14 Day Italy Itineraries

Ratings of Zicasso's Service

How Zicasso WorksCustom Italy Tours

  1. Describe your dream 14-day Italy itinerary.

  2. We match you with up to 3 top travel specialists (travel agencies). They compete to plan your vacation.

  3. Book the trip when you are satisfied.

Explore Italy like you never thought possible. Revel in the country’s most iconic cities, monuments, and cuisines, while also getting the distinct opportunity to uncover hidden treasures from exploring quaint villages to private tastings at countryside wineries. Discover the beauty of Italy and its many enchantments with a personalized 14-day itinerary from Zicasso.

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.

Custom Cultural Italy Tour in 2 Weeks

Custom Cultural Italy Tour in 2 Weeks

14 Day Custom Tour

From $3,845

Italy is like a great masterpiece waiting to dazzle the viewer. On first impression, she amazes you with her beauty. Upon a closer look, her details and history enrapture you—as you’re awestruck by the ruins of Rome, the majesty of the Vatican and the surreal waterways in Venice. Finally, you leave changed forever by the magic of this incomparable place. We invite you to indulge in the enchanting experiences that await you in this itinerary as well as our carefully selected collection of Italy tours on Zicasso.

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View of Florence, Italy with the Cathedral of Santa Maria del Fiore in the background

Perfect Two Weeks in Italy Tour

Perfect Two Weeks in Italy Tour

14 Day Custom Tour

From $3,943

Classic beauty and indelible charm will radiate from ancient ruins, Renaissance artwork, and captivating coastlines during your custom-tailored 2-week tour of Italy. The iconic wonder of Italy will seduce you with panoramas of the rugged Amalfi Coast and the glamour of St. Mark’s interior shimmering with gilded mosaics. The Colosseum reflects remarkable achievement of ancient engineering and the Uffizi Gallery displays the triumphs of spirited expression. Wander along the cherished shores of Lake Como and travel into the past while strolling down the streets of Pompeii. Embrace Italy as an embodiment of culture with classic style and timeless charisma.

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An Unforgettable Honeymoon in Italy

An Unforgettable Honeymoon in Italy

14 Day Custom Tour

From $3,845

Your first trip as a married couple should be remarkable. It should be filled with fine food and fun times, dictated by nothing but the slow circuit of the sun across a cloudless blue sky. It should be notable for its uniqueness, taking you to places you’ve never heard of and showing you things you could have never imagined. It should be as bold and as boundless as your love for each other, which means it can only be done in inimitable Italy.

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Milan Cathedral in Italy, the third largest church in Europe

Northern Italy to Sicily: Italy Tour for Second Timers

Northern Italy to Sicily: Italy Tour for Second Timers...

14 Day Custom Tour

From $3,495

Open your eyes to the expansive plains of Umbria and vast olive groves of Puglia, the seaside ambiance of Calabria and the flavors of Emilia-Romagna during your personalized Italy tour that will immerse you in the marvels of discovery. Savor the authentic beauty of medieval towns and Baroque cities preserved in time and steeped in tradition. Greek theaters decorate the landscape of Sicily and caves pockmark the soft tufa limestone of Basilicata. Travel from the Adriatic’s turquoise waters to the Tyrrhenian’s azure hues and the Ionian’s sapphire glow uncovering whitewashed homes, pastel-colored cathedrals, and an endless inviting ambiance.

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Amazing 14-Day Italy Itinerary with Capri

Amazing 14-Day Italy Itinerary with Capri

14 Day Custom Tour

From $3,845

Bask in the authentic charm and the simple wonder of Italy during your custom-tailored tour taking you from Rome to Capri, Lake Maggiore to Assisi. Travel across breathtaking horizons to uncover hidden sagas while gaining cultural insight into more than 3,000 years of history. Engage with the stories of the Medici family and witness the fruits of Michelangelo’s celebrated hands. Wander through lavish galleries showing the wealth of the former aristocracy and sample the treasured flavors of the remarkable wines. Engage with the extraordinary local specialties, travel the historical castles, and bask in the majestic landscapes discovered from the Amalfi Coast to Italian Alps. 

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Italy Tour of the Most Beautiful Towns & Villages

Italy Tour of the Most Beautiful Towns & Villages...

14 Day Custom Tour

From $3,845

The sensations of Italy come from traditions ingrained within the soil of the countryside and rising up through the towns and villages. On this 14-day tour through the north and south of the country you will find the most beautiful scenery displayed in Italy’s natural majesty. Climb through medieval villages and find the hidden waterfalls of Umbria, revel in the Tuscan hills and visit the marvelous art of the Renaissance. From natural magnificence to humanity’s endless striving for beatific perfection, you will find, wander, and wonder through it all. 

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Italy

14 Day Italy Itinerary at a Glance

A trip to Italy is a discovery of unrivaled history, culture, and cuisine. During your amazing 14-day vacation you can visit some of the country’s beautiful cities, tour ancient landmarks, and dine on the best cuisine in the world.

Regions

Italy is made up of 20 different regions. Each one is fascinating as it has its own customs, traditions, foods, and dialect. Rome and its many historical attractions are the highlight of the Lazio region, while Florence and Pisa are two of the highlights of Tuscany. The gorgeous city of Venice in the Veneto region and amazing Amalfi Coast in Campania are just a few more examples of the beautiful cities and landmarks that can be found all over the country.

Climate

Similar to other countries in the area, Italy has a Mediterranean climate. There are four seasons, and Winters are usually cold and wet while Summers are hot and dry. Snow is somewhat typical in northern regions, such as Piedmont, and the hottest climates can be found in southern regions such as Sicily. Spring and Fall bring greater chances for rain in most areas.

Population

Italy has a population of over 60 million people, and this number has remained relatively the same over the last couple of years. Greater amounts of the population are focused around main cities, while rural areas tend to be less populated. Some of the most populated cities in the country are Rome and Milan.

Religion

The main religion in Italy is the Roman Catholic branch of Christianity. Over 70% of Italians identify as Roman Catholic, and Vatican City, located outside Rome, is the center of the Roman Catholic faith. It is one of the most visited places in the country.

Language

Italian is the national language of Italy and the most common language you will hear during your trip. Local dialects are also spoken, especially in smaller towns and villages. It is also typical to come across people who speak English, particularly around tourist sites and major cities.

Currency

The European Euro is the national currency of Italy, and this replaced the Lira many years ago. The Euro is the most common form of payment, but major credit cards are also widely accepted in many places.

Where to Visit in 14 Days

During a 14-day Italian tour, you can visit many of the main cities and even explore the stunning island of Sicily. Two days each in Milan, Venice, Florence, and Naples, along with three days each in Rome and Sicily, is a great way to spend your time. Milan is a wonderful combination of history and a thriving business center. Some of the city’s attractions include the Milan Cathedral and La Scala Opera House. Venice, a floating city, is truly unique and provides the chance to visit St. Mark’s Square and the nearby islands of Murano and Burano. While in Florence, you can immerse in the art of the Renaissance through visits to the Uffizi and Accademia Galleries. Naples is full of culture, and close to the fascinating Mount Vesuvius volcano and island of Capri. Rome is full of historical attractions, including the Colosseum, Pantheon, and Roman Forum, and Vatican City is nearby as well. Sicily is a gorgeous island, and during your time here you can discover some of its exciting cities, including Palermo and Agrigento.

Best Time to Visit Italy

May, the first half of June, September, and October are considered the best times of the year to visit Italy. During these times the temperatures are ideal and comfortable, usually in the 60s and 70s Fahrenheit in most cities. These months are also typically less crowded than the Summer months of July and August. The main Summer months also experience the highest temperatures. Many Italians go on vacation during the first half of August, so this is an important consideration if planning a trip for that month.

Essential Experiences in Italy

There are so many cities to visit and things to see in Italy that it can be hard to decide on which attractions and landmarks you should explore. Here are some of the essential experiences you will not want to miss:

Witness the Intricate Design of the Milan Cathedral

The gorgeous Milan Cathedral is one of Italy’s largest Cathedrals and is adorned with stunning and intricate statues.

Enjoy a Picturesque Gondola Ride in Venice

A ride in one of Venice’s traditional boats is the ideal way to view the city and experience its unrivaled culture.

Visit the Remarkable Accademia Gallery in Florence

Florence is known for its collection of Renaissance art and museums, and the Accademia Gallery is the perfect place to see numerous priceless works of art, including Michelangelo’s David statue.

Uncover the Depth of History at the Colosseum in Rome

The ancient Roman Colosseum dates back centuries, and is a quintessential example of the grandeur of the Roman Empire.

Travel Considerations

Weather

If you are looking to travel to Italy when the weather is ideal, the best times to travel are Spring, early Summer, and Fall. Temperatures get extremely warm, in the 80s and 90s Fahrenheit, during the Summer months of July and August. Rain is a possibility at any time, but is especially likely in April and November. Your Zicasso travel specialist can help plan activities for any day the weather is a concern, and many attractions can still be enjoyed during inclement weather.

Transportation

There are several transportation options available to travel around Italy. High speed trains, buses, rental cars, and escorted tours are all accessible. If planning on renting a car, keep in mind that some tourist areas and older towns do not allow vehicles in certain locations. Trains and buses may also not provide options to visit smaller villages outside the main cities. Planning is essential when it comes to logistics for your vacation, and traveling with Zicasso will ensure all your transportation needs are taken care of so you can relax and enjoy your trip.

Packing

For a 14-day vacation to Italy, you will want to bring a variety of clothing and shoes. Pieces that can be layered, such as sweatshirts and light jackets, are good options for changing temperatures and climates. Comfortable shoes are also essential for touring and visiting attractions that include a lot of walking, such as the Roman Forum and Colosseum. If planning to travel on your own, try and keep luggage to a minimum as large and bulky bags can quickly become a hassle, especially in crowded areas and on trains and buses. Should you forget to pack something, there are endless numbers of stores and boutiques all around the country.

Weather Considerations:

Since you may encounter rain during your vacation, it is always suggested to bring umbrellas and raincoats. For the warmer months, hats, sunblock, and water bottles all come in handy. It is also a good idea to pack at least one jacket or coat so you are prepared for any changing temperatures from one city to the next.

Electrical Considerations:

Italy utilizes European standard electrical outlets. Electronics you may bring from home, such as cellphones and hair dryers, will not work with these outlets without adaptors and/or converters, so plan on packing a few of each for your trip.

Pharmaceutical Considerations:

Many of Italy’s main cities, including Rome, Florence, Milan, and Naples, have pharmacies readily available. Since not all medications may be found, we always suggest packing and bringing ample amounts of all medications and prescriptions with you on your trip.

Cultural Considerations

Italy is a main tourist destination, so the Italian people are very used to visitors and tourists, and are overall quite welcoming. Besides the main cities and landmarks, there are endless numbers of smaller towns and villages, parks, and open areas for you to enjoy as well. Public restrooms are not as commonly found as you may be used to, so take advantage of restrooms at restaurants and attractions. Any public restrooms that are available typically charge a small sum to use them.

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 traveling abroad, making sure you have the required travel documents with you is of utmost importance. Doing so will allow for a more relaxed and easygoing vacation. Here is a list of some of the essential documents you need:

  • Passport
  • Airline tickets/reservations
  • Hotel confirmations/reservations
  • Personal medical information, including health issues and medications
  • Emergency contact information
  • All required customs forms
  • Pre-purchased tickets for tours and attractions
  • Travel and medical insurance (see above section regarding this)

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

Finances & Tipping

You will find banks and ATM machines readily available in many of Italy’s main cities. Credit cards are also commonly accepted in most places, including restaurants and museums. In regards to tipping, it is common to leave a small tip of a few euros for waitstaff and tips of 5-10 euros for tour guides. Your Zicasso travel specialist can help with guidelines for any other staff you may wish to tip during your vacation. There are many street vendors that sell souvenirs and other small goods, and it is common to negotiate prices with these types of retailers.

Safety and Accessibility of Resources

Italy is a very safe country, and visited by millions of people every year. You can feel secure taking a vacation to Italy, and rest assured that if needed, emergency resources are available.

Crime Rate

After a peak in crime back in 2012 and 2013, crime rates have been decreasing in Italy every year since. It is considered one of the safest countries in Europe, and many landmarks and attractions are closely monitored on a regular basis.

Things to look out for

Similar to many places, tourists in Italy can unfortunately become targets for petty thefts. Pickpocketing has been known to occur, especially at busy sites such as the Trevi Fountain in Rome or St. Mark’s Square in Venice. You should always keep your personal belongings close and be aware of your surroundings to reduce the chances of this occurring.

Medical & First Aid

If you require medical assistance during your vacation, hospitals and urgent care centers are located around many of Italy’s main cities. Ambulance services are also available in many other towns and villages that can transport you to the closest hospital as well. In an emergency, it is suggested you get safely to the nearest hospital and notify the local embassy. This information is not intended as a substitute for personalized guidance from a doctor, and it is recommended that all travelers consult with a physician prior to traveling abroad.

Water & Food Safety

The food of Italy is some of the best in the world, and it is safe to enjoy. The country’s water is also safe, including water from public drinking fountains. If you have any food allergies, you should keep a list of them with you during your vacation.

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.

Reviews of Zicasso's Referral Service

4.88 stars based on 4471 reviews. See all our reviews.

Luxury Italy Travel Review: Siena, Florence, Chianti, Fiat...
"[Our travel agency] made the entire trip effortless, so

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Reviewed By Nicholas W.

Luxury Italy Travel Review: Sicily, Siracuse, Greek Temples...
"Getting things done, arranging the best, and satisfying

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Reviewed By Gerald H.

Italy & Sicily Family Travel Review: Mozzarella Making...
"...we felt like VIP the entire time."

Reviewed By Christina M.

Italy Honeymoon Trip, Florence, Rome, Truffle Hunting, Food...
"[The travel planners] did a great job gauging our tastes

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Reviewed By Amelia J.

Travel Review: Italy & Portugal 2-Week Anniversary Trip,...
"Our trip was simply magical...and it was everything my

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Reviewed By Randolph W.

Italy Travel Agent Review: 14-Day Honeymoon, Vatican Tour,...
"We were very impressed with the service that was provided

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Reviewed By Jennifer P.