Day 1 : Arrival Day
Welcome to Italy! We’ll pick you up from Rome* and travel by private transport to Città della Pieve, where you’ll settle into our historic boutique hotel in the heart of town. Once you arrive, we’ll welcome you with drinks and hors d’oeuvres. The remainder of the day is yours to unpack, take a swim, or have your first look around the neighborhood. This evening, we’ll gather for dinner at the hotel and get to know our fellow travelers.
*NOTE: Transportation to the hotel is included only if you arrive at Rome Fiumicino Airport (FCO) on Day 1 or are staying in Rome before the trip. If arriving on other dates or at other airports/cities, it is not included. We normally don’t include arrival transportation, but this trip is an exception because the hotel is quite far from a major airport or city.
Airport drop-off is not included. Your slowcation host can help arrange one of the following options:
1.) Private transfer: This can be shared with other travelers departing at similar times. The cost is approximately €400–€450 per vehicle, payable in cash to the driver.
2.) Taxi + train: A taxi to Chiusi costs approximately €25–€35, and can usually be paid by card. The train from Chiusi to the Rome airport (FCO) costs around €30–€50, and tickets can be purchased online by card.
Included :
- Transfers: Rome – Città della Pieve by private transport (approximately 2 hours)
- Activities: Welcome drink & hors d’oeuvres; Welcome dinner
- Meals: Dinner
- Accommodation: Historic boutique hotel
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Day 2 : Citta Della Pieve
This morning, we’ll get acquainted with Città della Pieve alongside a local guide. As we walk through its medieval streets, we’ll see the main landmarks, hear stories from the town’s past, and locate useful spots such as cafés, shops, banks, and pharmacies. We’ll also stop at the Saffron Museum to discover why this prized spice, known as “red gold”, has been part of local life for centuries, followed by a tasting.
Lunch features pici cacio e pepe: hand-rolled pasta tossed inside a large wheel of cheese until rich and creamy, then served straight from the wheel!
The afternoon is yours to spend at your own pace. Take a leisurely passeggiata through the narrow lanes and see why Città della Pieve received the Pio Alferano Prize as Italy’s “perfect city,” recognized for its beauty, art, and laid-back charm.
Included :
- Activities: Citta della Pieve walking tour; Saffron tasting; Free time
- Meals: Breakfast, Lunch
- Accommodation: Historic boutique hotel
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Day 3 : Cooking Class & Orvieto
We’ll spend the morning at a countryside villa surrounded by olive groves and vineyards for a hands-on cooking class. Guided by a local chef, we’ll prepare a selection of traditional Umbrian dishes, then sit down together to share the meal with a glass of regional wine.
Later, we’ll head to Orvieto, an ancient town built high on a plateau of golden stone. Your time here is free to visit the striking Duomo, walk through Etruscan caves hidden beneath the streets, or descend into the 16th-century St. Patrick’s Well. For something more leisurely, settle into a café in the main square with a coffee or glass of Orvieto Classico.
Included :
- Activities: Cooking class; Orvieto free time
- Meals: Breakfast, Lunch
- Accommodation: Historic boutique hotel
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Day 4 : Montepulciano and Pienza
Today, we’ll cross into Tuscany and arrive in Montepulciano. Take time to follow its medieval lanes, admire the Renaissance architecture, and look out over vineyards and the rolling countryside.
From there, we’ll be welcomed at a historic, family-run winery now led by a team of women winemakers. Inside its centuries-old cellars, we’ll hear how the estate’s wines are produced and sample its celebrated Vino Nobile di Montepulciano. A leisurely lunch featuring specialties from the region follows the tasting.
Our final stop is Pienza, a graceful Renaissance town overlooking the Val d’Orcia. Known as Pope Pius II’s “ideal city”, it’s a lovely place to stroll along its cobblestone lanes, go window-shopping, and try the pecorino cheese for which Pienza is known.
Included :
- Activities: Montepulciano free time; Winery tour, tasting & lunch; Pienza free time
- Meals: Breakfast, Lunch
- Accommodation: Historic boutique hotel
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Day 5 : Val d'Orcia
We’ll follow the country roads of Val d’Orcia past cypress trees and rolling farmland to a sheep farm away from the usual tourist route, where some of Italy’s best pecorino cheese is produced.
Brothers Giancarlo and Ulisse will welcome us to the property their family has worked for generations. They’ll share how they raise their sheep and turn the milk into pecorino, giving us a firsthand look at cheesemaking and daily life on a working Tuscan farm. We’ll finish with a generous tasting of their cheeses paired with wine. Their warmth and infectious enthusiasm make this one of the trip’s most memorable days.
Included :
- Activities: Sheep farm tour; Cheese making demonstration; Cheese and wine tasting
- Meals: Breakfast, Lunch
- Accommodation: Historic boutique hotel
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Day 6 : Farm-To-Fork Experience
This morning takes us to an innovative Umbrian farm featured on Stanley Tucci’s Searching for Italy. More than 1,500 varieties of fruits and vegetables grow here, including rare heritage produce rarely seen in ordinary markets. We’ll walk through the property to understand its nature-led approach before gathering for a seasonal brunch made almost entirely with ingredients harvested on-site, accompanied by views over the vineyard.
Included :
- Activities: Farm visit & brunch
- Meals: Breakfast, Brunch
- Accommodation: Historic boutique hotel
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Day 7 : Assisi
Assisi has long been a favorite among our past travelers, and its grand gateways, winding lanes, pale stone buildings, and Umbrian scenery make it easy to understand why.
With our guide, we’ll uncover the history of this important pilgrimage destination and enter the Basilica of Saint Francis. Built in honor of Assisi’s most famous native, the basilica houses remarkably preserved medieval frescoes by some of Italy’s most influential artists.
Following lunch, you’ll have time to discover Assisi independently. Look for the locally crafted jewelry inspired by St. Francis, found only here, or simply take in the atmosphere of this centuries-old spiritual center.
Included :
- Activities: Assisi tour; Basilica of Saint Francis; Assisi free time
- Meals: Breakfast, Lunch
- Accommodation: Historic boutique hotel
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Day 8 : Free Day
A full day has been set aside for you to shape around your interests. Take the train to Florence or Siena, choose another destination in Tuscany or Umbria, or remain in Città della Pieve for a slower day close to the hotel.
Your host can offer guidance on public transportation or help arrange a private transfer with sufficient notice. As this is a semi-independent trip, the day’s plans are completely up to you.
Included :
- Activities: Free day
- Meals: Breakfast
- Accommodation: Historic boutique hotel
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Day 9 : Free Day
Your final full day gives you another opportunity to follow your own plans. Check one more Italian destination off your list, return to a favorite corner of Città della Pieve, or claim a café table and watch daily life unfold over a long coffee or lunch in true Italian fashion.
Included :
- Activities: Free day; Farewell dinner
- Meals: Breakfast, Dinner
- Accommodation: Historic boutique hotel
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Day 10 : Departure Day
After breakfast, our time in Umbria comes to an end. Say goodbye to Città della Pieve and the new friends you’ve made along the way. We hope to travel with you again soon!
*NOTE: Airport drop-off is not included. Your slowcation host can help arrange one of the following options:
1.) Private transfer: This can be shared with other travelers departing at similar times. The cost is approximately €400–€450 per vehicle, payable in cash to the driver.
2.) Taxi + train: A taxi to Chiusi costs approximately €25–€35, and can usually be paid by card. The train from Chiusi to the Rome airport (FCO) costs around €30–€50, and tickets can be purchased online by card.
Included :
- Activities: Free time; Departure (at your own expense)
- Meals: Breakfast
*Itinerary is subject to change.
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10-Day Tuscany/Umbria Slowcation
USD $6,200 – Trip cost per person (What’s included and not included below.)
Deposit
Half the trip cost |
Final payment due
75 days before trip |
Rooms
Single occupancy |
*$300 of the deposit is a non-refundable administrative fee. You can see our full cancellation policy here.
Card payments are subject to a non-refundable processing fee. To avoid fees, you can pay by bank transfer.
Traveling solo?
Every traveler on this trip gets their own room at no extra cost. We do not offer roommate pairing on this trip. Rooms with two beds are limited in small-town Italian hotels, and this hotel is no exception. |
Three room categories are available, first-come, first-served. If you would like a larger room or a room with a balcony, upgrade fees will apply. Please see the ‘Rooms’ tab for more information about them.
What is included :
- 9 nights accommodation (single occupancy)
- Trip host
- Hotel transfer from Rome
- Private, climatized ground transportation
- Breakfast served daily
- 6 lunches, 2 dinners
- Activities as noted on the itinerary
What is not included :
- Visas (if needed)
- Supplementary insurance
- International airport drop-off
- International flights
- Some lunches & dinners
- Gratuities
- Souvenirs
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Our smile policy
We ask all travelers to treat fellow guests, trip staff, guides, hotel employees, and local residents with kindness, patience, and respect throughout the trip. One of the best parts of group travel is meeting people with different personalities, backgrounds, and travel styles, making every trip unique.
A flexible and positive attitude
If you are someone who is easily upset by minor inconveniences or expects everything to operate exactly as it does at home, this may not be the right style of trip for you. Travel does not always go exactly according to plan, so flexibility, an open mind, the ability to let the small things go, and a sense of humor will help you make the most of the trip.
Italy may feel different from home
We encourage you to embrace local customs and differences as part of the fun of traveling in another country. Daily life moves at a different pace in the Italian countryside: some businesses close during the afternoon, dinner is served much later than you’re used to, and restaurants may add a small per-person table charge. At the hotel, beds, pillows, water pressure, air-conditioning, and other amenities may also differ from what you’re used to at home.
Your trip host
Your trip host will accompany the group and assist with check-in, general questions, group coordination, and emergencies. Local guides will lead scheduled tours, and travelers should be comfortable with a reasonable level of independence since the host is not a personal assistant or concierge.
A semi-independent travel experience
This trip includes group activities and free time; if you skip an included activity, you’re responsible for arranging your alternative plans. Your host can offer recommendations, but alternative plans and anything outside the official trip itinerary or dates are yours to arrange and book.
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This trip has a low level of physical difficulty, depending on your fitness and mobility.
To participate comfortably in this trip, you should be able to do the following without assistance:
- Walk approximately 1–2 miles / 1.5–3 km over the course of the day including stairs, inclines, cobblestone streets, and occasional unpaved surfaces.
- Remain on your feet for up to 2 hours at a time while walking or standing, both indoors and outdoors.
- Carry or manage your personal belongings during transfers.
- Get in and out of a passenger van.
Note that some Italian towns we visit require some walking up and down hills and stairs.
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A slowcation lets you settle into one place without constantly packing, unpacking, and changing hotels. You’ll stay at one hotel throughout the trip, with an intentionally relaxed itinerary that balances included activities, free time, and completely free days.
Learn more: HOW SLOWCATIONS WORK.
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We recommend using your free days for a day trip to Florence, Siena, or elsewhere in Tuscany or Umbria, though you can also spend more time getting to know Città della Pieve. Your host can offer suggestions and transportation advice, and many past travelers have called Città della Pieve their favorite town to explore.
For local ideas, visit the Città della Pieve Information Page.
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The hotel is located at the entrance to Città della Pieve’s historic center, within walking distance of restaurants, cafés, shops, pharmacies, and the main sights. Set above the Chiana Valley near the Tuscan border, the town sees few international visitors, and we’re often the only tourists there. It also won the first Pio Alferano Prize as the most perfect city in Italy!
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Our hotel in Città della Pieve is a convenient base for visiting charming towns in both Umbria and Tuscany. Below are some noteworthy towns and approximate driving times :
- Orvieto: 30 minutes
- Arezzo: 45 minutes
- Perugia: 45 minutes
- Siena: 1 hour
- Montalcino: 1 hour
- Cortona: 1 hour
- Rome: 2 hours
- Florence: 2 hours
Some destinations can be reached by train, while others require private transportation. The nearest train station is in Chiusi, approximately 15 minutes from the hotel by taxi. The hotel reception can help reserve a taxi.
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Each group usually has 5–13 travelers. Keeping the group small makes it easier to get to know one another, interact with locals, visit places that can’t accommodate large groups, and remain flexible along the way.
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Most of our travelers are solo travelers in their late 30s through early 70s. Every group is different, and we welcome solo travelers, couples, and people of all genders and sexual orientations. The minimum age is 18.
See photos from previous trips HERE to get a sense of our groups.
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No. Single occupancy is included in the trip price, so every traveler has their own private room without paying an additional single supplement. We do not offer roommate pairing on this trip, and you do not need to bring a travel companion or share a room.
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A hotel transfer from Rome is included if you arrive at Rome Fiumicino Airport (FCO) on Day 1 or are staying in Rome before the trip. Detailed arrival instructions will be provided after booking. You can read more about airport pick-up in Rome here.
Departure transfers are not included. Your slowcation host can help arrange one of the following options:
1.) Private transfer: This can be shared with other travelers departing at similar times. The cost is approximately €400–€450 per vehicle, payable in cash to the driver.
2.) Taxi + train: A taxi to Chiusi costs approximately €25–€35, and can usually be paid by card. The train from Chiusi to the Rome airport (FCO) costs around €30–€50, and tickets can be purchased online by card.
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Most dietary restrictions, including vegetarian, vegan, and gluten-free diets, can be accommodated. Please tell us about any dietary needs or food allergies when booking. Options may be more limited in some restaurants, and we cannot guarantee an entirely allergen-free environment.
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Travel insurance is not required, but we strongly recommend it. Once the refund period outlined in our cancellation policy has passed, we cannot issue a refund due to illness, emergencies, or other personal circumstances; travel insurance may reimburse your non-refundable costs if you cancel for a reason covered by your policy.
See the ‘Insurance’ tab for more information and coverage options.
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The official currency of Italy is the euro (EUR).
Find out the live mid-market rate for your currency by using an online currency converter.
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The easiest way to get euros is from a bank-operated ATM. Avoid independent ATMs when possible, check your bank’s international fees, and always choose to be charged in euros rather than your home currency. You can also order euros from your bank before departure, although the rates and fees may be less favorable.
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Credit and debit cards are widely accepted in Greece, but it’s still a good idea to carry some cash. Small businesses, markets, taxis, and tips may require cash, while Visa and Mastercard are generally accepted more often than American Express and Discover.
Bring a backup card, check whether your bank requires a travel notice, and always choose euros rather than your home currency when paying or withdrawing cash.
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Tipping is appreciated but always optional.
- Trip host: Around €100–€150 per traveler at the end of the trip.
- Restaurants: Around 10% for good service.
- Hotel housekeeping: €1–€2 per day.
- Luggage porters: Around €2 per bag.
Tips for local guides and drivers are not included above and may be given separately at your discretion.
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We recommend budgeting approximately €600–€900 EUR for meals, optional activities, gratuities, and souvenirs not included in the trip price. You may want to budget more in case of an emergency or if you are an avid shopper.
IMPORTANT: Departure transportation from the hotel is not included and may cost approximately €55–€450, depending on the option chosen. See “Are arrival and departure transfers included?” for details.
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Most smartphones will work, but roaming charges depend on your provider and plan. Check your international options before departure, or consider a travel eSIM if your phone is unlocked and compatible.
Free Wi-Fi is available at the hotels and many restaurants and cafés, although speed and coverage may vary.
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The outlets are European-style plug types C and F and operate with 230V/50Hz. (See the picture below.) Converters and/or adapters might be necessary for your electronic devices.
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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)
- Lightweight clothing that dry quickly
- Warm clothing (for cooler days)
- Light and warm jacket/coat/cardigan (for cooler days and nights)
- Scarf (for colder days)
- Rain jacket
- Umbrella (for shade & rain)
- Sunglasses/hat
- Small backpack or across-the-shoulder bag (for day trips)
- Swimsuit (for hotel pool, not heated)
- Reusable water bottle
- Flashlight/headlamp
- Adapters/converters for electronics (bring 2 or more just in case)
- Prescription medication and/or over-the-counter medicine
- Sunscreen (biodegradable, if possible)
- Shampoo/conditioner/soap*
- Washcloth
- Extra bag for souvenirs (if needed)
*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.
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Laundry service is available at the hotel and takes less than 48 hours to complete. The price list will be available at the hotel reception.
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Italy is generally a safe destination, and Città della Pieve has a quiet, small-town atmosphere. As anywhere, stay aware of your surroundings and don’t leave valuables unattended.
Pickpocketing is more common in busy areas of Rome and Florence, particularly on public transportation and near major attractions. Keep valuables secure and avoid carrying phones or wallets in your back pockets.
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Please check the CDC Health Information for Travelers Website for current vaccination recommendations. If you have a pre-existing medical condition or questions about your individual health needs, consult your doctor before traveling.
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We offer private tours to Italy depending on the size of the group and availability.
Please reach out to us at info@globe-drifters.com for more information.
Flights
Your arrival and departure city are Rome (FCO).
*Please do not purchase any flights until you receive an email from us. You will receive an email within 24 – 48 hours of booking your trip.
Visa
US, Australian, Canadian, UK, and EU passport holders traveling to Italy for less than 90 days DO NOT need a visa.
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.
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.
Our hotel has a fascinating history beginning with Vittoria, a daughter of King Vittorio Emanuele II, who scandalously left her husband for a younger man. The couple settled in Città della Pieve, where their family acquired the property that eventually became this charming boutique hotel.
Located at the entrance to Città della Pieve’s historic center, the hotel is just a short walk from churches, museums, boutiques, restaurants, cafés, and the weekly market. Its comfortable, well-equipped rooms and attentive hospitality make it an inviting place to return to each day.
The hotel also has an excellent restaurant serving traditional local cuisine if you feel like staying in for the evening.
Other amenities include a swimming pool, sauna, small fitness center, wine cellar, and elevator.
This hotel has 30 rooms, all with en suite bathrooms. Each room is refined, uniquely decorated, air conditioning, as well as a TV, minibar, safety deposit box, hairdryer, and small toiletries kit.
There is no single supplement for this trip, and every person who signs up will get their own room.
There are 3 room categories available. Superior rooms do not require any upgrade fees, but the Deluxe and Deluxe with Balcony rooms do. Upgrade fees, photos, and brief descriptions are noted below. Please read the description of each room before making your room selection. All rooms are first-come-first-served. The sooner you book, the better chance you have of getting the room you prefer.
Superior Rooms
There are 7 Superior Rooms. All rooms have an en suite bathroom. Each room has a very small sitting area and is refined, uniquely decorated, and equipped with Wifi, air conditioning as well as a TV, minibar, safety deposit box, hairdryer, and small toiletries kit.
There is no upgrade fee for Superior Rooms.
Deluxe Rooms
There are 4 Deluxe Rooms and they are larger than the Superior Rooms. All rooms have an en suite bathroom. Each room has a small sitting area with a loveseat and is refined, uniquely decorated, and equipped with Wifi, air conditioning as well as a TV, minibar, safety deposit box, hairdryer, and small toiletries kit.
The upgrade fee is $365 for a Deluxe Room.
Deluxe Room with Balcony
There is only 1 Deluxe Room with Balcony and it is the same size as the Deluxe Rooms but it has a balcony. It also has an en suite bathroom. Each room has a small sitting area with a sofa and is refined, uniquely decorated, and equipped with Wifi, air conditioning as well as a TV, minibar, safety deposit box, hairdryer, and small toiletries kit.
The upgrade fee is $515 for the Deluxe Room with Balcony.
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, 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
