4 nights: Tuscan road trip - Siena - Up to 70% off | Voyage Privé

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  • Exploring the picturesque vineyards of Greve in Chianti, taking in the rolling hills and tasting the region’s finest wines at local estates.
  • Wandering through the medieval streets of Monteriggioni and San Gimignano, admiring their ancient towers and immersing in centuries of history.
  • Discovering the rich winemaking traditions of Montalcino and Montepulciano, sampling the renowned Brunello and Vino Nobile in breathtaking, hilltop vineyards.

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Carefully selected by our experts especially for you

Your itinerary in brief

Embark on a captivating 5-day journey through Tuscany, beginning with the charming town of Greve in Chianti, known as the gateway to the renowned Chianti wine region. Explore its vibrant central square and enjoy a traditional market experience before continuing to Siena, a city steeped in medieval beauty and rich history. Wander through its labyrinthine streets, visit iconic landmarks like the Torre del Mangia and Piazza del Campo, and indulge in local sweet treats. The next day, visit the medieval splendour of Monteriggioni, followed by the UNESCO-listed town of San Gimignano, with its impressive towers and artisanal delights.

 

The road trip continues to the scenic towns of Montalcino and Montepulciano, famous for their world-class wines, including Brunello di Montalcino and Vino Nobile di Montepulciano. Stroll through picturesque streets surrounded by lush vineyards and enjoy wine tastings at historic cellars, where age-old winemaking traditions are preserved. Throughout your journey, savour the beauty of Tuscany’s rolling hills, centuries-old towns, and exquisite wines, all while staying in the peaceful surroundings of Asciano.

 

Your itinerary: 

 

  • Day 1: Arrival - Greve in Chianti – Siena
  • Day 2: Monteriggioni – San Gimignano
  • Day 3: Montalcino – Montepulciano
  • Day 4: Siena
  • Day 5: Departure

 

Please note: your itinerary may have minor adjustments, but your overall trip experience will remain the same.

Your itinerary in detail

Day 1: GREVE IN CHIANTI - SIENA

DAY 1: GREVE IN CHIANTI – SIENA

 

  • Touch down at Pisa International Airport (PSA) or Florence Peretola Airport (FLR). 
  • Begin exploring the Tuscan countryside in Greve in Chianti. This quaint town is known as the gateway to Chianti. Its peaceful charm and vibrant central square host a traditional market every Saturday, offering an authentic taste of local culture.
  • Continue through rolling hills towards a city that simply oozes atmosphere and authenticity. Siena, with its stunning medieval beauty awaits discovery.

 

Overnight stay at Hotel Montaperti in Asciano or Hotel Le Colline in San Gimignano (or similar).

Please note: Pisa International Airport (PSA) is situated 57 miles from Asciano, while Florence's Peretola Airport (FLR) is 28 miles distant.

 

 

DAY 2: MONTERIGGIONI – SAN GIMIGNANO

 

  • Discover one of Italy's best-preserved medieval towns.

  • Surrounded by a 600-metre-long wall, Monteriggioni reveals narrow streets lined with stone houses. Enjoy immersing yourself in the unique atmosphere of the 13th century.
  • Travel to San Gimignano, a UNESCO World Heritage Site, famed for its striking medieval towers and preserved architecture. Stroll through cobbled streets, visit artisan shops, and savour a tasting of award-winning gelato, crafted by a local champion.

 

Overnight stay at Hotel Montaperti in Asciano or Hotel Le Colline in San Gimignano (or similar).

 

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Day 3: MONTALCINO - MONTEPULCIANO

DAY 3 : MONTALCINO – MONTEPULCIANO

 

  • Breakfast at your hotel before embarking on a scenic drive to Montalcino, a town renowned for its prestigious Brunello di Montalcino wine.
  • Explore the charming town with its roots dating back to the Etruscan period, shaped by centuries of rivalry between Florence and Siena.
  • Wander through picturesque streets surrounded by lush vineyards, offering an idyllic backdrop to discover Montalcino’s fascinating past and rich winemaking tradition.

  • Continue your journey to Montepulciano, perched atop a high tufa plateau, known for its exceptional Vino Nobile di Montepulciano.
  • Stroll through this enchanting hilltop town, renowned for its Renaissance architecture and stunning panoramic views.
  • Indulge in a wine tasting at a historic cellar (included activity), where you can sample the Vino Nobile crafted using age-old winemaking techniques.

 

Overnight stay at Hotel Montaperti in Asciano or Hotel Le Colline in San Gimignano (or similar).

 

DAY 4: SIENA

 

  • Enjoy breakfast before immersing yourself in the timeless beauty of Siena, a stunning medieval city exuding the elegance of the Gothic era.
  • Wander through its labyrinthine streets, flanked by narrow, red-brown palaces made from local Sienese clay, evoking an atmosphere where history seems to stand still.
  • Visit the historic centre, spread across three hills in the shape of a star, home to iconic landmarks such as the Palazzo Pubblico and the Torre del Mangia, a tower offering sweeping panoramic views of the renowned Piazza del Campo.
  • Take in the views from the Torre del Mangia, standing 88 metres tall above the city, and admire the famed Piazza del Campo, one of Italy's most beautiful squares.
  • Treat yourself to a tasting of traditional local sweets at a charming bakery (included activity), sampling cantucci (crunchy almond biscuits) and ricciarelli (soft almond cookies), crafted for generations. 

 

Overnight stay at Hotel Montaperti in Asciano or Hotel Le Colline in San Gimignano (or similar).

 

DAY 5: DEPARTURE

 

  • Enjoy a leisurely breakfast at the hotel before preparing for your departure from either Pisa International Airport (PSA) or Florence Peretola Airport (FLR). 

 

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Important information about your tour and visits:

The hotels, which comply with local standards, are indicative and may be changed locally for hotels of a similar category. The itinerary is subject to changes due to compelling reasons such as delayed flights, weather conditions or other cases of force majeure. The order of visits is also subject to change without affecting the overall experience of the itinerary.

Your hotels

Hand-picked just for you

Maximum room capacity

Enjoy a stay in a Standard Room in the following carefully selected luxury hotels (or similar):

 

  • Asciano: Hotel Montaperti (or similar)
  • San Gimignano: Hotel Le Colline (or similar)


 
If the hotels listed above are unavailable, you will be provided with comfortable accommodation in similar hotels. Local standards apply. 

Your dining choices

Your journey to Tuscany

Flights:

You will be able to choose your airline and flight times when you make your booking, in either Economy, Premium, or Business class, depending on the destination and carrier. This flight may include one or more stopovers.

 

Please review your flight options carefully as departure and arrival airports may differ, in order to offer the best price. 

Luggage information

Luggage, meals and other services on board may be subject to an additional fee on certain airlines. It is possible to view details of luggage allowances when you choose your flights at the next stage of the booking process. If luggage is not included with your flight, please go to the airline's website before your departure to purchase your luggage for an additional fee.

For domestic flights, airlines do not always offer the option of reserving luggage. In this case, you will need to pay for it at the airport counter.

You will receive all the information you need to check in for your flights after you have made your reservation.

Your destination

Tuscany

Overflowing with artistic treasures, Tuscany is a timeless haven where ancient history meets rolling landscapes. From Etruscan origins to Roman marvels and Renaissance brilliance, this region is a journey through the ages. Beyond its celebrated cities, Tuscany invites you to explore serene vineyards, sun-dappled olive groves, and quaint villages that define its rustic charm.

 

Must-sees:

 

  • Florence's Oltrarno District: Venture beyond the Arno River to discover artisan workshops, hidden gardens, and authentic trattorias.
  • San Gimignano’s Towers: A medieval skyline framed by Tuscany’s picturesque countryside.
  • Etruscan Legacy in Volterra: Wander ancient walls and explore artefacts in the Guarnacci Etruscan Museum.

 

Culinary culture:


Tuscany's culinary heritage is as rich as its landscapes. Indulge in seasonal Tuscan produce, from creamy pecorino cheeses to fragrant white truffles. Pair these delicacies with Chianti or Brunello di Montalcino wines from the region's renowned vineyards. Don’t miss rustic panzanella salads or ribollita, a hearty vegetable soup traditionally prepared with stale bread. For a sweeter note, try cantucci biscuits dipped in local Vin Santo.

 

Dive deeper:


Beyond Florence and Siena, Tuscany’s smaller towns reveal unique stories. In Pienza, you’ll find a Renaissance utopia shaped by Pope Pius II’s vision, while the Carrara marble quarries offer a glimpse into the artistry that crafted Michelangelo’s David. For a different perspective, take a cycling tour through the Val d’Orcia, a UNESCO World Heritage Site famed for its cinematic beauty.

 

Good to know:


The local currency is the euro (€), and Tuscany enjoys a mild Mediterranean climate, with spring and autumn being the ideal seasons to visit. Regional trains and buses connect towns efficiently, but renting a car offers the best flexibility for exploring the countryside’s hidden gems.

Weather

Jan
min : 2°C max : 9°C
Feb
min : 3°C max : 11°C
Mar
min : 5°C max : 14°C
Apr
min : 8°C max : 19°C
May
min : 12°C max : 23°C
Jun
min : 15°C max : 27°C
Jul
min : 18°C max : 30°C
Aug
min : 17°C max : 30°C
Sep
min : 15°C max : 26°C
Oct
min : 11°C max : 20°C
Nov
min : 7°C max : 14°C
Dec
min : 4°C max : 11°C

In more detail

Please find practical information about your trip:
This tour is not accessible to people with reduced mobility.

Pets are not permitted.
Your stay may be subject to an additional city or tourist tax payable directly to the hotel, which is not included in our nightly rate. Please check with hotel directly for further information.

Rates and times are indicative and are subject to change. Some facilities/services are subject to a surcharge, payable locally.


General terms and conditions of sale apply. 

The price includes:

 

  • 4 x nights accommodation in classic double rooms in the Asciano or San Gimignano area, including buffet breakfast
  • Daily use of outdoor pool of the hotel (open from 01/05 to 30/09/2025, weather permitting)
  • 1 x wine tasting in an ancient cellar in Montepulciano
  • 1 x ice cream tasting in San Gimignano
  • 1 x tasting of traditional biscuits at a typical bakery in Siena

 

The price does not include:

  • Car hire from Pisa International Airport (PSA) or Florence Peretola Airport (FLR) for the duration of the stay
  • Lunches and dinners
  • Beverages
  • Entrance fees to museums, cathedrals, castles, and other attractions
  • City tax, payable locally per person per day
  • Gratuities
  • Optional activity costs
  • Any items not specified in the 'The price includes' section.

A warm welcome

We offer you a warm welcome to your holiday destination, and our partners are committed to ensuring your well-being.

If booking as a solo traveller, room type is not guaranteed. You may be placed in a single, double or twin room, based on availability.

You may be asked to provide a credit/debit card deposit on arrival to cover any purchases made at the hotel.

Although we endeavour to provide up-to-date information, we cannot guarantee that all hotel facilities and services will be available during your stay, especially when travelling out of the main holiday periods.

Star rating standards may differ to that of the UK, depending on the country of travel.

The location shown on our map is to be used as a guide only and the actual location of the property may differ.

Your contact details may be passed on to the hotel so that they can make contact with you to discuss your booking in advance of your arrival.

Your contract

If you book a package which includes flights, your contract will be with Voyage Privé. The air holiday package(s) shown are ATOL protected by the Civil Aviation Authority. Our ATOL number is 10170.

If you book a package which does not include flights, then ATOL protection does not apply. Your contract will be with the provider of the accommodation and not Voyage Privé. Voyage Privé acts only as agent for the accommodation provider.

Please read our booking conditions before confirming your holiday. 

The Voyage Privé Promise

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  • Exclusive perks and discounts of up to 70% off
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