or pants even in the Summer months, as some attractions require shoulders and/or knees to be covered in order to visit. Although you may be tempted to overpack, try and keep luggage to a minimum, especially if you are traveling on your own between cities. Large bags can become a hassle in crowded areas and on trains and buses.

Weather Considerations:

Since you may encounter rain during your trip, it’s always a good idea to pack umbrellas and raincoats. If you visit Italy during the Winter months, you should bring at least one coat, and a pair of gloves. For the Spring and Summer months, hats and sunblock can let you enjoy the great weather while staying cool and protected.

Electrical Considerations:

You should plan on bringing a few adaptors and converters, as Italy uses European standard electrical outlets. These will be needed if you plan on bringing electronics from home, such as cellphones and laptops.

Pharmaceutical Considerations:

Pharmacies can be easily found around Italy’s major cities, and you should be able to find common medications and other pharmaceutical needs in most places. However, since not all medications may be available, we suggest packing and bringing ample amounts of all prescriptions and medications with you.

Cultural Considerations

During your trip to Italy, you will find the Italian culture fascinating, and feel welcome everywhere you go. In addition to the renowned landmarks, such as St. Peter’s Square and the Milan Cathedral, there are also gorgeous parks and open areas you can enjoy. Public restrooms usually charge a fee to utilize them, but they can sometimes be difficult to come across while out touring. It is always suggested to use restrooms at restaurants and museums when available, as well as at your hotel. An important note regarding meals is that many places close in the afternoon for a few hours when most Italians take a lunch break, and locals also tend to eat dinner later in the evening.

Travel Insurance

You’ve booked your dream vacation, now protect it with travel insurance. A wide range of factors can leave your vacation in limbo. Medical emergencies, inclement weather, and unexpected cancellations can cause turmoil for your trip, so in the unlikely event of a disaster, get the travel insurance coverage that provides peace of mind. To get a quote, visit our travel insurance page.

Flights Via Zicasso

Zicasso Air Desk is an international air ticketing service that eliminates the stress of finding and booking the right flights for your upcoming vacation by employing the same personalized service you can expect from planning a trip with Zicasso. Our competitive flight pricing, 24x7 Service & Support, and Complimentary Consultation of Routing vs. Pricing with an Expert Flight Specialist make finding the perfect flight for your trip effortless.

Travel Documents

When visiting Italy, you will need to make sure you have the necessary travel documents with you. Doing so will allow you to be prepared and enjoy a more easygoing trip. Here are some of the essential documents you should have with you:

  • Passport
  • Airline tickets/reservations
  • Proof of hotel reservations
  • Personal medical information, including health conditions and any medications
  • Emergency contact information, including names and phone numbers
  • Customs forms/documents
  • Travel and medical insurance (see above section regarding this)

Your Zicasso travel specialist can provide further requirements specific to your trip, though responsibility always lies with the traveler to ensure that all is in order.  Many times, travel requirements can change, so it is important to stay updated as your trip approaches.

Finances & Tipping

Finances and tipping are important to many travelers, and banks and ATM machines are widely available in many cities. Major credit cards are also accepted in most places, including restaurants and museums. In regards to tipping, it is not considered required in many instances. If you wish to tip, some general guidelines are a few euros for waitstaff and a range of 5-10 euros for tour guides. Some restaurants automatically add a surcharge to bills, and in this case no additional tipping is needed. Your Zicasso travel specialist can provide guidelines for any other staff you may wish to tip.

Safety and Accessibility of Resources

When traveling abroad for 3 weeks, your safety and health are of utmost importance. Italy is considered a very safe country, and you can feel secure touring its beautiful cities and landmarks. Should they be needed, emergency services such as hospitals and law enforcement are readily accessible.

Crime Rate

The crime rates in Italy have been declining in recent years, and the country is considered safe to tour, both during the day as well as at night. The most common crime typically encountered by tourists are petty thefts, so always be aware of your surroundings.

Things to look out for

Tourists can unfortunately become targets for minor thefts such as pickpocketing, so we always suggest keeping wallets and purses in front of you and secure while out in public. While shopping for souvenirs, you should also be familiar with typical prices for items to avoid being overcharged by street vendors and small shops.

Medical & First Aid

Emergency medical services, such as hospitals, urgent care centers, and ambulances, are readily available in most cities and their outlying areas. Should you fall ill or otherwise experience a medical emergency while in Italy, you should safely proceed to the nearest hospital and advise authorities, including the local embassy. It is strongly recommended that all international travelers consult with a primary care physician prior to traveling, and this information is not intended as a substitute for personalized guidance from a doctor.

Water & Food Safety

Italy’s food is delicious, and you can enjoy all the specialty dishes and sweet desserts feeling confident the food is safe to eat. The country’s water, including water from public drinking fountains, is also safe to ingest. Washing your hands before meals and snacks is a great way to reduce the chance of any germs spreading to your food.

Travel with Zicasso

When planning a luxury vacation, every detail matters, which is why our approach is different. We will match you with leading travel specialists who are the most qualified to make your dream trip happen. They know their country better than anyone, and each travel specialist in Zicasso’s network is among the finest travel agents and tour operators, comprising the top tier of the industry. Experience the wonder of an exceptional itinerary crafted just for you.

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