The 10 Best Multi-day Tours in Pienza, Tuscany

March 30, 2022 Janette Largent

Pienza, a town in Tuscany, is the "touchstone of Renaissance urbanism." In 1996, UNESCO declared the town a World Heritage Site and in 2004 the entire valley, the Val d'Orcia, was included on the list of Unesco’s World Cultural Landscapes. Pienza was the birthplace of Aeneas Silvius Piccolomini, who would become Pope Pius II. After he became Pope, Piccolomini had the entire village rebuilt as an ideal Renaissance town that would serve as a retreat from Rome.
Restaurants in Pienza

1. Under the Tuscan Sun Four Days Private Tour

Rome-Limousines

This four days tour allows travelers to enjoy the beauties of Tuscany as well as getting a bite of the famous Italian Christian tradition. Four days through breathtaking views, ancient medieval cities, historical vineyards, religious centers of world importance.

Inclusions: Air-conditioned vehicle, WiFi on board, Private transportation, Parking Fees, Tolls

Exclusions: Hotel must be booked by customers at Cortona town or nearby

Reviewed By Alice B

Thanks so much, we loved our tour. Very interesting and Alessandro was so welcoming, respectful and helped us have the best day. Would highly recommend! He even drove us about which was great while tired!

2. Luxury Italy Tour (7days) Rome, Naples (Pompei), Florence & Venice

Limousine Service in Italy

A week to discover the Italian historical, artistic and natural wonders. A private driver at your complete disposal from Rome to Naples (Pompeii, Capri, Sorrento, Positano), Tuscany (Florence, Siena, Pisa, Lucca) and Venice. Private guides and entrance fees are included. You can request to start your holiday from other cities other than Rome. We pick you up from all Italian airports and ports. The tour is totally customizable and you can ask our office to remove or add locations not present in our offer such as the Cinque Terre, Milan, Ferrari Museum, Ravenna, Verona etc. We will design the ideal tour for you according to all your requests. The price of the tour may vary based on the miles, the days you wish to add, the price of tickets and additional services.

Inclusions: Hotel, Apartment, Airport or Port pick up and drop off, English speaking driver at your disposal for 7 days for 24hrs a day., Private tours with licensed tour guides in Rome (8h), Naples (2h), Florence (3h) and Venice (4h), Luxury Mercedes V Class for the 7 days at your disposal 24hrs a day., Rome: Private walking tour of the Colosseum, Roman Forum, Vatican Museums, Sistine Chapel., Naples: Private walking tour of Pompei (2hrs) with a local tour guide., Florence: Private walking tour (3hrs) including the Accademia Gallery with a local tour guide., Venice: Private walking tour (4hrs) including Doge's Palace and St.Mark Basilica , Capri Private Boat tour (8hrs) in Naples. , Skip the line tickets in Rome, Naples, Florence and Venice.

Exclusions: Food and drink

Reviewed By nirmalm2013

We had a very enjoyable and informative all-day tour of Rome and Vatican City. Our guide, Nicola, was very knowledgeable and friendly. He arranged the schedule perfectly and gave us keen insights on each point of interest that we visited. Our driver, Claudio, expertly navigated the routes and was very friendly as well. We engaged Claudio to give us another half-day tour of Castel Gandolfo, which was superb. I strongly recommend Limousine Service in Italy for your travel needs.

3. 11-Day Private Tour of Albania and Italy with Accommodation

Albania Explorer TO & DMC

Europe Explorer Grand Tour “Imperial Route'', or the west side of Ancient Via Egnatia Road, is a great possibility for travelers looking for a special experience by visiting the best of Italy’s (Apennine peninsula) and the Illyrian (Balkan) Peninsula’s ancient and modern civilizations inheritance, which are considered to be the center of Western Civilization. In this tour you will explore and enjoy the rich cultural inheritance, nature, history, traditions, multi-ethnicity, multi-religion, etc. It is a specially designed program, trying to optimize all “must see’' places for Italy and Albania. Important Places to be Visited: Tirana, Durres, Foggia, Pescara, Ancona, Rimini, San Marino, Bologna, Florence, Pisa, Livorno, Siena, Pienza, Tarquinia, Civitavecchia, Rome, Caserta, Naples, Amalfi, and Bari.

Inclusions: Hotel: Accommodation 3* hotels on double occupancy in good locations of respective cities/places., Ferry: Tickets in cabins with private bathrooms., Transportation: Air Conditioned modern van/minibus/bus and other transportation listed in itinerary, Breakfast: Daily breakfast. All other meals not listed are at your expense., Guide: Professional bilingual English, speaking tour guide/leader, etc.

Exclusions: Admission/entry Fees, Travel insurance, visa fees (if applicable), Any charges for additional itinerary are not listed in itinerary, A mandatory service fee for tour guide/bus driver (min. 5-7 Euro /day per person), Excess baggage charges from Airlines, Personal expenses such as room service, telephone, laundry service charges, Losses or additional expenses, Lunch and Dinner charges (if applicable), Everything not mentioned in “Inclusions”

Reviewed By ArmyRangeratMIT

I love a good walking tour! It's the first thing I like to do when arriving to town since it gets you oriented to the major history and then gives you ideas of stuff to see.. We packed so much into the tour. The Square, government buildings, sculpture, orthodox church and mosque - wow so cool, and lots of other little things we eyed up to go back and enjoy.. Rate this one an "A"!

4. 4 Days Guided Tour "Val D'orcia and Chianti" All Inclusive by bus from Brescia

Brescia, Province of Brescia, Italy Aliantour in Europe

A journey in which the historical and artistic aspect is wisely mixed with the naturalistic and food and wine one. Four days full of history, art and culture for an unforgettable tour in Tuscany. A unique land to be enjoyed between Val d’Orcia and Crete Senesi, among excellent wines, truffles, cheeses and cured meats. So we want to recommend an itinerary that will allow you, together with our local guide, to discover all the beauties such as Montalcino, Montepulciano, Pienza, San Quirico d’Orcia, Castellina in Chianti, Siena and San Gimignano. You will be able to travel together with other people with the same passion for travel, allowing for a unique socialization experience. You will have a companion available who can be a point of reference for you; a person who knows the place and to whom you can rely on for any need. Our tours include state-of-the-art coaches and qualified guides. The choice of services is always oriented to the highest quality

Inclusions: Dinner, Breakfast, Dinner, Dinner, Breakfast, Breakfast, Chianti wine tasting in a typical cellar, Recent vintage coach for the whole period equipped with wi-fi, bathroom, air conditioning, Guide as per program: 2 full days + 2 half days, Guide from the starting point for the duration of the tour, 3 nights in a 4-star hotel in Chianciano Terme, assistance from our staff upon arrival at your destination, Medical insurance, Dinners served with a typical local three-course menu

Exclusions: Lunches during the tour, Drinks with meals, Any tourist taxes, Entrance not compulsory Roman Theater € 5.00, Non-compulsory admission to the Cathedral of San Gimignano euro 6.00, Admission not compulsory Church of San Francesco Arezzo euro 8.00, Non-compulsory admission to Piccolomini palace euro 7.00, optional entrance to the Chianti museum euro 5.00

5. 4 Days Guided Tour "Val D'orcia and Chianti" All Inclusive by bus from Milan

Milan, Metropolitan City of Milan, Italy Aliantour in Europe

A journey in which the historical and artistic aspect is wisely mixed with the naturalistic and food and wine one. Four days full of history, art and culture for an unforgettable tour in Tuscany. A unique land to be enjoyed between Val d’Orcia and Crete Senesi, among excellent wines, truffles, cheeses and cured meats. So we want to recommend an itinerary that will allow you, together with our local guide, to discover all the beauties such as Montalcino, Montepulciano, Pienza, San Quirico d’Orcia, Castellina in Chianti, Siena and San Gimignano. You will be able to travel together with other people with the same passion for travel, allowing for a unique socialization experience. You will have a companion available who can be a point of reference for you; a person who knows the place and to whom you can rely on for any need. Our tours include state-of-the-art coaches and qualified guides. The choice of services is always oriented to the highest quality

Inclusions: Dinner, Breakfast, Dinner, Dinner, Breakfast, Breakfast, 3 nights in a 4-star hotel in Chianciano Terme, Guide from the starting point for the duration of the tour, Chianti wine tasting in a typical cellar, Guide as per program: 2 full days + 2 half days, Recent vintage coach for the whole period equipped with wi-fi, bathroom, air conditioning, Dinners served with a typical local three-course menu, Medical insurance, assistance from our staff upon arrival at your destination

Exclusions: Any tourist taxes, Admission not compulsory Church of San Francesco Arezzo euro 8.00, Entrance not compulsory Roman Theater € 5.00, Drinks with meals, Lunches during the tour, Non-compulsory admission to Piccolomini palace euro 7.00, Non-compulsory admission to the Cathedral of San Gimignano euro 6.00, optional entrance to the Chianti museum euro 5.00

6. 4-day guided tour "Val D'orcia and Chianti" All Inclusive by bus from Piacenza

Piacenza, Province of Piacenza, Italy Aliantour in Europe

A journey in which the historical and artistic aspect is wisely mixed with the naturalistic and food and wine one. Four days full of history, art and culture for an unforgettable tour in Tuscany. A unique land to be enjoyed between Val d’Orcia and Crete Senesi, among excellent wines, truffles, cheeses and cured meats. So we want to recommend an itinerary that will allow you, together with our local guide, to discover all the beauties such as Montalcino, Montepulciano, Pienza, San Quirico d’Orcia, Castellina in Chianti, Siena and San Gimignano. You will be able to travel together with other people with the same passion for travel, allowing for a unique socialization experience. You will have a companion available who can be a point of reference for you; a person who knows the place and to whom you can rely on for any need. Our tours include state-of-the-art coaches and qualified guides. The choice of services is always oriented to the highest quality

Inclusions: Dinner, Breakfast, Dinner, Dinner, Breakfast, Breakfast, 3 nights in a 4-star hotel in Chianciano Terme, Guide from the starting point for the duration of the tour, Chianti wine tasting in a typical cellar, Guide as per program: 2 full days + 2 half days, Recent vintage coach for the whole period equipped with wi-fi, bathroom, air conditioning, Dinners served with a typical local three-course menu, assistance from our staff upon arrival at your destination, Medical insurance

Exclusions: Any tourist taxes, Admission not compulsory Church of San Francesco Arezzo euro 8.00, Entrance not compulsory Roman Theater € 5.00, Drinks with meals, Lunches during the tour, Non-compulsory admission to Piccolomini palace euro 7.00, Non-compulsory admission to the Cathedral of San Gimignano euro 6.00, optional entrance to the Chianti museum euro 5.00

7. 4-day guided tour "Val D'orcia and Chianti" All Inclusive by bus from Verona

Verona, VR, Italy Aliantour in Europe

A journey in which the historical and artistic aspect is wisely mixed with the naturalistic and food and wine one. Four days full of history, art and culture for an unforgettable tour in Tuscany. A unique land to be enjoyed between Val d’Orcia and Crete Senesi, among excellent wines, truffles, cheeses and cured meats. So we want to recommend an itinerary that will allow you, together with our local guide, to discover all the beauties such as Montalcino, Montepulciano, Pienza, San Quirico d’Orcia, Castellina in Chianti, Siena and San Gimignano. You will be able to travel together with other people with the same passion for travel, allowing for a unique socialization experience. You will have a companion available who can be a point of reference for you; a person who knows the place and to whom you can rely on for any need. Our tours include state-of-the-art coaches and qualified guides. The choice of services is always oriented to the highest quality

Inclusions: Dinner, Dinner, Breakfast, Breakfast, Dinner, Breakfast, 3 nights in a 4-star hotel in Chianciano Terme, Guide from the starting point for the duration of the tour, Chianti wine tasting in a typical cellar, Guide as per program: 2 full days + 2 half days, Recent vintage coach for the whole period equipped with wi-fi, bathroom, air conditioning, assistance from our staff upon arrival at your destination, Medical insurance, Dinners served with a typical local three-course menu

Exclusions: Any tourist taxes, Admission not compulsory Church of San Francesco Arezzo euro 8.00, Entrance not compulsory Roman Theater € 5.00, Drinks with meals, Lunches during the tour, Non-compulsory admission to Piccolomini palace euro 7.00, Non-compulsory admission to the Cathedral of San Gimignano euro 6.00, optional entrance to the Chianti museum euro 5.00

8. 4-day guided tour "Val D'orcia and Chianti" All Inclusive by bus from Padua

Padua, Province of Padua, Italy Aliantour in Europe

A journey in which the historical and artistic aspect is wisely mixed with the naturalistic and food and wine one. Four days full of history, art and culture for an unforgettable tour in Tuscany. A unique land to be enjoyed between Val d’Orcia and Crete Senesi, among excellent wines, truffles, cheeses and cured meats. So we want to recommend an itinerary that will allow you, together with our local guide, to discover all the beauties such as Montalcino, Montepulciano, Pienza, San Quirico d’Orcia, Castellina in Chianti, Siena and San Gimignano. You will be able to travel together with other people with the same passion for travel, allowing for a unique socialization experience. You will have a companion available who can be a point of reference for you; a person who knows the place and to whom you can rely on for any need. Our tours include state-of-the-art coaches and qualified guides. The choice of services is always oriented to the highest quality

Inclusions: Breakfast, Dinner, Dinner, Breakfast, Dinner, Breakfast, 3 nights in a 4-star hotel in Chianciano Terme, Guide from the starting point for the duration of the tour, Chianti wine tasting in a typical cellar, Guide as per program: 2 full days + 2 half days, Recent vintage coach for the whole period equipped with wi-fi, bathroom, air conditioning, Dinners served with a typical local three-course menu, assistance from our staff upon arrival at your destination, Medical insurance

Exclusions: Any tourist taxes, Admission not compulsory Church of San Francesco Arezzo euro 8.00, Entrance not compulsory Roman Theater € 5.00, Drinks with meals, Lunches during the tour, Non-compulsory admission to Piccolomini palace euro 7.00, Non-compulsory admission to the Cathedral of San Gimignano euro 6.00, optional entrance to the Chianti museum euro 5.00

9. 4-day guided tour "Val D'orcia and Chianti" All Inclusive by bus from Bologna

Via Stalingrado, 71, 40128 Bologna BO, Italy Aliantour in Europe

A journey in which the historical and artistic aspect is wisely mixed with the naturalistic and food and wine one. Four days full of history, art and culture for an unforgettable tour in Tuscany. A unique land to be enjoyed between Val d’Orcia and Crete Senesi, among excellent wines, truffles, cheeses and cured meats. So we want to recommend an itinerary that will allow you, together with our local guide, to discover all the beauties such as Montalcino, Montepulciano, Pienza, San Quirico d’Orcia, Castellina in Chianti, Siena and San Gimignano. You will be able to travel together with other people with the same passion for travel, allowing for a unique socialization experience. You will have a companion available who can be a point of reference for you; a person who knows the place and to whom you can rely on for any need. Our tours include state-of-the-art coaches and qualified guides. The choice of services is always oriented to the highest quality

Inclusions: Dinner, Breakfast, Breakfast, Dinner, Dinner, Breakfast, 3 nights in a 4-star hotel in Chianciano Terme, Guide from the starting point for the duration of the tour, Chianti wine tasting in a typical cellar, Guide as per program: 2 full days + 2 half days, Recent vintage coach for the whole period equipped with wi-fi, bathroom, air conditioning, Medical insurance, assistance from our staff upon arrival at your destination, Dinners served with a typical local three-course menu

Exclusions: Any tourist taxes, Admission not compulsory Church of San Francesco Arezzo euro 8.00, Entrance not compulsory Roman Theater € 5.00, Drinks with meals, Lunches during the tour, Non-compulsory admission to Piccolomini palace euro 7.00, Non-compulsory admission to the Cathedral of San Gimignano euro 6.00, Entrance not compulsory Chianti Museum euro 5.00

10. 4 Days Guided Tour of Chianti by Bus from Florence Train Station and Airport

Stazione Ferroviaria Firenze Santa Maria Novella, Piazza della Stazione, 50123 Firenze FI, Italy Aliantour in Europe

A journey in which the historical and artistic aspect is wisely mixed with the naturalistic and food and wine one. Four days full of history, art and culture for an unforgettable tour in Tuscany. A unique land to be enjoyed between Val d’Orcia and Crete Senesi, among excellent wines, truffles, cheeses and cured meats. So we want to recommend an itinerary that will allow you, together with our local guide, to discover all the beauties such as Montalcino, Montepulciano, Pienza, San Quirico d’Orcia, Castellina in Chianti, Siena and San Gimignano. You will be able to travel together with other people with the same passion for travel, allowing a unique socialization experience. You will have an escort at your disposal who can be a point of reference for you, a person who knows the place and to whom you can rely for any need. Our tours include state-of-the-art coaches and qualified guides. The choice of services is always oriented to the highest quality.

Inclusions: Dinner, Dinner, Breakfast, Breakfast, Dinner, Breakfast, 3 nights in a 4-star hotel in Chianciano Terme, Recent vintage coach for the whole period equipped with wi-fi, bathroom, air conditioning, Guide as per program: 2 full days + 2 half days, Chianti wine tasting in a typical cellar, Dinners served with a typical local three-course menu, Guide from the starting point for the duration of the tour, Medical insurance, Assistance from our staff upon arrival at your destination

Exclusions: Any tourist taxes, Admission not compulsory Church of San Francesco Arezzo euro 8.00, Entrance not compulsory Roman Theater € 5.00, Drinks with meals, Lunches during the tour, Non-compulsory admission to the Cathedral of San Gimignano euro 6.00, Admission not compulsory Palazzo Piccolomini euro 7.00, Optional entrance to the Chianti Museum € 5.00

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