4 - 7 night road trip: Wine and art from Siena to Florence - Florence - Up to 70% off | Voyage Privé

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  • Indulging in local wines with a tasting experience that invites you to savour the heart and soul of Tuscany's wine-making tradition.
  • Unwinding in the peaceful embrace of Reggello, a nature-filled paradise nestled among olive groves and cypress trees.
  • The thrill of discovering hidden courtyards and quiet piazzas, where every corner of Florence feels like a new secret to uncover.

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Your itinerary in brief

Set off on a Tuscan adventure that feels like stepping into a living postcard. Begin in Montecarlo di Lucca, where endless vineyards paint the landscape, and every turn reveals a new breathtaking view. Get lost in the dreamlike beauty of Asciano and the Crete Senesi, where rolling, clay-coloured hills stretch as far as the eye can see. Sip your way through unforgettable wine tastings, uncovering the heart of Tuscany in every glass.

 

Wander through the medieval magic of Siena, where time stands still, and let the Renaissance wonders of Florence sweep you off your feet. Unwind in the peaceful embrace of Reggello, surrounded by nature’s tranquillity. And end with a scenic journey through the rolling hills and vineyards of Chianti, where every moment feels like a postcard-perfect snapshot of the Tuscan dream. This is Tuscany as you've always imagined it—beautiful, captivating, and unforgettable.

 

You can choose from three enchanting itineraries, each offering a unique taste of Tuscany:

 

4-night tour:

Day 1: Arrival - Asciano
Day 2: Wine Tasting - Siena
Day 3: Reggello
Day 4: Florence- Reggello
Day 5: Departure

 

5-night tour:

Day 1: Arrival - Montecarlo di Lucca
Day 2: Asciano
Day 3: Wine Tasting - Siena
Day 4: Reggello
Day 5: Florence- Regello
Day 6: Departure

 

7-night tour:

Day 1: Arrival - Montecarlo di Lucca
Day 2: Lucca - Wine Tasting
Day 3: Asciano
Day 4: Wine Tasting - Siena
Day 5: Reggello
Day 6: Florence - Reggello
Day 7: Chianti hills
Day 8: Departure

 

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

Your itinerary in detail

4 night tour:

Day 1: Arrival - Asciano

 

Arrive in Asciano and check in at Hotel Montaperti 4*. Spend the afternoon exploring the Crete Senesi, a surreal landscape of clay hills and moon-like terrain. Recommended stop: the Abbazia di Monte Oliveto Maggiore, a breathtaking abbey surrounded by nature and famous for its Renaissance frescoes in the Grand Cloister. Return to your hotel for a relaxing evening. Tip: Enjoy dinner at a local restaurant in Asciano, where you can taste traditional dishes like "ribollita" or the famous "panzanella."

  • Check-in
  • Explore the stunning Crete Senesi landscapes
  • Visit the Abbey of Monte Oliveto Maggiore and its renowned frescoes
  • Night in Asciano

 


Day 2: Wine Tasting - Siena

 

After breakfast at the hotel, visit a local winery for a wine tasting of iconic Tuscan varieties like Chianti, Brunello di Montalcino, and Nobile di Montepulciano. In the afternoon, head to Siena, a UNESCO World Heritage site known for its medieval charm. Don’t miss Piazza del Campo, the Gothic Cathedral, and the Palazzo Pubblico with its Torre del Mangia, offering panoramic views of the city and surrounding hills. Enjoy a free evening in Siena, with time to explore and dine.

  • Breakfast
  • Savour the best Tuscan wines in a scenic winery
  • Wander the medieval streets of Siena and visit its iconic landmarks
  • Free evening to discover Siena’s vibrant dining scene
  • Night in Asciano

 


Day 3: Reggello

 

After breakfast, check out from the hotel and head to Reggello, where you’ll check in at Hotel Fattoria degli Usignoli 4*, nestled in the heart of nature, surrounded by forests and olive groves. Spend the afternoon relaxing at the hotel, with the opportunity for peaceful walks through the olive groves and vineyards. For art lovers, nearby Reggello’s San Pietro a Cascia church houses the famous “San Giovenale Triptych” by Masaccio. Enjoy a free evening to unwind.

  • Breakfast
  • Transfer to Reggello
  • Check in
  • Relax in the tranquil natural surroundings of Reggello
  • Explore the artistic heritage of Reggello with a visit to the San Pietro a Cascia church
  • Free evening to enjoy the peaceful ambience
  • Night in Reggello

 


Day 4: Florence- Reggello

 

After breakfast, take the train from Sant'Ellero to Florence, the jewel of the Renaissance. Using an audio guide, explore the stunning sights: the Duomo with Brunelleschi’s Dome, Giotto’s Bell Tower, and the Baptistery. Don’t miss Piazza della Signoria and the Uffizi Gallery, home to masterpieces like Botticelli’s “The Birth of Venus” and works by Leonardo and Michelangelo. Lunch will be at a traditional Florentine restaurant (drinks excluded), and in the afternoon, enjoy a leisurely walk across the Ponte Vecchio and through the artisan-filled Oltrarno district. Return to Reggello for the night.

  • Breakfast
  • Train to Florence
  • Audio guide & visit to iconic landmarks
  • Lunch (drinks excluded)
  • Stroll through the picturesque Ponte Vecchio and Oltrarno district
  • Transfer back to Reggello
  • Night in Reggello

 


Day 5: Departure

 

After a final breakfast, check out of the hotel and prepare for departure, taking with you unforgettable memories of Tuscany’s breathtaking landscapes, rich history, and world-class wines.

  • Breakfast
  • Check out
  • Say farewell to Tuscany, taking with you unforgettable memories of art, nature, and culture

 

5 night tour:

Day 1: Arrival - Montecarlo di Lucca

 

Arrive in the enchanting village of Montecarlo di Lucca. Check-in at La Torre Wine Relais 3*, a charming hotel nestled amidst vineyards with breathtaking views of the surrounding Tuscan countryside. In the afternoon, enjoy a delightful wine tasting at a local winery, discovering the rich flavours and aromas of the area’s signature wines, particularly the Montecarlo DOC red and white. Spend the evening relaxing at the relais, immersing yourself in the medieval charm of Montecarlo, renowned for its exceptional wine production.

  • Arrival and check-in at La Torre Wine Relais
  • Wine tasting experience with local Montecarlo DOC wines
  • Relax in the picturesque medieval village of Montecarlo di Lucca
  • Night in Montecarlo di Lucca

 


Day 2: Asciano

 

After a leisurely breakfast, set off for Asciano, nestled in the heart of the breathtaking Crete Senesi. Check in at the charming Hotel Montaperti 4*, your cosy sanctuary amid rolling hills. In the afternoon, immerse yourself in the surreal beauty of the Crete Senesi, where the landscape transforms into otherworldly clay hills and moonlit vistas. Explore the serene Abbazia di Monte Oliveto Maggiore, a hidden gem encased in pristine nature and famed for its stunning Renaissance frescoes. As the day winds down, return to your hotel for a tranquil evening, savouring the peace and beauty of this magical corner of Tuscany.

  • Transfer to Asciano
  • Check-in 
  • Explore the Crete Senesi and visit Monte Oliveto Maggiore Abbey
  • Night in Asciano

 


Day 3: Wine Tasting - Siena

 

Begin the day with breakfast at your hotel before heading to a local vineyard for a wine-tasting experience. Savour some of Tuscany’s most prestigious wines, including Chianti, Brunello di Montalcino, and Nobile di Montepulciano. In the afternoon, visit the medieval gem of Siena, a UNESCO World Heritage site. Must-see sights include the famous Piazza del Campo, the Gothic cathedral, and the Palazzo Pubblico with its Torre del Mangia, offering panoramic views of the city and the surrounding hills. Return to your hotel for the evening.

  • Breakfast
  • Morning wine tasting at a local vineyard
  • Afternoon visit to Siena, exploring Piazza del Campo, the cathedral, and Torre del Mangia
  • Evening at leisure in Siena
  • Night in Asciano

 


Day 4: Reggello

 

After breakfast, check out of your hotel and travel to Reggello, where you’ll check in at the Hotel Fattoria degli Usignoli 4*, a peaceful haven surrounded by nature, forests, and olive groves. Enjoy a day of relaxation in the serene environment, with options for leisurely walks among olive trees and vineyards. For art lovers, a visit to the nearby San Pietro a Cascia church is a must, home to Masaccio’s famous Triptych of San Giovenale.

  • Breakfast
  • Transfer to Reggello
  • Relax in nature, with opportunities for peaceful walks in the countryside
  • Visit the historical Pieve di San Pietro a Cascia, home to a Masaccio masterpiece
  • Night in Reggello

 


Day 5: Florence- Regello

 

After breakfast, take a train from Sant’Ellero to Florence, the heart of the Renaissance. Explore the city's treasures with an audio guide, visiting iconic landmarks such as the Duomo, the Campanile di Giotto, the Baptistery, and the Piazza della Signoria. The highlight of the day is the Uffizi Gallery, where you can admire masterpieces by Botticelli, Leonardo da Vinci, and Michelangelo. Enjoy a traditional Tuscan lunch at a local Florence restaurant (drinks excluded). In the afternoon, stroll along the Ponte Vecchio and wander through the Oltrarno district, famous for its artisan workshops. Return to Reggello for your final night.

  • Breakfast
  • Morning train ride to Florence and exploration with an audio guide
  • Visit the Duomo, the Uffizi Gallery, and Piazza della Signoria
  • Traditional lunch in Florence (drinks excluded)
  • Afternoon stroll across the Ponte Vecchio and the artisan district of Oltrarno
  • Transfer back to Regello
  • Night in Regello

 


Day 6: Departure

 

After breakfast, check out of your hotel and bid farewell to the unforgettable landscapes and rich culture of Tuscany as your tour comes to an end.

  • Breakfast and check-out
  • Departure

 

7 night tour:

Day 1: Arrival - Montecarlo di Lucca

 

Arrive in the enchanting Montecarlo di Lucca and check into La Torre Wine Relais 3*, a charming haven nestled among vineyards with breathtaking views of the Tuscan countryside. Unwind and enjoy the serene historical atmosphere of Montecarlo, a medieval village renowned for its exceptional wines.

  • Check-in
  • Relax and take in the scenic beauty of Montecarlo
  • Night in Montecarlo di Lucca

 


Day 2: Lucca - Wine Tasting

 

After breakfast, head to Lucca, a city steeped in history, and famous for its Renaissance-era walls. Take a leisurely walk along the city’s ancient ramparts for panoramic views. Must-see sites include the Piazza dell’Anfiteatro, Chiesa di San Michele in Foro, and the Cathedral of San Martino. In the afternoon, indulge in a wine-tasting experience at a local vineyard, where you’ll savour the unique flavours of the region’s Montecarlo DOC wines. Return to Montecarlo for a relaxing evening.

  • Breakfast
  • Walk along Lucca’s iconic Renaissance walls
  • Visit Piazza dell’Anfiteatro, San Michele in Foro, and the Cathedral of San Martino
  • Wine tasting of Montecarlo DOC wines
  • Night in Montecarlo di Lucca

 


Day 3: Asciano

 

After breakfast, travel to Asciano, nestled in the heart of the Crete Senesi region. Check-in at Hotel Montaperti 4*, your tranquil base. Spend the afternoon exploring the lunar-like landscapes of the Crete Senesi, characterized by unique clay hills and unspoiled beauty. A visit to the Abbazia di Monte Oliveto Maggiore is a must, renowned for its Renaissance frescoes and serene surroundings. Return to your hotel for a peaceful evening.

  • Breakfast
  • Transfer to Asciano
  • Check-in
  • Explore the striking landscapes of the Crete Senesi
  • Visit the Abbazia di Monte Oliveto Maggiore, with its stunning frescoes
  • Enjoy a relaxing evening at the hotel
  • Night in Asciano

 


Day 4: Wine Tasting - Siena

 

Start your day with a delicious breakfast at the hotel before heading to a local vineyard for a wine-tasting session. Sip on renowned Tuscan wines, including Chianti, Brunello di Montalcino, and Nobile di Montepulciano. In the afternoon, visit Siena, a UNESCO World Heritage site known for its medieval charm. Don’t miss the iconic Piazza del Campo, the Gothic Cathedral, and the Palazzo Pubblico with its Torre del Mangia. Enjoy a free evening in Siena before returning to your hotel.

  • Breakfast
  • Wine tasting of Chianti, Brunello, and Nobile wines
  • Visit Siena’s medieval treasures, including Piazza del Campo and the Gothic Cathedral
  • Night in Asciano

 


Day 5: Reggello

 

After breakfast, check out and transfer to Reggello, where you’ll check in at the serene Hotel Fattoria degli Usignoli 4*, surrounded by lush forests and olive groves. Spend the afternoon relaxing in the peaceful natural surroundings, or take a stroll through nearby olive orchards and vineyards. If you're interested in art, visit the Pieve di San Pietro a Cascia, which houses the famous "Trittico di San Giovenale" by Masaccio. Enjoy a free evening at the hotel.

  • Breakfast
  • Transfer to Reggello
  • Check-in
  • Relax in the peaceful natural setting
  • Night in Reggello

 


Day 6: Florence - Reggello

 

After breakfast, take a scenic train ride to Florence, the cradle of the Renaissance. Explore the city with an audio guide, visiting must-see landmarks such as the Duomo of Santa Maria del Fiore, the Campanile di Giotto, and the Uffizi Gallery, home to masterpieces by Botticelli, Leonardo da Vinci, and Michelangelo. Enjoy a traditional Tuscan lunch at a local restaurant, and spend the afternoon strolling along the Ponte Vecchio and exploring the artisan shops in the Oltrarno district.

  • Breakfast
  • Take a guided tour of Florence’s Renaissance landmarks
  • Visit the Uffizi Gallery and admire works by Botticelli, Michelangelo, and da Vinci
  • Traditional Tuscan lunch at a local restaurant (drinks excluded)
  • Afternoon walk through the historic Ponte Vecchio and Oltrarno
  • Transfer back to Reggello
  • Night in Reggello

 


Day 7: Chianti hills

 

After breakfast, embark on a scenic tour through the Chianti Hills, famous for its picturesque vineyards and rolling landscapes. Stop in charming towns such as Greve in Chianti, Panzano, and Radda in Chianti, each offering a taste of traditional Tuscan life. Enjoy a wine-tasting of the world-renowned Chianti Classico, paired with local specialities like pecorino cheese, olive oil, and cured meats. Return to Reggello for a relaxing evening.

  • Breakfast
  • Tour the scenic Chianti Hills and charming villages
  • Wine tasting in Greve, Panzano, and Radda in Chianti
  • Sample local delicacies like pecorino cheese and Tuscan salumi
  • Night in Reggello

 


Day 8: Departure

 

After a final breakfast, check out and depart, carrying with you the memories of a magical Tuscan adventure.

  • Enjoy a final breakfast
  • Check-out and depart, taking home unforgettable memories of Tuscany

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 https://voyageprive.workplace.com/ 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

You will stay at a handpicked selection of exceptional hotels, each offering a unique experience:

 

  • Montecarlo di Lucca: La Torre Wine Relais 3*
  • Asciano: Hotel Montaperti 4*
  • Reggello: Hotel Fattoria degli Usignoli 4*

 

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

Your dining choices

This is a bed and breakfast stay, with a traditional lunch included in Florence (drinks not included).

Your optional extras

eSIM with 1GB internet

Your optional extras

Enjoy easy access to the internet with a handy 1GB eSIM, bookable at the next stage of the booking process. Install your eSIM before departure in just a few taps.

Note: please check that your phone is eSIM-compatible before departure.

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Your journey to Italy

Flights:

You will be able to choose your airline and flight times when you make your booking. This flight may include one or more stopovers. The stopover may be technical (without a change of aircraft) or transit (with a change of aircraft).

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 destinations

Tuscany

Overflowing with artistic masterpieces, extraordinary architecture and a thrilling history that spans from the Etruscans to the Romans and the Renaissance, Tuscany is a breathtaking holiday destination that promises a never-ending list of things to do, places to see and rolling hills to explore.

 

A holiday to Tuscany comes with many possibilities. The capital of the region, Florence, draws in millions of tourists each year, all of whom come in search of promised romance and charm on the city's narrow, cobbled streets, which have remained unchanged for hundreds of years. Nestled on the banks of the Arno river, this UNESCO World Heritage Site is a prime place to indulge in quality, Tuscan produce, soak up rich culture, and feast on some of the world's finest art.

 

One of Tuscany's other main draws is its verdant countryside, where rustic vineyards, peaceful olive groves and quaint villages can be found in abundance. Here, a stroll in the hills can easily result in a stop in one of Italy's most authentic and sustainable trattorias, where local, seasonal dishes are sure to delight alongside delicious, full-bodied wine.

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

  • Accommodation as per the itinerary (see details)
  • Breakfast included
  • 1x wine tasting during your stay in Asciano (per person, per stay)
  • 1x roundtrip train ticket from Sant'Ellero to Florence (per person, per stay)
  • 1x lunch at a restaurant in Florence (per person, per stay, drinks not included)
  • 1x audio guide for the Florence tour (per person, per stay)
  • 1x wine tasting during your stay in Montecarlo (per person, per stay) for the 5 and 7-night stay
  • Car hire included (Fiat 500 or similar)
  • Offers with flights are ATOL/ABTA protected for your peace of mind

 

The price does not include

  • Optional activities and excursions
  • Vaccines and personal insurance
  • Drinks during meals
  • Tips and personal expenses
  • Laundry
  • Anything not mentioned in "the price includes"

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.

Car hire:

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. 

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