Italy's unrivalled cultural heritage, diverse landscapes and celebrated food and wine make it an unmissable destination. There are so many superb places to go, it can be difficult to know where to begin, but we can help you create an itinerary that reflects your interests, takes in the main sights and reveals some of Italy's lesser-known charms.
Whether you wish to travel with a group, hire a private chauffeur, or drive yourself, Taylored Tours will help make your trip to Italy memorable. If your desire is to discover artistic masterpieces in the churches and galleries of Florence, uncover Rome’s iconic sites, relax on the Amalfi Coast, or learn to cook traditional Italian pasta in Tuscany, Taylored Tours will set you on the right track. Your route will be ”taylored” to your own interests. Taylored Tours will help you discover the hidden side of Italy, as well as the key highlights.
A cultural powerhouse famed for its legendary art and architecture, glorious landscapes and gourmet food and wine, Italy offers you a wealth of experiences. CLICK HERE to see activities that offer a deeper insight into the country's most famous attractions and give a local perspective on life in this fascinating destination.
When is the best time to visit Italy?
The best time to visit Italy is during spring and fall, when the temperatures are comfortable and there are fewer crowds.
Temperatures start to warm up in spring, going from the late teens to mid-twenties, although it’s still advisable to wear layers in case of colder spells.
The summer months of July and August see higher temperatures and visitor numbers reach their peak. Temperatures are normally around 81 °F and often reach over 88 °F at the height of the day.
Temperatures cool down gradually, so September is still very pleasant, with an average of around 77℉. Expect crisp fall leaves and some sunnier days, but plan for wet weather too.
Temperatures in the south remain mild in winter. However, northern Italy is normally wet and cold, and it’s not unusual for snow to fall, especially in the mountains.
A rural region with beautiful countryside, mountains, and beaches. This is a great place to “get away from it all” enjoy an active, outdoor vacation in the Italian outdoors.
Located in the northwest corner of Italy in between France, Switzerland, and Piedmont, the Aosta Valley is mountainous and picturesque. The Alps cut through this autonomous region, adding to its allure. This is a great destination for history buffs who love castles and ruins, anyone who wants to get out of the heat (even the summers can be chilly here thanks to the mountains), and anyone interested in sampling the multicultural side of Italy.
The “instep” of Italy’s boot, Basilicata is large and rural. The area’s most-visited city is Matera, where the Neolithic cave dwellings pull fascinated visitors. Basilicata is also filled with forests, lakes, and small villages. It is a good destination for and active holiday if you are traveling on a budget.
Calabria sits near the tip of Italy’s boot and offers plenty of idyllic beaches. Like Basilicata, it is also mountainous and has a low population density, so it is a good option for travelers on a budget who are not looking for a crowded city experience.
Italy’s second most populous region, Campania is the place to go for a sun-soaked holiday on the bustling coast. From Naples to Pompeii and the Amalfi Coast, Campania covers it all.
A wealthy region that spans the north of the country, Emilia-Romagna covers cities including Bologna, Ferrara, and Modena. This is the region to visit for some of Italy’s most famous cuisine, most beautiful coastlines, and Renaissance cities.
This very small autonomous region is tucked away near Austria and Slovenia. It offers both seaside and Alps and is a great destination for a unique experience from the rest of Italy!
Italy’s central region and home to the capital city of Rome, Lazio offers sandy beaches, small mountains, medieval towns, lakes, and archeological sites. This destination is a must-see for history buffs and art lovers.
A hilly region with a long shoreline along the Adriatic, Le Marche’s tourism crowd is attracted for its beaches and mountains. This destination is ideal for hiking and other outdoor summer activities.
Famous for its seaside, Liguria has a storied history. Tourists are drawn to the area for the resort towns of Cinque Terre and Portofino but a huge draw is also the capital city of Genoa, which was the hometown of Christopher Columbus.
In the north of Italy, bordering Switzerland, Lombardy is the country’s wealthiest, most populous region. The capital, Milan, is the second largest city in Italy. Lombardy also offers the Lake District, which has destinations such as Lake Como, Maggiore, and Garda.
Molise is the country’s newest region. It is mainly agricultural and produces wine, olive oil, dairy, fruit, and vegetables. Tourism isn’t well-developed here yet, so it’s a great choice for off-grid vacationing in authentic small towns.
Though it is surrounded by the Alps on three sides, most of this region is actually on a flat plain. It produces rice and wine, making the region a must-visit for food aficionados. The area is also ideal for anyone who loves winter sports.
An island located west and south of Corsica features stunning beaches, gripping nightlife, and buzzy resort towns. Head inland for a tranquil agricultural area with a small-town feel.
The largest island in the Mediterranean, Sicily is its own world. Go for the sunny climate, natural beauty, ancient history, beaches, and unique culture.
This area is also known as Trentino-South Tyrol and is a gorgeous, autonomous region in northern Italy that used to be part of Austria-Hungary. It has its own special culture and is a great destination for active travelers who want to visit the mountains and see the sights!
Renowned for its food, wine, towns, and countryside, Tuscany is famous for the bounty of the region. If you are looking for a quintessential Italian getaway, look no further, Tuscany has it all.
Located next to Tuscany, Umbria also offers gorgeous countryside, hilltop towns, olive and wine vineyards, and a history that reaches back to the Etruscans. Umbria is a little less touristy than Tuscany and a great choice if you’re looking to get farther away from the crowds.
One of Italy’s most developed regions, this region produces some of Italy’s most famous wines including Prosecco, Valpolicella, and Soave. The region’s most popular towns to visit include Venice, Verona, Vicenza, Belluno, and Padua.
Located on the heel of Italy’s boot, Puglia is known for its beautiful beaches and countryside as well as its excellent food and unique architecture. A favorite summer destination for Italians, this is an ideal destination for anyone who wants a true taste of the Mediterranean lifestyle.
Take an incredible 6-night sojourn to the Tuscan countryside! Relax in classic villa accommodations while you spend your days exploring the Italian regions surrounding you. Discover new wines, learn how to make an authentic Italian pizza, and explore the Chianti region at your own leisure!
Your Italy escape will be much more than the Statue of David and a bottle of Chianti. Enjoy six nights based out of Tuscany. With your rental car you’ll be able to take any day trips you’d like. Explore Tuscany’s picturesque countryside or adventure to the nearby cities such as Siena, Pisa and Arezzo.
Experience the best of Florence with two unique culinary experiences included. You'll enjoy the villa's wine highlights and sample the Chianti Region wines one night, then enjoy an afternoon spent with a fun, hands-on lesson in pizza making the next!
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A Sample Self-Drive Itinerary