What to do and see in Pienza, Tuscany: The Best Day Trips from

January 3, 2022 Esmeralda Fenner

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. Valdorcia half day Tour: Pienza and Montepulciano

Piazza Dante Alighieri, 53026 Pienza SI, Italy Tour Guide Siena and Province
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5.0 based on 1 reviews

Tha Valdorcia half daytour includes some of the most beautiful towns of Tuscany like Pienza, birthplace of Pope Pius II, also known as 'the ideal town', and Montepulciano, once property of the powerful Medici family. Visitors will be given an overview to this area, so that in the afternoon they have the time to wonder around alone and taste the great local foods.

Inclusions: Professional guide, Professional art historian guide, Private tour

Exclusions: Food and drinks, Private transportation, Snacks

Reviewed By sd04walker

We enjoyed every second of the tour learning things that we would never have known without our local guide. Definitely recommend the experience!

2. Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

We Drive You Tuscany
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5.0 based on 5 reviews

* Only small, authentic, family-run activities * Off-the-beaten path itineraries * Private, exclusive, customizable, flexible, door-to-door tour of Southern Tuscany, Pienza, Val d'Orcia, Montalcino * Local, small wineries for private visit and wine tastings * 8 hours * Very knowledgeable English speaking local drivers

Inclusions: WiFi on board, Private transportation, Door-to-door pick-up and drop-off, Air-conditioned vehicle, Bottled water

Exclusions: Eventual entrance fees, Lunch, Gratuities, Wine tasting fees

Reviewed By 611lassed

We booked a wine tour for half a day only the night before and received the confirmation following morning! The driver picked us up at our place in Siena with a very nice and comfortable car. Our driver was Roberto, who spoke very well English and is a very funny and nice guy! He could answer all our questions on Italian cuisine and culture in a very passionate way. The wineries we visited were as authentic as you could imagine and they let us try all their best wines! We had an amazing afternoon and wished we’d booked for the entire day. Wedriveyou.it is highly recommended by us and make sure you ask for Roberto!

3. Val d'Orcia private tour: Montalcino, Pienza and Montepulciano

Ciao Florence Tours and Travels
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5.0 based on 3 reviews

Experience the heart of Tuscany by visiting the enchanting Val D’Orcia led by your private driver. Let your personal chauffeur do all the work and take you on a journey through the spellbinding Val D'Orcia countryside, a region known for its scenic beauty, picturesque villages, rolling hills and cypresses! Explore in total freedom the enchanting towns of Montalcino, Pienza and Montepulciano and savour the best wines in the world! The first stop will be Montalcino, land of the world-renowned Brunello wine, a labyrinth of cobbled streets, quaint wine shops and Romanesque-style churches. The following stop is Pienza, which stands high upon a hill and dominates all the Orcia valley with extraordinary views. The last stop reaches Montepulciano, home to the famous Vino Nobile vineyards and more recently famous for the filming of the vampire movie "New Moon". Enjoy your free time in the most elegant village of the entire Val D'Orcia.

Inclusions: 9 hours chauffeur driven hire, Pick up & drop off at your hotel, Bottled water, Free time in Montalcino, Pienza and Montepulciano, Wi-Fi

Exclusions: Guided tours in the villages - Free time only

Reviewed By J Adam K

Took the walking tour today with Safe as our guide. Wonderful experience. Safe spoke flawless English and his passion for Florence, art and history was addicting. We hope to do something similar in the future.

4. Tuscany Pienza and Montepulciano from Rome Private Day Tour

Rome-Limousines
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5.0 based on 1 reviews

This daily excursion from Rome allows travelers to discover and enjoy one of the most beautiful countryside of the world, the famous Valle d' Orcia of Tuscany, Unesco Heritage. It perfectly combines Art, Food, and Relax, principles of a good life.

Inclusions: Air-conditioned vehicle, WiFi on board, toll, Bottled water, Wine tasting, Cheese tasting

Exclusions: Lunch, tickets for monuments and ,museums

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!

5. Brunello and Montepulciano Wine Tour from Cortona

Tours of Tuscany
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5.0 based on 1 reviews

In you are in Cortona, come enjoy the “Brunello and Montepulciano Tour”.. with its picturesque villages, rolling hills and unforgettable red wines… this is a tour for the wine lover, foodie and travel enthusiast at heart! Tour Length: 7/8 hours. Dates: Every season.  Days of Week: Everyday. Departure Point: From your accommodation - pick-up and drop-off in Cortona or Siena province. Departure Time: 09.00/09.30 am – return 5.00/5:30 pm. Note: During this excursion transport will be made in a Mercedes 9 seats minivan which offers the maximum comfort, with air-conditioning, large panoramic windows and comfortable seats. Note2: The tour is normally in a SMALL GROUP, if you prefer to remain private please let us know Popularity: *****  (best seller wine and food tour in Tuscany)

Inclusions: 3 Wineries tour and tasting, Pairing lunch at a historic winery, Air-conditioned vehicle, WiFi on board, Bottled water

Exclusions: Gratuities

Reviewed By Sogufa

Amazing experience. Kindness and professionalism at the same time. Well organised and safe in all aspects.

6. Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch

Tours of Tuscany
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4.9 based on 27 reviews

This full-day tour will bring you a taste of the complex, full-bodied Brunello reds that make this region every wine lover’s dream. We will pick you up at your hotel & take you to some of the lesser-known vineyards with high-quality wines. After your first tasting, take some time to explore the hilltop town of Montalcino, where we will visit a second Brunello winery. Then we will continue to Pienza, a UNESCO World Heritage Site & a unique example of the ideal city according to Renaissance architecture. Then one last stop in the small town of Montepulciano, where you can taste the exquisite Nobile di Montepulciano wine & meet the winemakers that make the magic happen. Enjoy a special lunch featuring local specialities. Pick-up & Drop-off at your accommodation 3 wine tastings at boutique wine cellars Lunch with wine pairings & local specialities Visit Pienza & Montepulciano Small group: limited to 8 guests Don’t drive while you wine & dine! Let us take care of everything.

Inclusions: 3 Winery tour and tasting, Pairing lunch at a historic winery, Bottled water, Air-conditioned vehicle, WiFi on board

Exclusions: Gratuities

Reviewed By Sogufa

Amazing experience. Kindness and professionalism at the same time. Well organised and safe in all aspects.

7. Cities, Cheese and Wine Tour in Pienza & Montepulciano

Tours of Tuscany
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4.8 based on 17 reviews

Pienza and  Montepulciano Wine Tour - Experiences 1 day exciting trip in Valdorcia Tour Length: 7/8 hours. Dates: Every season.  Days of Week: Everyday. Departure Point: From your accommodation - pick-up and drop-off in Florence , Siena , Pienza , Montepulciano, Chianti Area or South of Siena province. Departure Time: From Siena or nearby 09.00/09.30 AM – Florence 08.00AM Note: During this excursion transport will be made in a Mercedes 9 seats minivan which offers the maximum comfort, with air-conditioning, large panoramic windows and comfortable seats. Unless you don't specify you want to remain private, is possible to be joined with some other people in the party ( maximum 1 van ) Popularity: *****  (best seller wine and food tour in Tuscany)

Inclusions: Tour and tasting in an historic wine cellar, from the oldest and famous of the Brunello area and famous worldwide. Visit the town of PIENZA - Cheese Tasting Light Lunch at a HISTORIC WINERY IN MONTEPULCIANO DOWNTOWN Visit of a third winery in the Nobile di Montepulciano Area Area Bottled water Lunch Wine Tastings, Lunch, Snacks, Alcoholic Beverages, Air-conditioned vehicle, WiFi on board

Exclusions: Gratuities

Reviewed By Sogufa

Amazing experience. Kindness and professionalism at the same time. Well organised and safe in all aspects.

8. Montepulciano, Montalcino, Pienza from Florence

Tuscany in Tour
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4.8 based on 5 reviews

The Val d ‘Orcia: a beautiful area in southern Tuscany, declared Unesco world heritage thanks to its incredible landscapes that make this area one of the most beautiful of all Tuscany.

Inclusions: Transportation on comfortable Mercedes Vclass minivan, Fuel surcharge, Driver/guide, Hotel pickup, Hotel drop-off, Private tour

Exclusions: Lunch, Wine tasting, Gratuities

Reviewed By AVV1284

Everything was planned by Max. I had a few issues few days before this trip, because Venice, our last leg of this trip, has just experienced the record setting flood, and I was worried and didn’t want to go through with it. Anyway, Max said to wait, and that he’ll be ready if ever i decide to change itinerary. Anyway, with Massimo as our driver throughout our 7days stay in Florence, doing daytrips to different places of Montalcino, Montepulciano, Sienna, Chianti, Pisa and of course some shopping at The Mall, everything was seamless, as Massimo is very knowledgeable and always on time. Max also arranged for our tour in Venice and Vicenza. It was a wonderful Christmas vacation in Florence and Venice. Everything was taken cared of. Thank you, Max and Massimo...

9. Montalcino and Pienza Tour from Rome

Discovery Tours Limousine Service Day Tours

We will drive via the A1 highway straight to the rolling hills of Tuscany, among olive groves and vineyards, in one of the most evocative region in Italy. Our first stop will be Montalcino, famous as the birthplace of one of the finest wines of Italy, the “Brunello Di Montalcino”, a red, Italian wine produced in the vineyards surrounding the town of Montalcino, located about 120 km south of Florence in the Tuscany wine region. A short visit is also deserved by Montalcino town, particularly the medieval fortress and the town center. Your private driver will suggest a fantastic restaurant for a delicious meal and extraordinary wine! After lunch, our next destination is Pienza, another beautiful Renaissance city in Tuscany, Pienza is a hilltop village famous not only for its architectures, but also for the excellent sheep’s milk cheese pecorino, produced in the area. Upon request before leaving Montepulciano we can organize a visit of one of the most famous local wineries.

Inclusions: Private transportation, Highly entertaining tour driver, Fuel, tolls, parking fees included, Fresh bottled water on board

Exclusions: On request: We can arrange a private Wine Tasting for an additional cost of 20-25 Euros per person, Gratuities (entirely at the client’s discretion), Meals & entrance fees

Reviewed By R8876FNjons

Gilberto and Max of Discovery Tours provided the day trip of a lifetime to Anzio where I followed in my father's footsteps to see where he served his country in World War 2. Discovery Tours handled all the logistics, trip planning and detailed information on the battle sites and Anzio campaign with consummate professionalism. I learned much and thanks to Gilberto and Max, have a much deeper and personal understanding of the challenges my father and all other servicemen and women faced during this critical time in history. I enthusiastically recommend Discovery Tours to enrich your travel experience in the wonderful country of Italy.

10. Montalcino and Pienza Tuscany Wine&Cheese Fullday from Rome

ItalyBestExcursions

Enjoy this unforgettable Experience and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer: • Montalcino • Pienza • Val D'Orcia countryside area. Included: - Montalcino with Winery visit, Wine Tasting guided tour - Pienza town with Pecorino Cheese Tasting guided tour in a farm Upgradable with licensed local tour guide in Private option. Private or Shared Tour available options. Worry-Free and Safe Private Tour Experience, operated only with: • Expert Professional English-Speaking Drivers • Selected local Expert Licensed Tour Guides (when booked) • Welcoming by private licensed fully-insured air-conditioned comfortable Vehicles

Inclusions: Hotel pickup and dropoff, Air-conditioned, fully insured and licensed legal vehicle with professional English-speaking Driver, Dedicated Local Licensed Expert Tour Guide (upgradable in Private option), Montalcino with Winery visit, Wine Tasting guided tour, Pienza town with Pecorino Cheese Tasting guided tour in a farm

Exclusions: Lunch, Food and drinks, Tipping is not included in our service fees, it is never mandatory although it is always appreciated

Reviewed By Bernadette E

Just back since Sunday after 7 nights on ship - boarded in Barcelona 3rd Nov - cannot praise ship - staff - food and - organisation skills - fantastic. It was my 60 th birthday pressie and have to say it was SPECIAL. Hopefully will see you all again next year

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