Siena
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Self-drive Tuscan Dream
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Siena
Pienza
Radda in Chianti
Natural springs, ancient mills and stunning countryside scenery, Bagno Vignoni
Hand-on cooking
San Gimignano
Florence
Italy

Self-drive Tuscan Dream (Tour code: 17034)

Starts and Ends
in Florence
Travel Periods
until 15 December 27
Experience
Travel Style
Independent Holiday Packages
Explore Tuscany at your own pace on this 7-day self-drive holiday through Chianti, Siena and the beautiful Val d’Orcia. Enjoy scenic drives, medieval villages, local flavours and authentic experiences along the way.

Highlights

Explore Tuscany's most celebrated wine regions, including Chianti, Montalcino and Montepulciano

Stay in the heart of the Siena countryside and Val d'Orcia region

Enjoy a hands-on Tuscan cooking class at a local farm

Discover UNESCO-listed treasures including Siena, San Gimignano and the breathtaking Val d'Orcia.

7 days
From
AUD 1,594
per person, twin share
Travelling with kids? Read more 
All services are subject to availability.

Overview

Experience Tuscany beyond the postcards on this 7-day self-drive journey through Chianti, Siena and the UNESCO-listed Val d'Orcia.

Follow winding country roads between medieval villages, vineyard-covered hills and historic towns, stopping to taste celebrated wines, local cheeses and regional specialties along the way. From the towers of San Gimignano and the grandeur of Siena to the Renaissance beauty of Pienza and the wine towns of Montalcino and Montepulciano, every day reveals a different side of Tuscany's rich history, culture and landscapes. 

Inclusions

3 nights in Siena at Precise Hotel Montaperti ★ ★ ★ ★ or similar
3 nights in the Val d'Orcia at hotel Corsignano ★ ★ ★ ★ or similar.
Daily Breakfast
Private Tuscan Cooking Class at a local farm or winery
Choose 2 included local experiences to personalise your Tuscany journey (full experience list available in the Important Notes).

Day 1 Florence Siena

Collect your rental car in Florence and begin your journey through the heart of Tuscany.

Drive through the famous Chianti wine region, stopping in picturesque villages such as Radda, Castellina or Greve to soak up the local atmosphere. Continue to the Siena countryside, with the option to visit the beautifully preserved medieval village of Monteriggioni along the way.

Overnight in the Siena at Precise Hotel Montaperti 4* or similar.

Florence → Siena
Chianti wine region

Day 2 Siena San Gimignano Siena

After breakfast, drive to San Gimignano (about 45 min). This UNESCO-listed town preserves the atmosphere of a 14th-century village and is famous for its medieval towers and the Piazza del Duomo with the “Devil’s Tower” and frescoed cathedral.

Return to Siena. Explore the historic centre, inscribed by UNESCO for its intact medieval urban fabric and masterpieces like Piazza del Campo (home of the Palio) and the outside of the Duomo decorated by Pisano, Donatello and Michelangelo. 

Today, guests may choose from the following included experience options:

  • Siena Cathedral admission
  • Pastries & Cantuccini tasting in Siena

Guests may select up to 2 included experiences throughout the itinerary. 

Overnight in the Siena at Precise Hotel Montaperti 4* or similar.

Breakfast

Day 3 Siena Crete Senesi Siena

Discover the stunning landscapes of the Crete Senesi, where rolling hills, cypress-lined roads and charming villages create some of Tuscany's most iconic scenery. Stop in Asciano for a stroll through its historic centre before continuing to the remarkable Abbey of San Galgano, a roofless Gothic masterpiece set in the heart of the countryside. Nearby, visit the Chapel of Montesiepi, home to Tuscany's legendary Sword in the Stone.

Today, guests may choose from the following included experience option:

  • San Galgano Abbey admission

Guests may select up to 2 included experiences throughout the itinerary. 

For those looking to enhance the day, optional experiences such as wine tasting, e-bike tour or a traditional Tuscan lunch can be added for a supplement.

Overnight in the Siena at Precise Hotel Montaperti 4* or similar.

Breakfast

Day 4 Siena Pienza & Bagno Vignoni Val d'Orcia

Leave Siena behind and travel into the breathtaking Val d'Orcia region.

Visit Renaissance Pienza, redesigned by Pope Pius II in the 15th century as the first “ideal Renaissance town” and recognised by UNESCO. Wander the piazza around the Cathedral and Palazzo Piccolomini and sample Pecorino di Pienza, celebrated during an annual festival.

Travel to the picturesque village of Bagno Vignoni, renowned for its historic thermal waters and beautiful central square. Take time to explore the village and enjoy a leisurely walk through the nearby Parco dei Mulini, where natural springs, ancient mills and stunning countryside scenery create a truly memorable setting.

Today, guests may choose from the following included experience options:

  • Pecorino cheese tasting in Pienza

Guests may select up to 2 included experiences throughout the itinerary. 

For those looking to enhance the day, optional experiences such as a wine tasting or a relaxing spa experience can be added for a supplement. 

Overnight in the Val d'Orcia at hotel Corsignano 4* or similar.

Breakfast

Day 5 Val d'Orcia Montalcino & Montepulciano Val d'Orcia

Today, discover two of Tuscany's most famous wine towns.

Start in Montalcino, surrounded by rolling vineyards and renowned for its world-famous Brunello wine.

Continue through the beautiful Tuscan countryside to the peaceful Abbey of Sant'Antimo before arriving in Montepulciano, where elegant piazzas, historic streets and centuries-old wine cellars invite you to explore at your own pace. 

Today, guests may choose from the following included experience options:

  • Wine & Food Tasting in Montepulciano

Guests may select up to 2 included experiences throughout the itinerary.

For those looking to enhance the day, optional experiences such as a guided cellar visit or a gourmet regional lunch can be added for a supplement. 

Overnight in the Val d'Orcia at hotel Corsignano 4* or similar.

Breakfast

Day 6 Val d'Orcia Castiglione del Lago Val d'Orcia

Today is all about discovering Tuscany at your own pace.

Drive through the rolling landscapes of Val d'Orcia, stopping in charming villages such as San Quirico d'Orcia and Castiglione d'Orcia before reaching the beautiful lakeside town of Castiglione del Lago. Wander through historic streets, admire sweeping countryside views and enjoy the relaxed atmosphere of one of central Italy's most picturesque regions.

For those looking to enhance the day, optional experiences such as a Lake Trasimeno boat cruise, wine tasting, e-bike tour or farm-to-table dining experience can be added for a supplement.

Overnight in the Val d'Orcia at hotel Corsignano 4* or similar.

Breakfast

Day 7 Val d'Orcia Florence

Depart Val d’Orcia and drive back to Florence (approx. 2 h).

Consider stopping at Murlo or Buonconvento for last glimpses of rural Tuscany before dropping off the car rental in Florence. End of our services.

Breakfast

Additional information

Official language
Italian
Local currency
EURO

FROM price reflects the lowest available price within the advertised travel period (e.g. April to October). Pricing varies depending on travel dates, availability and demand, and may not be available on all departures. Higher pricing applies during peak and shoulder periods. Final pricing is confirmed at the time of enquiry or booking. Please refer to Pricing & Price Conditions for full details, including inclusions, exclusions and other conditions.

Choose 2 included local experiences: Siena Cathedral admission, Pastries & Cantuccini tasting in Siena, San Galgano Abbey admission, Pecorino cheese tasting in Pienza, Wine & Food tasting in Montepulciano. Experience selections are subject to availability and must be requested at the time of booking.

Car Rental Includes: A 7-day intermediate automatic rental car (MG ZS or similar), featuring automatic transmission, air conditioning, seating for up to five passengers and space for three bags. The rental includes unlimited mileage, SCDW (Super Collision Damage Waiver), STP (Theft Protection), airport surcharge, taxes and applicable fees, giving you the freedom to explore Tuscany at your own pace. Vehicle upgrades are available for a supplement, subject to availability at the time of booking.

FAQs

Who are Entire Travel Group?

Welcome to Entire Travel Group. We offer exceptional travel experiences across our extensive range of Entire Holiday Packages, Entire Group Journeys, Entire Rail Journeys, and Entire Cruise Journeys. With our industry-leading Peace of Mind Booking Plan, you can Book Now with flexibility and confidence.

Entire Travel Group is celebrating over 50 years of passionately delivering unique and memorable travel experiences. We are an Australian, family-owned, award-winning business with a friendly team ready to match your expectations to the perfect holiday experience.

Entire Travel Group used to be known by the individual brands shown in the footer of the website. The company has not changed, but we have amalgamated under one brand - Entire Travel Group.

For more details please visit - About Us | Entire Travel Group

Is Entire Travel Group Australian owned and operated?

Entire Travel Group is proudly Australian family owned and operated and as it stands today represents 50 years of experience, progress, and evolution. We proudly support the community with our long-term commitment to many important charity organisations. We were awarded the best operator in our class at the most recent National Travel Industry Awards.

Is Entire Travel Group industry accredited?

Entire Travel Group is both ATIA and CATO Accredited. The Council of Australian Tour Operators (CATO) is the trade association representing the land supply sector of the Australian Travel Industry.

Does Entire Travel Group have industry awards?

Entire Travel Group was honoured at the 2023 National Travel Industry Awards with Most Oustanding Wholesaler - Product / Service.

As our team works tirelessly to deliver exceptional holiday experiences, it was exciting to have this acknowledged with the highest recognition. The award is also a testament to the quality of our partners around the globe, and we take this opportunity to thank them for their tremendous support of our customers.

Are the Entire Travel Group holiday packages exclusive?

In some cases, we are the sole representative in Australia for the overseas travel operator. In other circumstances the product developed has been exclusively built for Entire Travel Group and can’t be found elsewhere.

What’s unique about Entire Travel Group Holiday Packages?

  • They are not group tours with set departures - they are pre-designed, purpose built, independent holiday packages full of unique and memorable experiences.
  • Our holiday packages have been exclusively built for us in collaboration with our handpicked suppliers, who also offer full on-ground support for the clients.
  • We are offering unique travel experiences which cannot be found elsewhere.
  • Many packages include our “Freedom of Choice” options which allow you to tailor the holiday experience. Like a sommelier matching wine to a meal, we have used our experience to carefully select and offer the right experiences in each location.
  • They include our Peace of Mind Booking Plan.
  • A wide selection of our packages are compliant with the World Travel & Tourism Council (WTTC) Covid Safe Travels.

Our motto for Independent Holiday Packages is start your holiday when and with who you want!

Our Independent Holiday Packages are NOT group tours with set departure dates. Group Tours have specific set departure dates, and of course, you are travelling with unknown passengers in a coach. These tours are great for certain travellers and there are many reputable tour operators providing a wide range of options around the world.

At Entire Travel Group, our focus is Independent Holiday Packages. Available daily, they are pre-designed, purpose built, packaged itineraries full of memorable experiences delivered by our hand-picked local partners.

Our holidays suit every demographic, from couples to singles, to retirees to families and everyone else in between.

Why travel with Entire Travel Group?

Of Entire Travel Group's attributes, we have settled on "When Experience Matters" as the quality we believe adds the most value to our customers. We have the experience to ensure your itinerary makes the dream holiday possible. Our continually enhanced technology allows our team to provide a quality customer service experience, and our partnerships with outstanding operators ensure we are confident of the on-ground experience for our customers.

For more details please visit - About Us | Entire Travel Group

How does the Peace of Mind Booking Plan work?

Our Peace of Mind Booking Plan allows you to book with confidence in the new international travel environment. With low deposits, a cooling off period and a flexibility period where you can cancel and rebook later, we really do have you covered.

For more details please visit - Peace of Mind Booking Plan | Entire Travel Group

Is there a cooling-off period?

Look for packages with our Peace of Mind Booking Plan logo on the website.

  • We understand that occasionally plans may change, so we give you the confidence to proceed with a cooling off period.
  • You may cancel for any reason within 7 days, where you will receive a 100% refund of your $100 per person deposit.

For more details please visit - Peace of Mind Booking Plan | Entire Travel Group

What is Freedom of Choice?

At Entire Travel Group we understand that our customers have their own personal tastes and interests - so throughout our packages look for “Freedom of Choice” which gives you the ability to tailor your holiday from the various experiences offered on selected days. Like a sommelier matching wine to a meal, we have used our experience to carefully select and offer the right experiences in each location.

The Freedom of Choice options are included in the package price, and the price remains the same regardless of the choice you make on each day.

Our Freedom of Choice program offers flexibility, by allowing you to choose from different options on pre-selected days in the itinerary.

  • Our per person price includes one tour on each Freedom of Choice day in the itinerary.
  • The price of the package remains the same regardless of the choice you make on each day.

For more details please visit - Freedom of Choice | Entire Travel Group

What is Book Now?

Book Now offers you the ability to make a reservation on our website for Holiday Packages that include our Peace of Mind Booking Plan. But it’s not just a static offer – you have complete flexibility from travel dates, passenger numbers, single supplements, room upgrades, optional extras, flexible booking terms and more.

  • Our team will contact our overseas suppliers and confirm all arrangements.
  • A Confirmation from our reservation system will be sent in the coming days.
  • The Booking Number on this confirmation supersedes the website reference.

How secure is the Entire Travel Group's on-line payment portal?

  • Entire Travel Group have partnered with TravelPay to ensure secure on-line credit card payments.
  • TravelPay is a level 1 PCI DSS compliant, which gives you peace of mind that your payment card data is in safe hands.
  • Entire Travel Group does not store any credit card information.

For more details please visit - Security and Compliance - TravelPay

What forms of payment can be used at Entire Travel Group?

  • To confirm a booking using our on-line Book Now process, a credit card must be used to pay the refundable deposit.
  • For additional payments on the booking, Entire Travel Group supports bank transfer, credit card, TravelPay B2B, PaymentGate.
  • For further details please visit our Payments page.

Can you book my international airfares?

On some Islands Holiday Packages (e.g. Fiji), it is practical to include flights, so where we have done this it is indicated by the plane icon.

However, on the majority of our Holiday Packages, we do not include international flights.

We found that many customers may prefer to:

  • Travel on a specific airline of their choice
  • Have the flexibility to book flights with Frequent Flyer points
  • Select flight dates that may be different to our Holiday Package start/end dates
  • Use a Travel Credit already held with the airline
  • Use their travel agent for this service

We are able to assist with flights on any Holiday Package, so please just notify us during the Book Now process or contact our team.

Should I take travel insurance?

Travel insurance is strongly recommended. During the Book Now process please confirm you require assistance, and our team will be in contact with you.

What should I do before travelling?

Before you travel it is your responsibility to ensure you have the appropriate documentation including visas. If you are travelling on a passport other than Australian or New Zealand, you will require a permit to re-enter Australia. It is your responsibility as the traveller and/or travel booker to meet all government entry requirements.

For more information please visit - Before you travel | Entire Travel Group

How does a Travel Agent make a booking?

Please visit the Entire Travel Group's Agent Portal. We are here to support our industry partners with a range of informative updates, marketing collateral for campaigns and a reward & recognition program.

How do I start a Booking?

  • On any page that has Book Now simply follow the booking process.
  • You must select the Travel Agent tick box and provide correct details.
  • To confirm a booking only the refundable deposit is required.
  • An agency credit card must be used for this initial payment.

How do I contact Entire Travel Group?

For more information please visit - Contact us | Entire Travel Group

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