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Top to Toe of Italy

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You are viewing the 2026 itinerary. Select your departure year
202520262027
15 days From $5,495 $4,995 per person
4.5 stars(17 reviews)
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 Discover Italy's ancient and cultural destinations, dramatic coastlines and mouthwatering cuisine while traveling from Venice in the north to the traditional island of Sicily

Travel among a group of like-minded travelers led by a professional tour manager

Mobility Rating 4

2026 Tour code: TTG26

About the tour

From the alpine foothills to Sicily and all that lies between, uncover Italy's rich culture on an expertly crafted itinerary. See the highlights of Italy while traveling the country's length, delving into remarkable destinations, including Venice, Florence and Rome. 

Bask in the beauty of the Amalfi Coast and marvel at the remains of ancient Pompeii before venturing by train to Sicily - home to Mount Etna. 

Complete with delicious culinary experiences - a Sorrentine farm-to-fork lunch, pizza-making and a cannolo tasting - this journey offers an authentic taste of Italy. 

Unforgettable Experiences

Cruise along Italy’s iconic Amalfi Coast
Cruise along Italy’s iconic Amalfi Coast
Gaze upon one of Italy’s most desirable and dramatic stretches of coastline while on a memorable boat trip from Sorrento to the towns of Amalfi and Positano, with free time in each destination. 
Tour Italy’s historical cities
Tour Italy’s historical cities
Discover the best sights and cultural offerings of Italy's greatest cities while on expertly guided tours in destinations like Venice, Florence, Rome, Siena, Lucca, Pisa and Taormina. 
Indulge in a farm-to-table meal at an agriturismo
Indulge in a farm-to-table meal at an agriturismo
Experience farm-to-fork fresh produce and an introduction to delicious Sorrentine food as we enjoy lunch and a limoncello tasting at an agriturismo, a family-run farm operated for four generations on the Sorrento Peninsula. 
Step back in time in Pompeii
Step back in time in Pompeii
Uncover what remains of a city captured in time by the eruption of Mount Vesuvius in 79 A.D. on a guided tour featuring Pompeii's ancient streets, temples, baths, theaters, shops and markets – all remarkably preserved. 
Stay in coastal Sorrento
Stay in coastal Sorrento
Spend three nights unwinding in the laid-back coastal town of Sorrento, nestled between the Bay of Naples and hillsides of fragrant lemon orchards. 
View Europe’s most active volcano
View Europe’s most active volcano
Explore the craters and surreal landscape of Europe's most active volcano, Mount Etna, and admire its lava fields while following a highly scenic stretch of the Circumetnea Railway along the volcano's base. 

What’s included

Itinerary

Day 1 - Arriving on Italy’s east coast in Venice

Your vacation begins today as you arrive in the classical city of Venice on Italy's east coast. With centuries of history, breathtaking bridges and buildings, and a unique cityscape made up of more than 100 islands woven together by canals and lagoons, this city makes the ideal starting point for our Italian adventure.

Make your way to our five-star hotel on the island of Lido and check in for the first of two nights. This luxurious hotel is set away from the crowds of Venice yet has all the city's most popular attractions within reach. Take time to get settled in and enjoy views of the hotel's private beach before meeting your Tour Manager and the travel group this evening. Together, we sit down for dinner in the hotel's restaurant. Overnight Venice.

Includes
  • Dinner
Day 2 -  Touring Venice, the ‘Floating City’

This morning, we discover Venice on a guided tour. A boat transfer takes us through the winding waterways to Cornoldi Pier, where our excursion begins.

We tour the charming backstreets, viewing the church where composer Antoni Vivaldi was born, before marveling at the Bridge of Sighs and arriving in St. Mark's Square. Here, we view St. Mark's Basilica and Doge's Palace, as well as Caffè Florian, a coffee house that first opened in 1720.

In the afternoon and evening, you are free to explore independently and may opt to enter the basilica or Doge's Palace (payable locally). Venice's winding alleys and twisting lanes in the historic center are ideal for idly wandering, and there is incredible art and architecture to discover before perhaps settling down in a restaurant to enjoy some of the country's finest seafood. Experience it like a local by ordering some cicchetti, Venetian tapas, accompanied by one of the city's signature drinks - prosecco, Aperol spritz or bellini. Overnight Venice.

Includes
  • Breakfast
Day 3 -  Arrival in the Renaissance city of Florence

A private boat transfer takes us to the railway station this morning to travel by First Class rail to Florence. After checking into our central hotel, there is time to relax before we embark on a guided tour of this fascinating city.

Along the way, we view some of Florence's treasures, including the red-tiled Duomo and the free-standing campanile tower designed by Giotto. The dome and tower dominate Florence's skyline, but seeing the detail of the polychromatic exterior up close is a delight.

Moving to the medieval city center, we view the fortified 13th-century Palazzo Vecchio and the Loggia dei Lanzi in the Piazza della Signoria before concluding our tour at the famous 14th-century Ponte Vecchio.

Take a couple of hours to continue sightseeing at your own pace, then rejoin the group for dinner at a local restaurant this evening. Overnight Florence.

Includes
  • Breakfast, Dinner
Day 4 -  Looking to traditional Tuscany in Siena

 A new location lies ahead today as we take a day trip to medieval Siena, a Tuscan city where a labyrinth of narrow streets opens to charming piazzas.

After arriving by rail, we discover Siena's most popular destinations on a guided tour from the Fortress of Santa Barbara. We continue to the church of San Domenico, where we enjoy free admission, and then proceed to the Baptistery and the Duomo, which is one of Italy's most magnificent. Enjoy the medieval scenery and architecture as we continue along via di Città to Siena's city center, Tolomei Square and, finally, the city's most famous sight, Piazza del Campo.

Continue sightseeing at your own pace before we journey back to Florence by rail. You could sample some locally cured meats and cheeses or climb the spiral staircase at the Museo dell'Opera del Duomo for a panoramic view over Siena.

You have a free evening in Florence to explore the city's labyrinthine streets and pretty piazzas before perhaps choosing to eat at a trattoria, sampling traditional Florentine steak. Overnight Florence.

Includes
  • Breakfast
Day 5 - Another look at Tuscany in Pisa and Lucca

 After breakfast at the hotel, we travel by local rail to Pisa, beloved for its Leaning Tower. On arrival, we see this structure and many others on a guided tour. On entering the "Field of Miracles" through the Porto Nuevo, we view the white marble Romanesque cathedral, the circular Baptistry, and the Leaning Tower of Pisa itself. This popular tourist attraction has been slanted since it was built in the 12th century.

In the afternoon, we continue by train to the walled city of Lucca, where you are at leisure to explore the ancient ramparts and picturesque streets. The maze-like center has a Duomo and other frescoed churches, striking piazzas - including the Piazza Anfiteatro, once a Roman amphitheater - a botanical garden and art galleries all inside the city walls. You can opt for lunch in a local trattoria, maybe trying a typical Luccese soup or the local filled pasta, tordelli.

After returning to Florence early this evening, you can continue exploring independently, perhaps taking a stroll alongside the Arno River to experience the city at sunset. Overnight Florence.

Includes
  • Breakfast
Day 6 - To the Eternal City, Rome

 With a morning at leisure in Florence, you might want to wander Florence's impressive galleries, churches and Medici palaces, which display a fifth of the world's Renaissance art. If you plan to visit the Uffizi Gallery, book your tickets ahead of time to ensure admission. Alternatively, you may prefer to stroll across the river to Boboli Gardens to see fantastic views of Florence or visit the Mercato di San Lorenzo - the city's largest market.

In the early afternoon, we walk to the train station for our First Class journey to Rome, Italy's capital and Eternal City. This dynamic city is a melting pot of art, history and religion, with ancient sights around every corner. After checking into the hotel this afternoon, you can begin getting acquainted with Rome's many offerings while sightseeing independently.

Rejoin the group at the hotel this evening, and together, head to a local restaurant for dinner. Overnight Rome.

Includes
  • Breakfast, Dinner
Day 7 - Discovering La Dolce Vita in Rome

 This morning, we enjoy a grand introduction to Rome and its history on a guided tour. We transfer by coach to the Colosseum, Italy's most renowned classical site, where our excursion begins with a tour of its exterior. This immense structure is the largest ancient amphitheater ever constructed, believed to host around 50,000 spectators during gladiatorial contests.

Continuing our walking route, we learn about the powerful governing center of ancient Rome and its emperors while looking upon the outside of the Roman Forum, Piazza Venezia, the Roman Pantheon and the world-famous Trevi Fountain.

Our tour ends in Piazza Navona - a square with a Baroque fountain and border of ochre-hued buildings, cafés and restaurants. You are then free to continue soaking up Rome's beauty and unique style at your own pace this afternoon and evening.

For dinner tonight, you might like to search out some delicious Roman specialties, such as carbonara. Overnight Rome.

Includes
  • Breakfast
Day 8 - A free day in the ancient Italian capital

Savor a full free day with endless opportunities to experience the great city of Rome. Today is the perfect chance to experience nearby Vatican City. You might like to wander through St. Peter's Basilica or peruse the art and history that line the walls of the Vatican Museum. Of course, the biggest attraction in Vatican City is the Sistine Chapel, whose interior is covered in Renaissance frescoes by Botticelli, Ghirlandaio and, most famously, Michelangelo. If Vatican City is on your list, you must pre-book your visit online ahead of your vacation.

Staying in Rome, you could walk up the Spanish Steps to Villa Borghese Park, where you can relax in landscaped gardens or see art and sculptures in the Borghese Gallery.

Rome offers an array of eateries - many with alfresco seating. For lunch and dinner, maybe choose a trattoria to enjoy a plate of pasta with a glass of wine or dine like a local at an outdoor café. Overnight Rome.

Includes
  • Breakfast
Day 9 -  To Sorrento, the gateway to the Amalfi Coast

The delights of coastal Italy are on the horizon as we transfer to Rome's station for our First Class rail journey to Naples this morning. On arrival, we transfer by coach to Sorrento, stopping en route at a local agriturismo - a traditional farmhouse - established and run for four generations by the same family. Here, enjoy a lunch of fresh produce from the estate, including homemade limoncello and mozzarella, while surrounded by ancient olive groves, lemon orchards and vineyards.

Arriving in Sorrento late this afternoon, we check-in for the first of three nights at our hotel, which has delightful views across the town and bay towards Mount Vesuvius. We then get to know this alluring town, set in its own small bay within the vast Bay of Naples, on a short orientation tour. Sorrento is perched on a natural terrace above dramatic cliffs overlooking the sea, and its narrow, cobbled streets feature Renaissance palaces and Romanesque churches.

As the tour concludes, you are free to relax or continue exploring further for the remainder of the evening. Overnight Sorrento.

Includes
  • Breakfast, Lunch
Day 10 - Cruising the Amalfi Coast and an authentic pizza-making experience

 The rich culture and captivating beauty of the Amalfi Coast beckons as we set out on a cruise on the Tyrrhenian Sea. This scenic coastline is a UNESCO World Heritage Site stretching along the Gulf of Salerno, south of the Sorrento Peninsula.

A coach transfer takes us to Sorrento's port, where we board our boat. First, we sail to Amalfi, the "Jewel of the Amalfi Coast." With free time here, you could visit the cathedral, Duomo di Sant'Andrea, which overlooks the town's main piazza.

Our cruise continues to Positano, where pastel houses drape the rocky hillsides and tucked-away beaches open to turquoise water. Here, we are at leisure to soak up the atmosphere, wander the wisteria-veiled streets, and maybe enjoy lunch at a café in the harbor area.

We return to Sorrento in the late afternoon where you are free to dine independently this evening. Overnight Sorrento.

Includes
  • Breakfast, Dinner
Day 11 -  Pompeii: A city captured in time

 Enjoy a highlight of our journey this morning as we travel back in time to Pompeii, the city preserved by volcanic ash from the eruption of Mount Vesuvius in 79 A.D. Following a coach transfer to the station, we travel by local train to this fascinating archaeological site for a guided tour.

Our guide takes us through the remarkably intact streets of Pompeii, where we walk among the shops, villas, baths, temples and restaurants of this UNESCO World Heritage site. We also see Pompeii's amphitheater - the oldest in the world - and some of the city's extraordinary frescoes. Our tour provides a tangible understanding of daily life in an ancient city, and after, you are free to continue exploring its ash-preserved wonders independently.

After retracing our journey by train and shuttle back to Sorrento there is time to relax before a three-course dinner at our hotel this evening. Overnight Sorrento.

Includes
  • Breakfast, Dinner
Day 12 -  Traveling to Sicily by train

 With an early start, we have breakfast at the hotel and then leave Sorrento behind, transferring to the town of Salerno, where we catch the train to Sicily in First Class. The route provides excellent views of the Tyrrhenian Sea as we travel the full length of the Calabrian Coast and into the unspoiled region of Calabria, known as the "toe" of Italy.

In Villa San Giovanni, the train is shunted on to a ferry specially equipped with rails for a journey across the Strait of Messina. You are welcome to stay in your seat on the train or relax on board the ferry while enjoying great views of Sicily. Upon docking, we return to the rails for the final leg of our journey to Taormina and then continue by coach to our hotel in nearby Giardini Naxos.

Our accommodation here is an elegant beachfront hotel with a private beach. The laid-back coastal town has a good choice of restaurants for dinner this evening, serving local specialties, including swordfish, and the baked pasta dish pasta 'ncasciata. Overnight Giardini Naxos.

Includes
  • Breakfast
Day 13 -  Exploring Mount Etna: Europe’s most active volcano

 A highlight of our Sicilian trip awaits today as we visit the island's most iconic sight. An active volcano with a height of more than 10,000 feet and a circumference of around 93 miles, Mount Etna is as captivating as it is massive.

Our coach transfer takes us to Rifugio di Sapienza, the highest point of vehicular access on Mount Etna. Here, you can view the Silvestri Craters, the elemental volcanic scenery, and the otherworldly landscape of basalt rocks formed from drying lava flows. For another perspective on the scenery, you could book a cable car ride or a Jeep excursion higher up Mount Etna (payable locally).

This afternoon, we get a different view of Mount Etna as we continue to Adrano by coach to join the Circumetnea Railway to Randazzo. This route is the most scenic stretch of the narrow-gauge railway that travels around the base of the volcano and reveals lava fields that often encroach on nearby towns.

Returning to our hotel this afternoon, you have a free evening to relax on the beach or find dinner locally. Overnight Giardini Naxos.

Includes
  • Breakfast
Day 14 -  Touring the ancient Greek city of Taormina

 Our day starts with breakfast at our hotel before we transfer by coach to the historic town of Taormina. During our two-hour guided tour, we see the Greek theater, which is believed to date from around the third century B.C. Dug out of Mount Taurus, this vast venue could seat upwards of 5,000 spectators who would gather to watch Greek tragedies or comedies and, during the later Roman period, gladiators. While the amphitheater is impressive in its own right, it also offers beautiful views of the Ionian Sea and Mount Etna.

Our tour concludes at a local cake shop or "pasticceria," where we indulge in a sweet taste of Sicily - a cannolo. Meaning "little tube," these crisp, ricotta-filled pastries are the island's most famous dessert.

There is the option to spend your afternoon in Taormina following the tour and return the short distance to Giardini Naxos independently this evening. Tonight, we gather in the hotel's restaurant for a three-course dinner - our final meal together in Italy. Overnight Giardini Naxos.

Includes
  • Breakfast, Dinner
Day 15 -  Tour conclusion

 From the Floating City of Venice on Italy's east coast to the rolling fields of Tuscany, the ancient capital city, the colorful villages of the Sorrento Peninsula and, finally, the cultural island of Sicily, this adventure has truly presented Italy from the "top to toe." Complemented by rich culture, delicious cuisine and stunning scenery, each day has been filled with Italian wonders.

Catch glimpses of the Ionian Sea and soak up the atmosphere during your final breakfast in Sicily. Your Italian adventure draws to a close as you check out of the hotel and begin your trip home, transferring to the airport or railway station in Taormina independently for your onward journey.

Includes
  • Breakfast

Additional information

Departure times

Departure times vary based on selected rail vacation. This information will be provided in your final documents. For more information please speak with your rail specialist.

Mobility information

Due to the nature of our tours, they are generally unsuitable for those with restricted mobility. Please reference our Mobility Ratings Information, and if you’d like to discuss any particular vacation with us in this respect, then please don’t hesitate to call us at 1-877-929-7245.

Hotels

Hotel Cellai, Florence

Hotel Cellai, Florence

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Hilton Sorrento Palace

Hilton Sorrento Palace, Sorrento

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Bettoja Hotel Mediterraneo, Rome

Bettoja Hotel Mediterraneo, Rome

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Hotel Excelsior Venice Lido Resort, Venice

Hotel Excelsior Venice Lido Resort, Venice

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Hellenia Yachting Hotel, Giardini Naxos

Hellenia Yachting Hotel, Giardini Naxos

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Trains

The Circumetnea Train
Trenitalia

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Reviews

4.5 stars4.5 / 5 · 17 reviews

  1. 5 stars
    (10)
  2. 4 stars
    (6)
  3. 3 stars
    (0)
  4. 2 stars
    (1)
  5. 1 star
    (0)

Tina Dino

5 stars

Submitted 28 Oct 2024

Best tour ever! Wouldn’t travel any other way!

from Vacations By Rail
Hi Tina - Welcome home! It's wonderful to hear that you enjoyed your Italy vacation. The photos you shared are terrific! We hope to help plan your next vacation with you.
1 comment

Collected by Trustpilot

Jodi Altman

5 stars

Submitted 25 Oct 2024

The top to toe of Italy tour that we went on was fantastic! Everything was planned and perfectly choreographed by our tour guide, Judith! The folks in our group were so sweet and really fun to get to know! I can't wait to plan another trip with this company!

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DB

5 stars

Submitted 05 Oct 2024

A great way to see as much of Italy as possible in one trip.

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Eloise De Beer

5 stars

Submitted 14 Oct 2023

We had a fabulous Tour Manager in Lydia. She was always available and approachable and friendly to all. We stayed in excellent hotels, tours, and great meals were included. There's only a couple things I'd change. We were too long on the Amalfi Coast, and wished we could spend some time exploring Sorrento on our own. My roommate and I paid for 2 extra nights in the first hotel, in Murano, and you would think at $269 per night, breakfast would be included.

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BARBER, TINA

5 stars

Submitted 11 Oct 2023

Overall, this was a fabulous 15-day trip. Our tour manager, Lydia, is a top-notch facilitator and made sure our needs were met. The train connection from Pisa to Lucca was a bit too tight and a couple of folks had to hop on the next train, which wasn't as crowded. The itinerary timing could be adjusted here for future bookings. I highly recommend the Top to Toe of Italy tour.

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Louis Amblard

5 stars

Submitted 30 Sep 2023

It's was pretty well organized

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