Under the Tuscan Sunshine: Cortona and Montepulciano Tuscany Tour

Private Tuscany Tour from Rome to Cortona and Montepulciano

duration:10 Hours

Payment method:Cash, Paypal, Credit card

starting time:8:00 AM


  • Experience an extraordinary day tour to Tuscany from Rome to two captivating hill towns
  • Indulge in the comfort of our deluxe vehicles driven by your personal English-speaking driver
  • Admire the captivating beauty of the Tuscan countryside, an eternal muse for artists, writers, and poets alike
  • Fall in love with Cortona, the enchanting hilltop town that inspired the renowned "Under the Tuscan Sun"
  • Discover the captivating allure of Montepulciano, where ancient charm and exquisite wines create an unforgettable experience
  • Marvel at the Temple of San Biagio, a magnificent gem of Tuscan Renaissance architecture
  • Experience the ultimate tour enjoyment, comfort, and privacy with our private tours solely for you and your companions
  • Convenient pick up from your Rome hotel at 8:00 AM, and arrival back at your hotel at about 6 PM
  • Enjoy an unparalleled level of personalized attention from your private driver on our Tuscany tours
  • This tour does NOT include a Tour Guide, you will Self Tour when away from the Vehicle
  • * Please read ALL the information on the tour page before booking to ensure this tour meets your expectations. If you have any unanswered questions let us know. Tour Requests are confirmed based on availability


  • Cortona
  • Montepulciano


  • Private Deluxe Vehicle
  • English speaking Driver
  • All Italy VAT Taxes
  • Highway Tolls and Parking Fees

not included

  • Admission Tickets if visiting sites that require them
  • Tour Guide / Walking Tour
  • Lunch
  • Gratuities


Escape to the idyllic landscapes of Tuscany and experience the captivating charm of Cortona and Montepulciano on our private "Under the Tuscan Sunshine" day tour from Rome. Get ready to be whisked away in your private deluxe vehicle, accompanied by your personal English-speaking driver, as you set off to explore these enchanting towns.

Immerse yourself in the irresistible charm that radiates from every corner of Cortona and Montepulciano as you enjoy free time on your own for independent exploration. Wander through their ancient streets and feel the vibrant pulse of these historic places. Marvel at the awe-inspiring panoramic vistas that stretch before you, capturing the essence of Tuscan beauty in its purest form.

Delight in the treasures of Tuscan culture as you indulge in the region's renowned wines and cuisine for lunch at a local restaurant of your choosing. Taste the tantalizing flavors of local Tuscany, each sip and bite a celebration of the region's heritage.

With convenient pick-up and drop-off at your Rome hotel, this extraordinary adventure promises to create lasting memories of Tuscany's irresistible magic.



  • For up to 4 participants from Rome Hotel: 590 Euros
  • For up to 6 participants from Rome Hotel: 650 Euros
  • For up to 8 participants from Rome Hotel: 700 Euros


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** You may also do a QUICK PRICE CHECK using the Price Check & Booking form on the Right Side of this page.  Once you receive the PRICE QUOTE based on the information you input, you may proceed to SUBMIT your Tour Request. 

*** Dates on the Booking Form Calendar that are NOT Selectableare NOT AVAILABLE.


CORTONA - Enchanting hilltop town

Amidst the picturesque landscapes of Tuscany, Cortona beckons you to bask in the warm embrace of the Tuscan sun. Take in the breathtaking vistas, immerse yourself in the timeless allure of this extraordinary town, and create cherished memories that will forever be etched in your heart.


Under the Tuscan Sunshine Cortona day trip from Rome


Embrace the freedom to explore Cortona on your own. Stroll through the charming squares such as Piazza della Repubblica and Piazza della Signoria, and meander along the narrow medieval streets adorned with inviting cafes, boutiques, art galleries, and shops brimming with local treasures.

For history and art enthusiasts, Cortona offers a wealth of cultural treasures to explore. Step into the MAEC Etruscan Academy Museum housed within the majestic Palazzo Casali in Piazza della Signoria, and immerse yourself in the ancient wonders of Etruscan civilization. Alternatively, visit the Diocesano Museum in Piazza del Duomo, where a rich collection of religious art and artifacts awaits your discovery.


Day trip from Rome to Cortona and Montepulciano Under the Tuscan Sun


Delight in the abundance of regional products, from exquisite wines to gastronomic delights, allowing your senses to savor the true essence of Cortona. While in Cortona, savor a leisurely lunch, delighting in the flavors of delectable Tuscan delicacies at a charming local restaurant of your choosing.


MONTEPULCIANO - Majestic Renaissance gem

Montepulciano, often hailed as the pearl of the Renaissance, boasts a remarkable collection of palaces, churches, and ornate decorations that serve as a living testament to the height of the Renaissance. This captivating hill town invites you to immerse yourself in its labyrinthine historical streets, lined with magnificent architecture that transports you back in time. Explore the town's hidden gems, from local artisan shops to gastronomic boutiques, where you can indulge in the finest culinary delights and sample exquisite wines. 

 Cortona and Montepulciano Tuscany Tour from Rome


On top of Montepulciano is Piazza Grande, a picturesque square that captures the essence of the town's rich history and architectural beauty.  At the heart of the square stands the impressive Duomo, also known as the Cathedral of Santa Maria Assunta. Its magnificent facade showcases a blend of Renaissance and Gothic elements. Flanking the Duomo, you'll find the Palazzo Comunale, the town's historic town hall.

As you wander through Piazza Grande, you'll be surrounded by other palazzi, each displaying its unique architectural charm. These palazzi reflect different periods of history, from the Medieval to the Renaissance, creating a harmonious blend of styles. Enjoy a leisurely stroll, savoring the architectural wonders and taking in the captivating views of the surrounding countryside from the edge of the town.

And of course, no visit to Montepulciano would be complete without stopping at local wine shops (enoteche) in town to savor the world-famous Vino Nobile di Montepulciano (Noble Wine of Montepulciano) that have earned Montepulciano the prestigious title of the "King of all Wines" as proclaimed by Francesco Redi in his poem "Bacchus in Tuscany."

The Noble Wine of Montepulciano is a classic red wine with a rich history dating back to the 15th century. The wine’s velvety texture and captivating flavors have enchanted aristocracy and wine enthusiasts for centuries.  Let the allure of Montepulciano weave its spell and create memories that will last a lifetime.


Under the Tuscan Sunshine Cortona Montepulciano Tuscany Tour from Rome


Among Montepulciano's architectural treasures is the splendid Temple of San Biagio, located at the base of the hill outside the town.  A true masterpiece of Tuscan Renaissance, the sanctuary was designed by the eminent architect Antonio da Sangallo the Elder, the temple was built between 1518 and 1545 and occupies a striking position in the midst of a flat meadow at the base of the hilltop town.

This masterpiece design features a Greek cross plan, central dome, semicircular apse, and two bell towers, all adorned with striking travertine. You have the option if you wish to visit this sanctuary, tickets can be purchased at the nearby gift shop. Inside the sanctuary, a captivating marble reredos takes center stage, showcasing a fresco of the Madonna and Child with Saint Francis. As you wander through this architectural marvel, immerse yourself in its captivating history and artistic grandeur. 

  • NOTE that the Temple of San Biagio may have limited visiting hours, especially during the winter months (off-season) when it only opens on weekends


Bid farewell to Montepulciano as you once again join your driver for a leisurely journey back to Rome with an estimated arrival time of around 6 PM. Relax and soak in the pastoral landscapes as you traverse the picturesque Italian countryside, cherishing every precious memory created during your extraordinary day in the heart of Tuscany.
Thank you for choosing Stefano’s RomeCabs for your Tuscany tours from Rome. We look forward to showing you beautiful places in Italy!

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Important Information




Payment for this Tour can be made in EUROS directly to your driver on the Date of Tour, or prepaid in advance via PayPal or Credit Card online upon request. PayPal processes all online credit card payments for safety and security. (See Cancellation policy below)



We kindly ask that cancellations be made via E-mail at least 7 days prior to Date of Service

Cancellations are accepted only via E-mail so your cancellation is on record. We do not accept cancellations by phone, text message, or 3rd parties.

** Cancelations for PREPAID SERVICES will be refunded the Reduced Net Rate we receive from your prepayment.  Reduced Net Rate: actual service price minus PayPal/Credit Card fees retained by PayPal/Credit Card as they do not reimburse us the fees they retain from your payment.



This Cortona and Montepulciano Tuscany Day Tour includes an English-speaking Private Driver who is not a Licensed Tour Guide.

Italy's strict laws prohibit Drivers from providing tour guide services and from accompanying guests away from the vehicle to sightsee on foot. Your Driver will be happy to offer basic touristic information while at the vehicle, but will be obliged to remain with the vehicle while you SELF-TOUR the sites included in this tour.


MEETING POINT at your Rome Hotel / Accommodation

For day tours from Rome, your private driver will meet you inside the lobby of your hotel or in areas permitted by hotels.

For Apartments or B&Bs without a lobby, your driver will meet you outside the main entrance of your Pick Up Address.

* If your hotel or accommodation is on a street or in an area restricted to vehicle traffic, your driver will park as close as lawfully possible and meet you on foot at your Address, and accompany you to your parked vehicle.

Museum Visit in Cortona (Optional)

If you wish to visit any museums in Cortona, please note that Museums are CLOSED on Mondays and December 25. Admission Tickets to museums can be purchased on-site inside the museums.

Wine Tastings at Local Wine Shops in Montepulciano

Wine tasting in Montepulciano is possible only in town at various wine shops operated by local wine producers. Wine tastings may cost anywhere between 5-15 Euros per person, and are paid directly to the wine shop. Please taste wine responsibly, and never on an empty stomach.

Visiting the Temple of San Biagio in Montepulciano:

Visiting San Biagio requires admission tickets that can be purchased at the gift shop near the sanctuary.  Tickets are approximately 3.50 Euros Per Person. Family Rate for 2 parents with up to 2-3 children over the age of 5 years old: 10 Euros. Children under the age of 6 have free entrance.

Temple of San Biagio Opening Hours:

  • Monday to Saturday:  10:00 AM - 1:30 PM / 2:00 PM - 6:30 PM
  • Sundays: 11:30 AM - 1:30 PM / 2:00 PM - 6:30 PM
  • CLOSED on December 25



FAQ about Cortona and Montepulciano Tuscany tour from Rome:

Q1. What is the price for the Cortona and Montepulciano Tuscany tour from Rome? 

A1:  Prices vary depending on the number of persons in your party. Our current price list is published right on this tour page.

Q2:  What payment methods are accepted for the tour?

A2:  Please read the Payment Options on this page for more information.

Q3:  What time does the tour start?

A3:   The tour starts at 8:00 AM with pick up at your hotel accommodation in Rome and will conclude at approximately 6 PM with your arrival back at your hotel.

Q4:  What is included in the tour price?

A4:   The tour includes a private deluxe vehicle, an English-speaking driver, all Italy VAT taxes, highway tolls, and parking fees.

Q5. Does the tour include a tour guide?

A5: No, the tour does not include a tour guide. Guests will self-tour the sites when away from the vehicle. Cortona and Montepulciano are delightful towns that are best explored independently explore the towns and enjoy the Tuscan atmosphere.