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9-Day Umbria and Tuscany Foodie Escape

Customisable Itinerary
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Trip Overview

Take a trip to one of the most charming regions of Italy. This 9-day itinerary goes through the rolling hills of Tuscany is truly a fairytale holiday!

Experience the medieval magic of ancient Tuscan towns, embark on winery tours set in idyllic countryside settings and stay in quaint farmhouses where you will be fully immersed in the Italian village lifestyle.

This Italy trip includes authentic Tuscany food tour, tastings of some of the best wines in the world and unique experiences such as truffle hunting in Certaldo or harvesting olives in Montepulciano!
Food & Drink
Sightseeing
Culture & Arts

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Itinerary

Day 1

Arrival in Rome

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Arrival in Rome

Welcome to Italy! Upon your arrival at Rome Fiumicino Airport, you will pick up your rental car and embark on your 9-day adventure. Depart for Civita di Bagnoregio, a delightful rural town built on a tufa rock. After lunch at a local winery, you will drive to Orvieto, a stunning Etruscan city, where you can explore its cobbled streets and medieval piazzas. After, head towards Perugia where you will spend the night.

  • accommodation icon
    Accommodation

    Castello di Monterone

  • activities icon
    Activities

    Local Olive Mill and Winery

    Orvieto

  • transportations icon
    Transportations

    Rental Car from Rome Fiumicino Airport to Civita di Bagnoregio

    Rental Car from Orvieto to Perugia

  • meals icon
    Meals

    Lunch

  • destination icon
    Destinations

    Civita di Bagnoregio

    Orvieto

    Perugia

Day 2

Vineyards and Medieval Towns

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Vineyards and Medieval Towns

After enjoying breakfast this morning, you will drive to the wine and oil museum located in Torgiano. Here you will learn about the importance of these two items in Italian culture and history. After, you will embark on an exciting winery tour through a panoramic vineyard to discover Sagrantino and Montefalco wines. After, visit the charming town of Assissi, named after one of Italy's patron saints, before heading back to your hotel.

  • accommodation icon
    Accommodation

    Castello di Monterone

  • activities icon
    Activities

    Wine and Oil MuseumOptional Activity

    Wine Tour in Montefalco

    Assisi

  • transportations icon
    Transportations

    Rental Car from Castello di Monterone to Wine Museum

    Rental Car from Wine Museum to Montefalco

    Rental Car from Montefalco to Assisi

    Rental Car from Assisi to Castello di Monterone

  • meals icon
    Meals

    Breakfast and lunch

  • destination icon
    Destinations

    Perugia

    Torgiano

    Montefalco

    Assisi

Day 3

Bevagna and Spello

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Bevagna and Spello

Begin your day heading towards Bevagna with your guide. This pretty village has been a settlement since the time of the Ancient Romans, with fascinating architecture still standing from that time. After, drive towards an olive mill to learn about olive oil production in Umbria where you will enjoy a light lunch. In the afternoon, visit Spello, another delightful medieval Umbrian town.

  • accommodation icon
    Accommodation

    Castello di Monterone

  • activities icon
    Activities

    BevagnaOptional Activity

    Umbria Olive Mill

    Spello

  • transportations icon
    Transportations

    Rental Car from Castello di Monterone to Bevagna

    Rental Car from Bevagna to Umbria

    Rental Car from Umbria to Spello

    Rental Car from Spello to Castello di Monterone

  • meals icon
    Meals

    Breakfast and lunch

  • destination icon
    Destinations

    Perugia

    Bevagna

    Spello

Day 4

Chianciano and Montepulciano

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Chianciano and Montepulciano

This morning you will leave Perugia behind as you set off towards the Chianciano area, known for its superb wines and olive oil production. Visit a family olive mill in the region to learn more about this process and take part in the olive harvest! After, you'll drive to Montepulciano for a visit to this beautiful medieval town and a tour of a local winery here. in the afternoon you will check in to a charming farmhouse where you will get a chance to immerse yourself in the Tuscany experience.

  • accommodation icon
    Accommodation

    Cretaiole

  • activities icon
    Activities

    Olive Mill in Chianciano

    Montepulciano City and Winery Tour

  • transportations icon
    Transportations

    Rental Car from Castello di Monterone to Chianciano

    Rental Car from Chianciano to Montepulciano

    Rental Car from Montepulciano to Cretaiole

  • meals icon
    Meals

    Breakfast and lunch

  • destination icon
    Destinations

    Perugia

    Chianciano Terme

    Montepulciano

    Pienza

Day 5

Enchanting Tuscany Food Tour

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Enchanting Tuscany Food Tour

Wake up in your charming farmhouse and drive to the pretty town of Pienza, which was converted to an ideal Renaissance town in 1459. Your Tuscany food tour starts here! Visit a dairy farm and get to sample the famous Pecorino cheese from here. After lunch, make your way to Bagno Vignoni and San Quirico d'Orcia to get an enchanting glimpse of Tuscany. The Val d’Orcia is famous all over the world and boasts of countless locations of great historical and artistic value.

  • accommodation icon
    Accommodation

    Cretaiole

  • activities icon
    Activities

    Pienza

    Pienza Dairy Farm

    Val d'Orcia

  • transportations icon
    Transportations

    Rental Car from Cretaiole to Pienza

    Rental Car from Pienza to Bagno Vignoni

    Rental Car from Val d'Orcia to Cretaiole

  • meals icon
    Meals

    Breakfast and lunch

  • destination icon
    Destinations

    Pienza

    Tuscany

Day 6

Olive Mill in Montisi and Siena City Tour

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Olive Mill in Montisi and Siena City Tour

Check out of your accommodation in Montepulciano to head to your next destination: the beautiful village of Montisi, where you'll visit a local olive mill and learn more about how olives are pressed for oil. After, you'll spend some time in the lively city of Siena, a jewel of central Italy and an essential stop on any Tuscan itinerary. In the afternoon, head to your next agriturismo in the San Gimignano area.

  • accommodation icon
    Accommodation

    Farmhouse Villa Palagetto

  • activities icon
    Activities

    Siena Cathedral

    Half-Day Tour to Siena and San Gimignano

  • transportations icon
    Transportations

    Rental Car from Cretaiole to Siena

    Rental Car from Siena to Farmhouse Villa Palagetto

  • meals icon
    Meals

    Breakfast

  • destination icon
    Destinations

    Pienza

    Siena

    San Gimignano

Day 7

Lucca Farm and Pisa

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Lucca Farm and Pisa

Begin your day leisurely driving to Lucca, stopping at a local winery and farm that produces evo oil. You will visit the preservation cellars and the oil and wine-making rooms at the farm as well as a light lunch matched with 4 wines. After lunch, go on a 2-hour walking tour of Lucca's historic centre. Then, continue for an afternoon visit of Pisa, where you can stroll around the famous Miracle square and visit the leaning tower.

  • accommodation icon
    Accommodation

    Farmhouse Villa Palagetto

  • activities icon
    Activities

    Tuscany Farm and Winery

    Lucca

    Leaning Tower of Pisa

    Pisa Baptistery

  • transportations icon
    Transportations

    Rental Car from Siena to Lucca

    Rental Car from Lucca to Pisa

    Rental Car from Pisa to Farmhouse Villa Palagetto

  • meals icon
    Meals

    Breakfast and lunch

  • destination icon
    Destinations

    San Gimignano

    Lucca

    Pisa

Day 8

Truffle Hunting and The Tuscan Town of San Gimignano

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Truffle Hunting and The Tuscan Town of San Gimignano

Your day today will start with an adventure to the small medieval town of Certaldo, located in the heart of Tuscany. With your guide, you will embark on an exciting truffle hunting adventure, which you will get used in a meal for lunch later! After eating, you will have the afternoon and evening to explore the Tuscan hill town of San Gimignano, which is a charming place to wander around during the sunset hours.

  • accommodation icon
    Accommodation

    Farmhouse Villa Palagetto

  • activities icon
    Activities

    Certaldo Truffle Hunting

    San Gimignano

  • transportations icon
    Transportations

    Rental Car from Farmhouse Villa Palagetto to Certaldo

    Rental Car from Certaldo to San Gimignano

    Rental Car from San Gimignano to Farmhouse Villa Palagetto

  • meals icon
    Meals

    Breakfast and lunch

  • destination icon
    Destinations

    San Gimignano

    Certaldo

Day 9

Goodbye Italy!

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Goodbye Italy!

After one last breakfast at your farmhouse, it is time to leave Italy. Drive back to the airport in Rome where you will drop off your rental car and catch your departing flight home.

  • transportations icon
    Transportations

    Rental Car from Farmhouse Villa Palagetto to Rome Fiumicino Airport

  • meals icon
    Meals

    Breakfast

  • destination icon
    Destinations

    San Gimignano

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What’s included?

  • 8 nights accommodation
  • 17 activities
  • 8 breakfasts and 7 lunches
  • Ground transportation
  • Licensed English speaking guides

What’s not included?

  • Airport transfer
  • Alcohol beverages
  • Domestic flights
  • Entrance fees
  • Entry visas / airport departure tax
  • Gratuities
  • International flights
  • Laundry
  • Personal expenses
  • Travel insurance
  • Trekking permits
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