8 Day Italy Itineraries

Ratings of Zicasso's Service

How Zicasso WorksCustom Italy Tours

  1. Describe your dream 8 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.

Uncover discoveries long held to legend as you venture to Italy for an experience unlike any other. From ancient monuments and tantalizing mythology to winding vineyards and a thriving culture, an 8-day Italy itinerary has so much to offer. Enjoy the luxury of expert guidance as you plan your trip of a lifetime with Zicasso’s travel specialists.

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.

8 Day Luxury Tour of Sicily Highlights: Taormina, Syracuse, Agrigento, Palermo

8 Day Luxury Tour of Sicily Highlights: Taormina, Syracuse,...

8 Day Custom Tour

From $4,795

A marble balcony overlooks the azure water of the Mediterranean Sea. Snow caps the conical summit of Mount Etna. Baroque churches create an elegant and lavish atmosphere along the streets of hillside towns. Gold-trimmed walls reflect endlessly into the collection of mirrors hanging in the dining hall of a lavish palace. Your luxury tour of Sicily highlights takes you through the majesty of the island’s past in the comforts of contemporary five-star hotels. Take in Greek ruins and stunning panoramas, ancient markets, and private tours, showing you how plush history can be.


Adriatic to Mediterranean: Explore Venice, Lake Garda & Cinque Terre Tour

Adriatic to Mediterranean: Explore Venice, Lake Garda...

8 Day Custom Tour

From $2,195

Let Italy enchant you with its long tradition of beautiful cities and elegant towns set in the dream-like landscape between the Adriatic and Mediterranean. Marble palaces offer insight into the former prestige of noble families as storybook castles protect the shores of a glassy alpine lake while mountain outcroppings preserve the beauty of medieval fishing villages that overlook the sea. Your custom tailored tour will immerse you in the traditions of Venice, Lake Garda, and Cinque Terre, as you indulge in the cuisine, marvel at the sites, and wander along the cobblestone streets and meandering trails. Embrace the grandeur of Italian heritage and bask in the luxury. 


Tuscany Tour for Lovers: Siena, Cortona, Volterra, San Gimignano and Certaldo

Tuscany Tour for Lovers: Siena, Cortona, Volterra,...

8 Day Custom Tour

From $2,195

Medieval city walls and historic towers make each town in the Tuscan countryside feel like a fairytale, and you will feel like royalty. On your custom tailored Tuscany tour for lovers, each day takes you to the intimate villages and enchanting landscapes, from lush valleys to glistening seaside. Taste the traditions of elegant, regional cuisine and savor the treasured company of your partner. You will find the charms of history and the enchantment of sunsets over castle walls, sipping wine in a piazza, sharing gelato, and discovering all the different ways that Tuscany is for lovers.


Grottammare village on the Adriatic Sea in Marche, Italy.

Soulful Italy: Umbria, The Marches, and Abruzzo Tour

Soulful Italy: Umbria, The Marches, and Abruzzo Tour...

8 Day Custom Tour

From $2,195

Discover central Italy's hidden gems on this 8-day tour. Often overshadowed by Lazio and Tuscany, the regions of Abruzzo, Marche, and Umbria are stars in their own right. From the natural beauty of Gran Sasso National Park to small squares of towns like Ascoli Piceno, there is much to seek and enjoy on this journey. Book your memorable tour today.


Gastronomic Traditions of Italy Tour: Cheese Making, Olive Oil Pressing & More

Gastronomic Traditions of Italy Tour: Cheese Making,...

8 Day Custom Tour

From $2,195

Encounter a side of unseen Italy in the undisturbed region of Abruzzo. Medieval castles remain strong, overlooking a valley of lush vines. The Apennine Mountains form extraordinary backdrops to historic hillside towns. Fishermen continue using ancient fishing techniques along the coastline. Shepherds traverse the undulating landscape, faithfully following their flock. Farms produce an abundance of flavorful cheeses, and vineyards make inspiring wines. Your custom tailored Italy tour immerses you in historical culture set in a divine landscape where the mountains meet the eastern shore.


Basil & Chocolate: Indulging in Italian Riviera and Umbrian Countryside Tour

Basil & Chocolate: Indulging in Italian Riviera...

8 Day Custom Tour

From $2,195

The charm of the Italian Riviera emanates from contemporary luxuries hidden within the serene seaside villages. The enchantment of Umbria rises from the medieval streets, bucolic hills, and overlooked towns that burst out of iconic vineyards. Your custom tailored tour combines the majesty of land and sea to take you on a remarkable journey through ancient city walls and continued traditions, tranquil hiking trails and opulent marinas. A statue of Neptune adorns the cliff that overlooks the Mediterranean as a powerful waterfall erupts from an emerald forest. Unwrap the wonder of the Riviera and Umbrian regions to enjoy pebbled beaches and perfect panoramas. 


A villa and vineyard in Piedmont, northern Italy

Pleasures of Piedmont Tour: Wine, Truffles & Celebration

Pleasures of Piedmont Tour: Wine, Truffles & Celebration...

8 Day Custom Tour

From $2,195

In Italy, you can stand in an ancient cave-turned-wine-cellar and taste wine with roots dating back to the Roman Empire. Your handcrafted Piedmont Italy tour of wine and truffles takes you around Piedmont, filling each day with the sumptuous flavors of the region, from food to history. The eclectic aromas of the Truffle Festival mix with the enthusiastic calls of the crowd, each person aching to taste the unique concoctions created simply for the event. A sea of vineyards traipses over the hillside and the pleasurable flavors of the countryside can be as rich or delicate as an award-winning restaurant in the city.


True Flavors of Northern Italy: Food & Wine Tour of Veneto

True Flavors of Northern Italy: Food & Wine Tour...

8 Day Custom Tour

From $2,195

The cuisine of a region explains much of its culture, tradition, and respect for the landscape. Sip a glass of indulgent wine with a view of the snow-capped peaks of the Dolomite Mountains, just before you sit down to a gourmet meal. Wander the cobblestone streets of a Renaissance city adorned with shining frescoes as the aromas of olive groves and grapevines sweep across the landscape that connects the foothills to the lakeshores. The marvels of the wine and food in Veneto are at your fingertips during your custom tailored tour dedicated to the splendor of farm to table cooking and soil to bottle vineyards.


Tuscany Tour of Charming Villages, Ancient Towns & Unforgettable Landscapes

Tuscany Tour of Charming Villages, Ancient Towns &...

8 Day Custom Tour

From $2,195

There are few greater moments than sitting on a hillside at a quiet café with a view overlooking the red-tiled roofs of a historic city. You can hear the bells of the cathedral chime at dusk. The aromas of freshly cooked pasta and rich locally grown wine add to the unforgettable ambiance. Images of Renaissance statues and oil paintings decorate the fantasy. Your custom-tailored Tuscany tour to Florence, Siena, and Arezzo turns dreams into realities, taking you through the treasured hills and medieval towns of, where every moment is luxurious, illuminating, and unforgettable.


Beautiful town of Alberobello with trulli houses among green plants and flowers in the Apulia region of southern Italy.

Off-the-Beaten-Path Puglia Discovery Tour

Off-the-Beaten-Path Puglia Discovery Tour

8 Day Custom Tour

From $2,195

This 8-day tour of Puglia is a great way to venture off the beaten path in one of Europe's most visited tourist destinations. This tour is an immersive exploration of the Italian region that time forgot, from the rural countryside to the scenic seaside. A blend of active and leisure time on this tour makes sure that you are able to fully enjoy this unforgettable journey in one of the most idyllic vacation destinations on the planet.


Vatican Dome of San Pietro Basilica and the Sant'Angelo bridge over Tiber river in Rome, Italy.

Rome and Neapolitan Coast Tour

Rome and Neapolitan Coast Tour

8 Day Custom Tour

From $2,195

On this handcrafted 7-day tour, witness the Italian heritage that shines through iconic monuments and contemporary restaurants that preserve the country's culinary roots. Allow yourself to marvel at the country's phenomenal art and architecture and appreciate the mesmerizing landscapes of each iconic destination.


Sun rising on San Marco Square in Venice.

Rich Jewish Heritage of Italy Tour

Rich Jewish Heritage of Italy Tour

8 Day Custom Tour

From $2,315

Trace the deep roots of culture on this 8-day Jewish heritage Italy tour. The histories of the Jewish community and Italy have intertwined for over 2,000 years, showcasing the ways the cultures have merged to create a unique blend of distinctive cultural practices, artistic aesthetics, and delicious cuisine. Your Italy trip to Rome, Venice, and Florence will uncover where Jewish traditions converged and conflicted through time.



8 Day Italy Itinerary at a Glance

Italy is rich in history, full of culture, home to some of the world’s best cuisine, and truly an amazing destination. From the ancient landmarks of Rome to the art masterpieces of Florence and gorgeous landscapes of Venice, Italy has something for everyone, and is the perfect place for a memorable vacation.


Italy is comprised of 20 regions, each distinct with its own traditions, foods, and dialects. Some of the most well-known regions are Lazio, Tuscany, Veneto, and Lombardy. These four regions are home to some of Italy’s major cities and attractions, and are thus quite popular for tourists. The capital city of Rome and attractions such as the Colosseum and Roman Forum are found in Lazio, while a visit to Tuscany will bring you to the captivating city of Florence and attractions such as the Florence Cathedral and Ponte Vecchio. One of the most visited destinations in Veneto is the unrivaled city of Venice, home to winding waterways and floating gondolas. Lombardy is equally intriguing, and offers the fashion capital of Milan and attractions such as La Scala Opera House.


Italy has an overall Mediterranean climate, with warm Summers in 80s and 90s Fahrenheit, pleasant Spring months in the 70s Fahrenheit, and cool winters in the 50s Fahrenheit and even lower. Northern Italy, in regions such as Piedmont, the climate is on average cooler than more southern regions such as Calabria and the island of Sicily. Rain can be common in the months of April and November, and snow is also a possibility in northern regions that are home to some of Italy’s mountain ranges, such as the Alps.


Italy has a population of over 60 million people, and ranks in the top five most populated European countries. Some of the most populated regions are Lombardy, Lazio, and Campania. Most of the population in Lombardy revolves around Milan, its capital city which is home to a thriving business and fashion world. Rome and Naples highlight the popular areas of Lazio and Campania, and are also important and influential cities.


Christianity is the dominant religion in Italy, with Roman Catholicism being the most popular faith followed by Italians. Roughly 70% of the Italian population identify as Roman Catholic, and Vatican City, located near Rome, is the center of the Roman Catholic Church and home to the Pope.


Italian is the official language of Italy. There are also many regional dialects, so you may encounter some of these as you travel from one area of the country to the next. People in the major cities, especially around tourist sites, may also speak English.


The national currency of Italy, like many other European countries, is the Euro. In addition, most major credit cards are also accepted, especially at tourist attractions and restaurants in major cities.

Where to Visit in 8 Days

An 8-day trip to Italy provides enough time to visit and explore some its wonderful cities and historic attractions. Two days each in Rome, Florence, Milan, and Venice, are a great way to spend your eight days. In Rome, you can tour a plethora of unparalleled sites, such as the Colosseum, Roman Forum, and nearby Vatican. Florence is home to some of the world’s best art and museums, including the Uffizi and Accademia Galleries, and Milan is a thriving city with a stunning Cathedral and the country’s oldest shopping mall. Venice is truly a unique destination, as it is the floating city on water, and where you will find St. Mark’s Square and an endless number of gondolas and historic bridges.

Best Time to Visit Italy

The best time to visit Italy in regards to weather is from mid-April through mid-June, and again from September through October. During these months the temperatures are not too warm or too cold, and it is usually less crowded than the Summer months of July and August. July and August are also the hottest months of the year. Much of Italy closes for vacation during the first half of August, so this is important to keep in mind if planning to travel during that time.

Essential Experiences in Italy

There are so many amazing destinations in Italy, and each city can immerse you in some of the country’s history, culture, and delicious cuisine. Here are some of the essential experiences you will not want to miss:

Colosseum in Rome

The Roman Colosseum dates back centuries, and will transport you back to the grandeur of Ancient Rome as you tour the rows of seating and learn about the mighty gladiators that once graced this legendary arena.

David Statue in Florence

The museums of Florence are second to none, and the Renaissance can be relived through some of the city’s priceless art. Michelangelo’s David statue is a true masterpiece, and a quintessential piece of Tuscan art and history.

Gondola Ride in Venice

Venice is like no other city, and a gondola ride around its winding canals provides the perfect vantage point to discover its attractions and gorgeous atmosphere. 

Travel Considerations


The coldest months in Italy are usually between December and February, while the warmest months, with temperatures reaching temperatures in 80s and 90s Fahrenheit, are the second half of June, July, and August. Rain may be encountered in any city at any time, but is more likely to occur in the months of April and November. If inclement weather is encountered, your Zicasso travel specialist can provide plenty of alternatives that will still allow you to enjoy your destinations. Many attractions, such as museums and churches, are still open even if the weather is not ideal.


Italy is very accessible, and offers many options for transportation from one city to the next. High speed trains, buses, rental cars, and guided tours are readily available. Handling logistics and luggage can sometimes get tricky on your own, but you can rest assured that Zicasso can assist with all your transportation needs so your trip is smooth and enjoyable.


Whether you visit in Fall, Winter, Spring, or Summer, it is best to pack a variety of clothing for your trip. Light jackets and sweatshirts are great pieces that can easily be taken on and off while out touring. You will also want to be sure to pack shawls, scarves, and lightweight pants even if visiting in the Summer, as certain attractions, such as the Vatican, require shoulders and knees to be covered. If you plan on taking trains and buses, it is best to keep your pieces of luggage to a minimum, as large suitcases can be quite bulky and become a hassle to handle.

Weather Considerations:

With the chance for rain and other inclement weather a possibility, umbrellas and raincoats are essentials for your trip. Comfortable shoes, hats, and sunblock are also great pieces to have while out walking and visiting attractions.

Electrical Considerations:

It’s a good idea to pack a few adaptors and converters, as European standard electrical outlets are utilized throughout Italy. The adaptors and converters are needed to charge and use electronics from home.

Pharmaceutical Considerations:

Pharmacies can be easily found around major cities such as Rome and Florence. However, not all medications may be available, so it is always recommended to bring ample amounts of medications and prescriptions with you on your trip. A small first aid kit is also a good item to keep on hand.

Cultural Considerations

The Italian people are lively, and often very welcoming to tourists and visitors. Besides the main attractions, there are also plenty of public parks and open spaces available for you to enjoy during your trip. Restrooms can sometimes be difficult to find, especially outside of the main cities and landmarks, so take advantage of restrooms at restaurants, museums, attractions, and your hotel. For any public restrooms that are available, it is customary to pay 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

Bringing the necessary travel documents with you is essential for your trip to Italy, and being prepared will help ensure a smooth and enjoyable vacation. Here is a list of some of the most important documents to have with you while traveling:

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

Your Zicasso travel specialist can provide requirements that are specific to your trip, although responsibility always lies with the traveler to ensure that all is in order.  Travel requirements can and do change often to no notice, so all are wise to stay updated as your trip comes near.

Finances & Tipping

Italy utilizes the Euro currency, so you will want to exchange some money either before your trip or shortly after arriving in Italy. Banks and ATM machines are readily available, especially in the major cities. Negotiations and bartering are common when purchasing souvenirs or shopping at outdoor vendors, so you can be comfortable trying to get a lower price at these types of merchants. Overall, tipping is not very popular in Italy and is not considered required. For exceptional service at restaurants, a tip of a few euros is acceptable. Note that some restaurants automatically add service charges to the bill, in which case no additional tip is needed. Your Zicasso travel specialist can help with more specific guidelines for hotel staff and tour guides you may want to tip.

Safety and Accessibility of Resources

Italy is a very safe country, and you can feel secure while traveling from one city to the next. Evening and night time tours and attractions are also considered safe to enjoy. If needed, emergency resources such as law enforcement and hospitals are readily available in most areas. 

Crime Rate

Italy’s crime rate has been declining for a number of years and it is considered one of the safest countries in Europe. It is always important to keep aware of your surroundings and keep personal items, especially wallets and purses, close to you and secure while out touring.

Things to look out for

Tourists can sometimes become targets for petty thefts, such as pickpocketing. This is especially true around tourist sites and busy attractions, so always be observant of who is around you. You should also always take care to only purchase items from reputable vendors, to avoid the possibility of being overcharged or possibly purchasing counterfeit goods.

Medical & First Aid

If needed, hospitals and pharmacies are easily found in Italy’s major cities, including Rome, Florence, Milan, and Venice. It is suggested to keep a list of any current health conditions and medications with you so this information can be easily accessed in case of an emergency. If you experience an emergency medical situation, it is best to get to the nearest hospital and notify the embassy if necessary. This information is not intended to be a substitute for personalized guidance from a doctor, and it is strongly recommended all travelers consult with a primary care physician prior to traveling.

Water & Food Safety

The water and food of Italy is safe to eat and drink, and absolutely delicious. The country is known for its cuisine, and you will find many dining options and amazing restaurants everywhere you go. Water from drinking fountains is also considered safe to drink.

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.

Italy Travel Review: Venice, Florence, Tuscany, Cinque Terre,...
"Our tour guides in each city were extremely knowledgeable,


Reviewed By Ashley P.

Travel Review: Italy Tour, Sicily, Palermo, Agrigento, Catania,...
"All the arrangements made by the travel company worked


Reviewed By Paul R.

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

Reviewed By Christina M.

Italy Travel Agent Review: Puglia Region, Wine Tasting,...
"The entire experience was professionally coordinated."

Reviewed By Nadine P.

Travel Review: Italy Vacation, Florence, Rome, Palermo,...
"Every detail was seen too."

Reviewed By Trudi W.

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


Reviewed By Gerald H.