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Tuscan Escape Reunion

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The reunion trip that brings you Tuscan vineyards and Italian food markets, exclusively for 35-45 year old travellers

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  • Duration

    7 days

  • Places

    10 places

  • Meals

    6 Breakfasts, 1 Lunch, 1 Dinner

  • Transport Style


  • 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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    Your Trip Host has designed every trip to be packed with incredible, local experiences, made even more amazing as you share it with other incredible 18-35 year old travelers.

About this trip

Ready for a Tuscan experience trip like no other? In Rome, get acquainted with your squad of awesome 35-45 year old travellers (and maybe swap some sweet memories of Contiki trips gone by!) After a guided foodie tour in Trastevere, we’ll hit the road. Destination: picture-perfect Siena & sun-soaked Tuscan vineyards! Staying at a stunning property in the village of Borgo di Cortefreda, there’ll be plenty of time for day trips to Florence, Lucca, Pisa & all the Tuscan favourites. Over one extraordinary week, drink up as much Renaissance art & architecture as you want (or just stick to your Aperol Spritz!)

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  • Only $200 deposit to book

    Reserve your space now with a deposit of only $200, pay the rest 45 days before departure

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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



  • Horseback Riding

    Free Time Add-On


  • Learn about Florence's leather craft with a demonstration



Tuscan Escape Reunion

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
  • Locally guided tour of Pisa
  • 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

Map & Itinerary

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

DAY 1 - Start 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.

DAY 2 - Rome to Siena via Orvieto


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


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.


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.

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


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?

DAY 4 - Siena with Day Trip to 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!

DAY 5 - Siena with Day Trip to Pisa & Lucca



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 with a local expert. 


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.


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...

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



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!

DAY 7 - End 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?

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

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