In Italy with Cosimo


Beginning in the 17th century, English aristocrats embarked on the “Grand Tour.” And central Italy has been the key destination.
Focusing on Florence-Rome, we designed this trip to incorporate some of the iconic things to do and visit parts more off the beaten path where you can immerse yourself in the true Italian experience.

The tour begins in the heart of the historic renaissance. Experience the opulence of Medici rule and immerse yourself in the wonders of Leonardo Da Vinci, Michelangelo and Botticelli, to name a few.

Come by and bask in the sunshine of Tuscany’s rolling hills, taste the region’s famous wines, and enjoy the cuisine for which Tuscany is famous.

Concluding in the historical epicenter of the Roman Empire, Rome will leave you spellbound.

Designed by Cosimo Ceccherini, an Italian-born Florentine who now divides his time between New Zealand and Italy, you’ll experience fantastic personally curated private tours with some of the best expert guides, food lessons, wine tastings, and plenty of aperitifs. Be prepared not only for wonderful sightseeing, but also for jokes and laughter.

It will be a small group of up to 16 people. The tour was designed with the Italian institution of “strolling” in mind, relaxed and unhurried. However, most museum visits are scheduled in the early hours of the day to avoid the large crowds they tend to attract.

From noon to mid-afternoon deliberate leisure time: you may want to avoid the heat and adopt the Italian tradition of “pisolino” (beauty nap). Get ready to experience central Italy up close and personal.

Tour Description.

This is the beginning of our journey where you will be welcomed by Cosimo in your first four-star hotel.

After check-in you will be introduced to your personal Florence guide for a walking tour of the historic center. Although it is famous for its large squares, it is in the narrow alleys that you can enter the true depth of the city.

Nothing in Florence is random. Everything has a why and it is through the stories and anecdotes you share with your guide that will reveal the mysteries and secrets of the city.

The day ends with a welcome dinner at one of Florence’s renowned restaurants where you will be introduced to traditional Tuscan cuisine and taste Chianti wines.

The day begins at the Uffizi, famous for being the first gallery founded in the world. Here our personal tour guide will lead us through the fascinating development of the Renaissance.

Afterwards there is free time for eating, shopping and sightseeing before we return together to visit Palazzo Vecchio. Much more than Florence’s city hall, this was the heart of the Medici’s strong control over the city, and its walls hold many secrets that will be shared with you.

The tour culminates with an optional climb to the tower for breathtaking views of the city.

A visit to Florence would not be complete without a visit to the Academy of Fine Arts. Replicas of Michelangelo’s David can be found all over the city, but here you will see the original and learn more about its fascinating background.

We will be happy to provide suggestions for some free time in the afternoon, but later in the day we will gather for a traditional pasta class that will conclude with dinner. Savor the fruits of your labors paired with local wines.

Today we set out in comfortable mini vans to reach Florence’s historic competitor, Siena. Famous today for the Palio di Siena, a horse race held in the main square, Siena’s history is deep and complex. Upon arrival we will be met by a local guide who will take you through the city and unveil some of its mysteries. After a shared lunch, we will check into the hotel and gather in the early evening for one of Italy’s great institutions: the aperitivo.

We will be happy to provide suggestions for some free time in the afternoon, but later in the day we will gather for a traditional pasta class that will conclude with dinner. Savor the fruits of your labors paired with local wines.

In the 13th century, how did powerful families gain superiority and demonstrate their wealth? They built a tower. There are more towers left in the medieval village of San Gimignano than any other village in Italy, and this produces a fascinating landscape.

After learning about the tumultuous history of San Gimignano, we will travel through the rolling hills of Chianti to arrive in Panzano.
Dario Cecchini is an eighth-generation butcher whose family clients included Leonardo Da Vinci and Dante Alighieri. Still running a butcher shop, Dario has expanded his operations to include restaurants in Panzano featured in Chef’s Table. A table has been reserved for you!

We will be happy to provide suggestions for some free time in the afternoon, but later in the day we will gather for a traditional pasta class that will conclude with dinner. Savor the fruits of your labors paired with local wines.

We leave Siena bound for Rome, traveling through the vineyards and olive groves of the Val D’Orcia. Recognized as a UNESCO World Heritage Site since 2004, it has been a source of inspiration for many Renaissance painters.

The first stop will be a historic winery in Montalcino, owned by a local family from which you will learn all about Brunello di Montalcino, including how to appreciate it by drinking different vintages.

After wine tasting, we will venture a few more kilometers to Pienza, a papal village famous for its pecorino cheese. Here we will enjoy a gourmet lunch in a former 15th-century convent with breathtaking views of the Val D’Orcia.

Next we will travel to Montepulciano, a typical medieval Tuscan village that boasts green landscapes marked by rolling hills and castle walls. Situated on a limestone hill 2000 meters above sea level, it is world famous for its “Vino Nobile.” There we will visit a historic winery called “The Underground City” located on the lower floor of a local wine shop.

We will arrive in Rome in the early evening where you will be checked in to your accommodation.

We begin the day with a guided walking tour of the historic center of the Eternal City, rich in art, architecture, culture and…. fountains (Rome has more fountains than any other city in the world).

After getting your bearings, you will be free to explore the wonders of Rome at your leisure. Cosimo will be able to provide suggestions for sightseeing, shopping and grazing.

We will meet again in the evening for appetizers and pizza.

A visit to Rome would not be complete without visiting the world’s smallest state: the Vatican. The Sistine Chapel and the Vatican Museums are two of the most iconic places in Rome. Rich in history, culture and religious power, there is no other place in the Eternal City where so many artistic treasures are concentrated. The majestic views will be complemented by our personal guide’s wealth of knowledge.

After some free time at noon we will explore another hidden gem of Rome, the Coppedè District. Designed and built in the 1920s, this Gaudi-style suburb will welcome you with bizarre and surreal buildings containing sculptures and architectural decorations with Masonic and esoteric symbolic meanings. Its mysterious and magical dimension is unlike any other part of Rome.

Our trip ends with a farewell dinner at a nearby local restaurant, located in the cloister of Caprera Square.


At Keys of Italy we believe that quality lodging is an essential part of the tour experience.
The hotels for this tour have yet to be determined, but you can expect accommodations of the following four-star caliber.

Check availability:

What the tour includes

An experienced tour leader for all 8 days ensures stress-free travel.

Transportation throughout the tour in premium mini van.

8 nights in 4-star boutique accommodation with breakfast included.

Private guided tours with specialized guides and all entrance fees to museum galleries, cooking classes and wine tastings

  • Welcome dinner in Florence
  • Pasta dinner
  • Lunch in Siena
  • Aperitif in Siena
  • Lunch in Panzano at Dario Cecchini’s restaurant
  • Wine tasting in Montalcino with sommelier/enologist
  • Wine tasting in Montepulciano with sommelier/enologist
  • Lunch in Pienza
  • Aperitif and pizza in Rome
  • Farewell dinner

What it does not include

  • Visa if required

  • Travel insurance (required)

  • International airfares

  • Drinks and meals other than those included above

  • Optional tours you may want to take. We will be there to help you

  • Money for personal expenses

  • Transportation to hotel meeting point of arrival and last day after check-out

Anything not mentioned under “what’s included”

Reservation and cancellation

The following rates apply:

Non-refundable deposit of €500 to secure reservation
Full payment is due by April 1
In case of cancellation before May 1, payments already made (minus the deposit) will be refunded;

  • Between May 1 and June 1, 70% will be refunded;
  • June 2 to June 16 will be refunded 50%;
  • As of June 17, there is no refund.

In the event that fewer than 6 reservations are made, Keys of Italy reserves the right to cancel the tour based on a full refund of payments made.

Credit card and money transfer fees may apply.

Look here

Some pictures:



Cosimo was born and raised in Florence.

After completing his qualifications in the hotel industry, he traveled the world finally settling in New Zealand where he was proud to become a citizen.

Cosimo traveled through New Zealand, living and working in several cities.

He and his partner recently bought a villa in the Italian countryside and had the experience of renovating it.

Integrating his knowledge of Italy and New Zealand and his love of traveling the world, Cosimo is uniquely positioned to ensure a truly memorable tour, no matter where you call home. Italy: look at it, feel it, taste it!

If you would like to make hotel reservations in Florence a few days before your arrival, or in Rome after the tour is over, we can help you.
If you wish to continue exploring Italy, we can help you prepare an itinerary. We strongly recommend doing this a few months in advance.

Since numbers are limited, we recommend advance reservations. The closing date is May 4.

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