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Tuscan Escape

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Group riding bikes in Italy

The one that stirs your passion for authentic Italian life under the Tuscan sun

Travel Style

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  • Duration

    7 days

  • Places

    10 places

  • Meals

    6 Breakfasts, 1 Lunch, 1 Dinner

  • Transport Style

    Coach

  • Group Size

    Maximum 24 people

  • Team

    Expert Trip Manager & Local Guides

Rome, Siena, Vatican City, Orvieto, Chianti Region, San Gimignano, Florence, Pisa, Lucca, Perugia

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About this trip

Starting in Rome, we’ll live la dolce vita for seven unforgettable days on this adventure up through sun-soaked Tuscany for a truly authentic taste of this iconic region. Whether you get your kicks from food, history, culture or Chianti, this is the one you’ve been waiting for - with mouthwatering cuisine, idyllic vineyards & a chance to try artisan crafts, we’ll re-live the Renaissance in Florence and Lucca, marvel at the medieval beauty of Siena and pose for the perfect picture in Pisa all across one extraordinary week.

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Map & Itinerary

  • Start location
  • End location
  • Trip day
  • Via location
  • River route
  • Plane route

Nights spent per location

  1. Vatican City

  2. 1 1 night

    Rome

  3. via via

    Orvieto

  4. 2 2 nights

    Siena

  5. via via

    Chianti Region

  6. via via

    San Gimignano

  7. via via

    Florence

  8. 2 2 nights

    Siena

  9. via via

    Pisa

  10. via via

    Lucca

  11. via via

    Perugia

  12. 1 1 night

    Siena

+2 more

DAY 1 - Start Rome

Rome

If you reverse the Italian word for Rome (Roma), you get Amor (love)… and we’re all set to fall in love with this ancient Italian capital the moment we set foot in it. ‘Ciao’ your new Contiki pals and we’ll hop on our coach for a city tour to catch all the classic sights, from the Colosseum to St Peter’s Square. Next we’ll cross the River Tiber to taste our way through Trastevere on a guided foodie walking tour, sampling pizza, pasta, wine and more in this bohemian district known for trattorias, pubs and artisan shops. Full of our first introductions to Italian life, we’ll join the locals for a passeggiata (promenade) to stroll off a few of the carbs before a satisfied slumber tonight.

INCLUDED EXPERIENCES

  • Food walking tour of Trastevere with Local Guide

DAY 2 - Rome to Siena via Orvieto

Rome

Sorry Rome, we’d love to linger but there are so many more experiences to soak up!

Orvieto

En route to Siena, we have time to explore the picturesque hilltop town of Orvieto, followed by an included lunch at Casa Segreta in the nearby village of Baschi. We’ll join the Polegri family on a short tour of the vineyards and olive orchards that make up their azienda agricola (farm), then enjoy a meal on the veranda overlooking the Tiber Valley. Expect bruschetta with homemade extra virgin olive oil, homemade focaccia with homegrown rosemary and vegetables, alongside a risotto or pasta made with vegetables grown on the farm. All accompanied by a glass of their very own wine and a handmade dessert of the day. Buon appetito! We’ll stop again at Terme di Saturnia where you’ll have time to bask in the famous thermal baths. Enjoy the benefits of thermal hydro-massage in one of Europe’s biggest hot spring pool complexes, lulled by the sights and sounds of the surrounding countryside.

Siena

The day is still unfolding and we’ve already done so much! After arriving at our accommodation in Siena there’ll be time to explore what is possibly Italy’s most beautiful medieval city. The historic centre has been declared a UNESCO world heritage site and its heart is the Piazza del Campo, the sweeping central square that hosts the world-famous Palio horse race. We’ll settle in here for the night, ready for more adventures tomorrow.

Stay

Borgo di Cortefreda or La Certosa di Pontignano

INCLUDED EXPERIENCES

  • Stop off at a local organic farm for a lunch under the Umbrian sun with pasta, olives, wine and More (MAKE TRAVEL MATTER® Experience)

  • Visit Terme di Saturnia Thermal Baths

DAY 3 - Siena with Day Trip to Chianti and San Gimignano

Siena

Chianti Region

Bathed in the golden glow of the Tuscan sun, there’s no better way to uncover this historical region than by tasting it. Today we’ll hop on our bikes to ride from Radda to Gaiole to visit local vineyards and explore Chianti wineries, and discover for ourselves this rich ruby red tipple the locals have been perfecting here for centuries.

San Gimignano

Another place famous for its wine, next we head to the enchanting hilltop town of San Gimignano. Known as the Town of Fine Towers, it’s yet another UNESCO World Heritage Site, renowned for its medieval architecture & sweeping views of the entire Chianti valley. Once you’ve stopped staring there’ll be free time to explore, have dinner and, hey why not, maybe another glass of wine?

Stay

Borgo di Cortefreda or La Certosa di Pontignano

INCLUDED EXPERIENCES

  • Visit local vineyards on two wheels and taste the famed Chianti wine

DAY 4 - Siena with Day Trip to Florence

Siena

Florence

Our destination today is home to red roofs, Renaissance architecture and rustic cuisine. Florence is often referred to as a 'walking museum', and today we'll find out why. With a locally guided walking tour, we'll explore the city on foot, swooning at Giotto's Bell Tower and the remarkable architectural feat that is the Duomo, pausing at the stalls and jewellry shops on the Ponte Vecchio and posing for a selfie with the replica statue of David (fig leaf and all). This afternoon we’ll have the chance to get involved with local handicrafts at a leather craft demonstration, part of Florence's artisan history, learning about this ancient tradition from a master craftsman and using the opportunity to customise your own leather accessory. Later there’ll be free time for more sightseeing, shopping or food, and meat-eaters won’t want to miss the chance to sample a Bistecca Fiorentina, a Tuscan speciality. Before we leave the city today don’t forget to touch the nose of ‘Il Porcellino’, the bronze boar in Piazza del Mercato, the traditional way to make sure you return to Florence!

Stay

Borgo di Cortefreda or La Certosa di Pontignano

INCLUDED EXPERIENCES

  • Learn about Florence's leather craft with a demonstration

  • See the Duomo, Basilica Santa Croce, Giotto’s Bell Tower, the Baptistery & Piazza della Signoria on a locally guided walking tour of Florence

FREE TIME ADD-ONS

  • Take part in a leather making work-shop in the Headquarters of the Leather Trade, the heart of the city of Florence. With the dedicated assistance & guidance of our Master Craftsman customise your own personal Genuine Leather accessory from scratch while learning about the secrets of this Ancient Tradition.

  • Florentine Steak Dinner

DAY 5 - Siena with Day Trip to Pisa & Lucca

Siena

Pisa

We can't be in this part of the world without a sneaky visit to the Leaning Tower of Pisa. Depriving you of the chance to perfect the ‘holding-up-the-tower’ shot would be criminal. Our visit includes a guided tour and entry to the tower, the cathedral and the Baptistry.

Lucca

We’ll stop for lunch in lovely Lucca, with its charming piazzas, Renaissance architecture and historic cafes. Well-preserved 16th century walls surround the historic centre and cobbled streets, perfect for a leisurely stroll or a cycle followed by a cheeky gelato.

Siena

Further south you can choose to find some dinner in Montalcino, another beautiful historic town known for – you guessed it – the production of delicious red wine. Don’t go knocking this one back too easily though, thanks to its individual grape variety, Brunello di Montalcino is one of Italy’s priciest wines...

Stay

Borgo di Cortefreda or La Certosa di Pontignano

INCLUDED EXPERIENCES

  • Guided tour and entry to the tower, the cathedral and the Baptistry.

FREE TIME ADD-ONS

  • Dinner in Montalcino - home to Brunello wines

DAY 6 - Siena with Day Trip to Perugia (Umbria)

Siena

Perugia

Somehow Umbria feels even more authentically Italy than anywhere else we’ve been so far. A little less explored than Tuscany and still dotted with fairytale towns, we can see why Umbria is known as Italy’s ‘green heart’. We’ll visit its capital Perugia, where fine old buildings perch on the beautiful hilltop. This afternoon you can choose to go horseback riding or hiking through the hills, or sign up for an authentic cooking class to learn the secrets of local specialties. Plus, a top tip - instead of wine, Perugia has become famous for chocolate. Get involved!

Stay

Borgo di Cortefreda or La Certosa di Pontignano

FREE TIME ADD-ONS

  • Horseback Riding

  • Hiking through the hills

  • Cooking Class

DAY 7 - End Rome

Rome

It’s said that all roads lead to Rome and that’s where we’re headed back to today. Has it really only been a week since we last set foot in the Eternal city? But don’t worry, there’s still time to pull in some adventures with a stop at Ostia, Italy’s largest ancient excavation site after Pompeii. Dating from the second to fourth centuries AD its impressive mosaics and frescoes and well-preserved ancient buildings like the theatre and the Baths of Neptune paint a vivid picture of urban life in Imperial Rome. Back in modern day Rome this afternoon, it’s time to say our sad goodbyes – or ‘Arrivederci’ - until we meet again on our next adventure. How does a reunion in Greece sound?

INCLUDED EXPERIENCES

  • Visit Ostia, the ancient harbour city of Rome and discover the vast archaeological site

Top Experiences

8 included & 6 free time add-ons available to add later

  • See the Duomo, Basilica Santa Croce, Giotto’s Bell Tower, the Baptistery & Piazza della Signoria on a locally guided walking tour of Florence

    Included

    Florence

  • Horseback Riding

    Free Time Add-On

    Perugia

  • Learn about Florence's leather craft with a demonstration

    Included

    Florence

Tuscan Escape

8 Inclusions

Experiences that are included with your trip

  • Food walking tour of Trastevere with Local Guide
  • Visit Casa Segreta (Secret House) located in the picturesque village of Baschi. We will go on a short tour of the azienda agricola along the vineyards and olive orchards before meeting the Polegri Family who will introduce us to the plants and fruits they grow along with the farming techniques used to harvest their produce. Under the veranda overlooking the Tiber Valley we'll enjoy a meal of bruschetta with their homemade extra virgin olive oil, homemade focaccia with homegrown rosemary and vegetables, a risotto or pasta made with vegetables grown on the farm, topped off with a glass of their very own wine and a homemade dessert of the day. (MAKE TRAVEL MATTER® Experience)
  • Visit Terme di Saturnia Thermal Baths
  • Visit local vineyards on two wheels and taste the famed Chianti wine
  • Learn about Florence's leather craft with a demonstration
  • See the Duomo, Basilica Santa Croce, Giotto’s Bell Tower, the Baptistery & Piazza della Signoria on a locally guided walking tour of Florence
  • Guided tour and entry to the tower, the cathedral and the Baptistry.
  • Visit Ostia, the ancient harbour city of Rome and discover the vast archaeological site

6 Free Time Add-Ons

Optional experiences that you can choose from and pay for on your trip

  • Take part in a leather making work-shop in the Headquarters of the Leather Trade, the heart of the city of Florence. With the dedicated assistance & guidance of our Master Craftsman customise your own personal Genuine Leather accessory from scratch while learning about the secrets of this Ancient Tradition.
  • Florentine Steak Dinner
  • Dinner in Montalcino, home to Brunello wines
  • Horseback Riding
  • Hiking through the hills
  • Cooking Class

Where You'll Stay

Learn more about the accommodation available on this trip

  • Borgo di Cortefreda in Tuscany

    Borgo di Cortefreda

    Tuscany, Italy

    Borgo di Cortefreda is a charming village in the heart of the Tuscan countryside with a beautiful view of the Chianti hills. Surrounded by small medieval villages and wineries while being close to the cities of art, Siena and Florence. There is a rustic-chic restaurant and patio that serves Tuscan fare and also an outdoor pool with a poolside bar to enjoy.

    5 nights

  • 6 nights

    All accommodation is included on this trip

    1 night in Hotel, 5 nights in Contiki Special Stay

Frequently Asked Questions

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