Life is beautiful




14 days, starting at $ 7,400 per person

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Explore the true wonders of three distinctly different areas of Italy as you make your way through historical Rome, medieval Siena, and charming Assisi.

life is beautiful


Chambray glossier tbh XOXO chicharrones narwhal truffaut forage butcher hot chicken. Selvage chartreuse artisan plaid.

Explore the true wonders of three distinctly different areas of Italy as you make your way through historical Rome, medieval Siena, and charming Assisi.


combinable itineraries

Flexible total days

customizable experiences


14 days 

 in magical

14 days 

in magical


Welcome to Rome! 

The Adventure Begins

Your private driver will whisk you from the airport to your hotel in time to prepare for the most delicious orientation possible this evening. A private culinary tour makes a plethora of sweet and savory stops in Rome’s most popular neighborhoods - all before culminating in a traditional, multicourse Roman dinner. The perfect first night. 

Your adventure begins by departing the airport of your choice.

DAY 1 


Discover the treasures that lie within the walls of Vatican City in great company today. A passionate, expert local guide will help you uncover centuries of art, history, and religion in the Vatican Museums, St. Peter’s Basilica, and the Sistine Chapel. Customizable to any interests, this is an absolute must-do in Italy. 

Roman Splendor


Rome As You Please

Today offers a perfect opportunity to explore Rome at your own pace. The options are as endless as the city is Eternal. 

DAY 4 


Discover one of Tuscany’s most beautiful areas, the Val D’Orcia en route to your new hotel in Siena. This day has been designed with full flexibility in mind, so that you can stay as long or move on as quickly as you like in the hilltop towns or verdant valleys we suggest exploring. Your dedicated private driver is at your service, ensuring today is absolutely perfect.

Explore the Val D'Orcia


The Eternal City

One of Italy’s most iconic sites, the Colosseum, acts a portal into another time and you will begin your rich discover of Ancient Rome there today with your private guide. Followed by the expansive Roman Forum and other incredible sites of ancient importance, this is the ideal introduction to the essential foundation of the Eternal City.

Florentine Highlights

Spend your single day in Florence with a well-balanced mix of the “must-sees” and the hidden treasures, as your private guide leads you through one of Italy’s most enchanting cities. Of course a trip to Florence wouldn’t be complete without meeting the city’s most famous resident - Michelangelo’s David. This day is made possible with round trip train ride from Siena.

DAY 7 


Today is your final day in Siena. Continue to explore the beauty and charm that Siena offers to locals and visitors alike. Of course, recommendations are always available if you find yourself wanting something truly unique to wrap up your time in such a beautiful city.

Leaving Siena, your private driver will bring you to Perugia where you will get a taste of how life was and how it remains to be today. Your private guide will show you local artisans and workshops, lead you underground to the Rocca Paolina, and then a tasting of the region’s best gourmet chocolate. Your day ends as your driver delivers you to your new hotel in Assisi.

Siena as You Please

Mysteries and Masterpieces of Perugia


DAY 10

Step back in time with a new friend, as your expert private guide leads you through the stone alleyways and medieval architecture that create Siena’s singular beauty and charm. History will be brought to life right before your eyes, and you’ll glean a vast array of insider tips and tricks to make the most of your time here. 

Panoramic Tour of Siena

Assisi as You Please

Your final full day in Assisi has been left open for your enjoyment. As always, we have several suggestions for effortlessly enjoyable day trips you may want to include. 

DAY 11 

DAY 12

En route to Rome, today starts with touring two of Umbria’s best vineyards. Enjoy your wine, enjoy the drive, and then enjoy the spa. Once back in Rome, you will check in to your resort where a truly wonderful evening waits for you to wrap up your dream trip in complete relaxation. Take this time to reflect on the amazing two weeks you have just experienced. 

A final private transfer will take you to the airport as 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!

Umbrian Wine Tour and Roman Spa

Arrivederci, Italia!

DAY 13

DAY 14

Intro to Assisi and Tastes of Umbria

Today, simply meet your private driver outside of your hotel and relax. Your local guide will share Assisi’s famous landmarks, as well as some truly wonderful hidden gems! Following your tour, our dear friends are waiting to welcome you to their award-winning organic vineyard. You will enjoy a delicious lunch paired with the vineyard’s own wines.

Enjoy our top suggested hotels, with upgrade options
Or, self-book with our guidance

your home away from home


Always exclusively with private expert guides and local specialists




Only ever with dedicated private drivers and first class arrangements.

For effortlessly enjoyable travels

Every detail taken care of

You are welcome to combine days of this itinerary with any other itinerary from our Select Portfolio Collection.

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Any portion of this itinerary is able to be customized to your personal preferences, tastes, interests, and pace.

Invest in a lifetime of made-for-you memories
in the most memorable location of all

14 Days starting at


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life is beautiful

Invest in a lifetime of
made-for-you memories
in the most memorable place of all