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Itinerary

Some trips show you a country. This one takes you straight into the Italy everyone dreams of visiting at least once in their lifetime.

We start in Venice, among canals, narrow alleyways, St. Mark’s Square, and a welcome Spritz to toast the beginning of our adventure. From here, we travel by high-speed train to Florence and dive into the heart of the Renaissance, exploring the Duomo, Ponte Vecchio, one of the city’s most famous schiacciata sandwiches, and the art of making fresh pasta from scratch.

Then, for one day, we leave the city behind and head into the rolling hills of Chianti, surrounded by vineyards, picturesque villages, and a local winery where we’ll discover and taste one of Tuscany’s most iconic products.

The final chapter of our journey takes us to Rome: the Trevi Fountain, the Pantheon, Piazza Navona, Trastevere, and of course the Colosseum, Roman Forum, and Palatine Hill.

Three iconic cities, one full day in the Tuscan countryside, and only two major travel days: enough time to see Italy’s must-see highlights while still having time to slow down, grab an aperitivo, taste the local food, and simply enjoy being here.

A map of Italy with a plotted travel route starting in Venice and ending in Rome, passing through San Marino.
A narrow canal flows between tall, weathered buildings with balconies and shutters under an overcast sky.

Welcome to Venice

Flights to and from Italy are not included in the package, giving everyone the freedom to choose the airline, airport, and schedule that works best for them.

We recommend flying into Venice Marco Polo Airport (VCE) and making your own way to our hotel.

We’ll meet as a group in the late afternoon. Once we’ve dropped off our bags and met our new travel crew, there’s only one proper way to kick off a trip to Italy: with a toast.

We head out through Venice’s narrow alleyways, bridges, and hidden squares for our first taste of the city before stopping for our Welcome Drink: a classic Venetian Spritz.

It’s the perfect chance to break the ice and officially kick off our Italian adventure.

The rest of the evening is ours to enjoy. We can decide together where to have dinner and start soaking up the atmosphere of Venice by night.

An aerial view of a city with a large domed basilica and terracotta-roofed buildings next to a canal with boats.

La Serenissima

After breakfast, it’s time to really get to know Venice.

Together with a local guide, we explore the heart of the city, weaving through narrow alleyways, small squares, bridges, and historic neighborhoods while learning about the history and traditions of one of the most unique cities in the world.

We make our way to St. Mark’s Square, Venice’s grandest gathering place, and step inside the magnificent St. Mark’s Basilica, famous for its golden mosaics and extraordinary history.

From here, we continue through the city toward some of Venice’s most iconic sights, eventually reaching Rialto Bridge and the Grand Canal.

Venice at Your Own Pace

The afternoon is free.

You might choose to take a gondola ride, visit a museum, do some shopping, or simply get lost among the canals and stop at a traditional bacaro for cicchetti and a glass of local wine.

In the evening, we meet back up and decide together where to have dinner.

The Florence Cathedral's dome and bell tower rise above the city's terracotta roofs, with mountains in the background under a blue sky.

Next Stop: Florence!

After breakfast, we say goodbye to Vly.enice and make our way to Santa Lucia train station.

We travel by high-speed train from Venice to Florence, avoiding a long bus ride and arriving right in the heart of our next destination.

Once in Florence, we drop off our bags at the hotel and start exploring.

We walk through Santa Maria Novella, Piazza del Duomo, the Cathedral of Santa Maria del Fiore, the Baptistery, Piazza della Signoria, and Ponte Vecchio.

Florence feels like an open-air museum, and today is all about getting our first taste of one of the most beautiful cities in Ita

Time for a Florentine Schiacciata

Lunch comes with a true Florence essential: a traditional Florentine schiacciata from one of the city’s most famous sandwich spots, filled with Tuscan cured meats, cheeses, and local ingredients.

In the afternoon, we continue exploring the city with our Coordinator.

The evening is free, giving us time to choose where to have dinner and experience Florence after dark.

A person's hands catch strands of fresh fettuccine pasta coming out of a manual pasta maker over a wooden board.

The Heart of Florence

After breakfast, we have another full day to dive deeper into Florence.

The morning is free, so everyone can experience the city in their own way.

Art lovers can visit the Accademia Gallery to see Michelangelo’s David or explore the masterpieces inside the Uffizi Gallery. Those looking for a slower morning can wander through the Central Market, explore the Oltrarno neighborhood, go shopping, or simply enjoy a coffee with a view of the Duomo.

Let’s Make Pasta!

In the afternoon, we leave the museums behind and turn our attention to another form of Italian art: food.

During our fresh pasta cooking class, we learn about traditional ingredients and techniques and get hands-on as we make pasta from scratch.

Tagliatelle, ravioli, or other Italian specialties whatever is on the menu, this is guaranteed to be one of the most fun and social experiences of the trip.

Before or after the cooking class, depending on timing, we can make our way up to Piazzale Michelangelo for one of the best panoramic views over Florence.

A person holds a glass of red wine over a checkered tablecloth with a wine bottle in a wicker basket.

Picture-Perfect Tuscany: The Rolling Hills of Chianti

Today we completely change scenery.

After breakfast, we leave Florence by private transportation and head into the Tuscan countryside, surrounded by rolling hills, vineyards, cypress trees, and charming villages.

Our destination is Chianti, one of Italy’s most famous wine regions.

Wine and Tuscan Landscapes

We visit a local winery to discover how wine is produced here, from the vineyard all the way to the bottle.

Then, of course, comes the part we’ve all been waiting for: a guided Chianti wine tasting.

During the day, we’ll also have time to stop in one of the area’s picturesque villages, wander through its streets and squares, and take in the slower pace of the Tuscan countryside.

Lunch is not included, so we can decide as a group whether to stop at a trattoria, an agriturismo, or grab something more casual along the way.

In the late afternoon, we return to Florence.

Our final evening in the city is free.

A low-angle daytime view of a large, ornate fountain with intricate statues built against a classical building.

All Roads Lead to Rome!

After breakfast, we say goodbye to Florence and get ready for our second major transfer of the trip.

We travel by high-speed train from Florence to Rome, arriving right in the center of the Italian capital.

After dropping off our bags at the hotel, we head straight out to discover the Eternal City.

The Rome We’ve Always Seen in the Movies

Together with a local guide, we explore the historic center and some of Rome’s most iconic landmarks.

We walk through the Spanish Steps, the Trevi Fountain, the Pantheon, and Piazza Navona, while hearing the stories, legends, and fascinating details behind the city.

And yes — throwing a coin into the Trevi Fountain is basically mandatory. According to tradition, it means you’ll return to Rome one day.

Rome by Night

In the evening, we can head over to Trastevere, one of Rome’s most atmospheric and lively neighborhoods.

Tonight’s mission is simple: find a great local trattoria and settle the ultimate Roman debate carbonara, amatriciana, or cacio e pepe and of course a glass of red wine

The exterior of a large ancient stone amphitheater with multiple tiers of arches, illuminated by the setting sun.

Ave, WeRoaders!

Today we travel back almost 2,000 years.

After breakfast, we head to one of the most famous landmarks in the world: the Colosseum.

We step inside the legendary amphitheater and discover the world of gladiators, public spectacles, and Imperial Rome.

From here, we continue to the Roman Forum, once the political, religious, and commercial heart of the city, before making our way up Palatine Hill, where according to legend, Rome itself was founded by Romulus.

It’s a morning completely immersed in the history of Ancient Rome and one of the absolute highlights of the trip.

Today we travel back almost 2,000 years. After breakfast, we head to one of the most famous landmarks in the world: the Colosseum. We step inside the legendary amphitheater and discover the world of gladiators, public spectacles, and Imperial Rome. From h

The afternoon is free.

Those who want to keep exploring can head to St. Peter’s Basilica and Vatican City, visit the Vatican Museums, go shopping, return to the Trevi Fountain, or simply enjoy their final hours in Rome with no schedule at all.

Toward the end of the day, we can meet again and head to the Pincian Hill for one last sunset over Rome before our final evening together.

Dinner is free, so we’ll decide together where to spend our last night and toast to the past seven days.

A large crowd gathers on a wide street leading to the grand facade and dome of a historic basilica under an overcast sky.

Ciao Ciao

After our final breakfast together, it’s time to say goodbye.

The trip ends in Rome, with no scheduled group activities today, giving everyone the freedom to arrange their flight home from Rome Fiumicino Airport (FCO) or continue traveling through Italy.

Eight days ago, we were strangers meeting over a Spritz in Venice.

Since then, we’ve crossed Venice, Florence, the rolling hills of Chianti, and Rome together.

Not bad for one week.

What's included

What's not included

Roundtrip flight to/from destination
  • Food and beverages when not specified
  • All the extras you'll be able to fit in your backpack
  • Anything not mentioned in the "What's included" section

Optional activities

  • Winery visit and wine tasting
  • Fresh pasta cooking class

Additional info

Learn more about accommodation, transport, and other useful travel information.
  • Rooms with single or double beds and a private bathroom.
  • Train schedules are subject to change due to circumstances beyond our control, such as delays
  • Info on private roomsShow all details

Why WeRoad

  • Small groups, on average 11 people

  • Move or change your trip for free up to 31 days before departure

  • Book with $ 0. Pay the $ 100 deposit only once the trip is confirmed

The Group Leaders

Our Group Leaders are chosen because they’re people just like you: passionate travelers who share the experience authentically, while having the skills to take care of the organisation, and help you get the most out of every moment of the trip.

Find your flight

For this trip, we recommend arriving and departing from these airports.

ArrivalVenice (VCE)
ReturnRoma (RMA)
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WeRoadX

This is a WeRoadX

A trip designed and created entirely by an experienced WeRoad Travel Group Leader.

This is a trip designed and created entirely by an experienced WeRoad Travel Group Leader. They organise the whole trip: from defining the itinerary to selecting accommodation and on-site experiences. On the WeRoad website you can book the trip and manage it in MyWeRoad, just like any other WeRoad.

FAQs – Frequently Asked Questions

About this trip

About WeRoad

About Italy