Tuscany

Flexible Booking Policy

Top vacation destinations in Tuscany

Castellina in Chianti

Florence

Siena

Lucca

A slice of heaven packed with beautiful scenery and centuries of history, resplendent with vineyards

Halfway down the Italian peninsula, Tuscany is a region of dramatic landscapes, rolling hills, mountains, and coastlines. This unique destination combines these beautiful natural landscapes with Renaissance art and architecture, and sumptuous cuisine. What more could you want? Not only is this the home of beloved works of art, including Michelangelo's “David,” the region is also blessed with excellent weather. That means the wine, olive oil, and vegetables, are always fresh and flavorful. Besides, you're doing them a favor tucking into the wild boar ragu pasta, the animals are a pest to winegrowers. Above all, Tuscany is a food and wine lover's dream.

This region balancing urban life, high art, history, and deliciously timeless cuisine is certainly a must-visit for anyone who enjoys la dolce vita. Every trip to Tuscany is unforgettable, especially if you have the flexibility of traveling on your own, as this opens up the possibility of staying in out of the way places surrounded by this gorgeous landscape, on wine estates and farms, in historic palazzos, or and medieval castles. You can day-trip to the cities of Siena and Florence, getting insight from knowledgeable local guides we can arrange for you. Hike through the hills, visit quaint hilltop villages, relax on the beaches of the Tyrrhenian Sea, and relax and enjoy the fruits of the vine in Chianti’s vineyards. It’s hard not to have a wonderful time in Tuscany.

Popular Tuscany Vacation Itineraries

Name: JayWay Travel Italian Vacation Packages
Brand: JayWay Travel
Rating: 4.95 (84 reviews)

Our suggested itineraries in Tuscany allow you to enjoy a multi-destination tour with ease. Our Tuscany vacation packages make traveling in Italy and neighboring countries hassle-free. We take care of getting you from place to place, accommodation, excursions and activities.

A Week in Central Italy

Rome, Castellina in Chianti, Florence

8 Days

Classic Italian Beauty

Rome, Florence, Venice

10 Days

A Dream Italian Honeymoon

Rome, Castellina in Chianti, Florence, Venice

10 Days

Accessible Italy

Rome, Castellina in Chianti, Florence, Milan

10 Days

History, Art & The Scent of Lemons

Rome, Florence, Sorrento

10 Days

Under the Radar Italy

Naples, Bologna, Lucca, Milan

11 Days

Italian Highlights

Rome, Castellina in Chianti, Monterosso Al Mare, Venice

11 Days

Magical Italian Exploration

Rome, Positano, Naples, Florence, Castellina in Chianti, Florence, Venice

14 Days

The Best of Italy and Slovenia

Rome, Florence, Venice, Bovec, Ljubljana

14 Days

Italian Splendor

Rome, Florence, Venice, Como, Milan

14 Days

Italian & Greek Showstoppers

Rome, Florence, Venice, Santorini, Athens

14 Days

The Varied Charms of Italy and Switzerland

Rome, Florence, Milan, Lugano, Lucerne, Zurich

15 Days

A Grand Tour of Italy

Naples, Positano, Rome, Florence, Monterosso Al Mare, Milan, Venice

15 Days

UNESCO in Italy

Venice, Milan, Florence, Rome, Naples, Alberobello, Brindisi, Siracusa

18 Days

Adventures in Italy

Venice, Como, Monterosso Al Mare, Florence, Rome, Sorrento, Matera, Lecce

19 Days

Glowing Reviews from Our Guests

5.0 / 5

Average of our Guest's Ratings of our Italian vacation packages, based on 84 reviews

Kyle & Chelsea

Arizona

Would absolutely recommend JayWay Travel to anyone of our friends. We had a great vacation and had zero issues with all of our arrangements.

Year : 2022
Visited : Italy
Itinerary : Rome, Sorrento, Naples, Florence, Castellina in Chianti, Florence, Venice
Rating :

5 / 5

Year : 2022
Visited : Italy
Itinerary : Rome, Sorrento, Naples, Florence, Castellina in Chianti, Florence, Venice
Rating :

5 / 5

Veronica & Kevin

Georgia

JayWay Travel is excellent to work with. They handle everything so you don’t need to worry about a thing.

Year : 2022
Visited : Italy
Itinerary : Milan, Lake Como, Venice
Rating :

5 / 5

Year : 2022
Visited : Italy
Itinerary : Milan, Lake Como, Venice
Rating :

5 / 5

Mike, Viviana & Nicholas

Georgia

Absolutely fantastic. Very professional with great people and impressive website tools. Extremely organized information. It was very easy to navigate through the whole trip. I am so glad I didn’t try to do this myself. Service surpassed my expectations. I will use JayWay Travel again and refer to many friends.

Year : 2022
Visited : Italy
Itinerary : Milan, Venice, Florence, Sorrento, Rome
Rating :

5 / 5

Year : 2022
Visited : Italy
Itinerary : Milan, Venice, Florence, Sorrento, Rome
Rating :

5 / 5