Italy Vacations

Italy is one of the most visited countries in the world, and for good reason. It’s the center of historical sites, food, art and culture and offers something for everyone. There are many regions to visit. We have broken areas down as follows: Rome, Florence, Tuscany, Venice and Northern Italy, Southern Italy and Sicily.

Colosseum at sunset in Rome, Italy
Colosseum at sunset in Rome, Italy

Rome, Florence and Tuscany

This region is the most visited part of Italy, and is deserving of that claim. In Rome there is so much to see and do you can easily spend 4-7 days exploring it. Besides the most obvious historical sites (which will take you 3 days), there are many piazzas (district squares), museums, galleries and restaurants that you really need to see in order to get the true feel of Rome. There are many hotels and restaurants to suit every taste and budget. Special tours of the main sites can be pre-arranged and pre-paid to save you a lot of time.

Florence is the cultural capital of Italy and is the gateway to Tuscany. Florence is known for its art, culture and history. You will want to visit the Duomo, the Ponte Vecchio and Michaelangelo’s David at the Accademia. The city’s breathtaking views from the Pitti Palace of Florence will delight you. With its Renaissance architecture, world renowned paintings and sculptures, shopping and great food, Florence is a must stop on any itinerary.

Vineyard in Europe
Vineyard in Europe

Tuscany is the most famous of the many wine regions. Beautiful rolling hills and quaint old world towns dot the landscape throughout the area. Hotels are small, and there are many villas available for your stay. Siena is the main town in Tuscany and is a great place to stay and do your day excursions. There are many different wine areas to explore within Tuscany. You can easily spend 3-5 days in this area.

Venice and Northern Italy

We recommend a flight into Milan, for a visit of a couple of days. What used to be an industrial city, Milan has transformed itself into a unique place to visit. The Duomo and La Scala Opera House are two sites not to be missed.

The real allure in this area is Venice, the city of canals. At least two days is needed to see the famous sites of St. Mark’s Square, the Doge’s Palace and the bridge of Sighs.

More time is needed to be spent exploring Northern Italy. It is without a doubt the most beautiful scenery in all of Italy. It’s famous for its many little quaint towns in the Lake Maggiore and Lake Como areas with its great view of the Dolomites, also known as the Italian Alps. To explore Venice and the lake area region you need at least one week.

Southern Italy and Sicily

The south of Italy, just past Naples, brings you to one of the most famous coastlines in the world — the Amalfi coast. The rugged but scenic coastal drive is a must on your stay. Visit Pompeii, the preserved city destroyed over 2000 years ago. After Pompeii, proceed to Sorrento with its view of Mt Vesuvius. Sorrento is a perfect place to stay and do side trips. At Sorrento, you can explore the Isle of Capri or sail to Positano, one of the most picturesque villages on a cliff overlooking the Mediterranean. Also, plan to make a stop of the mountain side town of Ravello.

Sicily is one of the fastest growing tourist areas in Italy. With old world towns, beautiful coastal views and a growing wine region, this is an area you should consider visiting. Palermo, the capital of Sicily, is a good point in which to explore the area and its many archaeological sites. Another stay should be in Taormina with its view of Mt. Enta, one of the most active volcanoes in the world. Besides interesting sites along the way, stop at one of the many wineries in the region.

Coastal view of beautiful Amalfi in Italy
Coastal view of beautiful Amalfi in Italy


As you can see, there is so much to do and see in Italy. You must determine how much time you want to spend. For those travelers who only visit Italy once, there are tours in the 8-10 day range that take in the major cities of Venice, Florence and Rome. There are comprehensive tours taking in two of the three regions of your choice that are two weeks duration.

If you are planning more than one trip to Italy, I would suggest concentrating on just one of the regions for 7-10 days.

There are all sorts of specialty tours besides the general excursions. These include food and cooking classes, art tours, villa stays and private car with driver tours.

You can take either an escorted or independent tour. Escorted tours offer a great variation of tours and range from 16 people to 25 to 40. We have vendors that offer private escorted tours for 2-6 people.

Independent tours are recommended if you go it alone. The advantage is you only do what you want. Also, we suggest you know some Italian, especially if you are not staying in the main cities. In addition, with independent tours, you must handle all luggage, hotel and train check-ins and sightseeing on your own.

Shadyside Travel is able to offer you both escorted and independent tours in all price ranges.

Contact Us For Escorted and Independent Tours for your Italy Vacations

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