Tuscany and Umbria, Italy: A Creative Experience

Sierra Club Outings Trip # 14625A, International


  • Walk through picturesque countryside and historical hill towns
  • Visit Etruscan museums, famous cathedrals, and churches with Renaissance art
  • Enjoy sensory art activities while creating a journal


  • All transportation to hill towns, museums, cathedrals, island on Trasimeno Lake
  • Double lodging in villas
  • All meals except three lunches on your own (accommodating vegetarians and vegans)


DatesMay 20–30, 2014
Price$3,125 (12–15)
$3,645 (or fewer)
StaffLynne Simpson

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Trip Overview

The Trip

We’ll travel to Tuscany and Umbria to enjoy the enduring charm that has enticed many travelers through the ages and to fully use our senses to be aware of it all. “Sensazione” is the Italian word for fully experiencing life through our senses. Throughout our travels, we will expand and stimulate our creativity as we record in a journal what we see, do, taste, and feel: the tastes of cheeses, olive oils, and fresh tomatoes; smells of Spello’s “infiorata” flower displays; visions of Italians in animated conversations with kinesthetic punctuations; and sounds of church bells in towers ringing out the hours. No skill in drawing or creative writing is necessary, just a willingness to experience the moment with freshness and curiosity. We will start the trip in Rome and end in Florence. We’ll be staying near Cortona in a quiet charming villa decorated with antiques, and a hillside residence overlooking Assisi so that we can enjoy the lavish sense of beauty and the tranquility of the nearby countryside. We’ll be surrounded by nature -- the oaks and protecting cypress -- as we walk around St. Francis meditation garden, the island of Polvese on Trasimeno Lake with a naturalist, and Boboli Gardens. Following a boardwalk at a bird sanctuary gives us a close-up look at reed wrens, gulls, and ducks. Our small tour bus will transport us to guided tours of Assisi, Cortona, Florence, Spello, and Orvieto, where we can visit cathedrals and museums to see the art of Botticelli, Signorelli, Pinturicchio, Giotto, and Fra Angelico. And we’ll notice that art stands out everywhere in the embellished details of geometric decoration on buildings designed by Middle Age and Renaissance builders. Relaxing walks will take us down narrow, winding cobblestone streets, through open markets, and past small specialty shops to see the ceramics, jewelry, fashion, leatherwork, and handicrafts of the area. In Assisi, the pink town on Mt. Subasio, we can learn about the life of St. Francis, who is sometimes called the first conservationist or environmentalist. At the end of each day, while eating a delicious Italian meal prepared just for us, we’ll enjoy the golden sunlight of the evening, illuminating an historic medieval town.

This promises to be a journey with a variety of activities and experiences, with time for reflection and contemplation centered around one of the most artistically rich areas in the world. And as we travel, we can just be present; we will enrich our experience by recording our impressions in a journal, using our own creativity.         


Day 1: Our trip starts this morning in the heart of Rome at 10 a. m. when we'll board our bus to travel through the countryside and view vineyards, wildflower studded hillsides, and some environmentally protected natural landscapes on our way to Orvieto. There, our guide will take us on a tour of the town, which sits atop a sheer-cliffed mesa to the famous Duomo, decorated with a fresco by Signoreli. We’ll enjoy a lunch of famous Tuscan antipasti before taking our bus to our residence in Assisi, Umbria’s most famous town and one of its loveliest. After settling in, we’ll enjoy a welcome dinner together.

Day 2: After our buffet breakfast, we will gather for an introduction to our sensory activities and begin our journals with our artist guide. In the afternoon, we’ll tour Assisi and the famous Basilica of Saint Francis with a friar. The lower church holds the crypt of St. Francis, while the upper church holds the 28 fresco panels of Giotto that depict the life of St. Francis. We will enjoy healthy, delicious meals every day in the dining room of our residence.

Day 3: Our early morning, one-mile walk will take us downhill through the winding streets of the medieval town, while the sun rises over the countryside and the modern town of Assisi lies below us. Our destination is the Basilica of Saint Chiara, where we'll enjoy the singing of the cloistered nuns. In contrast we can view the front of the Roman Temple to Minerva from the 1st century BC, with Corinthian columns and travertine steps. It is the best surviving Roman temple front on the Italian peninsula, as good as any ruin in Rome for helping your imagination conjure up the classical world. After gathering and sharing together, with direction by our resident artist, we'll take our afternoon walk to San Damiano. The small chapel among the olive groves was used for a cloister by Chiara, who was inspired by St. Francis. It is a pink and white striped beauty with a rose window. Today it holds a copy of the crucifix that spoke to St. Francis and told him “to rebuild my church.” Later there will be an opportunity to join activities led by our artist to increase our creativity.

Day 4: Our tour today will be in Monte Subasio regional park, where we walk through the peaceful Eremo delle Carceri located in a beautiful setting on the edge of a ravine, deep in the woods. As we walk through the woods and pass rock caves, we can imagine what it might have been like for the first Umbrians living and meditating here. We’ll take time in this pleasant garden for our own contemplation and reflection. Participants can walk the 2.5 miles to the Eremo and back, or take a taxi. The evening leaves us time to focus on recording in our journals what we have experienced.

Day 5: Today our early morning walk takes us down the path of “Light” to Santa Maria degli Angeli and the Porziuncola built in 1569. Now it is in the center of the modern town of Assisi -- an example of Baroque design completed in 1684 after an earthquake. The grandiose façade was added in 1927. Inside is a garden with the thornless roses, a museum, and statue of St. Francis by Andrea della Robbia. It is a day of discovery for us as we examine details and the geometric embellishment that the Middle Age and Renaissance builders added to decorate windows, facades, and mosaics. In the evening we enjoy a musical play about the life of Santa Chiara.

Day 6: On our last day in Assisi we have time to explore the Rocca Maggiore, a fortress above the town that's filled with scenes of medieval life, musical instruments, and artifacts. Palazzo del Comune in the center of town is surrounded by shops and the best gelateria for an afternoon gelato. You might chose to walk through the forest to the ruins of Santa Croce before our evening gathering atop our residence to observe the radiance of the sunset.

Day 7: After packing and enjoying our buffet breakfast, we board our tour bus for a short ride to medieval Spello, built of the same pink and cream Umbrian stone as Assisi. It overlooks the spacious Valle Umbra and has three excellently preserved Roman gates with statues from the Roman Republic. The 13th century church of Santa Maria Maggiore, with its Romanesque campanile and some 11th century carving incorporated into its 17th century façade, has inside the three frescoed scenes by Pinturicchio: Annunciation, Nativity, and Dispute of the Temple. Our guide will tell us about the symbols and hidden meanings included by the artist. The floor of the church is made of historic painted ceramics. Outside while walking the narrow cobbled streets under hidden archways and up stairways, we will observe the traditional contest to decorate every balcony, doorway, and windowsill with floral displays. It will be our chance to choose a trattoria, restaurant, or outside café for lunch before meeting back at our bus for our ride to our countryside villa near Cortona. A welcome dinner will be served on the veranda by our host and hostess at the villa.

Day 8: Our bus will take us through the Tuscan landscape of rolling hills, poplars and parasol pines, vineyards, and winding lanes that can be seen in the paintings of artists, where each tree and rock take on a mystic significance. Our Italian guide will meet us at the top of Cortona for an espresso on a terrace that has a commanding view of the countryside. We’ll wind down through the small town as we hear about the history, view art, see churches, and recognize movie scene locations from the film, Under the Tuscan Sun. After a lunch on our own, we will visit the Museo dell’Accademia Etrusca, with its exhibits of Greek vases, Egyptian mummies, and the most famous Etruscan relic -- a bronze chandelier that dates back to the 5th century BC. Upstairs there is a fine collection of paintings. After our bus returns us to our villa, there will be time in the late afternoon for a swim or walk in the country before we eat dinner and gather to add to our journals.

Day 9: A day of exploration in nature begins when we take up our binoculars and walk out on the boardwalk over Trasimeno Lake with an environmental naturalist to identify birds and their habitat. We can watch the banding procedure that is used to gather information on the migration of the birds that travel south over the Sahara Desert for the winter. A tour boat will take us across the lake to Isola Polvese, the largest of the lake’s three islands, for a picnic lunch and a two-mile walk around the island and through the Roman amphitheater to a special plant garden. It was near this lake that a famous battle of the Second Punic War took place between Hannibal and the Romans, but today it is a tranquil, shimmering shallow lake embedded in gentle rolling hills. It is possible to stop for an olive oil tasting at a press along the shore of the lake before we return to our villa and a final dinner. This will be an opportunity to share our created journals with pictures, sketches, and writings of this journey.

Day 10: Today our bus takes us west to Florence so we can check into our hotel and then visit the famous Piazza del Duomo and examine the bronze doors of the Baptistry and the great church with Brunelleschi’s dome. Our guide takes us on a tour across the Ponte Vecchio over the Arno River to the Pitti Palace, formerly palace of the Medici, and the Boboli Gardens with its fountains and statues. We chose our own lunch café before free time and then an afternoon reservation at the Accademia to see the famous David statue. Sunset is the perfect time to gather at the Belvedere overlooking all of Florence for our closing dinner.

Day 11: Our last meal will be our buffet breakfast this morning. Our bus will pick us up at 11 a.m. to transport us to the Florence airport or Florence train station, Santa Maria Novella. You can buy tickets on the spot for many fast trains departing frequently for other cities in Italy, or you can continue your stay in Florence at one of the hotels or bed and breakfasts.           



Getting There

Flights from the United States are direct to Rome. It is easy and usually the same price to fly into one city and out of another. However, a fast train from Florence to Rome takes one hour for a flight out of Rome. The Rome airport is outside of the city, so you will have to take a bus, underground train, or taxi (40-50€) into Rome. If you are flying from the west coast of the U. S., you will lose a day in flight, so you must leave a day earlier than the day that you want to arrive. If you experience jet lag (in Italian it is “fuso orario”), the trip leader suggests arriving a day or two before the trip starts and staying in Rome at a small hotel. There is a nice hotel near the Rome Airport in Fuciamo where the leader has stayed before for a reasonable price: www.cancellirossi.it. You will receive a pre-trip letter that gives the location where we will meet in Rome to begin the trip. At the end of the trip, our bus will return you to the Florence airport or train station around midday.

Accommodations and Food

We will be staying in three different locations -- a residence in Assisi, a villa or agriturismo near Cortona, and a hotel in Florence. The “agriturismo” began in the 1980s as a way to encourage farmers to stay on their land, produce food, and offer accommodations to tourists. As a peaceful home base for exploring the region, it is similar to the bed-and-breakfast, though in Italy they often tend to be elegant and surrounded by countryside. They are family-run accommodations and provide breakfasts each day and gala dinners. They have beautiful garden grounds, swimming pools, and ideal terraces with views of open hillsides -- the perfect setting for comfortable relaxation after a walk or tour. Rooms are double-occupancy; a roommate will be provided for solo travelers. All rooms have a bathroom. All meals and tips will be provided in the trip price except for three lunches on your own in towns, so that you can sample cafes, restaurants, osterias, trattorias, or Italian fast food takeout. Mineral water, water naturale, table wine, coffee, tea, and morning juice are included with meals, but specialty wines and drinks will be at your own expense. Our residence and villa offer some vegetarian dishes and will attempt to satisfy special dietary needs. We can buy corn or rice pasta and bring it to the chef to cook. Please inform the leader of dietary restrictions when completing your application.

Trip Difficulty

This trip is easy to moderate and suitable for the active and those seeking a more relaxed vacation. It is open to all as long as you are in reasonably good health, get regular exercise, enjoy nature, and want to learn about Italian culture, art, and history. We’ll be transported by private minibus to towns, historic sites, and trailheads for tours. Our walks or hikes will be one to five miles, with an elevation gain of not more than 800 feet at a leisurely pace on established trails and paths. However, the trails may be narrow and there are some uneven steps to climb in Assisi and Cortona. There are taxis available for hire in Assisi if the return walk seems too strenuous. Streets in historic towns are made of cobblestones and are often uneven. It is essential to have comfortable and supportive shoes. As always, the better physical shape you are in, the more you will enjoy the trip. Before the trip, plan some walks and hikes on paths and pavement going up and downhill.

Equipment and Clothing

The climate in Tuscany in spring is usually pleasant, with temperatures in the 60s to 80s (Fahrenheit) in the daytime and an average of 25 days without rain. Dress will be casual and comfortable. When going into the museums and churches, arms and legs must be covered -- a blouse or shirt with sleeves and a skirt or pants that cover the knees. Our villa has a swimming pool, so bring a bathing suit. Raingear or an umbrella is always a good idea. If you find it difficult to walk on uneven surfaces, a walking stick will be helpful. Your leader will provide additional pre-trip information -- including a comprehensive packing list -- to registered participants.


Book of Creativity:

  • Gelb, Micharel J., How to Think Like Leonardo da Vinci, Random House.


  • Eco, Umberto, The Name of the Rose, Harcourt, Brace & Company.
  • King, Ross, Michelangelo and the Pope's Ceiling, Walker Publishing Co.
  • Mayes, Frances, Under the Tuscan Sun, Broadway.
  • Castagno, Dario and Robert Rodi, Too Much Tuscan Sun, Globe Pequot.
  • Kazantzakis, Nikos, Saint Francis, Loyola Classics.

About Italy:

  • Calcagno, Anne, Travelers' Tales of Italy, Traveler' Tales Guides.
  • Richards, Charles, The New Italians, Gardners Books.
  • Francke, Linda Bird, On the Road with Francis of Assisi: A Timeless Journey Through Umbria and Tuscany and Beyond, Random House.
  • Gary Paul Nabhan, Songbirds, Truffles, and Wolves, Penguin Books, 1994.

Films and Videos:

  • Brother Sun Sister Moon, Franco Zeffirelli, Paramount Home Video, 1993
  • Life Is Beautiful, Roberto Benigni, 1991
  • Johnny Stecchino, Roberto Benigni, 1991
  • Tea with Mussolini, Franco Zeffirelli, 1999


Sierra Club is an environmentally focused entity. We are concerned about conservation and sustainability of resources both locally and globally. Our work is accomplished by volunteers, aided by a salaried staff, encouraging grassroots involvement. Our outings seek to empower participants toward environmentally understanding parallel concerns at home and abroad. Environmental topics on this outing are alternative energy sources, eating locally grown produce, recycling, and preserving wild land. "0 kilometer cibo" is practiced everywhere in Italy -- using food grown locally means delicious and fresh meals. The small nearby growers deliver produce daily to the towns of Tuscany. They have a green practice of using no pesticides, and we’ll be staying at a villa that has received a "green" award.

The Italians truly appreciate the beauty of their countryside, and we can observe how they are preserving it. We will discuss environmental issues concerning Lake Trasimeno with the staff at Oasi delle Valle. We'll have the opportunity to walk with guides on trails and a naturalist in a preserve and in a regional park. We can observe their selective logging practice and hear about their research on forest health. On our minibus trips, we can observe the production of clean energy with solar farms and wind turbines.

Recycling bins dominate corners within each town, and each family is responsible for carrying and depositing refuse, and recycling all their waste. Households have recently been given compost cans to take to a central bin. There are even bins that are marked "Humana" for things that can be recycled for use by someone else. We will be bringing our own drinking bottles for refilling water, cloth bags for carrying purchases, and a plate and utensils for eating at picnics, so that we don't add to the waste.



Lynne Simpson went on her first outing with the Sierra Club in 1968 and so enjoyed that experience that she signed on to cook and to lead for the National Outings program. In her time with outings, she has led in Hawaii, Europe, Asia and Africa. She has also led backpacks, river trips, and service trips within the United States. Part of her college education included a year in France; she speaks fluent French and so her Italian can be classified as "Itfranglais."Lynne's other interests include art (she is a printmaker), cooking, snorkeling, stand up paddleboarding and French poodles.

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