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Jeff Caplinger

Owner/Licensed Guide




(click to enlarge map)




Overnight Stays: 


Rome (2 nights), Montecatini Terme (3 nights),

Chianciano Terme (2 nights)



Also Visiting: 


Rome, Spoleto, Assisi, Tuscany, Florence




At A Glance:



(Day 1) Depart Charleston (other airport if not departing CHS) (am), Depart New York City (pm)

(Day 2) Arrive in Rome and See the Best of Rome’s Sights and Trevi Fountain.
             Step Back in Time with a Tour of Ancient Rome: Colosseo and Roman Forum

(Day 3) Tuscany: olive Oil Tasting & Tuscan Cooking Class + Cortona ”Under the Tuscan    

             Sun” and Trasimeno Lake

(Day 4) Umbria - Assisi. The Basilica of St Francis, Spoleto (Charleston's sister-city),

(Day 5) Siena and Val d’Orcia UNESCO area - Pienza: Pecorino Cheese Tasting and

             Montepulciano Twilight saga

(Day 6) Chianti - “Life is beautiful” Wineries Tour with a typical Tuscan lunch and Wine

             Tasting in a Renaissance Castle

(Day 7) Florence - Discover the Renaissance  + Lucca (by night)

(Day 8) Cortona ("Under The Tuscan Sun") (am), The Vatican (pm)


(Day 9) Arrivederci Italia!  Depart Rome for home





Full Itinerary:



DAY 1 - Friday - Depart Charleston (other airport) and NYC
Depart Charleston (or your designated airport) mid-morning.  Lunch on-your-own at JFK International Airport.  Boarding your overnight flight from New York City,   you’re off  on your Italian adventure.   Buon viaggio!


DAY 2 - Saturday - Arrive in Rome
Benvenuti a Roma!  We are pleased to offer complimentary transfers from the Fiumicino – Leonardo da Vinci Aeroporto (Rome airport) to the hotel at scheduled times. Your AAC representatives (Jeff and Lisa) will be traveling with you to ensure a smooth transition.  Enjoy a sightseeing tour by bus. Walking tour of Baroquean Rome: stroll through picturesque cobblestone alleyways and discover the enchanting sites, such as the Piazza Navona, the Pantheon, the Spanish Steps, the Trevi Fountain, the Colosseo and Roman Forum. Hail Caesar!  (1 night accomodations) Lunch, Dinner



DAY 3 - Sunday - Tuscany

This morning we will visit an oil mill and experience the true flavors of Tuscany as you partake in your very own cooking class. Prepare a hand made pasta meal like "grandma" would in a warm and down-to-Earth atmosphere with local ingredients accompanied by an Italian Chef. Take good care in your creations as this will be your meal for lunch.  Tuscany is a region renowned for its art, culture, history and legends.  In the afternoon will continue to explore the Tuscan countryside.  Breakfast, Lunch, Dinner


DAY 4 - Monday - Umbria (Assisi, Spoleto)

We will continue through the Apennine Mountains in Umbria and arrive at the mystical town of Assisi on the slopes of Mount Subasio. See the sights of St. Francis' birthplace, including the medieval ramparts and the Basilica of St Mary of the Angels, built on the site where St. Francis died. Assisi, the home of one of the Catholicism’s most beloved saints and the birthplace of the Franciscans. The town is dominated by the impressive expanse of the incredible Basilica di San Francesco, a UNESCO World Heritage Site since 2000 and one of the key sites for Christian pilgrimage in Europe. Take in the incredible gothic interior of the Upper Church and the impressive portico before marveling at the simply spectacular nave, whose floods are covered with patterned marble and whose walls and ceilings reflect the brightness of the countryside beyond, shimmering blue and serene green, passionate red and soothing gold. From the incredible art to the unbeatable legacy, this is a church that is not to be missed.  We will eat lunch in a Umbria trattoria.


Nestled in a wide valley surrounded by the mountains of Umbria, is Charleston's sister-city... Spoleto.  Spoleto is one of Italy's most beautiful hill-towns with it's majestic landscape and ancient city walls contributing to Spoleto's inviting atmosphere and making it a wonderful place to tour.  Its rich history includes the first Roman settlement of Spoletium which began in 241 BC. Its splendid architecture includes the Duomo, the Teatro Caio Melisso and the Ponte delle Torri, the Bridge of the Towers, an awe-inspiring medieval bridge spanning 262 feet above the gorge below.  Its legendary art includes medieval frescoes and the Festival dei Due Mondi, The Festival of Two Worlds, which celebrates opera, dance, theatre, visual arts and sciences each summer. We will begin our walking tour at Duomo Square, to take in the exquisite design of Cathedral of Santa Maria. Breakfast, Lunch, Dinner


DAY 5 - Tuesday - Val d’Orcia (Pienza, Montepulciano, Siena, Montecatini Terme)

After breakfast we load the coach and say ciao to Chianciano Terme. Today we travel through the provinces of Tuscany toward its northern side. The morning will be dedicated to Val d’Orcia UNESCO area with visits to Renaissance villages of Pienza for a pecorino cheese tasting and Montepulciano, known today as a location of the Twilight saga.  We will have lunch in a local osteria.


After lunch the tour continue with a 1.5 hour ride to the remarkable medieval town of Siena, whose historic city center is also World Heritage Site.  Riddled with winding cobblestone lanes and Siena has a number of impressive structures, like the Torre del Mangia that juts dramatically within the city’s skyline. You will witness one of Europe’s greatest medieval squares: Piazza del Campo, where the red brick Palazzo Publico is striking and impressive, covered with flags and vivid banners during the twice annual horse race known as the Palio.


After departing Siena, we will arrive in the garden-town of Montecatini Terme in about 1.15 hours for your 3-night stay. With its wonderful parks, suggestive old village, trendy coffee bars and wine-bars, its palaces that still recall our ancient history and bygone memories offer a holiday characterized by wellbeing, culture and relaxation.  (3 nights accomodations) Breakfast, Lunch, Dinner

DAY 7 - Wednesday - (Chianti Classico Area, San Gimignano)

Today we transport you through the verdant undulations of Tuscany until you reach the Chianti Classico area, the garden of Tuscany, where we will visit the vineyards and wineries of a Renaissance castle and we will enjoy a wine tasting followed by an authentic Tuscan lunch experience made with locally sourced fresh produce. In the afternoon we drive through the Chianti vineyards to the medieval village of San Gimignano and its famous skyline dominated by 13 towers, almost unchanged since the middle ages. You will wander through the streets of this medieval town rich of works of art, shops and restaurants. Before returning to the hotel we will be back to the origins of the art genius Leonardo da Vinci's birthplace. Breakfast, Lunch, Dinner


DAY 8 - Thursday - Florence (Lucca by night)
After breakfast, we’re off to Florence via the Highway of the Sun. As we traverse the gently rolling countryside to the capital of Tuscany and the center of the most important art movement in the Western world, the home to the Dante, Medici, Machiavelli, da Vinci and Michelangelo. Florence enjoys a unique artistic heritage. Experience the delights during your sightseeing tour on foot with our knowledgeable guide. Admire the Baptistery, renowned for its carved bronze-gold doors, the marble Cathedral of Santa Maria del Fiore, Giotto's impressive bell tower, Ponte Vecchio the oldest bridge of Europe and the Piazza Signoria where you will see the famous statue of David by Michelangelo.  We will have lunch in a Tuscan ristorante.


Enjoy free time to explore or to shop for high quality Italian leather goods and 18-carat gold jewelry, then check-in to our hotel.


Tour by night : After dinner enjoy a walking tour of the historical city of Lucca, surrounded by the most impressive renaissance walls of Europe, Lucca was the capital of the Roman empire during the Triumvirate. You will see the still inhabited Roman amphitheatre, and the birthplace of the opera composer Giacomo Puccini.  (3 nights accomodations) Breakfast, Lunch, Dinner


DAY 8 - Friday - (Cortona, Rome, The Vatican)

In the morning we will take you to Cortona, one of the oldest hill towns in Tuscany, where you will recognize the scenery from the movie "Under the Tuscan Sun".  Following lunch, we will transport back to Rome and visit The Vatican.  Our tour starts from the center of the Christian Religion and residence of the Holy Father, St. Peter Square. It is a colossal architectural work surrounded by a colonnade composed of 284 columns and 88 pillars. At the top of the colonnades there are 140 statues 3.20 meters high, depicting saints, martyrs and popes. Then, the tour goes on acceding St Peter Basilica, one of the largest churches in the world. Designed by Bernini and Carlo Maderno, it is the burial site of its namesake Saint Peter and it is the most notable building in the Vatican City State, overlooking Rome’s skyline from its impressive Dome.

The most exciting and impressive room of the Vatican Museums is without a doubt the Sistine Chapel. Its majestic frescoes, depicting the Last Judgement and the creation of Adam, is a masterpiece you have absolutely to see at least once in your lifetime. Today it is the site of the Papal conclave, the process by which a new Pope is selected. We conclude our day with a wonderful send-off dinner as we reflect on our Italian adventure. Breakfast, Lunch, Dinner


DAY 9 - Saturday - Flight home from Rome
Sadly, today you say Arrivederci!  This morning your trip home starts at the Fiumicino – Leonardo da Vinci Aeroporto (Rome airport). We hope you enjoyed your Italian adventure, your guide, your driver and your traveling companions. Buon viaggio and please join All About Charleston again in the very near future. Boxed Breakfast


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