Wander Through Ancient Italy and Sicily – 2025

You meet your guide at Malpensa Airport (MXP) and your guide takes you to your hotel in the city center.  After check-in, you go on a walking tour. You see a combination of ancient Italian architecture and modern buildings. You stop at the gothic Milan Duomo Cathedral, the Medieval Sofrzesco castle, and the historic Teatro alla Scala in red velvet and gold. The evening is at the Galleria Vittorio Emanuele II, Italy’s oldest shopping center.

Site Visits / Activities:

• Lesiure Walk
• Duomo/Cathedral
• Galleria Vittorio Emanuele II
• Teatro alla Scala
• Castello Sforzesco

Hotel: TBA

Meals: Welcome Supper

After breakfast, you travel by train through Italy’s Lombardy region to Lake Como. The region is known for its breathtaking scenery with snow-capped alps encircling the long lake. Lake Como offers some of the most picturesque scenery in Italy. You visit the old town with medieval walls, charming alleys and of course the lakefront. In the afternoon you cruise on Lake surrounded by the region’s natural beauty.

Site Visits / Activities:

• Train ride to Lake Como
• Leisure walk through Town
• Boat Ride on the Lake

Hotel: TBA

Meals: Breakfast

You have a free morning on your own in the city center of Milan. After lunch, you take a train to Venice known as the City of Canals or the Floating City. There are almost no roads, just winding canals, bridges, and magnificent architecture. Upon arrival, you take a water taxi from the train station through the canal to your hotel and check in. The rest of the afternoon is a tour of many historic sites along the canal.

Site Visits/ Activities:

• Canal ride/ Leisure walks
• Rialto Bridge
• St. Mark’s Basillica/Campanile
• St. Mark Square
• Gondolas at Canal Grande
• Palazzo Ducale (Doges Palace)
• Ponte dei Sospiri (Bridge of Signs)
• Jewish Ghetto
• Chiesa di Santa Maria Assunta

Hotel: TBA

Meals: Breakfast

Following breakfast, you go island hopping. There are 118 small Islands that make up the providence, Venice. You ride on a boat through the canals and across the lagoon to Murano and Torcello Islands have the atmosphere of Venice’s traditional fishing village with a history of the earliest days. You have lunch at one of the islands. In the afternoon you stop at Lido, a long Island with sandy beaches and a nice neighborhood.

Site Visit / Activities:

• The Islands (Murano, torcello and Lido Islands)
• Basilica di Santa Maria della Salute
• Gallerie dell’ Accademia

Hotel: TBA

Meals: Breakfast

After breakfast, you travel to Bologna by train. Along the way, you stop at Ravenna, an old town with amazing Byzantine architecture and beautiful mosaic artwork. You visit the antique Basilica of San Vitale, which boasts some of the best-preserved mosaics, and the Piazza del Popolo, a square with a 1300 BCE Egyptian obelisk from Heliopolis erected in the center. You arrive in Bologna by evening.

Site Visits/ Activities:

• Explore the Old town of Ravenna
• Basilica of San Vitale
• Piazza del Popolo

Hotel: TBA

Meals: Breakfast

On this day, you go on a historic tour of Bologna. This small city is famous for its immense culture and artistic heritage. You stop at the Quadrilatero, an old city hub with markets since medieval times. It includes the Piazza Maggiore, the Fountain of Neptune, the two towers, the Piazza di Port Ravegnana, and more. And not to forget there’s delicious Bolognese cuisine to try.

Site Visits / Activities:

• Explore the old Town of Bologna
• The Fountain of Neptune
• Piazza Maggiore
• Two Towers
• Piazza di Porta Ravegnana
• Palazzo Vecchio
• Torre della Garisenda

Hotel: TBA

Meals: Breakfast

You have a full day in Florence. You start at the Uffizi Gallery, a prominent art museum in the Historic Center of the city. The gallery is known for its collection of ancient artworks. Two known paintings, “Birth of Venus” and “Annunciation” are exhibited there. In the afternoon you explore the old city with the Cathedral of Santa Maria del Fiore with a red-colored terracotta dome. You can see it from different corners of the old city.

Site Visits / Activities:

• Uffizi Gallery
• Old Town of Florence
• Piazza della Repubblica
• Ponte Vecchio
• Cathedral
• Piazza della Signoria
• Palazzo Vecchio
• Loggia dei Lanzi

Hotel: TBA

Meals: Breakfast

You have a second day in the city. You visit the Galleria dell’ Accademia,  the museum that houses Michelangelo’s famous sculpture, David. And you go on a leisure walk to Oltrarno crossing the Arno River into the chic neighborhood with artisan shops and cafes. You pass the Santa Croce, enter the Boboli Gardens, and stop at the Piazzale Michelangelo for a panoramic view of Florence with the red dome cathedral.   

Site Visits / Activities:

• Explore the old town of Florence (Roma and Via dei Calzaiuoli roads)
• Galleria dell’ Accademia
• Oltrarno Walk
• Santa Croce Church
• Boboli Gardens
• Piazzale Michelangelo

Hotel: TBA

Meals: Breakfast

You check out of Florence and travel in a minibus around Tuscany. You stop at one of Italy’s most beautiful villages, Montefioralle with chianti vineyards. You have free time to explore the streets, taste some wine and have lunch at some local restaurant. Following you drive through Tuscany countryside to the charming walled city of Lucca. You explore the inside of the city with gates built at different periods of our time.

Site Visits / Activities:

• Explore the old town of Montefioralle and have lunch
• Driving break at the old town of Luca

Hotel: TBA

Meals: Breakfast

You rise early for the Mercato Centrale Pisa, a lively market with local produce, artisan breads, Italian meats, and local delicacies. After the market, you explore the city of Pisa by bus, taxi, and foot. You see the world-renowned leading tower, the Pisa, take a break at Borgo Stretto a neighborhood with colored townhouses and wooden shutters, and you continue the discovery of many more architectural wonders.

Site Visit / Activities:

• Mercato Centrale Pisa (early AM)
• Pisa Cathedral
• Leaning Tower
• Pisa Baptistery
• Piazza dei Miracoli
• Camposanto
• Santa Maria della Spina
• Borgo Stretto (lunch)
• Palazzo della Carovana
• Casa Ammannati (Casa natale di Galileo Galilei)
• Palazzo Blu

Hotel: TBA

Meals: Breakfast

You check out of Pisa and drive through the countryside of Tuscany to this charming town, Volterra. It’s a very small town and the oldest city in Italy. It’s built on a hilltop with stunning views. Your guide takes you to a local farmstead for a lunch break. After lunch you continue your drive, stopping at San Gimignano, another medieval walled city but with towers that rise above the city. San Gimignano is a UNESCO world heritage site.

Sight Visits / Activities:

• Tuscany tour
• Volterra
• Lunch at a local farm restaurant

Hotel: TBA

Meals: Breakfast

You wake up in Monteriggioni, a castle town in the Chianti region. The region is known for its wine. Why not enjoy a wine-themed breakfast? Then drive to Siena for the Piazza del Campo which is of Europe’s greatest medieval squares with the Palazzo Pubblico, a “public” palace. After lunch drive to Cortona, a hilltop town with a museum reflecting the Etruscan past. Evening is in Montepulciano known for its thermal baths.

Site Visits / Activities:

• Old Town of Siena
• Piazza del Campo
• Palazzo Publico
• MAEC (Museum of the Etruscan and Roman City of Cortona)
• Montepulciano spa facilities

Hotel: TBA

Meals: Breakfast

You go on a day trip to the Orcia Valley, a UNESCO World Heritage Site that recognizes the development of the town with magnificent landscapes of rolling hills and cypress trees that inspired many artists. The valley is home to some of Italy’s most famous wines and pecorino cheese. You stop to explore the medieval village and have lunch at the local farmstead. You return to Montepulciano for the evening.

Sight Visits / Activities:

• The Orcia Valley 
• Lunch at a local  farm restaurant
• The old medieval town of Montepulciano

Hotel: TBA

Meals: Breakfast

You drive out of Tuscany stopping at Pitgliano, a tuff rock town built from volcanic ash deposits, that is “cemented” into a bedrock on steep hills. Dwellers dug out living spaces/caves and tunnels. A cave city was created in the bedrock. The town is nicknamed “Little Jerusalem” because it’s home to Jewish families who moved in around the 16th century. You see Lake Bolsena, a crater lake before you enter Rome.

Site Visits / Activities:

• Pitigliano with the carved volcanic stone town
• Lake Bolsena with the largest volcanic lake view in Europe

Hotel: TBA

Meals: Breakfast

After breakfast, you embark on your city tour of old Rome. You stop to see the Borghese, a gallery with an elegant art museum and a beautiful garden. Then You go on a city tour to see great landmarks including the famous Trevi Fountain, the iconic Spanish Steps, the Piazza del Campidoglio, which is Italy’s most beautiful square, and many other historic sites in the same area.  The evening is in the city center.

Site Visit / Activities:

• The Borghese Gallery
• Streets of Medieval Rome
• Trevi Fountain
• Spanish Steps
• Piazza del Popolo
• Altare della Patria
• Campidoglio
• Piazza Venezia

Hotel: TBA

Meals: Breakfast

You visit the Vatican, a city-state in Rome. The city is the headquarters of the Roman Catholic Church. You visit the Vatican museum which houses ancient Roman sculptures and Renaissance frescoes. After lunch, you visit the Pantheon, the world-renowned monument with the world’s largest unsupported concrete dome, and the Church of Saint Ignatius of Loyola with some of Rome’s best Italian Baroque decorations.

Sight Visits / Activities:

• Vatican Museum
• St. Peter’s Basilica
• Piazza San Pietro
• Castel Sant’Angelo
• Pantheon
• Piazza Navona
• Chiesa di Sant’Ignazio di Loyola

Hotel: TBA

Meals: Breakfast

After breakfast, you begin your tour of Ancient Rome. You visit the ruins of the Roman Forum and discover how the ancient Romans utilized this space. And you see the Colosseum, the largest ancient amphitheater ever built. It hosted events like the gladiators games. After lunch, you see the Bocca della Verità (aka the Mouth of Truth), the Jewish Ghetto, the Tiber Island, and the Trastevere, a bohemian neighborhood.

Site Visits / Activities:

• Foro Romano
• Closseo
• Palatino
• Ciro Massimo
• Aventino
• Campo de’ Flori
• Jewish Ghetto
• Bocca della Verità
• Tiber Island
• Trastevere

Hotel: TBA

Meals: Breakfast

You check out and travel to Naples an old town with several medieval castles. You see the Basilica of Santa Chira, a church complex with a monastery, tombs, and a museum. Discover the Palazzo del Plebiscito, with the Teatro di San Carlo, the world’s oldest opera house, and the beautiful 19th-century Galleria Umberto I. You walk down Spaccanapoli, a long narrow street that from above seems to divide the city. After Naples, travel to Pompeii.

Site Visits / Activities:

• Castel Nuovo
• Castel dell’Ovo from the window
• Chiostro di Santa Chiara
• Teatro di San Carlo
• Galleria Umberto I
• Palazzo del Plebiscito
• Old Town of Naples
• Spaccanapoli Street
•  Pompei ruins

Hotel: TBA

Meals Breakfast

After breakfast you walk to the port of Sorrento and take a high speed boat to Amalfi coastline, one of Italy’s most scenic spot. The area is a UNESCO site with majestic terrain, high cliffs, turquoise waters and lemon groves. You go see the Grotta dello Smeraldo aka Emerald Grotto, a beautiful cave with fascinating natural structures, and you wander the streets of Amalfi, Italy’s oldest Maritime town. Why not try a lemon gelato?

Site Visit / Activities:

• The old town of Amalfi
• Grotta dell smeraldo
• boat rides
• Town of Positano

Hotel: TBA

Meal: Breakfast

You check out early for your flight to Sicily, an Italian island famous for sandy beaches, delicious wine, and ancient Greek and Roman structures. Upon arrival, you check in at your hotel and then embark on a city tour of the capital, Palermo. Your guide will take you to various markets with food for tasting. And to other landmarks including the Port Nuova, a historical gate, and the Fontana Pretoria (the Fountain of Shame).

Sight Visits / Activities:

• La Vucciria Market
• The Capo Market
• Ballarò Market
• Fontana Pretoria
• Porta Nuova
• Catacombe dei cappuccini (optional)

Hotel: TBA

Meal: Breakfast

In the morning, you tour old Palermo, stopping at the Norman Palace that was the seat of the Kings of Sicily and the Palazzo Conte Frederico, which is one of the oldest homes still inhabited by the same family.  In the afternoon you go to Erice, a historic town on a hilltop with two castles, one built by the Arabs and the latter by the Normans. Following you take a funicular down to Trapani, an old port city.

Site Visits / Activities:

• The old town of Palermo
• Palazzo Conte Federico
• Norman Palace
• Cappella Palatina
  
• Town of Erice
• Take the funicular down to Trapani
• Town of Trapani

Hotel: TBA

Meals: Breakfast

After breakfast, you take a ferry boat to Favignana Island. The Island is a paradise, known for its beautiful beaches and crystal clear waters. You have free time on the island to enjoy the beach and swim in the water or go snorkeling. There are many nature trails for cycling and walking. The island has a small hub with artisan shops, restaurants, and cafes.

Site Visits / Activities:

• Port of Trapani
• Ferry to Favignana Island
• Free time on the artisan island

Hotel: TBA

Meals: Breakfast

You check out and drive northwest to Segesta. The city once belonged to the indigenous Elymians, a tribal people who inhabited the area during the Bronze Age. You stop at the Parco Archeological Di Segesta park to learn about these people. In the afternoon you stop at a farmstead for a homestyle lunch. Then continue your drive to Agrigento for your hotel l that looks out to the Valley of the Temples.

Site Visits / Activities:

• Parco Archeologico di Segesta
• View of the Valley of the Temples

Hotel: TBA

Meals: Breakfast

After breakfast, you check out and drive to the ancient city of Akragas in the Valley of Temples. It is an archeological site with preserved Greek temples dating back to the 6th century BC. You stop at some temples. Then after lunch, you leave the site for Ragusa Ibla, a hilltop town with baroque structures. You check in your hotel there and hop on a trolley for a ride through the old town with narrow streets and ethereal beauty.

Site Visits / Activities:

• Valley of the Temples
• Old Town of Ragusa
• Leisure Walk through town
• Trolley Ride

Hotel: TBA

Meals: Breakfast

You go on a day trip to Modica, a charming old town in deep canyons carved by rivers that traverse the valley a long time ago. There are 17 ancient bridges with no river flowing. You explore the city on the trolley and get off to see key landmarks. Some structures and tombs in the city date back to 2200 BC. Many churches are built in the Baroque style. The city is famous for its chocolate which has been produced for years.

Site Visits / Activities:

• Old town of Modica
• Trolley tour of Modica
• Leisure walk of Ragusa Ibla

Hotel: TBA

Meals: Breakfast

After breakfast and check out, you drive to Noto, the city with the most Opulent Baroque architecture. It’s also a town of the Bishop’s authority with many churches and religious buildings. You explore the streets and enter some of the churches. In the afternoon you drive to Syracuse and check in at a hotel on Ortega Island. The island is a labyrinth of ancient streets packed with over 2,500 years of history.

Site Visits / Activities:

• Corso Vittorio Emanuele (main street)
• Piazza Immacolata/Church of San Francis
• Piazza Municipio/Palazzo Ducerio
• Piazza XVI Maggio/Chiesa di San Domenico
• Ortigia Island
• Old town of Ortigia

Hotel: TBA

Meals: Breakfast

You check out Syracuse and drive to an elegant and charming town Taormina. It’s near Mount Etna, a volcano with nature trails for leisure walks. The town is known for the Teatro Antico di Taormina, an ancient Greco-Roman theater that is still used today. Near the theater, you can see the cliff that drops into the sea and forms a cove with beaches.  Taormina is an Italian food heaven with many places to eat and drink.

Site Visits / Activities:

• Explore Taormina
• Leisure walk
• Greek Theatre 
• View of the Bay of Naxos
• View of Mt. Etna

Hotel: TBA

Meals: Breakfast

After breakfast, you hop on a bus or cable car to Caselmola, one of Italy’s most beautiful villages. It is nestled on a mountain overlooking the Ionian Sea. You go up to the entrance of Sant Antonio Square for a breathtaking panoramic view of the Strait of Messina. From the top, you move down the village passing by small galleries and artisan shops, cafes, and bars, too. After lunch, you may follow a nature trail back to Taormina. Or take the bus back to Taormina for the rest of the afternoon. It’s your last day in Italy.

Site Visit / Activities:

• Cable Car ride up to Caselmola Village
• Sant’ Antonino Square panoramic view
•  Explore the Old town of Caselmola
• Trail walk down to Taormina

It’s time to say good bye.  Your guide takes you to the airport and drops you off.