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.
Stay longer to add time in Rоme and Vеnice!
What's Included
- Round-trip economy class airfare to Rome (FCO)
- Manual shift car rental for duration - upgrade to automatic available
- 6 nights in Tuscany at Castello Di Montegufoni
- 2 nights in the Rome area at Grand Hotel Fleming, or similar (with breakfast)
Great Ways to Explore
Enjoy views of rolling hills and winding roads in Tuscany.
- Unwind at Castello Di Montegufoni, a 12th-century castle.
Discover the highlights of the Chianti region.
- Enjoy day trips to nearby Tuscan cities, like Florence.
Immerse yourself in the beauty, heritage, and flavors of Italy.
This Italian adventure unfolds like a tapestry of celebrated cities, layered history, and landscapes that feel eternal. The journey opens in Rome, where ancient monuments, sweeping piazzas, and the artistic riches of the Vatican create a vivid and immersive introduction to Italy’s cultural heartbeat.
From the capital, the road leads north into Tuscany, gradually giving way to rolling hills, vineyards, and medieval hill towns that invite unhurried exploration. The centerpiece of this experience is a stay at Castello di Montegufoni, a 12th‑century castle nestled in the Chianti countryside. After days spent wandering Rome’s archaeological wonders, the castle becomes a peaceful retreat—surrounded by terraced gardens, vineyards, and panoramic views that blend medieval character with Renaissance grace. With its spacious rooms, on-site pool, and welcoming restaurant, Montegufoni offers a restful home base between your Tuscan excursions.
From this ideal location in Chianti, many of Italy’s most iconic destinations are within easy reach. Florence’s masterpieces, Pisa’s famed tower, Siena’s Gothic charm, and Arezzo’s timeless streets all make for effortless day trips. Each day brings a mix of art, history, and scenic drives through postcard-worthy countryside, balanced with time to savor regional dishes and the celebrated wines 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.
Enhance your vacation with:
- Florence Walk and Talk Tour
- Fattoria San Michele a Torri Wine Tasting
What's Included
- Round-trip economy class airfare to Rome (FCO)
- Manual shift car rental for duration - upgrade to automatic available
- 6 nights in Tuscany at Castello Di Montegufoni
- 2 nights in the Rome area at Grand Hotel Fleming, or similar (with breakfast)
Great Ways to Explore
Enjoy views of rolling hills and winding roads in Tuscany.
- Unwind at Castello Di Montegufoni, a 12th-century castle.
Discover the highlights of the Chianti region.
- Enjoy day trips to nearby Tuscan cities, like Florence.
Immerse yourself in the beauty, heritage, and flavors of Italy.
Package Overview
This Italian adventure unfolds like a tapestry of celebrated cities, layered history, and landscapes that feel eternal. The journey opens in Rome, where ancient monuments, sweeping piazzas, and the artistic riches of the Vatican create a vivid and immersive introduction to Italy’s cultural heartbeat.
From the capital, the road leads north into Tuscany, gradually giving way to rolling hills, vineyards, and medieval hill towns that invite unhurried exploration. The centerpiece of this experience is a stay at Castello di Montegufoni, a 12th‑century castle nestled in the Chianti countryside. After days spent wandering Rome’s archaeological wonders, the castle becomes a peaceful retreat—surrounded by terraced gardens, vineyards, and panoramic views that blend medieval character with Renaissance grace. With its spacious rooms, on-site pool, and welcoming restaurant, Montegufoni offers a restful home base between your Tuscan excursions.
From this ideal location in Chianti, many of Italy’s most iconic destinations are within easy reach. Florence’s masterpieces, Pisa’s famed tower, Siena’s Gothic charm, and Arezzo’s timeless streets all make for effortless day trips. Each day brings a mix of art, history, and scenic drives through postcard-worthy countryside, balanced with time to savor regional dishes and the celebrated wines 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.
Upgrade & Include Even More!
Enhance your vacation with:
- Florence Walk and Talk Tour
- Fattoria San Michele a Torri Wine Tasting
Deal Of The Week
Number of Nights:
Day 1. Welcome to Rome!
Welcome to Rome!
After picking up your rental car—yours to enjoy for the entire trip—you’ll begin your drive toward the stunning Tuscan retreat of Castello di Montegufoni. The route carries you out of the city and into sweeping countryside, where rolling hills and open vistas invite leisurely stops for photos or simply to take in the view. Be sure to plan your timing so you can arrive before check‑in closes and 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
Your hotel in Montegufoni Castle places you in the heart of the Chianti region, known for its vineyards and postcard-worthy scenery. With your rental car, you have the flexibility to explore at your own pace. Consider a 30-minute drive to Florence, a city celebrated as the birthplace of the Renaissance. Wander through its historic streets, admire the architecture, and begin discovering the cultural depth that defines this remarkable city.
Scenic Tuscany
Day 3. Tuscany
Spend more time immersing yourself in Florence today. Visit the Duomo and admire its striking facade and impressive dome, then explore the Pitti Palace, once home to powerful Florentine families. Art lovers will appreciate time at the Uffizi Gallery, which houses works by masters such as Michelangelo and Botticelli. Balance sightseeing with relaxed cafe stops and leisurely walks along the Arno River.
Duomo • Florence
Day 4. Tuscany
Today offers the opportunity to journey to Pisa, just under two hours away by car. The city is best known for the Leaning Tower, but the surrounding Piazza dei Miracoli is equally impressive, with its cathedral and baptistery. Take time to explore the area beyond the main sights, enjoying a slower pace before returning to Tuscany.
Leaning Tower of Pisa • Pisa
Day 5. Tuscany
Enjoy a scenic drive through the Tuscan countryside, where winding roads lead past vineyards, olive groves, and hilltop towns. Stop as often as you like to take in the views or explore local villages. Notable towns in the region include Siena, with its famous piazza, and Ravenna, known for its historic charm and artistic heritage.
Siena
Day 6. Tuscany
For a more relaxed final day in Tuscany, drive south for about an hour to the city of Arezzo. This elegant city features medieval towers, Renaissance architecture, and atmospheric streets. Spend time in Piazza Grande, the bustling heart of the city, and enjoy browsing shops or stopping for a leisurely lunch before returning to your accommodation.
Italian gelato
Day 7. Tuscany - Rome
Head back to Rome today! Once you’ve settled in, ease into your Italian adventure by exploring the Frascati area. This lively town on the outskirts of Rome is known for its historic center, local wine culture, and relaxed atmosphere. Take a stroll through the streets, enjoy an early aperitivo, and soak up your first evening in Italy.
Rome,
Italy
1 of 3 hotels
Located in the vicinity of Ponte Milvio and surrounded by ancient Roman residences, Grand Hotel Fleming it is the perfect place to enjoy the city's wealth in a relaxing environment. Located a 10-minute drive from the Foro Italico, Olympic Stadium and Auditorium, the hotel offers easy access to public transportation or taxis to the city center.
An elegant corner of Rome and a beloved celebrity hideaway, the Grand Hotel Fleming is an ideal location for a romantic weekend in Rome. Each of the 302 rooms are tastefully decorated and feature an en suite bathroom, in-room safe, air-conditioning, minibar and more. Wake up to a delicious buffet breakfast each morning, then relax with an Italian meal at the restaurant in the evening. The hotel's staff is happy to assist with booking tours, taxis and airport transfers.
Rome,
Italy
2 of 3 hotels
Start your day of adventuring with warm croissants, fresh cheeses, Italian cappuccinos and freshly-squeezed juice from the breakfast spread at Pineta Palace Hotel Roma. Catch a bus mere feet from the hotel that run to Cornelia Metro Station and the Vatican Museums. Then, link up to from the FR3 Line to the Trionfale, an excellent choice for travelers interested in ancient landmarks, art and monuments.
The Pineta Palace offers air-conditioned rooms with a classic décor and a private balcony. Some also provide city views. The restaurant serves classic Italian cuisine for dinner. The hotel's restaurant, "Il Focolare dei Cinque Sensi", offers the best in Roman and Mediterranean cuisine thanks to the genuine simplicity of top quality ingredients and passion of the chef. Complete your meal by choosing from a wide selection of national wines or relax with a cocktail at the lounge bar, which has the option of a scenic outdoor terrace. As the adventure winds down for the day, return to the hotel for a drink or snack from the bar, escape momentarily from the bustle of Rome, and unwind in the quiet surroundings.
Rome,
Italy
3 of 3 hotels
Located close to the GRA and in the bustling EUR district, Hotel Cristoforo Colombo's renovations are complete and ready to impress. The hotel has a large parking area, a seasonal outdoor pool, and well-appointed facilities equipped to meet your every need. The property is a complex comprised of three buildings, all refreshed with marble finishes and bright color schemes. Relax in the hotel's casually elegant bar or enjoy a meal from the restaurant. The professional staff is available around the clock to help with needs such as tour schedules, museum tickets, or even restaurant suggestions.
Day 8. Rome
Rome is a city where history surrounds you at every turn. Take the metro to the Colosseum and spend time exploring this iconic landmark, once the stage for gladiatorial combat and grand public spectacles. Walking through the ruins, it’s easy to imagine the scale and intensity of life in ancient Rome.
Just next door lies the Roman Forum, where temples, arches, and government buildings once formed the heart of political life. Continue on to the Pantheon, one of the best-preserved monuments from antiquity, admired for its remarkable dome and enduring architectural influence.
Roman Forum
Day 9. Depart Italy
Gather your keepsakes and bid Italy a warm ciao. Make your way back to Rome Airport, return your rental car, and prepare to board your flight home.
Fly home!
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Tuscany, Italy
Castello di Montegufoni
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