Caldwell Italy Itinerary 2025

Travelers to Italy will thoroughly enjoy our 13-day tour through Tuscany, Umbria, and Rome, with its outstanding art and architecture, palazzos and piazzas, and pasta and pizza! Throughout our journey, we’ll also read the Apostle Paul’s letter to the Romans to discover its relevance for our lives today.

Days 1 & 2, October 13 &14 – Arrival
Depart US, arrive Florence, San Gimignano

Arrive at the Florence airport and transfer to San Gimignano for the next five nights.  (D)

 Day 3, October 15 – Siena

Siena is one of the most appealing towns in Tuscany, with its well-conserved medieval streets and the square, the Piazza del Campo. The piazza's focal point is the Palazzo Pubblico, which dates back to 1250. We also visit the monumental Duomo, Siena's cathedral. Return to San Gimignano for overnight. (B, D)

 Day 4, October 16 – Tuscan Countryside

We slow down the pace but not the experience. We explore the beautiful countryside of Tuscany with its verdant vineyards. Take an optional vineyard tour with a Tuscan farmhouse lunch included, as well as a local wine-tasting event. Or, take the day to explore the countryside and soak up the local atmosphere, stroll the streets of San Gimignano, or climb one of its towers. The medieval towers of San Gimignano are among Tuscany's most famous views and are a World Heritage Site. (B, D)

 Day 5, October 17 – Florence

Florence is truly one of the amazing cities of Italy. Some of Michelangelo's most significant works can be found here. We visit the Academia and view the majestic David, then to the Duomo, Brunelleschi's sloping, red-tiled dome, predominant on Florence's skyline and the world's fourth-largest cathedral. The Gates of Paradise on the Baptistery are not to be missed.

Then to the Basilica of Santa Croce, with its walls lined with the tombs of Michelangelo, Machiavelli, Galileo, and Bardi. Return to San Gimignano for overnight (B, L, D)

Day 6, October 18 – Tuscan Cooking

Again, we slow down the pace but not the experience. Take an optional Tuscan cooking class and prepare a full Tuscan menu as you spend time with a local chef. After a day of festive cooking, enjoy the dinner that you have prepared. You may also choose to visit the many fine churches of San Gimignano or shop for ceramics, local wines, or watercolors of the sunflower fields of Tuscany. (B, D)

 Day 7, October 19 – Umbria Countryside &  Montefalco

Leaving Tuscany, we visit the region of Umbria and one of the numerous vineyards in the quaint village of Montefalco to sample Sagrantino di Montefalco, which boasts the highest content of polyphenols (antioxidants) of any red wine. We also visit a fine linen factory dating back eight centuries before enjoying the local Umbrian cuisine. Overnight Montefalco. (B, D)

 Day 8, October 20 – Umbria Countryside & Assisi

Walled Assisi is miraculous with its many churches, and we visit the churches of St. Clare and St. Francis. St Francis was born here, and work began on his basilica two years after his death. It's a magnificent tribute to the patron saint of animals, with frescoes by Giotto, Cimabue, and Martini. Overnight in the province of Umbria. (B, D)

Day 9, October 21 - Rome: The Eternal City | Jubilee Year

All roads lead to Rome…for thousands of years, tourists, merchants, and pilgrims have journeyed to the city of seven hills on the Tiber. Rome has unarguably one of the richest histories of any city on earth, all the while incorporating some of the finest architecture still surviving. Upon arrival in Rome, we enjoy a walking tour through the heart of the city. (B, D)

 Day 10, October 22 - Rome: Forum, Palatine Hill, Colosseum

The tour begins with a visit to the magnificent landmark of the Roman Empire, the Colosseum, followed by a walking tour through the ancient Roman Forum, the very center of the mighty Imperial Roman.  (B)

Day 11, October 23 - Rome

Optional tour of the Vatican Museum and St. Peter’s Basilica. Or a free day in Rome to explore the Eternal City. Enjoy an evening stroll and one of Rome’s many tavernas. (B)

Day 12, October 24 – Rome: Martyrdom of Apostle Paul

We travel along the Appian Way and visit the Catacombs. Here, we share in communion in the underground resting place of the early Christian community. Concluding Paul’s life, we see the church where St. Paul was buried. We end our time with our farewell dinner. (B, D)

Day 13, October 25 – Depart to USA

We board our bus for transfer to the airport and return flight to the USA. Return home with wonderful memories, shared experiences, and new friends!