Day 1 : Italy Arrival
Welcome to Italy! Airport pick-up has been arranged to take you to your private villa in the hills of Umbria. Your trip leader will be waiting for you at the villa and will show you to your room. There will be welcome drinks and hors d’oeuvres waiting for you upon arrival. You have the rest of the day to explore your new home.
Later that evening, there will be a welcome dinner. The dinner will be traditionally Tuscan and served at the villa as you get to know your fellow travelers.
Included :
- Transfers: Rome – Villa (approx. 2 hours)
- Activities: Villa transfer
- Meals: Welcome drink and hors d’oeuvres, Dinner
- Accommodation: Villa
NEXT DAY Day 2 : Citta Della Pieve
Start the day with an orientation walk of the nearby town of Città della Pieve (approximately 20 minutes by foot from the villa). Your trip leader will point out local landmarks, restaurants, cafes, grocery stores as well as the bank, pharmacy, post office and anything else that you might need during your stay. Afterward, we suggest a passeggiata (leisurely stroll) to take in the sights, sounds and smells of the outdoor cafes and local shops sprinkled around this ancient town.
As you explore, you will see why Città della Pieve won the first Pio Alferano Prize as the most perfect city in Italy. The prize judges said this about the 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.”
Later that evening, we suggest dinner together at one of the many restaurants in town.
*There will be a daily shuttle that is included in the trip cost and goes from the villa into town at 7:oo PM.
Included :
- Activities: Citta della Pieve orientation walk; Free time
- Meals: Breakfast
- Accommodation: Villa
NEXT DAY Day 3 : Montepulciano and Pienza
Head to Montepulciano (approximately 1 hour drive from the villa) which is renowned for its Vino Nobile Montepulciano wines. You will get a chance to taste these famous wines at a wine cellar that dates back to the 16th century. A wine connoisseur will guide you through the cellar and teach you all about the history of the cellar and the aging process. After the wine tasting, you will have some free time in Montepulciano to do some shopping or discover it by train as you pass by some unbeatable landscapes.
Next up is Pienza (approximately 20-minute drive from Montepulciano), a beautiful Renaissance town surrounded by panoramic views of Orcia Valley. This town has been defined as the ideal city thanks to Pope Pius II who endeavored to transform his hometown into the “perfect town”. You will have some time to wander around Pienza’s hidden alleyways and cobblestone streets and enjoy the small shops in the town center. Don’t miss out on Pienza’s specialty: a pecorino sheep’s milk cheese which you can taste and buy at stores in the town.
Included :
- Activities: Montepulciano wine cellar tour & tasting; Montepulciano free time; Pienza free time
- Meals: Breakfast, Lunch
- Accommodation: Villa
NEXT DAY Day 4 : Assisi
Make your way to Assisi (approximately one hour drive from the villa) which many of our past travelers have said is their favorite town in all of Italy! Assisi is a hilltop town in the beautiful region of Umbria with charming lanes, massive gates and stone buildings. The town is famous for being the birthplace of St. Francis of Assisi, one of Italy’s most venerated saints, and has attracted pilgrims from all over the world for over 700 years. The gigantesque Basilica Saint Francis was built in his honor right after his death and is covered in some of the best preserved and vibrant frescoes in all of Italy. After lunch, enjoy some free time to explore and do some shopping. Be on the lookout for unique jewels inspired by Saint Francis that are only made in Assisi.
Included :
- Activities: Assisi tour; Basilica of Saint Francis; Assisi free time
- Meals: Breakfast, Lunch
- Accommodation: Villa
NEXT DAY Day 5 : Free Day
Today is a free day to do as you wish and we highly recommend a hands-on cooking class. Prepare some of Tuscany’s most popular dishes at the villa with an Italian chef. Get ready to learn how to make the best tiramisu you’ve ever had!
Alternatively, you could visit the beautiful town of Orvieto sitting upon a plateau overlooking the valley. The city is filled with a wide variety of museums and monuments that are all located within walking distance from each other and built over a vast honeycomb of caves, tunnels and cellars. Also, don’t miss Orvieto’s beautiful duomo (cathedral)!
The choice is yours and your trip leader will be there to help with logistics and reservations as well as suggested activities.
Included :
- Activities: Free day (trip leader can recommend activities for you)
- Meals: Breakfast
- Accommodation: Villa
NEXT DAY Day 6 : Val d'Orcia
Get ready for an authentic experience far away from the main tourist attractions. Travel along the winding roads of Val d’Orcia where some of Italy’s best pecorino cheese is produced. Surrounded by towering cypress trees over softly rolling hills stretching toward the blue sky, Val d’Orcia is right from a postcard.
Spend the day in the heart of the Tuscan countryside with Giancarlo and his brother, the owners of a family sheep and cheese farm. They will welcome you to share their passion for nature and pecorino secrets with you. Learn about how they work the land, raise the animals and produce cheese as you see, smell, feel and taste every step of this family’s everyday life over the generations. Not only will you experience one of the best cheese tastings in Italy, but their enthusiasm and infectious smiles will put a smile on your face too!
Included :
- Activities: Sheep farm tour; Cheese making demonstration; Cheese and wine tasting
- Meals: Breakfast, Lunch
- Accommodation: Villa
NEXT DAY Day 7 : Free Days
All remaining days are completely free to do as you wish. You can choose to relax by the veranda with a glass of wine or explore some more.
We recommend a day trip to Maggiore Island (approximately 20-minute drive from the villa followed by a short boat ride), one of three islands on Trasimeno Lake. Visit the church from the 14th century, walk around the narrow village streets, shop in the small craft shops, go for a peaceful walk in the olive groves overlooking the lake and try the fish caught fresh from the lake.
Or you might choose to rub shoulders (literally!) with the locals and visit the famous Saturnia Hot Springs. Bring your water shoes and get ready to relax in thermal waters, cascades and natural pools that remain a toasty 96Fº year-round.
Alternatively, we suggest a day trip to Siena or Florence which are both easily accessible by train. You could also go truffle hunting closer to the villa and try your hand at finding a tasty treat. Or pamper yourself at a thermal water spa with over 20 wellness experiences.
The choice is yours and your trip leader will be there to help with logistics and reservations as well as suggested activities.
Included :
- Activities: Free day (trip leader can recommend activities for you)
- Meals: Breakfast
- Accommodation: Villa
NEXT DAY Italy 10-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, and this villa is no exception. We have made the single supplement as affordable as possible as many of our clients are solo travelers.
If you decide at the booking stage that you want a single room throughout the trip, you can purchase a single supplement. The single supplement fee for the 10-day trip is $350. If you decide later that you would like your own room, you can buy the additional supplement and pay at check-out.
*There is no single supplement for rooms #1, #2 & #3 in the villa and room #3 in the casa due to size limitations. Please see the ‘Rooms’ tab for more information on this. At check-in, you will be asked to give your room preferences and all rooms are assigned on a first-come-first-served basis.
What is included :
- 9 nights accommodation (double occupancy) in a private villa
- Trip leader
- International airport pick-up from Rome*
- Breakfast served daily
- Welcome dinner
- 3 lunches
- Activities as noted on the itinerary
- Daily evening shuttle from villa to town
*Villa transfer is only included for guests arriving on Day 1 or if you’re arriving on another day and staying in Rome. If you have made your own arrangements before the trip, your villa transfer will not be included.
What is not included :
- Most dinners & lunches
- Gratuities
- Optional activities and excursions
- Souvenirs
- International airport drop-off
- International flights
- Supplementary insurance
During the first few days of your slowcation, there are activities and excursions that are included in the trip cost. These are a great chance to help you get to know your fellow travelers and get familiarized with your new surroundings.
There will also be sign-up sheets for optional activities and excursions that you can join, but it is completely your choice of what to do in your free time. Again, it is your choice which activities you want to participate in and you are free to plan events, host dinners, or organize trips/excursions for the group or just for yourself.
In the main salon of the villa, there will be a whiteboard that you can post announcements on. If you would like to host a happy hour before dinner one night or if you want to cook for a night with your fellow travelers, just can add this announcement to the whiteboard.
Find out more about how our slowcations work by clicking here: HOW IT WORKS.
Each group usually consists of 8 – 14 travelers. We prefer small group travel because based on our experience, small groups are more easily able to integrate into local society and generally have more authentic contact with the locals.
A small group number also means that you will receive more personalized treatment from the trip host who can thoroughly attend to the needs of each person. Small groups are also more mobile and flexible as travel plans can be easily altered. If the group discovers a special event or festival that they would like to attend, it is easier to organize with a smaller group.
Città della Pieve is the town closest to our villa. It is a wonderful place to relax and we are usually the only tourists in town! It is a 20-minute walk from the villa into town. When going into town, there is a gradual incline for about 5 minutes and then, it flattens out. If picking up groceries, we will have a small shopping bag/cart with wheels that many Italians use to take their groceries home so you will not have to carry them.
Città Della Pieve is a charming medieval town of just over 7,000 residents that dates back to the 1300s. It is situated on a hill that is about 1,660 feet above sea level and overlooks Chiana Valley. The town is located in Umbria and is just under 2.5 miles from the neighboring region of Tuscany.
It has all the amenities you need while maintaining all the characteristics of a small, quaint town. There are several eateries and cafes to choose from and its grand wall that was for protection from invaders is magnificent. Città della Pieve also won the first Pio Alferano Prize as the most perfect city in Italy and is home to the current Italian Prime Minister, Mario Draghi.
Additionally, Città Della Pieve has several beautiful churches, a lovely art museum, an opera house, and other interesting historical sites that will keep you busy during your stay.
The closest train station to our villa is Chiusi which is a 15-minute drive from the villa.
Here are some of the cities closest to the villa and the time it takes to get there from the villa:
- Montalcino – 1 hour
- Chianti – 2 hours
- Siena – 1 hour
- Cortona – 1 hour
- Montepulciano – 45 minutes
- Orvieto – 30 minutes
- Assisi – 1 hour
- Perugia – 45 minutes
- Arezzo – 40 minutes
- Rome – 2 hours
- Florence – 2 hours
- Bagno Vignoni (hot spring) – 40 minutes
- Civita di Bagnoregio (the dying town) – 1 hour
The villa is halfway between Florence and Rome and on the border of Umbria and Tuscany making it ideal for exploring the region. You can check out the location of the villa on the map in the corresponding tab above.
Most of our travelers are in their late 30s – early 70s with many being solo female travelers. Generally, we get a good mix of diverse people and every trip is unique thanks to the energy created by the group. Past travelers have told us that the group dynamic was one of the highlights of the trip.
The minimum age on our tours is 18.
If you would like to see pictures from our past trips to see who goes on our trips and what we do, please click the link below:
Tuscany/Umbria Villa Slowcation Photos
When most people arrive, they want to hit the ground running, so we have included excursions at the beginning of each trip. That way, you have activities to do upon arrival and then, you can arrange your optional excursions for later dates. These excursions are included in the cost of the trip. Thereafter, you will have your choice of activities at an additional cost. It is completely up to you how you spend your free days.
NOTE: Payment for the optional activities offered at the villa is in cash only.
There will be a sign-up sheet for activities that might interest you (cooking class, sheep farm, cheese tasting, truffle hunting, antique shopping, etc.) You can choose to join based on your interests. Most of the popular places in the area are easily reachable by train or if enough people sign up, you can rent a van for the day. Your trip leader and your Italian guide will be there to facilitate and arrange activities and excursions as well as make any necessary reservations.
Most everything in this area does not require advanced purchase so just arrive and let us handle it for you while you enjoy your Slowcation!
If you would like to read up on different activities and landmarks in Città della Pieve, click the following link: Città della Pieve Information Page.
The official currency of Italy is the euro (EUR).
Find out the live mid-market rate for your currency by using a currency converter online.
We strongly recommend using ATMs while in Italy as they usually offer the best exchange rates. The easiest way is to pull money out from the ATM at the airport upon arrival and throughout your trip. It is always a good idea to carry some cash on you in case your bank puts a hold on your ATM card.
You can find ATMs at almost all bank branches as well as at most large supermarkets, some petrol stations, shopping malls, airports, and post offices. There is a bank very close to the villa so you won’t have any issues finding an ATM.
It’s important to tell your bank and/or credit card company that you’ll be using your card in Italy. Some banks block transactions in foreign countries or currencies if they haven’t been forewarned about your travel plans.
Since euros are a popular currency, most banks in your home town/city will exchange your local currency for euros. This a very convenient way to get euros, but be aware that some banks might not have favorable exchange rates or charge additional fees to exchange. It is best to check with your bank to see what fees are associated with exchanging money in your home town.
We recommend having access to anywhere between 600 to 900 euros during the duration of your stay based on past customers’ feedback. We strongly advise budgeting more than you plan to spend in case of an emergency.
Passport holders of Australia, Canada, and the United States do not need a visa for a stay of 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.
If you hold a passport from another country, it’s best to contact your nearest embassy or consulate about entry requirements.
As a general rule, passports should have at least six months of validity when traveling internationally. Most countries will not permit a traveler to enter their country unless the passport is set to expire at least six months after the final day of travel.
When using your phone overseas, be sure to check with your provider to get informed about data and call roaming prices. When you land in Italy, you will usually get a message from your provider that will give you the price of data, calls, and texts in that country. See the example below:
Welcome to Italy! Your plan gives you unlimited data at up to 2G speeds and texts at no extra cost. Calls at 20 cents/min. Want our fastest data and unlimited calls? Get an International Pass for just $5/day.
You may consider contacting your service provider to learn about what kind of international plans they offer for calls, texts, and data.
You can connect to Wifi at most cafes and restaurants. The villa has Wifi in some general living areas and some rooms, but it is spotty, slow, or absent in some areas of the villa as well as some bedrooms. If you absolutely need an internet connection, then it might be best to get an international plan for the duration of your stay.
In Italy, there are three associated plug types: types C, F, and L. Italy operates on a 230V supply voltage and 50Hz.
Below are examples of the three different plug types in Italy (C, F, and L):


Below are a few things that we suggest bringing to make your trip more comfortable:
- Comfortable walking shoes (good traction & ankle support for cobblestone streets)
- Sunglasses/hat
- Sunscreen (biodegradable, if possible)
- Warm coat/scarf/ warm clothes
- Swimsuit (for spa or hot springs)
- Water shoes (for hot springs)
- Mosquito repellent
- Shampoo/conditioner/soap*
- Small backpack or across-the-shoulder bag for day trips
- Any prescription medication and/or over-the-counter medicine
- Adapters
- Flashlight/headlamp
- Reusable water bottle
*All rooms are equipped with a hairdryer. Some small toiletries such as hand soap and shampoo are also provided in your room but it’s best to bring or buy your own as they are sample sizes.
The 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.
Basic essentials are provided at the villa such as:
- Dish soap
- Dishwasher soap
- Paper towels
- Toilet paper
- Sponges
- Laundry detergent
- Trash bags
- Spices (there are fresh rosemary, basil, and sage plants on the property that you can pick from for cooking)
- Coffee w/creamer and sugar and tea bags
Coffee will be served at breakfast from 8-9 AM and they have a proper coffee machine for lattes, cappuccinos, etc. We will also provide coffee and creamer in case you are an early riser and would like yours before 8 AM.
There is a groundskeeper on the property who will come to the villa every other day to take out the trash and to do general upkeep of the grounds. Maid service comes in weekly to change bed linens and towels as well as to clean the rooms.
Inside the villa, there is a pantry that has both red and white wine from the vineyards surrounding your villa for sale. Also in the pantry is a small selection of local beer and olive oil. All of these items are for purchase and will be done on the ‘honor code‘. Anything you take from the pantry you must make a mark next to your name on a corresponding list and then we will tally your bill at the end of your stay.
The tap water in Italy is safe to drink and many consider tap water in the Città della Pieve to be superior as it comes clean and fresh directly from the mountains. By drinking tap water instead of bottled water, you can help alleviate the plastic waste epidemic.
If you go to larger cities such as Rome or Florence, you can buy bottled water if you would like. Many travelers have said that they don’t enjoy the taste of the water in the bigger cities, but it is still safe to drink.
Italy does not have a strong tipping culture. In restaurants, taxis, and for personal services, all tips are at your discretion. If you do decide to tip, around 10-20% of the total bill is appreciated.
Tipping your trip leader: If you feel he/she did an exceptional job, then you can tip anywhere between 8 – 15 euros a day based on past travelers’ feedback.
Drivers: when going on an excursion, a suggested amount to tip your driver is around 5 euros a day.
Breakfast staff: A waiter/waitress will be there every morning to prepare your breakfast and favorite hot drinks. We recommend tipping 20-30 euros at the end of your stay.
For more information about tipping your guide, please see our blog on tipping your tour guide.
Most areas of Italy that you will visit on this trip experience fewer crimes compared to bigger U.S. and European cities. As with any travel destination, it is important to be aware of your surroundings with a secure over-the-shoulder day pack that closes tightly. This way your belongings won’t easily become the property of any purse snatchers or pickpockets. When going to larger cities such as Rome and Florence pick-pocketing is much more common and you should not put anything in your back pockets, especially if you are on a crowded bus/train or at a crowded tourist spot as thieves target these areas.
Please review the CDC Health Information for Travelers Website before traveling to Italy to see any recommended vaccinations.
If you suffer from pre-existing medical conditions or are concerned about what vaccinations may be right for you, we strongly advise that you visit a medical professional or your personal physician before your trip.
Yes, we offer private tours to Italy for groups of 5 or more people. The itinerary can be entirely tailored to your needs while you will enjoy a personalized experience with our guides and your friends and family.
If planning a family reunion or a trip with friends we can take care of all the details and work with you to create an amazing experience!
Please contact us at info@globe-drifters.com for more information.
Visa
Nationals of Australia, Canada, and the United States do not need a visa for a stay of up to 90 days. Your passport must be valid for at least six months after the date you plan to exit Italy or the Schengen Area.
If you are not a citizen of one of the above-mentioned countries, please check with your nearest embassy or consulate for information on visas and travel to Italy.
Flights
Your arrival and departure city are Rome (FCO).
Please do not book any flights until you receive a confirmation from us.

Our villa is a historic Tuscan farmhouse dating back to the 1700s. The villa was recently converted into a prestigious holiday home while preserving 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 centrally located to many unique sites.
The property has 2 main living areas: the main villa with 7 rooms and an adjacent house with 3 rooms. Each room has an ensuite bathroom. You can find pictures and a detailed description of the rooms under the ‘Rooms’ tab above.
Pool (The villa has 2 pools on the property)
There are 7 bedrooms in the main villa and there are 2 bedrooms in the casa. All rooms have ensuite bathrooms of varying sizes. After you book, you will pick your top 3 room choices. Most rooms are similar in quality and size, but some rooms have extra features like sitting areas. Some rooms do not require a single supplement and 1 room is reserved for 2 people who are sharing. Please read the description of each room before making your room selection. All rooms are assigned on a first-come-first-served basis. The sooner you book the better chance you have of getting the room you prefer.
Villa Room #1
This room has no single supplement as it is a smaller sized bedroom and bathroom. The beds can be converted into a full bed or left as two twin beds. This room is located on the ground floor.
Villa Room #2
This room has no single supplement as it is a smaller sized bedroom and bathroom. The beds can be converted into a full bed or left as two twin beds. This room is located on the ground floor.
Villa Room #3
This room has no single supplement as it is a smaller sized bedroom and bathroom. There is 1 full bed. This room is located on the ground floor.
Villa Room #4
This room is located on the 2nd floor with a large bathroom, fireplace, and a full bed.
Villa Room #5
This room is located on the 2nd floor with a large bathroom, a whirlpool bath, and a full bed.
Villa Room #6
This room is located on the first floor (about 5 stairs to climb) featuring a fireplace, sitting area, a very large bathroom, and a full bed.
Villa Room #7
This room is reserved for 2 people sharing. If you are single you can not choose this room. This room can be a full bed or converted into 2 twin beds. It is located downstairs and has its own very large sitting area, bathroom, kitchen. a TV, and a fireplace.
Casa Room #1
This room is located in the casa adjacent to the villa. The casa has 3 rooms in it with a large sitting area, kitchen, and pool table in the common areas. If you want more privacy the casa is ideal. This room is located on the 1st floor with a sitting area, full bed, and private entrance.
Casa Room #2
This room is located in the casa adjacent to the villa. The casa has 3 rooms with a large sitting area, kitchen, and pool table in the common areas. If you want more privacy the casa is ideal. This room is located on the 1st floor with a full bed.
Bathrooms
All villa and casa rooms have ensuite bathrooms. All bathrooms have a toilet, sink, shower and some have a bidet. There is a half bath in the main villa and the casa 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