Tuscany and Umbria

April 6, 2026 -
April 10, 2026

Experience the road with total peace of mind – join an intimate group guided by a professional, with luxury cars and full-service support. Every detail is taken care of, so you can simply live the moment

Luxury journey of Southern Tuscany and Umbria – An Unforgettable Experience

Join us for an exclusive journey through Tuscany and Umbria where luxury driving meets rich culture and breathtaking scenery.

Cruise through historic towns and discover hidden gems off the beaten path, and unwind in handpicked luxury hotels.

This experience combines stunning landscapes, world-class wine tastings, and unforgettable culinary moments.

Each day brings a new region, from charming wine villages to wild nature, all curated for the ultimate Italian adventure.

dividng the page subject

THE ROUTE

· Truffles, Towers & the Tuscan Horizon

Your luxury journey begins in Florence with a breathtaking view from Piazzale Michelangelo. From there, drive into the Tuscan hills to San Miniato for a truffle hunt with local experts and their dogs, followed by a rustic truffle lunch.
In the afternoon, explore the medieval charm of San Gimignano, then head to your countryside hotel for a relaxed evening and gourmet dinner.

 

 

 

Key Roads & Highlights:

  • Florence from Piazzale Michelangelo

  • Truffle hunting in San Miniato

  • Lunch with fresh truffles

  • Walk through San Gimignano

  • Key Road: SP40

florance cathedreal

DAY

1

· Truffles, Towers & the Tuscan Horizon

Your luxury journey begins in Florence with a breathtaking view from Piazzale Michelangelo. From there, drive into the Tuscan hills to San Miniato for a truffle hunt with local experts and their dogs, followed by a rustic truffle lunch.
In the afternoon, explore the medieval charm of San Gimignano, then head to your countryside hotel for a relaxed evening and gourmet dinner.

 

 

 

Key Roads & Highlights:

  • Florence from Piazzale Michelangelo

  • Truffle hunting in San Miniato

  • Lunch with fresh truffles

  • Walk through San Gimignano

  • Key Road: SP40

florance cathedreal

DAY

1

· Wine Roads & Stone Towns: Through Chianti and Medieval Hilltops

After breakfast, the journey continues along the scenic Chianti roads to the picturesque town of Greve in Chianti. Enjoy a coffee and pastry at a local pasticceria before heading to a top local winery for a guided tour and a refined lunch paired with Chianti Classico wines.
In the afternoon, explore the charming walled village of Monteriggioni, then make your way to the hotel for a relaxing evening.

Key Roads & Highlights:

  • Drive through the Chianti hills

  • Morning stop in Greve in Chianti

  • Winery tour and lunch in a Chianti estate

  • Visit to the medieval village of Monteriggioni

  • Key Road: Chiantigiana (SR222)

360_F_484608974_Nbmm1GnDHdijGfdFJapZovtrqZDnwEdK

DAY

2

· Wine Roads & Stone Towns: Through Chianti and Medieval Hilltops

After breakfast, the journey continues along the scenic Chianti roads to the picturesque town of Greve in Chianti. Enjoy a coffee and pastry at a local pasticceria before heading to a top local winery for a guided tour and a refined lunch paired with Chianti Classico wines.
In the afternoon, explore the charming walled village of Monteriggioni, then make your way to the hotel for a relaxing evening.

Key Roads & Highlights:

  • Drive through the Chianti hills

  • Morning stop in Greve in Chianti

  • Winery tour and lunch in a Chianti estate

  • Visit to the medieval village of Monteriggioni

  • Key Road: Chiantigiana (SR222)

360_F_484608974_Nbmm1GnDHdijGfdFJapZovtrqZDnwEdK

DAY

2

· Deep into Tuscany: Rolling Hills, Renaissance Towns & Bold Wines

205Km
127Mi

Start the day with a scenic drive to Pienza, the jewel of Val d’Orcia and home of the region’s finest pecorino. Visit a local dairy for a tour and cheese tasting.
Continue to Montepulciano for a stroll through its elegant streets and a relaxed lunch.
In the afternoon, head east to Passignano sul Trasimeno for a coffee by the lake, then drive to your hotel near Perugia or Assisi, where a peaceful evening and dinner await.

Key Roads & Highlights:

  • Visit and tasting at a cheese farm in Pienza

  • Walk and lunch in Montepulciano

  • Coffee by the lake in Passignano sul Trasimeno

  • Key Roads: SR2 (Via Cassia), SP146

  • Evening arrival near Perugia or Assisi

Sunrise,Over,Val,D'orcia,,Near,San,Quirico,D'orcia,,Siena,,Tuscany,

DAY

3

· Deep into Tuscany: Rolling Hills, Renaissance Towns & Bold Wines

205Km
127Mi

Start the day with a scenic drive to Pienza, the jewel of Val d’Orcia and home of the region’s finest pecorino. Visit a local dairy for a tour and cheese tasting.
Continue to Montepulciano for a stroll through its elegant streets and a relaxed lunch.
In the afternoon, head east to Passignano sul Trasimeno for a coffee by the lake, then drive to your hotel near Perugia or Assisi, where a peaceful evening and dinner await.

Key Roads & Highlights:

  • Visit and tasting at a cheese farm in Pienza

  • Walk and lunch in Montepulciano

  • Coffee by the lake in Passignano sul Trasimeno

  • Key Roads: SR2 (Via Cassia), SP146

  • Evening arrival near Perugia or Assisi

Sunrise,Over,Val,D'orcia,,Near,San,Quirico,D'orcia,,Siena,,Tuscany,

DAY

3

· Spirit, Stone & Scenic Beauty

Begin the day in Rasiglia, the “village of streams,” where clear spring water flows between ancient stone houses. Continue to Spello, known for its colorful flower-filled balconies and Roman roots, for a relaxed stroll and lunch.
In the afternoon, explore Orvieto, dramatically perched on a volcanic cliff and famous for its cathedral and underground tunnels.
End the day with a scenic drive to your countryside hotel near Saturnia, home to natural hot springs.

Key Roads & Highlights:

  • Rasiglia – the fairytale “village of streams”

  • Spello – Roman charm and floral alleys

  • Guided tour of Orvieto’s cliffside old town

  • Arrival near Saturnia’s thermal springs

  • Key Roads: SS3, SS71, SR74


Tuscany

DAY

4

· Spirit, Stone & Scenic Beauty

Begin the day in Rasiglia, the “village of streams,” where clear spring water flows between ancient stone houses. Continue to Spello, known for its colorful flower-filled balconies and Roman roots, for a relaxed stroll and lunch.
In the afternoon, explore Orvieto, dramatically perched on a volcanic cliff and famous for its cathedral and underground tunnels.
End the day with a scenic drive to your countryside hotel near Saturnia, home to natural hot springs.

Key Roads & Highlights:

  • Rasiglia – the fairytale “village of streams”

  • Spello – Roman charm and floral alleys

  • Guided tour of Orvieto’s cliffside old town

  • Arrival near Saturnia’s thermal springs

  • Key Roads: SS3, SS71, SR74


Tuscany

DAY

4

· Il Grand Finale: Waterfalls, Art & the Eternal City

177Km
186Mi

Begin the final day in Pitigliano, the dramatic town carved into volcanic rock, with a guided walk and tastings of its local delicacies.
Continue to the breathtaking Civita di Bagnoregio, known as “the dying city,” perched atop a crumbling cliff and reachable only by footbridge. Enjoy a memorable lunch in its timeless setting.

In the afternoon, head toward the Castelli Romani hills for a final stop in Nemi, a lakeside village famous for wild strawberries. Enjoy an aperitivo overlooking the lake before the final drive to Rome, where you return the cars and close an unforgettable journey.

Key Roads & Highlights:

  • Guided walk and tastings in Pitigliano

  • Visit and lunch in Civita di Bagnoregio

  • Aperitivo by the lake in Nemi

  • Final drive through the Castelli Romani hills

  • Key Roads: SR74, SP6, Via dei Lagh

lagi di piediluco

DAY

5

· Il Grand Finale: Waterfalls, Art & the Eternal City

177Km
186Mi

Begin the final day in Pitigliano, the dramatic town carved into volcanic rock, with a guided walk and tastings of its local delicacies.
Continue to the breathtaking Civita di Bagnoregio, known as “the dying city,” perched atop a crumbling cliff and reachable only by footbridge. Enjoy a memorable lunch in its timeless setting.

In the afternoon, head toward the Castelli Romani hills for a final stop in Nemi, a lakeside village famous for wild strawberries. Enjoy an aperitivo overlooking the lake before the final drive to Rome, where you return the cars and close an unforgettable journey.

Key Roads & Highlights:

  • Guided walk and tastings in Pitigliano

  • Visit and lunch in Civita di Bagnoregio

  • Aperitivo by the lake in Nemi

  • Final drive through the Castelli Romani hills

  • Key Roads: SR74, SP6, Via dei Lagh

lagi di piediluco

DAY

5
dividng the page subject

WHAT'S INCLUDED

  • Driving a variety of high-end supercars

  • Accommodation in boutique and five-star hotels across Italy

  • Meals at gourmet restaurants, as well as traditional and authentic local cuisine

  • Driving tours through some of the most beautiful roads and landscapes in the world

  • Fuel & Refueling service | Private parking

dividng the page subject

WHAT'S NOT INCLUDED

  • Flights
  • Tolls
  • Traffic fines and other reports
  • Refundable Security deposit up to 3,500€ – 6500€ (depend on the car ) in Case of Damages

 

 

 

dividng the page subject

WHAT TO BRING

  • Driver license, local and international
  • A valid credit card with an available credit limit sufficient to cover the required security deposit.
  • Passports and ID documents
  •  Recommended: Phone chargers and cables

Travel on your own terms – with the full support of luxury planning. We craft your perfect route, recommend five-star hotels, and provide smart Maps links – giving you a seamless, independent journey without sacrificing elegance or ease.

Luxury journey of Southern Tuscany and Umbria – An Unforgettable Experience

Join us for an exclusive journey through Tuscany and Umbria where luxury driving meets rich culture and breathtaking scenery.

Cruise through historic towns and discover hidden gems off the beaten path, and unwind in handpicked luxury hotels.

This experience combines stunning landscapes, world-class wine tastings, and unforgettable culinary moments.

Each day brings a new region, from charming wine villages to wild nature, all curated for the ultimate Italian adventure.

dividng the page subject

THE ROUTE

· Truffles, Towers & the Tuscan Horizon

Your luxury journey begins in Florence with a breathtaking view from Piazzale Michelangelo. From there, drive into the Tuscan hills to San Miniato for a truffle hunt with local experts and their dogs, followed by a rustic truffle lunch.
In the afternoon, explore the medieval charm of San Gimignano, then head to your countryside hotel for a relaxed evening and gourmet dinner.

 

 

 

Key Roads & Highlights:

  • Florence from Piazzale Michelangelo

  • Truffle hunting in San Miniato

  • Lunch with fresh truffles

  • Walk through San Gimignano

  • Key Road: SP40

florance cathedreal

DAY

1

· Truffles, Towers & the Tuscan Horizon

Your luxury journey begins in Florence with a breathtaking view from Piazzale Michelangelo. From there, drive into the Tuscan hills to San Miniato for a truffle hunt with local experts and their dogs, followed by a rustic truffle lunch.
In the afternoon, explore the medieval charm of San Gimignano, then head to your countryside hotel for a relaxed evening and gourmet dinner.

 

 

 

Key Roads & Highlights:

  • Florence from Piazzale Michelangelo

  • Truffle hunting in San Miniato

  • Lunch with fresh truffles

  • Walk through San Gimignano

  • Key Road: SP40

florance cathedreal

DAY

1

· Wine Roads & Stone Towns: Through Chianti and Medieval Hilltops

After breakfast, the journey continues along the scenic Chianti roads to the picturesque town of Greve in Chianti. Enjoy a coffee and pastry at a local pasticceria before heading to a top local winery for a guided tour and a refined lunch paired with Chianti Classico wines.
In the afternoon, explore the charming walled village of Monteriggioni, then make your way to the hotel for a relaxing evening.

Key Roads & Highlights:

  • Drive through the Chianti hills

  • Morning stop in Greve in Chianti

  • Winery tour and lunch in a Chianti estate

  • Visit to the medieval village of Monteriggioni

  • Key Road: Chiantigiana (SR222)

360_F_484608974_Nbmm1GnDHdijGfdFJapZovtrqZDnwEdK

DAY

2

· Wine Roads & Stone Towns: Through Chianti and Medieval Hilltops

After breakfast, the journey continues along the scenic Chianti roads to the picturesque town of Greve in Chianti. Enjoy a coffee and pastry at a local pasticceria before heading to a top local winery for a guided tour and a refined lunch paired with Chianti Classico wines.
In the afternoon, explore the charming walled village of Monteriggioni, then make your way to the hotel for a relaxing evening.

Key Roads & Highlights:

  • Drive through the Chianti hills

  • Morning stop in Greve in Chianti

  • Winery tour and lunch in a Chianti estate

  • Visit to the medieval village of Monteriggioni

  • Key Road: Chiantigiana (SR222)

360_F_484608974_Nbmm1GnDHdijGfdFJapZovtrqZDnwEdK

DAY

2

· Deep into Tuscany: Rolling Hills, Renaissance Towns & Bold Wines

205Km
127Mi

Start the day with a scenic drive to Pienza, the jewel of Val d’Orcia and home of the region’s finest pecorino. Visit a local dairy for a tour and cheese tasting.
Continue to Montepulciano for a stroll through its elegant streets and a relaxed lunch.
In the afternoon, head east to Passignano sul Trasimeno for a coffee by the lake, then drive to your hotel near Perugia or Assisi, where a peaceful evening and dinner await.

Key Roads & Highlights:

  • Visit and tasting at a cheese farm in Pienza

  • Walk and lunch in Montepulciano

  • Coffee by the lake in Passignano sul Trasimeno

  • Key Roads: SR2 (Via Cassia), SP146

  • Evening arrival near Perugia or Assisi

Sunrise,Over,Val,D'orcia,,Near,San,Quirico,D'orcia,,Siena,,Tuscany,

DAY

3

· Deep into Tuscany: Rolling Hills, Renaissance Towns & Bold Wines

205Km
127Mi

Start the day with a scenic drive to Pienza, the jewel of Val d’Orcia and home of the region’s finest pecorino. Visit a local dairy for a tour and cheese tasting.
Continue to Montepulciano for a stroll through its elegant streets and a relaxed lunch.
In the afternoon, head east to Passignano sul Trasimeno for a coffee by the lake, then drive to your hotel near Perugia or Assisi, where a peaceful evening and dinner await.

Key Roads & Highlights:

  • Visit and tasting at a cheese farm in Pienza

  • Walk and lunch in Montepulciano

  • Coffee by the lake in Passignano sul Trasimeno

  • Key Roads: SR2 (Via Cassia), SP146

  • Evening arrival near Perugia or Assisi

Sunrise,Over,Val,D'orcia,,Near,San,Quirico,D'orcia,,Siena,,Tuscany,

DAY

3

· Spirit, Stone & Scenic Beauty

Begin the day in Rasiglia, the “village of streams,” where clear spring water flows between ancient stone houses. Continue to Spello, known for its colorful flower-filled balconies and Roman roots, for a relaxed stroll and lunch.
In the afternoon, explore Orvieto, dramatically perched on a volcanic cliff and famous for its cathedral and underground tunnels.
End the day with a scenic drive to your countryside hotel near Saturnia, home to natural hot springs.

Key Roads & Highlights:

  • Rasiglia – the fairytale “village of streams”

  • Spello – Roman charm and floral alleys

  • Guided tour of Orvieto’s cliffside old town

  • Arrival near Saturnia’s thermal springs

  • Key Roads: SS3, SS71, SR74


Tuscany

DAY

4

· Spirit, Stone & Scenic Beauty

Begin the day in Rasiglia, the “village of streams,” where clear spring water flows between ancient stone houses. Continue to Spello, known for its colorful flower-filled balconies and Roman roots, for a relaxed stroll and lunch.
In the afternoon, explore Orvieto, dramatically perched on a volcanic cliff and famous for its cathedral and underground tunnels.
End the day with a scenic drive to your countryside hotel near Saturnia, home to natural hot springs.

Key Roads & Highlights:

  • Rasiglia – the fairytale “village of streams”

  • Spello – Roman charm and floral alleys

  • Guided tour of Orvieto’s cliffside old town

  • Arrival near Saturnia’s thermal springs

  • Key Roads: SS3, SS71, SR74


Tuscany

DAY

4

· Il Grand Finale: Waterfalls, Art & the Eternal City

177Km
186Mi

Begin the final day in Pitigliano, the dramatic town carved into volcanic rock, with a guided walk and tastings of its local delicacies.
Continue to the breathtaking Civita di Bagnoregio, known as “the dying city,” perched atop a crumbling cliff and reachable only by footbridge. Enjoy a memorable lunch in its timeless setting.

In the afternoon, head toward the Castelli Romani hills for a final stop in Nemi, a lakeside village famous for wild strawberries. Enjoy an aperitivo overlooking the lake before the final drive to Rome, where you return the cars and close an unforgettable journey.

Key Roads & Highlights:

  • Guided walk and tastings in Pitigliano

  • Visit and lunch in Civita di Bagnoregio

  • Aperitivo by the lake in Nemi

  • Final drive through the Castelli Romani hills

  • Key Roads: SR74, SP6, Via dei Lagh

lagi di piediluco

DAY

5

· Il Grand Finale: Waterfalls, Art & the Eternal City

177Km
186Mi

Begin the final day in Pitigliano, the dramatic town carved into volcanic rock, with a guided walk and tastings of its local delicacies.
Continue to the breathtaking Civita di Bagnoregio, known as “the dying city,” perched atop a crumbling cliff and reachable only by footbridge. Enjoy a memorable lunch in its timeless setting.

In the afternoon, head toward the Castelli Romani hills for a final stop in Nemi, a lakeside village famous for wild strawberries. Enjoy an aperitivo overlooking the lake before the final drive to Rome, where you return the cars and close an unforgettable journey.

Key Roads & Highlights:

  • Guided walk and tastings in Pitigliano

  • Visit and lunch in Civita di Bagnoregio

  • Aperitivo by the lake in Nemi

  • Final drive through the Castelli Romani hills

  • Key Roads: SR74, SP6, Via dei Lagh

lagi di piediluco

DAY

5
dividng the page subject

WHAT'S INCLUDED

  • Experience the thrill of driving a supercar of your choice
  • Accommodation in boutique and five-star hotels across Italy
  • A Google Maps file featuring the complete itinerary, along with recommendations and highlighted hotspots suggested by our professional guides
dividng the page subject

WHAT'S NOT INCLUDED

  • Flights
  • Tolls
  • Fuel
  • Meals
  • Traffic fines and other reports
  • Refundable security deposit up to 3,500€ – 6500€ (depend on the car ) in Case of Damages

 

dividng the page subject

WHAT TO BRING

  • Driver license, local and international
  • A valid credit card with an available credit limit sufficient to cover the required security deposit.
  • Passports and ID documents
  •  Recommended: Phone chargers and cables
dividng the page subject

BOOK A TOUR NOW

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