May 13 – May 17, 2024

Living La Dolce Vita in the Italian Countryside

Join Malaka Hilton and Salvatore Ferragamo in the decadence of Tuscany, as they savor fine wines and recline in luxurious estates. Experience the timeless beauty of Tuscany as you reside in private villas and indulge in the culinary, historical, and serene nature of the Italian countryside. Enjoy a summer getaway of museums, wineries, cooking classes, exquisite views, and more.

Call 1.888.722.3401 for most accurate pricing & availability (scroll down for journey details)

Arrival: Tuscany

May 13, 2024 – Arrival Transfers

Upon your arrival at the airport, you will be welcomed by your driver who will accompany you to the exquisite Il Borro estate.

To commence your memorable stay, an exclusive welcome reception awaits you at the villa, graciously hosted by the Ferragamo and Hilton families.

Following this reception, savor a delectable casual dinner, ensuring a delightful culinary experience in the enchanting surroundings of the villa.

May 14, 2024 – Day 2

Your morning is at leisure to enjoy some of the offerings at Il Borro:

Il Borro offers a series of unique experiences designed to give a taste of authentic Tuscany. From wine tours to cooking classes, from the artisans’ workshops to horseback riding, biking and a whole variety of excursions in and about the countryside.

This afternoon, prepare for an extraordinary wine experience like no other, hosted by the esteemed Salvatore Ferragamo. Immerse yourself in the world of fine wines as you partake in an exclusive wine tasting session, personally guided by Salvatore himself. Indulge your senses as you savor a selection of exquisite wines, allowing their aromas and flavors to transport you to new heights of appreciation.

Following this captivating experience, the evening is yours to enjoy at your leisure. Relish the freedom to choose from a wide array of dining options, each offering their own unique culinary delights.

May 15, 2024 – Day 3

Today embark on a truly exquisite full-day wine tasting journey. Dive into the rich viticultural heritage of the Chianti region as you embark on an exclusive excursion to visit two distinct wineries. Indulge your refined palate as you sample an impressive array of meticulously crafted wines, each showcasing the distinctive terroir and winemaking expertise of this renowned area.

As the day draws to a close, savor the memories of your enchanting wine tasting experience as you are chauffeured back to the exquisite comfort of Il Borro.

Chianti Region

May 16, 2024 – Day 4

Spoiled for choice, today you have a few options to “design your own dream day”.

Then, indulge in an extraordinary evening as you bid farewell to a remarkable stay. Tonight, be swept away by an exquisite Farewell wine pairing dinner, hosted by the Ferragamo family at their opulent Villa.

Tour Option 1

Travel to Florence for a walking tour

Meet your private guide and driver in the hotel lobby of Il Borro. Reach Florence and start your walking tour along the streets. Admire the beauty of cathedral of Santa Maria del Fiore, more commonly known as the duomo because of its magnificent dome. The fourth largest church in the world, the cathedral was designed by Cambio in 1296, but it was the great renaissance architect Brunelleschi who gave it its crowning glory. Also see the adjacent 14th century gothic campanile or bell tower, designed by Giotto and the baptistry in romanesque style, with Ghiberti’s bronze doors, representing scenes from the life of Christ. Continue to piazza della signoria and palazzo vecchio, and the lovely 14th century gothic loggia dei lanzi (foot soldiers). In the piazza you can also admire the fountain of Neptune by Ammannati and the copy of Michelangelo’s David. After that, reach the accademia museum with your private guide for a visit, there you can behold the real David statue of Michelangelo. At the end of the tour drive back to Il Borro.

Tour Option 2

Siena on Your Own

Take your time to absorb the beauty and history of Siena at your own pace, creating your own narrative as you explore its treasures. From panoramic viewpoints offering breathtaking views to charming boutiques filled with artisanal crafts, every step reveals a new facet of Siena’s allure.

Tour Option 3

Guided Siena and San Gimignano

Meet your driver and guide in the hotel lobby and board your private vehicle. Your first stop will be in Siena – the “beloved” – a mystical, gentle, passionate and generous art centre. Admire the beautiful Palazzo Pubblico, reach the cathedral and the campanile. Before leaving Siena, do not forget to buy the most typical cookies of the region, “the Ricciarelli”, made with almond paste. Enjoy a thirty minutes drive through this region blessed with lush vineyards, olive groves and cypress trees, that will take you to the gentle San Gimignano. You will have lunch in a beautiful farm extended on the hills overlooking this small town and surrounded by secular woods among oliveyards, vineyards and orchards. You will have the chance to taste genuine farm products of the place. After lunch, you will have a tour of San Gimignano, which is also known as “San Gimignano Dalle Belle Torri”, from the numerous towers of nobility of the area. These towers were thought for a long time to have been built for defensive purposes and as a sign of the power of the noble families who were split in the internecine fighting between the Ghibellines and the Guelphs. At the end of the tour the driver will take you back to the hotel to freshen up before dinner.

The Ferragamo and Hilton families have been friends for almost two decades, traveling the world together and hosting groups at Il Borro and other exotic locations. One of their most memorable trips was a wine pairing dinner at the foot of the Great Pyramid, followed by a wine tasting on a private 777 en route to a safari!

Continue your journey in Tuscany and travel to Castiglion del Bosco for an extra two days of decadence!

Call Jolene DiRocco at 941-951-1801 at extension 106 now to reserve your space on this unique journey today! You may e-mail at

Cost starting from $4,950 per person. For most accurate rates & availability, please call our office.

  • 25% deposit required to secure space.
    • Second 25% deposit due Nov. 13, 2023
    • Final balance due Feb. 12, 2024
  • A $250 per person Admiral Travel booking fee will apply. (VIPLane members complimentary)
  • All payments are non-refundable.
  • We highly recommend trip insurance and are happy to assist with this.


  • Your arrival and departure transfers will be in a sedan with capacity for two checked bags and two carry-ons.
  • 4 nights at Il Borro in a Level 3 room
    • Upgrade to the Master Suite at $2,000 per person (1 suite only) – SOLD OUT
    • Upgrade to a Level 1 room at $1,200 per person (3 rooms in this upgrade option) – SOLD OUT
    • Upgrade to a Level 2 room at $800 per person (3 rooms in this upgrade option)
      • All upgrades are based on double occupancy and for the 4 night stay
  • Touring, events, and dinners as listed on the itinerary


  • International or domestic flights unless otherwise mentioned
  • Beverages, snack, lunches, dinners unless otherwise noted
  • Room outside of normal check-in/check-out times
  • Porterage at airport and hotels unless otherwise noted
  • Optional excursions, activities, museums or pre and post trips not mentioned
  • Any service not specifically listed under “included” – such as the optional excursions
  • Insurance
  • Unforeseen admission to nature sites is not included in the price
  • Other items of personal nature


  • Founder’s Journey will always be priced at or below published rates, but never higher.
  • Travel with like-minded individuals on these exclusive departures.
  • Enjoy a welcome cocktail party to meet your fellow travelers.
  • On many occasions, optional shore events are offered as an option that only our group is invited to join.
  • Special global relationships that the Hiltons have formed over the years will allow you privileged access opportunities.
  • Trips are offered well in advance to give ample time for your future planning.
  • Minimum numbers must be met in order for the ATI Hosts to host the journey.
  • ATI Hosts reserve the right to adjust the duration of their participation should any schedule conflicts arise.
  • The order of events are subject to change.