A royal escape in Italy
Castello di Montegufoni—a beautifully restored 12th‑century fortress set amid rolling Tuscan hills and terraced gardens—creates a truly memorable backdrop for your Italian getaway. Blending medieval charm with touches of Renaissance elegance, the estate offers an on‑site restaurant, a refreshing pool, and easy access to golf, hiking trails, and spa experiences. With an included rental car, it becomes an ideal home base for exploring the surrounding Chianti region and beyond. This upgrade includes a tour of Florence as well as a Wine Tasting.
Stay longer to add time in Rоme and Vеnice!
What's Included
- Round-trip economy class airfare into Rome (FCO)
- Manual shift car rental for duration* - upgrade to automatic available
- 6 nights in Tuscany at Castello Di Montegufoni
PLUS!
- Florence Walk and Talk Tour
- Fattoria San Michele a Torri Wine Tasting
Great Ways to Explore
Enjoy views of rolling hills and winding roads in Tuscany.
- Stay at Castello Di Montegufoni, a 12th-century castle.
Explore the serene Chianti region.
- Take day trips to nearby Tuscan cities, like Florence.
Immerse yourself in the beauty, heritage, and flavors of Italy.
This Italian getaway unfolds at a relaxed, thoughtful pace, centered around a stay at Castello di Montegufoni—a 12th‑century castle tucked into the rolling hills of Tuscany’s Chianti region. With its spacious rooms, inviting pool, on-site dining, and the quiet beauty of the surrounding countryside, Montegufoni serves as a welcoming haven to return to after each day’s adventures.
From this base in Chianti, travelers can easily reach many of Italy’s most treasured cities. Florence, Pisa, Siena, and Arezzo are all within comfortable driving distance, making it simple to fill each day with Renaissance masterpieces, charming historic squares, and scenic routes lined with vineyards and olive groves. The journey balances exploration with indulgence, leaving plenty of time to enjoy regional dishes, sip local wines, and soak in the timeless atmosphere of Tuscany.
**Please Note**
The drive from Rome to Montegufoni is approximately 2.5 - 3 hours. In order to arrive at your accommodation in time for check-in, be sure to choose a flight which allots time for travel.
Check-in at Castello Di Montegufoni is NOT available after 6:00pm November through March, and after 7:00pm April through October. If arriving after those times, you must call the property to get instructions to get your keys and reach your apartment, but there is no one available to assist.
At Castello Di Montegufoni, the following taxes and fees are not included and must be paid directly to the property:
- Cash security deposit of €150 (refundable).
- Mandatory final cleaning fee of €60 for a one-bedroom villa, €70 for a two-bedroom, €80 for a three-bedroom.
- Local Tax of apx. €2 per person, per day for the first six days of your stay- applies only to adults over the age of 15.
- Heating fee of €20 per day for a one-bedroom villa, €25 per day for a two-bedroom, €30 per day for a three-bedroom. This fee is mandatory when staying November through April; in other month, this fee only applies if the heat is used.
- Gratuities, some local city taxes, daily housekeeping, and meals are NOT included.
- Fees vary based on accommodation type and are subject to change.
Please note that some recommendations in the following suggested itinerary may not be included in your package. Check What's Included above for full details on inclusions.
What's Included
- Round-trip economy class airfare into Rome (FCO)
- Manual shift car rental for duration* - upgrade to automatic available
- 6 nights in Tuscany at Castello Di Montegufoni
PLUS!
- Florence Walk and Talk Tour
- Fattoria San Michele a Torri Wine Tasting
Great Ways to Explore
Enjoy views of rolling hills and winding roads in Tuscany.
- Stay at Castello Di Montegufoni, a 12th-century castle.
Explore the serene Chianti region.
- Take day trips to nearby Tuscan cities, like Florence.
Immerse yourself in the beauty, heritage, and flavors of Italy.
Package Overview
This Italian getaway unfolds at a relaxed, thoughtful pace, centered around a stay at Castello di Montegufoni—a 12th‑century castle tucked into the rolling hills of Tuscany’s Chianti region. With its spacious rooms, inviting pool, on-site dining, and the quiet beauty of the surrounding countryside, Montegufoni serves as a welcoming haven to return to after each day’s adventures.
From this base in Chianti, travelers can easily reach many of Italy’s most treasured cities. Florence, Pisa, Siena, and Arezzo are all within comfortable driving distance, making it simple to fill each day with Renaissance masterpieces, charming historic squares, and scenic routes lined with vineyards and olive groves. The journey balances exploration with indulgence, leaving plenty of time to enjoy regional dishes, sip local wines, and soak in the timeless atmosphere of Tuscany.
**Please Note**
The drive from Rome to Montegufoni is approximately 2.5 - 3 hours. In order to arrive at your accommodation in time for check-in, be sure to choose a flight which allots time for travel.
Check-in at Castello Di Montegufoni is NOT available after 6:00pm November through March, and after 7:00pm April through October. If arriving after those times, you must call the property to get instructions to get your keys and reach your apartment, but there is no one available to assist.
At Castello Di Montegufoni, the following taxes and fees are not included and must be paid directly to the property:
- Cash security deposit of €150 (refundable).
- Mandatory final cleaning fee of €60 for a one-bedroom villa, €70 for a two-bedroom, €80 for a three-bedroom.
- Local Tax of apx. €2 per person, per day for the first six days of your stay- applies only to adults over the age of 15.
- Heating fee of €20 per day for a one-bedroom villa, €25 per day for a two-bedroom, €30 per day for a three-bedroom. This fee is mandatory when staying November through April; in other month, this fee only applies if the heat is used.
- Gratuities, some local city taxes, daily housekeeping, and meals are NOT included.
- Fees vary based on accommodation type and are subject to change.
Please note that some recommendations in the following suggested itinerary may not be included in your package. Check What's Included above for full details on inclusions.
Deal Of The Week
Number of Nights:
Day 1. Welcome to Rome!
You’ve arrived in Rome! Collect your rental car, which will be yours for the duration of the journey, and set off towards your magnificent Tuscan accommodation, Castello Di Montegufoni. The drive winds through breathtaking countryside, offering countless opportunities to stop and capture the scenery at your leisure. Please remember to arrive in time for check-in to avoid any late arrival fees.
Check-in - Castello di Montegufoni
Tuscany,
Italy
Castello di Montegufoni, a 12th-century castle set in the Tuscan hills, offers the perfect home for your Tuscan adventure. Set in the midst of a large and very charming terraced park overlooking beautiful Italian gardens, it still retains a certain medieval flavor which blends smoothly with Renaissance refinement and solidity. In addition to the 15 spacious and comfortable accommodations, the Castle offers a swimming pool, and restaurant specializing in sumptuous local Chianti fare. Golf, horseback riding, hiking, biking, and spa facilities can all be found within easy reach.
In addition to the 15 Castle apartments, Castello di Montegufoni offers Dependance apartments located only footsteps from the Castle. Offering access to the full range of facilities such as the pool, restaurant, and on-site activities, these modernized apartments have a large living room with a dining area and a kitchen corner. Dependance apartments have 2 - 4 bedrooms, one or more bathrooms, a freezer, and many have an outdoor area with gazebo furnished with table and chairs. Some apartments include air-conditioning, a dishwasher, a microwave, and a fireplace. Depending on Castle apartment availability, you may be accommodated in a Dependance apartment rather than a Castle apartment.
The hotel restaurant is open from March 1st through October 30th (closed on Tuesdays, opens at 12:00 pm). The hotel bar is open from April 1st through September 15th.
**Please Note**
At the Montegufoni Castle, the following taxes and fees are not included and must be paid directly to the property:
- Cash security deposit of €150 (refundable).
- Mandatory final cleaning fee of €50 for a one-bedroom villa, €60 for a two-bedroom, €70 for a three-bedroom.
- Local Tax of apx. €1 per person, per day for the first six days of your stay- applies only to adults over the age of 15.
- Heating fee (if used) of €20 per day for a one-bedroom villa, €25 per day for a two-bedroom, €30 per day for a three-bedroom.
- Gratuities, some local city taxes, daily housekeeping, and meals are NOT included.
- Fees vary based on accommodation type and are subject to change.
Day 2. Tuscany
Spend time exploring more of your castle hotel! Unwind by the pool or enjoy gorgeous views of the Tuscan countryside with a glass of wine in hand.
In the evening, indulge in a delicious Italian dinner back at your accommodation.
Castello di Montegufoni
Day 3. Tuscany
Today invites a scenic drive to Pisa, a little under two hours away. While the Leaning Tower is the city’s star attraction, the entire Piazza dei Miracoli—home to the cathedral and baptistery—is equally striking. After taking in the famous landmarks, wander into the quieter streets beyond the main square, where the pace slows and the crowds thin.
Enjoy the change of scenery before making your way back to the Tuscan countryside.
Leaning Tower of Pisa • Pisa
Day 4. Tuscany
Today, head to Florence and enjoy your tour taking you to "must-see" sights like the Duomo, Ponte Vecchio, and Piazza della Signoria. After the tour, consider heading to Parco delle Cascine, a spacious riverfront park.
This 1.5 hour walking tour of Florence is just what you need to be introduced to the city and its splendor! You'll hear tantalizing gossip of Michelangelo; discover what Leonardo had in mind to revolutionize the town, and more astounding events that shocked the Florentines.
Walk through the center of Florence and discover its unique secular heritage and breathtaking beauty with an expert and fun tour guide. This tour explores the historic and architectural evolution factors from the Roman foundation through medieval centuries and its Renaissance glorious period up to modern time Florence.
Your guide will take you to some of the most important spots where the greatest minds and artists have stood and been inspired. During this walk, you will see Piazza della Signoria with the town hall Palazzo Vecchio, the Duomo, the Baptistery with its ‘Gates of Paradise’, Giotto’s independent bell tower, Brunelleschi’s Dome, Santa Trinita and Orsanmichele Church, Ponte Vecchio Bridge and the secret Vasari Corridor, as well as famous shopping streets and the Oltrarno – the fourth and last district, the manual crafts neighborhood.
Day 5. Tuscany
Today, enjoy your included wine tasting. Use the rest of the day to rest, relax, and indulge in the amenities at your castle hotel.
Set amongst vineyard and olive groves, the agricultural estate of Fattoria San Michele a Torri Srl is a gem of the "Chianti" wine producing area. The trhion covers an area of 500 acres of land, of which approximately 125 acres are occupied by vineyards, and 75 by olive groves.
This is a habitat particularly suited to winemaking, which produces smooth, perfumed wines of great character. The area produces red and white wines, Vinsanto, and Olive Oil.
During your visit to the vineyard, you will have the opportunity to see both the new and old wine cellars. See the olive oil producing room “orciaia” with an explanation of how the olive oil is made. You will also enjoy a tasting which will include: 3 red wines (Chianti Colli Fiorentini, Chianti Classico & Super Tuscan), and bruschetta with extra virgin olive oil, salami and cheese.
Please Note: Transportation to and from Fattoria San Michele is not included.
Day 6. Tuscany
For a slower-paced final day in Tuscany, consider heading about an hour south to the city of Arezzo. This refined destination is known for its medieval towers, Renaissance elegance, and atmospheric streets lined with local shops and cafés.
Spend some time in Piazza Grande, the lively centerpiece of the city, before enjoying a relaxed lunch or a bit of browsing. When you’re ready, make your way back to your accommodation and savor the last quiet moments of your Tuscan stay.
Italian gelato
Day 7. Tuscany
For your final day in Tuscany, set off for the charming city of Lucca. Nestled along the Serchio River, Lucca is celebrated for its remarkably well-preserved Renaissance walls, which fully encircle the historic centre and offer a lovely elevated walk with views over terracotta rooftops and church spires. Wander through its elegant piazzas and narrow streets before visiting Casa di Puccini, the birthplace and former home of the famed composer, now a fascinating museum dedicated to his life and music.
Lucca
Day 8. Depart Italy
Pack your souvenirs and say ciao to Italy. Return your rental car before boarding your flight home.
Fly home!
We have selected the most economical flight schedule for you. Please note that shorter and more convenient flight options may be available at an additional cost.
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