Tuscany/Umbria Villa (1 Week)

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 back to 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 just in time for an amazing Tuscan sunset. Tuscany is the dream vacation that you never got around to doing but now is your chance!

Day 1 : Italy Arrival

Welcome to Italy! 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 week. Once you arrive, why not head into town for the farmer’s market that takes place every Saturday?

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
  • Accommodation : Villa




Day 2 : Umbria

Today is a free day to do as you wish. The villa where we will be staying is in the town  Città della Pieve (approximately 15  minutes on foot from the villa). Why not wander the streets and take in the atmosphere? It’s a captivating town with a vibrant civic life despite its small size with a population of just over 7,000.

There are several excellent outdoor cafes sprinkled around this small town and upon visiting it, you will see the grand wall that used to protect this medieval city that dates back to the 1300s. Città della Pieve also won the first Pio Alferano Prize as the most perfect city in Italy! 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 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.”




During your stay, you will have a local host/guide who will help arrange anything you might need and give suggestions based on your interests. For example, if you need a taxi to the train station and the train schedule to go to Siena, the concierge has you covered.

The location of the villa is halfway between Florence and Rome and is also 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 under the “Map” 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 where you can go 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 – 40 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

Many of us on the trip will not know one another and some will be traveling solo. Thus, upon arrival, there will be an introduction so that 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 on which you can post announcements. If you would like to host an aperitivo before dinner one night, you can add this announcement to the whiteboard. Maybe one night you would like to cook dinner for everyone. You can put the announcement up on the board and invite your fellow travelers. 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.

Included :

  • Activities : Free day (Guide can recommend activities for you)
  • Meals : Breakfast
  • Accommodation : Villa

Day 3 : Pienza and Montepulciano Tour

Today we will head to Pienza which is an hour from our villa. Upon arrival you will have some time to wander around this village with its small alleyways and cobblestone streets. There are many cheese and meat shops as well as stores that will keep you entertained for hours. In 1996, UNESCO added this town to its ‘World Heritage’ list and once you visit, you will see why.

Next, let’s head to Montepulciano which is just a short 20 minute drive from Pienza. Montepulciano is well-known for its Renaissance buildings and lovely churches, but it is especially renowned for the “Vino Nobile” Montepulciano wines. We will get a chance to taste these famous wines at the Talosa Cellar which dates back to the 16th century and a visit here s is like stepping back in time. The brick passageways contain a series of vaults and niches where the barrels are placed. The origin of the cave can be attributed to the Etruscan civilization (5th century BC). You will be guided by a wine expert through the winery and your guide will explain the cellar’s history, aging process and barrels, private collection of old vintages, and a history of Etruscan period while exploring the Etruscan tomb in the cellar. At the end of the guided tour, guests will be seated for a wine tasting. Along with the wine tasting, you will be given lunch as well as some cheese and meats to pair with the wine.  

After the wine tasting and lunch, you will have some free time to walk around Montepulciano and then we will head back to the villa.





Included :

  • Activities : Pienza tour; Montepulicano tour; Wine cellar tour and tasting
  • Meals : Breakfast, Lunch
  • Accommodation : Villa

Day 4 : Assisi Tour

Today, we will visit Assisi which is an hour drive from our villa. We will drive up, up, up to the very top of Assisi and then we can work our way down as we explore what many of our past travelers have said was their favorite town in all of Italy! Assisi is a superb hill town in the beautiful region of Umbria in Italy. To visitors, medieval “hill towns” are like storybook towns that time forgot; they did not develop into big cities over the centuries, but rather kept their narrow lanes, massive gates, stone buildings, and other features we find so charming. But Assisi is much more than a pretty hill town. Thousands come to worship in Assisi’s magnificent churches and to pray to Francis of Assisi, a much-beloved saint.

After our tour of Assisi, let’s stop for some lunch and then make our way back to our villa.


Included :

  • Activities : Assisi tour
  • Meals : Breakfast, Lunch
  • Accommodation : Villa

Day 5: Umbria

Today is a free day to do as you please. We suggest visiting the small town of Orvieto that is just 2 train stops away. Once you arrive at the train stop, you can take the funicular up to the top and then make your way to the amazing church that sits in the middle of town. You can also take an English guided tour of the underground caves and afterwards go shopping for pottery for which this town is famous. Of course, it is completely up to you what you would like to do today. If you want, why not just sit around one of the two pools on the property? Today is your day and of course, your Italian guide will be there to help with any arrangements.

Included :

  • Activities : Free day (Guide can recommend activities for you)
  • Meals : Breakfast
  • Accommodation : Villa

Day 6 : Cortona 

Cortona is a small, charming town in southern Tuscany and upon arrival we will leisurely walk down the main street that is filled with shops and cafes. The city, enclosed by stone walls dating back to Etruscan and Roman times, sits on the top of a hill. This dominant position over the valley offers a spectacular view of the whole town which is most famous for being the filming spot for ‘Under the Tuscan Sun’ and en route to Cortona where we will stop for a quick picture at the villa where the movie was filmed. It is now a private rental, but we can peak over the stone wall to see this magnificent property that now is a popular spot for weddings. Once in Cortona, we will have free time to go shopping, take some pictures of the magnificent vistas and eat gelato! We will meet together for lunch in the plaza. 

The next stop is the Church of Santa Margherita. The story of Saint Margherita is an interesting one and we can learn more about it when we are there. 

End your visit with a stop just outside Cortona’s walls at a hermitage (monastery) founded in 1211 by St Francis of Assisi and his followers. The monastery is still functioning and a small community of friars still live there today. Afterwards, we will head back to our villa.















Included :

  • Activities : Cortona tour; Hermitage visit
  • Meals : Breakfast, Lunch
  • Accommodation : Villa

Day 7 : Umbria

Today is another free day to do as you wish. You could take a day trip to Siena or Florence or you could take a cooking class that is in the town near the villa. The guide will be there to help with arrangements. Today is our last day so why don’t we all come together for a last group dinner at our villa?

Included :

  • Activities : Free day (Guide can recommend activities for you)
  • Meals : Breakfast
  • Accommodation : Villa

Day 8 : Italy Departure

Say goodbye to Umbria and Tuscany and the villa you called home for the last week 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

*Itinerary is subject to change.

Italy 8-Day Trip

$2,900 – 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 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.  

If you decide at the booking stage that you want a single room throughout the tour, you can purchase the “single supplement”. The single supplement fee for this trip is $700. If you would like your own room, you can buy the additional supplement at check out.

*There is no single supplement for rooms #2 & 3 due to size limitations. Please see the ‘Rooms’ tab for more information on this or email : info@globe-drifters.com.  


What is included :

  • 7 nights accommodation in private villa (Double occupancy)
  • Local Italian guide/concierge
  • International airport pick-up from Rome
  • Breakfast served daily
  • Welcome dinner
  • 3 lunches
  • Globe Drifters representative
  • Activities as noted on itinerary

What is not included :

  • Most dinners & lunches
  • Gratuities
  • 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 from 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, 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. June is a great time to visit this area as all the cafes and restaurants open their outdoor terraces.


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 euros 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 where 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 $300 – $700 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…


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. We advise getting an international plan for the duration of your trip.  


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 June can vary, but are generally warm during the day and cool at night. These months have generally little rainfall and cool to warm temperatures with average daily highs in the 70s – 80s°F throughout the month and with the possibility of cooler (60s°F) temperatures at night.

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
  • Bathing suit
  • Small, across the shoulder day bag or small backpack
  • Flashlight
  • Water bottle
  • 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. Please understand that dryers are not common in Europe and the one at our villa can take over 3 hours to dry a small load. The fastest way for your clothes to dry is to put them on a clothes line or drying rack which are also available on the property.


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. Most servers are paid a decent living wage and does not depend on your tips in order to make ends meet.

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 fee.

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 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 as well.

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.

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

Tuscany May 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 available 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. Your arrival city should be Rome which is about 2 hours away from our villa. You can depart from either Florence or Rome.

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. Many travelers choose to visit this area during a shoulder season — April and May or October and November — when these provinces are less crowded.

This trip will take place in May and temperatures are at their best during this time. 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

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, 3
  • Camere Zona Centrale : Rooms #4, 5
  • Camere Lato Ovest : Rooms #6, 7
  • 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 Description

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 your room in the 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.

You can take a virtual tour of the villa by clicking HERE. Note that it is all in Italian.

Main Villa

Room #1 – Ground floor with access to the patio/lawn area. Twin beds.  —  

Room #2 – Ground floor with access to the patio/lawn area. Storage space for clothes is limited in this room so we are waiving the single supplement fee for this room. 

Room #3 –  Ground floor with access to the patio/lawn area. Storage space for clothes is limited in this room so we are waiving the single supplement fee for this room. —  

Room #4 – 2nd floor with fireplace.

Room #5 – 2nd floor 

Room #6 – Basement with adjacent private sitting area containing TV, fireplace, private kitchenette and direct access to the garden.  —  


Room #7 – 1st floor with adjacent private sitting area with fireplace.  — 


Adjacent Casa

Casa Room #1 – 2nd floor with private sitting area. 

Casa Room #2 – 2nd floor

Casa Room #3 –  Ground floor. Private area outside the room.

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 23
MAY 30, 2020
USD $2,900

Price based on double occupancy. Single Supplement can be purchased for an additional $700.

MAY 30
JUNE 6, 2020
USD $2,900

Price based on double occupancy. Single Supplement can be purchased for an additional $700.


  1. Unable to make this one due to virus. Please keep me informed about later in the year trips. I have been to Italy but never stayed in a villa. Sounds awfully exciting!

  2. If we book now, and need to cancel later for any reason, how does that work? How do refunds work?

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