The Adventure Begins

Depart from your preferred airport in the United States for the most convenient start to your trip as possible.

A special stop en route to your first hotel makes an unforgettable welcome to Italy - and with the services of your private driver who will meet you upon your arrival at the airport, it couldn’t be easier to enjoy!

Siena is at once too beautiful to be believed, and so approachable you feel like you’ve always been there. With the insight and trips from your private guide you’ll discover the highlights and hidden gems of your new home away from home, including the world famous Duomo di Siena, and living like a local in no time.

Welcome to Tuscany 

Stunning Siena

Val D’Orcia 

Truly an area of the quintessential Tuscany the world dreams of visiting, the Val D’Orcia offers a wide array of small towns where it is still easy to get away from the crowds and experience traditional Italian life. The full day services of your dedicated private driver make it effortlessly enjoyable to do just that, whether you spend all day in one town or plan to visit a few.

Siena boasts some of the most amazing museums in the country, let alone the region. Simply choose which area interests you most: religious art, the tradition of Siena’s famous palio, art history, ancient history, or even torture! We’ll do the rest to make this an easy but enjoyable self-paced day between two full length day trips.  

An absolute favorite of ITD clients, this day in the Chianti countryside is truly unforgettable. Starting and ending with private transfers through gorgeous scenery, the highlights include a private guided tour of a wine estate, engaging wine tasting, and a cooking class with local food enthusiasts that is non-stop fun...and then topped with a long, leisurely feast of the spoils!

Your Personal Siena

Cooking in Chianti 

Siena As You Please

Your final full day in Siena has been left open for your enjoyment, which is just as likely to be stumbled upon as scheduled. Options are available for a variety of activities, should you wish. 

En route to your new hotel in Lucca, an unforgettable adventure awaits you. With one of the region’s most passionate guides, you will uncover the mysteries of the Etruscans through a visit to incredible ruins, a small, but world-renowned museum, and even an alabaster studio where you can try your hand at carving this beautiful stone for one-of-a-kind mementos!

Lucca has a rich history - in more ways than one - that you simply cannot discover fully without a local expert by your side. Fortunately, your guide is a passionate and incredible well-connected local, so you can rest assured that whether you’re more interested in art, religion, or cuisine, you are sure to find the best of the best. And in Lucca, that’s saying a lot! 

Etruscans En Route 

Luxurious Lucca 

Countryside Surprise 

Today combines a visit to an unspoiled medieval hamlet - complete with a castle and scalable walls, an olive oil and kiwi (yes, kiwi!) farm - in the morning, with a visit to one of the most iconic Italian architectural masterpieces in Pisa in the afternoon. Enjoy the non-stop thrill of being surrounded by countless hidden gems all day long.

Your final full day has been left free to enjoy more of what Lucca has to offer. The town’s great connections to other cities make an impromptu day trip easy as well. Of course, we are always happy to design a special final day, should you wish. 

A final private transfer will take you to the airport if this signals the end of your travels. If you are extending your time in Italy, then it’s just on to the next great experience!

At Your Leisure in Lucca 

Arrivederci, Tuscany!