Tuscany/Umbria Villa (2 Weeks)

Under The Tuscan Sun

Tuscany conjures up dreams of what life would be like at a slower pace; where you can soak in the culture, food and amazing vistas of the Italian countryside. Go to the local markets to pick out some cheese and wine and stroll through the narrow passageways of medieval villages dating from the 14th century that few tourists get to see and that dot the countryside by the hundreds. Head back to your 18th century luxury villa by foot or bike as you pass olive groves and truffle fields just in time for an amazing Tuscan sunset. Tuscany is that dream vacation that you never got around to doing but now is your chance!

Day 1 : Italy Arrival

Welcome to Italy! Today you arrive in Italy and airport pick-up has been arranged for you to take you to your private villa in the hills of Umbria. Your host will be waiting for you at the villa and will show you to your room. You have the rest of the day to explore your new home for the next two weeks and the surrounding 5 acres of property. Later that evening, there will be a welcome dinner at the villa. The dinner will be Tuscan-style and served on the veranda. You can also have your first Italian aperitivo before your meal as you watch the Tuscan sun set over the rolling hills!

Included :

  • Activities : Airport pick-up
  • Meals : Dinner @ 7:30 PM
  • Accommodation : Luxury private villa

Day 2 – 14 : Tuscany/Umbria

The next 14 days are at your leisure. If you would like to see pictures of our villa, please refer to the tab above labeled ‘Accommodation’.  Every morning, a private chef will prepare a wholesome breakfast with traditional, local products of the region in the beautiful dining salon in the western part of the villa.

Below is a picture of the breakfast salon in the villa.

Every morning you will be served an Italian-style breakfast consisting of :

Fresh bread, croissants, croissants with chocolate, biscuits, jams, Nutella, fresh pastries, cakes, prosciutto, salami, cheese, butter, fruit juices, fresh milk, American coffee, espresso coffee and cappuccino.

The villa where we will be staying is 1 kilometer from a town called Città della Pieve (approximately 15  minutes on foot). This small town is nestled on the Tuscany/Umbria border and lays claim to one of the narrowest streets in Italy, called via Baciadonna. It’s so narrow that one can lean out the window and kiss the girl in the building across the street! Wander the streets and take in the atmosphere; it’s a captivating town with a vibrant civic life despite its small size (population just over 7,000). There are several excellent eateries and appealing cafes sprinkled around this small town and upon visiting, you will see the grand wall that was used to protect this medieval city that dates back to the 1300s. The town’s theater is a beautiful jewelry box of an opera house decked out with satins and velvets and lined with private viewing boxes. A performance here feels like a truly spectacular event. If you’re lucky, you can catch a performance during your stay! Città della Pieve also won the first Pio Alferano Prize as the most perfect city in Italy and it is only 1 kilometer from our villa! A quote from the prize judges about this town : “Città della Pieve is a perfect city : it offers the ideal condition of being isolated and close. It is at the center of art with the masterpieces of Perugino, but without the anxiety of a frenetic tourism. In the sheltered rooms of beautiful houses, villas, hotels, taverns and restaurants, day and night, a slight euphoria animates the spirit and shakes the body when in this city.”

Below is a picture of via Baciadonna, said to be the narrowest street in all of Italy!

Most villas in the Tuscany/Umbria regions are approximately 5 – 15 kilometers away from the closest village/town which makes it nearly impossible to walk into town. You would need to rent a car and deal with parking. We chose this villa due to its close proximity to the town. You will more than likely be the only visitors in town which is a great escape from the throngs of tourists in Siena and Florence. Sip on an espresso at one of the numerous outdoor cafes or go shopping at the local market for tonight’s dinner.

Below are pictures of the town of Città della Pieve.

During your stay you will have a local host who will check in daily and help arrange anything you might need. If you would like to rent a bike or a car, no problem! Your concierge will have it dropped off at the villa for you. Do you need a taxi to the train station and the train schedule to go to Rome? This can be can easily arranged for you! Two weeks before your trip, we will send you a list of excursions in and around the area. How about a parmesan cheese and balsamic vinegar factory tour? Maybe a visit to a saffron farm? The location of the villa is half way between Florence and Rome and on the border of Umbria and Tuscany making it ideal for exploring a variety of places. You can check out the location of our villa on the map in the corresponding tab above. Please see below for travel times to different towns and cities from the villa as a reference :

Chiusi – 20 minutes by car. This is the nearest train station from our villa and the trains can take you to Siena, Florence, Rome, Pisa, and much more. Most of the larger cities and towns offer direct access by train.

Montalcino – 1 hour
Chianti – 50 minutes
Siena – 50 minutes
Cortona – 30 minutes
Beach (Grosseto) – 2 hours
Montepulciano – 30 minutes
Assisi – 1 hour
Perugia – 45 minutes
Arezzo – 40 minutes
Rome – 1.5 ~ 2 hours
Florence – 1.5 ~ 2 hours

Because the villa is halfway between Florence and Rome, you can arrive in and depart from either city. You can read more about this in the ‘Flights and Visa’ tab above. 

Many of us on the trip will not know one another and some will be traveling solo, so upon arrival, there will be an introduction so we can learn about each other and what excursions interest us during our stay in Italy. In the main salon of the villa, there will be a whiteboard and bulletin board. If you would like to host an aperitivo before dinner one night, you can add this announcement to the whiteboard. If you have signed up for a cooking class, you can put a sign up sheet on the bulletin board to see if anyone else would like to join in. Maybe one night you would like to cook dinner for everyone? You can put the announcement up on the board to invite your fellow travelers. Our villa has a traditional wood-fired pizza oven on the patio, so how about a pizza and pool day? If you want to invite others in the house, you can just post a note about it along with a sign up sheet. When more people join, the cost of that activity is less! Of course, it is your choice what activities you want to participate in, but you are free to plan events, host dinners or organize trips/excursions for the group or just for yourself.  

 Below is the wood-fired oven at our villa.

Day 15 : Italy Departure

Say goodbye to Umbria/Tuscany and the villa you called home for the last two weeks as you head back home. Hopefully, along the way you made some amazing memories and friendships. See you all again on our next adventure!

Included :

  • Activities : Departure (At your own expense)
  • Meals : Breakfast

Italy 15-Day Trip

$2,700 – Trip Cost (See below for inclusions and exclusions.)

I’m a single traveler. Will I be charged a single supplement?

Unfortunately, many villas located in the Italian countryside do not have many rooms with 2 beds, this villa being no exception. Thus, we have made the single supplement as affordable as possible as many of our customers are solo travelers.  This villa has 8 rooms with a double bed and 2 rooms with twin beds. All rooms have their own bathroom.  Room selection is done on a first-come-first served basis.  If you want a room with twin beds it is best to book sooner rather than later.  You can see pictures of the rooms on the corresponding tab appropriately named ‘Rooms.’

If you would like your own room throughout the tour, you can purchase the “single supplement”. The single supplement fee for this trip is $650. If you would like your own room, you can buy the additional supplement at check out. We strongly encourage buying the single supplement if traveling solo and again we have made it as affordable as possible to encourage those traveling solo to not be discouraged with a costly single supplement fee.

What is included :

  • 14 nights accommodation (Double occupancy)
  • Local Italian guide/concierge
  • International airport pick-up
  • Breakfast served daily
  • Welcome dinner

What is not included :

  • Most dinners & lunches
  • All activities
  • Gratuities
  • Alcoholic beverages
  • Souvenirs
  • International airport drop-off
  • International flight
  • Supplementary insurance
Group Size

Each group will consist of 10 – 16 travelers. The group size will depend on how many single supplements are purchased.


We researched hundreds of villas in and around the Tuscany and Umbria regions. During our research, one of the main issues was the distances between the villas and nearby towns/villages. Most villas in this region were 7 kilometers on average to the closest town. This means that a car would have to be rented for the duration of the trip. Renting a car would be a very expensive additional cost. Another issue was that the villages within walking distance from the villas only had 100 or so residents. While it sounds quaint, these villages lacked basic amenities such as banks as well as restaurants, bars, cafes and shops. Our villa stands out because the town of Città della Pieve, which is just 15 minutes away on foot and is a town of just over 7,000 residents. This means that it is big enough to have all the amenities you need, but still has all the characteristics of a small and quaint Tuscan town. Città della Pieve is a medieval town and dates back to the 1300s. It has a lovely art museum, opera house and other interesting historical sites that will keep you busy. It also has a bank and numerous restaurants, bars, cafes and shops. Both May and August are great times to visit this area as all the cafes and restaurants open their outdoor terraces.

During your stay you will have the option of renting a car, which is a great way to get out and see the Italian countryside. You can rent a car for just a day and the car will be delivered to you at the villa for added convenience. Also, if there is a group of you that would like to venture to the more far flung countryside areas, you can split the car rental cost to make it more affordable. Structured tours (i.e. cheese factory, food tours, vineyard visits, cooking classes, etc.) include pick-up and drop-off in the cost, so you will not need to worry about transport for these. The closest train station is 20 minutes away and can take you to numerous cities and towns throughout Italy.  Two weeks before the trip we will send you more details about optional excursions. 


Italy uses the Euro and other currencies will not be accepted for legal tender. The most convenient way to handle money is to use a debit card for withdrawals from an ATM and/or to bring money to exchange. If you need to buy Euro on arrival, you can exchange a small amount at the airport. If exchanging currency at the airport, it’s usually best to exchange only a small amount and then seek a better deal elsewhere as airports usually offer unfavorable exchange rates. Your villa is only 1 kilometer from the town of Città della Pieve. In the town, there is a bank and an ATM, so you will easily be able to withdraw or exchange money during your stay. In some small shops, cash may be the only acceptable form of payment. Therefore, it is a good idea to always carry some cash with you, just in case!

ATMs are common in towns and cities. As a general rule, using ATMs for cash withdrawal is one of the smartest ways to get money. The exchange rates applied are usually fair and they’re convenient to use. However, do make sure you know what fees your home bank charges and watch out for the fees added by the ATM operator. If your bank adds a per transaction fee, for example, then taking out larger sums less frequently would be a more sensible way to reduce overall costs. The majority of ATMs offer English language or other language options for the convenience of foreigners.

We suggest bringing or having access to anywhere from $800 – $2,000 while on the trip, either in cash or on your debit card depending on your spending habits. WE HIGHLY ADVISE BUDGETING MORE MONEY THAN YOU EXPECT TO SPEND IN CASE OF AN EMERGENCY.


There are plenty of souvenirs to be found in Italy, most being edible and drinkable! Local craft markets can be found in the towns and cities all over the Umbria/Tuscany regions and they offer items such as ceramics, handmade stationery, leather goods and much more. Some of the more delicious souvenirs include balsamic vinegar, truffle honey, saffron, olive oil, wines, etc… can be found all around the region.


If you have a smart phone, it will likely work in Italy, but coverage may be spotty. Be sure to check with your provider to get informed about data and call roaming while abroad. You also may consider contacting your service provider to learn about what kind of international plans they offer for calls, texts, and data, especially since you will be abroad for 15 days.


In general, hotels, restaurants and other public places in just about any area in Italy offer wifi. Bear in mind that although it’s available, it’s not always as fast as you may be used to. Our villa has wifi and you will be able to access it during your stay.

What to Bring 

Temperatures in Umbria/Tuscany in the months of May and August/September can vary, but are generally warm during the day and cool at night.

You can read more about the weather in the ‘When to go‘ tab above.

Below are a few things that we suggest bringing to make your trip more comfortable :

  • A positive attitude and open mind
  • Sunscreen
  • Hat/Sunglasses
  • Any prescription medication and over the counter medicine
  • Walking shoes or sneakers
  • Warm jacket/coat for night
  • Cardigan or light jacket
  • Warm pajamas
  • Small, across the shoulder day bag or small backpack
  • Small hair dryer (if needed)
  • Flashlight
  • Swimsuit
  • Shampoo/conditioner/soap
  • Adapter

Italy’s electrical outlets are euro plug-type round pin sockets with 220-240 volts and 50 Hz frequency. Be prepared to pack the necessary adapters and converters if you plan on bringing electronic devices.


Our villa has a washer and dryer on the premises as well as laundry detergent, so you will be able to do laundry during your stay.  If you would like to send it out to be cleaned, this can also be arranged.


Tipping at restaurants in Italy : Most Italians do not leave a tip at meals, but if you are happy with the service, you can leave a 10% tip. If you weren’t thrilled with the service and it was just adequate, you do not need to tip. 

Remember to look at the breakdown of your bill. You will very likely see a cover charge, called a coperto, in the amount of about 2-3 euros per head. This is completely normal and should be an expected charge on your bill anytime you sit down anywhere, even if all you order is a glass of water. The key words there are “sit down”. If you stand at a bar, you will not get charged the cover. Know that your server is already being paid a living wage and does not depend on your tips in order to make ends meet.

Also note that some restaurants add an additional service charge, listed on the bill as servizio. A servizio is usually about 10% and should not be a surprise at the time you receive the bill. It is usually noted on the menu and often applies to specific scenarios like for parties of 8 people or more. This charge is the tip, so if you ever see a charge for servizio, do not leave any additional tip. 

Tipping your taxi driver :  Tipping cab drivers is unusual in Italy, but appreciated, especially if they help you with your luggage and provide you with useful info about getting around in that particular place. For drivers who quote a fixed fare – for example an airport fare or a pre-paid fare – there is no need to add a tip. A good rule of thumb is to round up. If your taxi fare is 9 euros, you can just give him/her 10 euros, but again, this is not necessary and most Italians do not tip drivers.

Tipping your tour guide/concierge : Again, it is not necessary to tip your guide, but if you feel he/she did an exceptional job, then you can tip anywhere from 5% – 15% of the total cost. During your stay at the villa, you will have an Italian host who will arrange everything you will need during your stay and will check in daily to help with arrangements. If you use his/her services frequently and he/she helped you arrange extraordinary excursions, then a tip would be appreciated. This depends on your own preferences and if the services provided exceeded your expectations.

Tipping the villa staff : It also is not customary to tip your villa staff, but if they go above and beyond for you and provide an exceptional service during your two week stay, then you can tip. During your stay at the villa, there will be a cook who comes in everyday to prepare us breakfast (this is included in the trip cost) and if you feel he/she did a good job, feel free to tip at the end of your stay. The only other staff you will see during your stay besides your Italian host is the cleaning staff who will come every Saturday to clean and change linens. If you also feel that they did an exceptional job, you are more than welcome to tip them but again it is up to you. 

Many Italians will only leave a tip for very exceptional service, so it is completely up to you who and when to tip.

Medical Facilities

The U.S. Embassy in Italy’s website has a list of doctors and medical facilities in various cities throughout Italy. In the unlikely case of a medical emergency, you will be taken to a medical facility of good standing.

Special Events

During your stay, there will be several festivals and events being held in and around the regions of Umbria and Tuscany. Our Italian host will inform us of any special events. You can also see below for some events happening during your stay.

May Trips

The Oldest and the Biggest Antique Fair

Many years ago, Ivan Bruschi gave life to one of the oldest and biggest antique fairs in Tuscany…maybe even all of Italy. He transformed his love for the old, unique and precious into an event that fills the streets of Arezzo every first Sunday of the month and the Saturday that precedes it that month. So mark your calendars for May 5 & 6th – and be sure to leave some time to explore the museums and churches in Arezzo.

Arezzo Antiques Fair

Below is a link to more festivals taking place in the month of May :

Tuscany May Festivals

August/September Trip

Traditional games & Winemaking tradition

On the last Sunday of August, this exciting race takes place along the tiny, steep streets of the village between the 8 contrade (districts) and whoever is the fastest to push their heavy wooden wine barrel (called botti in Italian) along the uphill streets of the historical center to the finish line in front of the Duomo in Piazza Grande wins the Bravio (a painted banner depicting the patron saint). Click here for more detailed information.

Arezzo medieval games

It’s one of the most eagerly awaited events that Tuscans love to celebrate, during which the whole city turns back into a medieval town to recreate the atmosphere of yesteryear. Festivities start a week earlier, giving life to a rich calendar of daily events and culinary meet-ups that end with the Joust on the first Sunday of September. A competition between the 4 quarters of the city to win the Gold Lance, with parade in historical costumes, drummers and flag-throwers. Click HERE for more information.

Below are links to more festivals taking place in the months of August and September :

Tuscany August Festivals

Tuscany September Festivals

The tap water in Italy is safe to drink and by drinking the tap water instead of bottled water, you can help alleviate the plastic waste epidemic. Many consider the tap water in Italy to be superior, especially in the region we are staying. Most restaurants in Italy will ask if you would like water upon being seated. There is usually a choice between sparkling and flat water. Most restaurants do not serve tap water, but you can ask and they will usually oblige.
In our villa there is a small pantry with basic goods such as toilet paper, bottled water, laundry detergent and of course wine! If you prefer bottled water, it will be for purchase at the villa. This will be on an honor system and whatever you take from the pantry must be written down and your bill will be tallied up at the end of your stay.

Nationals of Australia, Canada and the United States do not need a visa for a stay up to 90 days. Your passport needs to be valid for at least six (6) months after the date you plan to exit Italy or the Schengen Area. Nationals of the European Union (EU) countries can stay for an unlimited period.

If you are not a citizen of one of the above mentioned countries, please check with your nearest Italian embassy or consulate for information on visas and travel to Italy.


Once you have booked your flights, please send us your flight information. There are 2 possible cities that you can fly into : Rome or Florence. Our villa is exactly halfway between both cities (2 hours by car). It is your choice which airport to arrive at and depart from.

Please note that if your flight lands within 30 minutes of another travelers’ flight, you will share a taxi to the villa. If the time exceeds 30 minutes, you will not have to wait for other travelers  and will be taken directly to the villa.

*Please do not book any flights until you receive a confirmation from us which will be sent to you within 1 ~ 2 business days after paying your deposit. 

When to Go to Tuscany/Umbria

Like many of its European neighbors, Tuscany and Umbria’s tourist season peaks during the summer months and can lead to an uncomfortable mix of high temperatures and crowds. Even then, the weather can vary from region to region in Tuscany and Umbria, as its mountains and hills tend to remain cooler than its valleys and coastline.

The first trip will take place in May. You can expect daytime temperatures in the 70s and nighttime temperatures in the mid-50s to low 60s.

You can read more about the weather by clicking the link below :

Tuscany/Umbria in May

The second trip will take place at the end of August and beginning of September and the temperatures are warm during the day and cool at night. You can expect daytime temperatures in the 80s and nighttime temperatures in the 60s.

You can read more about the weather by clicking the link below :

Tuscany/Umbria in September

Tuscany/Umbria in August

You can zoom in and out on the map by pressing the plus and minus buttons to the right.  If you would like to look up the location on your Google Maps you can type in ‘Villa Podere Baiocco‘.

Villa Baiocco is a historic Tuscan farmhouse dating back to the 1700s. The villa was recently converted into a prestigious holiday home without losing the farmhouse’s unique character and charm. Surrounded by 20,000 square meters (5 acres) of well-kept gardens, it offers the peace and tranquility of the Italian countryside with the convenience of being very close to many sites.

The property has 2 main living areas : the main villa with 7 rooms and an adjacent house with 3 rooms, each room with an ensuite bathroom. You can find pictures and a detailed description of the rooms under the tab above labeled ‘Rooms.’ 

You can take a virtual tour of the villa by clicking HERE. Note that it is all in Italian so please refer to the following in order to understand what you’re looking at :

  • Camere Lato Este : Rooms #1, 2, 4
  • Camere Zona Centrale : Rooms #6, 7
  • Camere Lato Ovest : Rooms #5, 3
  • Parco – Piscina : Patio & pool
  • Sala de Pranzo : Dining room
  • Cucina : Kitchen
  • Sala Colazioni : Smaller dining room
  • Palestra : Fitness room
  • Sala Massagi : Massage room
  • Parcheggio : Parking area
  • Entrata : Property entrance
Villa Exterior :

Pool (The villa has 2 pools on the property) : 

Villa Interior :


Exterior of the house:

Interior of the house : 


We recommend that you purchase trip/travel insurance for your trip. We work with Travelex, which offers travel protection plans to help protect you and your travel investment against the unexpected. Travel protection plans include coverage for Trip Cancellation, Trip Interruption, Emergency Medical and Emergency Evacuation/Repatriation, Trip Delay, Baggage Delay and more. Otherwise, you are welcome to shop around online for a provider and policy that best suits your needs.

For more information on the recommended plans or to enroll, click on the image below or contact Travelex Insurance Services at 800-228-9792. Globe Drifters’ reference location number is 09-0984.

The product descriptions provided here are only brief summaries. The full coverage terms and details, including limitations and exclusions, are contained in the insurance policy. Travelex CA Agency License #0D10209. All products listed are underwritten by, Berkshire Hathaway Specialty Insurance Company, NAIC #22276. 11.17 E7N


Below is information from the CDC and its recommendations regarding vaccinations for travel to Italy.

CDC Italy

Room Descriptions

There are 7 rooms in the main villa. 2 rooms have twin beds and 5 rooms have double beds. In the second house, there are 3 bedrooms all with double beds. All rooms have ensuite bathrooms. After you book, you will be asked about room preferences in a questionnaire. Room selection is on a first-come, first-served basis. Most rooms are similar in quality and size, but some rooms have extra features like sitting areas. For example, one room has direct access to the garden and a few rooms have a small living area connected. There are only 2 rooms with twin beds available. Once they are taken, you will either need to share a bed with a partner or pay the single supplement. *Please note that casa rooms will become available for booking once all villa rooms have been filled.

You can take a virtual tour of the villa by clicking HERE. Note that it is all in Italian so please refer to the following in order to understand what you’re looking at :

  • Camere Lato Este : Rooms #1, 2, 4
  • Camere Zona Centrale : Rooms #6, 7
  • Camere Lato Ovest : Rooms #5, 3
  • Parco – Piscina : Patio & pool
  • Sala de Pranzo : Dining room
  • Cucina : Kitchen
  • Sala Colazioni : Smaller dining room
  • Palestra : Fitness room
  • Sala Massagi : Massage room
  • Parcheggio : Parking area
  • Entrata : Property entrance
Main Villa
Room #1 – Ground floor with access to the patio/lawn area.  This is 1 of 2 twin rooms. 

This room is sold out for all trip dates.

Room #2 – Ground floor with access to the patio/lawn area.  This is 1 of 2 twin rooms. 

May 4 – 18, 2019 Trip : AVAILABLE  //  May 18 – June 1, 2019 : AVAILABLE  //  August 24 – September 7, 2019 Trip : AVAILABLE

Room #3 – 1st floor with adjacent private sitting area with fireplace. 

This room is sold out for all trip dates.

Room #4 –  Ground floor with access to the patio/lawn area.

This room is sold out for all trip dates.

Room #5 – Basement with adjacent private sitting area containing TV, fireplace, private kitchenette and direct access to the garden.

This room is sold out for all trip dates.

Room #6 – 2nd floor with fireplace.

May 4 – 18, 2019 Trip : SOLD  //  May 18 – June 1, 2019 : SOLD  //  August 24 – September 7, 2019 Trip : AVAILABLE

Room #7 – 2nd floor with whirlpool tub/shower combination.

May 4 – 18, 2019 Trip : AVAILABLE  // May 18 – June 1, 2019 : SOLD  //  August 24 – September 7, 2019 Trip : SOLD

Casa Room #1 – 1st floor with private sitting area. Living area, pool table, full kitchen and half bath shared with 2 other rooms (Casa Rooms #2 and #3).

May 4 – 18, 2019 Trip : AVAILABLE // May 18 – June 1, 2019 : AVAILABLE // August 24 – September 7, 2019 Trip : AVAILABLE

Casa Room #2 – 1st floor. Living area, pool table, full kitchen and half bath shared with 2 other rooms (Casa Rooms #1 and #3).

May 4 – 18, 2019 Trip : AVAILABLE // May 18 – June 1, 2019 : AVAILABLE // August 24 – September 7, 2019 Trip : AVAILABLE

Casa Room #3 –  Ground floor. Living area, pool table, full kitchen and half bath shared with 2 other rooms (Casa Rooms #2 and #1).

May 4 – 18, 2019 Trip : AVAILABLE // May 18 – June 1, 2019 : AVAILABLE // August 24 – September 7, 2019 Trip : AVAILABLE

All villa and casa rooms have ensuite bathrooms. Room sizes vary, but most are very similar in size and quality. All bathrooms have a toilet, sink, shower and some have a bidet.

Trip Date

MAY 18, 2019
USD $2,700

Price based on double occupancy. Single Supplement can be purchased for an additional $650.

MAY 18
JUNE 1, 2019
USD $2,700

Price based on double occupancy. Single Supplement can be purchased for an additional $650.

USD $2,700

Price based on double occupancy. Single Supplement can be purchased for an additional $650.