Escape to Tuscany
There is a reason the region of Tuscany shines the brightest for many travelers who love Italy most: The exquisite rolling countryside with its gentle hills and forests scattered among perfect medieval hilltop fairy tale castles and villages, clear rivers and energetic lush vineyards.
We begin our magical sojourn in Florence, the perfect example of a romantic Italian city, and justly renown for history, art, literature, architecture, and fashion. The warm red-gold roofs nestling in the bowl of hills, the silver ribbon of the Arno river winding gracefully through, the enormous cathedral presiding majestically over its flock, the stern tower of the Palazzo Vecchio soaring above as guardian—all these come together harmoniously to make an enchanting picture.
In a charming small hotel overlooking the Arno river, and close to the center, we spend our mornings in Florence visiting its most famed sites with a local guide, leaving afternoons free for you to visit (or revisit) other famed museums or architectural gems, and in the evening gorge in esteemed cafes.
We travel to our next stop by train with views of the verdant Tuscan countryside, to Montepulciano, known as the “perfect Renaissance town,” and the site for many films, including Much Ado About Nothing, Midsummer Nights Dream, the Twilight Saga, and many others. Montepulciano’s chief attraction is architectural, with a number of small palaces, and also the number of excellent wineries. We will make treks into the countryside to farms and return to optional tastings at the local famed wineries. We stay in the old town at a family-owned, converted 16th century convent.
Our final destination, is Lucca, a townof many surprises. Lucca perfectly preserved its Medieval town wall and its become a charming center of daily life, with gardens, old armaments and promenades that are charming and entertaining. Beside the historical sites, we’ll tour a local chocolate factory and take an tasty and entertaining cooking class.
Itinerary Oct. 6-15 , 2026
Day 1: Depart USA from your local airport.
Oct. 6, Day 2: Florence Arrive by air in Florence Italy where you are met by your trip organizers and transferred to our hotel on the banks of the Arno River. Time to wander before dinner at one of Florence's tasty, nearby restaurants.
Wed. Oct. 7, Day 3: Florence Breakfast, then a guided walking tour of city, including the most important sights: Palazzo Vecchio, the Duomo and Baptistry, culminating at lunch at a typical Trattoria. Afternoon free to visit and enjoy of of Florence numerous museums, churches, palaces or shops.
Oct. 8 Day 4: Florence Spend the morning with Michelangelo, visiting his family home, Casabuonarroti, then feasting on his visual work including the sculpture of David at the Academia, and sculptures at the Bargello. Afternoon free to visit the Uffizi or other sights. Evening feast of Florentine delicacies.
Afternoon walk to San Miniato al Monte, arguably the prettiest church in Florence. Take in the panorama of the city and the surrounding hills, before admiring the Romanesque architecture, the frescoes and art treasures within. We’ll hear the monks sing vespers in Gregorian chants before departing. Next we stop at the adjoining cemetery to take in the wonderful collection of Italian funerary art, then visit the small shop run by the monks that sells medicinal elixirs and tasty liquors. Dinner at another of Florence fine restaurants
Fri. Oct 9 Day 5: Montepulciano Depart by train to Chiusi, where we transfer by taxi to the exquisite medieval town of Montepulciano. Check into our charming hotel, a beautifully converted convent. We take a brief guided walking tour of the historic town, culminating in wine tasting at one of the excellent wineries: Lucevan le Stelle. Dinner together.
Sat. Oct 10 Day 6: Montepulciano Breakfast, followed by a walk through vineyards, orchards, and farms to Fattorino Pulcino, a delightful monastery-turned-farm-plus-restaurant for lunch and to shop for local food products: Pecorino cheese, cold cuts, honey, homemade jams and cakes. Walk back, or return by public bus. Late afternoon optional wine tasting continues at another local winery. Dinner on your own.
Sun. Oct 11 Day 7 Morning is your last chance to explore Montepulciano. See the Art show at the museum at the old Fortezza. 6th-century Duomo on Piazza Grande, then walk about 2 hours to the neighboring hill town of Monticchiello, passing through the neighboring countryside and ended with an aperitivo. Afterwards (almost more importantly), private car back to Montepulciano
Mon. Oct 12 Day 8 Montepulciano Morning bus to Pienza,” In 1996, declared a World Heritage Site and in 2004 the entire valley, the Val d'Orcia, was included. Pienza was the birthplace of Aeneas Silvius Piccolomini, who would become Pope Pius II. After he became Pope, Piccolomini had the entire village rebuilt as an ideal Renaissance town that would serve as a retreat from Rome.
In 1996, UNESCO declared the town a World Heritage Site and in 2004 the entire valley, the Val d'Orcia, was included on the list of Unesco’s World Cultural Landscapes. The route, Il Sentiero dell’Arte e dell’Anima, or the Path of Art and Soul, was unveiled in March, with contributions by renowned Italian artists. We’ll tour the benches together and then return to the exquisite village for free time to wander, shop and have lunch.
Final happy hour gathering at one of our rooms before dinner at our favorite trattoria.
Oct. 13 Day 9: Lucca Travel by private mini bus to Lucca, stopping along the way at San Giminano for lunch, and time to wander this “masterpiece of creative human genius, an exceptional example of breathtaking architecture and landscape’
Arrive in Lucca and check into our hotel. Meet our local guide in the Center for a tour of the most importanthistorical sites: Piazza Antifeatro, the Cathedral,Guinini Tower, and Puccini’s birthplace, followed by dinner
Oct 14 Day 10: Lucca-historic walking tour this morning we walk the 2 mile perfectly preserved medieval walls of the lovely city, and encounter the fortifications and the botanical gardens. In the afternoon a cooking class of Luccan specialties, followed by a feast.
Oct 15 Day 11: Final Day in Tuscany. Free day to enjoy in whatever way you wish.
Oct. 16 Day 12 Departure Transfer by private motor coach to the Florence international airport, or stay on and extend your visit to Italy.
Note: Anyone may opt out of any activity, however there will be no refunds. Anyone who leaves the tour at any time, for any reason, is on their own.
Hotels:
Florence: www.booking.com/HotelSilla
Montepulciano: www.albergoilmarzocco.it/
Lucca: La Luna hotel: https://www.hotellaluna.it
Included:
3 nights at Hotel Silla Florence
Entrance fees: Duomo, Palazzzo Vecchio, & Baptistry, Casa Buenoroti, Bargallo and Academia in Florence
Professional Local Guide in Florence
Taxi to train station
Train Florence to Chiusi and Taxi to Il Marzocco
4 nights Albergo Marzocco
Guided tour Monteculciano
Day trips to Fattoria Pulciano andMonticchiello
Private bus transfer to Lucca with lunchstop in San Gimignano
3 nights
Excursions to Pucini’s birthday, the Cathedral, tower and museum, in Lucca
Private Bus to Florence airport
Breakfast every day and one dinner
Pre-trip information package
Services of Made Surya and Judy Slattum, Trip organizers, and local guides in each locale.
Not Included:
RT Air and airport transfer in Florence
Most meals (breakfast included at all hotels)
Tips, Laundry, extra excursions.
Details:
Cost: TBA Cost will be posted no later than Oct. 31, 2025.Based on two people sharing a twin or double bedded room.
Passport and Visa: A passport, valid six months from date of entry to Italy. Visa is not required for citizens of the USA. No health requirements.
Roommates: Because we are so limited in the number of rooms we have reserved,single rooms will be limited. Minimum 8, maximum 12 participants.
Accommodations: Generally rooms have two single beds or double with modern facilities. All accommodations are locally owned, clean and comfortable.
Food: In recent published reports, the Mediterranean diet was judged to be the healthiest in western countries, with its emphasis on fresh fruits and vegetables, light oils, low-fat dairy products, protein rich olives, and light use of meats.
Weather: October is a beautiful month to visit Italy. Harvest season in full swing, including vineyards and olives, and it's warm but never hot.
Tour Organizer/ Leader:
Made Surya & Judy Slattum MFA are professional tour organizers who have led study tours to Italy since 1995.
