Tuscany: Food & Wine Tasting, Italy

Indulge in a taste of Tuscany’s best: wine culture, local delicacies, and countryside charm

Private Itinerary
5 Days

Journey Highlights & Signature Inclusions

Experience the best of Tuscany on a journey through its picturesque landscapes and charming towns. Explore Cortona’s medieval streets, the breathtaking Val d’Orcia, and the historic gems of Pienza and Montepulciano. Indulge in exquisite food and wine tastings and elevate your culinary skills with a Michelin-star cooking experience.

  • 4 nights in exquisite 4 and 5-star hotels
  • 4 breakfasts (B), 2 lunches (L), 1 dinner (D)
  • Winery tour and tasting in Cortona
  • Guided private tour of Cortona
  • Michelin Star cooking experience with dinner
  • Wine tasting at a winery in Montepulciano including lunch
  • Pienza cheese farm visit and tasting
  • Montalcino winery lunch and tasting
  • Deluxe VIP transfers as indicated
  • Note: hotel city taxes, if applicable, are not included

Discover The Itinerary

Explore your itinerary in detail, featuring carefully selected hotels, unique experiences, and premium inclusions designed to elevate your travel experience.

Day 1
Day 2
Day 3
Day 4
Day 5

DAY 1: Cortona

Welcome to Tuscany’s rolling hills and a gastronomy focused tasting of the region. Check in to your amazing hotel just outside the town. Freshen up before joining an introductory sampler – a winery tour and wine tasting – followed by an evening to relax.

Il Falconiere Relais & Spa Toscana

Overnight Hotel / or similar

DAY 2: Cortona

Cortona is a hilltop town with predominantly medieval architecture, steep narrow streets, significant museums and a historic centre. While the origins of the settlement are Umbrian, it was the Etruscans that developed the town and eventually became a Roman colony. Learn more of the history and the gastronomic significance of the surrounding region on a private guided walking tour. In the afternoon, enjoy a Michelin Star cooking class experience designed by Silvia Baracchi, celebrating traditional Tuscan recipes, followed by dinner.

Il Falconiere Relais & Spa Toscana

Overnight Hotel / or similar

Breakfast, Dinner

Meals Included

DAY 3: Cortona – Montepulciano – Val d’Orcia

Enjoy breakfast before journeying through the Tuscan countryside into the picturesque Val d’Orcia. Stop in Montepulciano, a major producer of produce including pork, cheese, ‘pici’ pasta and of course wine. Enjoy time to stroll the hamlet, before a local winery visit for lunch and a tasting of Nobile di Montepulciano wines, the first Italian DOCG wine characterised by gorgeous ruby red colour and fruity aromas. Continue to your next retreat for a relaxing evening.

Boutique Hotel Villa Liberty, Borgo Capitano Collection

Overnight Hotel / or similar

Breakfast, Lunch

Meals Included

DAY 4: Val d’Orcia – Pienza – Montalcino – Val d’Orcia

Indulge in a progressive day of food and wine. For appetisers, visit a cheese farm for a Pecorino di Pienza cheese tasting. Afterward, transfer to Montalcino for the main dish, a Brunello wine tasting lunch. Montalcino produces top-notch wine with unrivalled complexity. Finish with leisure time in the hilltop town of Montalcino to browse the quaint shops that include quality wines from the region. Retire at your retreat for a final evening of relaxation.

Boutique Hotel Villa Liberty, Borgo Capitano Collection

Overnight Hotel / or similar

Breakfast, Lunch

Meals Included

DAY 5: Val D’Orcia

After breakfast, depart for your ongoing journey.

Breakfast

Meals Included

Upcoming Departures

Enjoy your private itinerary

Experience the freedom of a private, fully customisable itinerary with Ormina Tours. This itinerary can start on any date, with options to adjust activities, upgrade experiences, and tailor every detail to suit your travel style, ensuring a seamless and unforgettable journey designed just for you.

  • Depart on any date you choose
  • Fully customisable
  • Unique activities
  • Comfort and privacy
From $4,498 AUD PPFrom price (Private driver)

Upgrade Options

  • Upgrade to a 5-star hotel in Val d’Orcia: recommended – La Posta Hotel & Thermal Spa or ADLER Spa Resort THERMAE
  • Extend your stay to spend a day in Bagno Vignoni – a charming town and a UNESCO World Heritage Site offering natural thermal waters
  • Include transfers into Cortona and out of Val d’Orcia for a seamless journey

Frequently Asked Questions

What services does Ormina Tours provide?

Ormina Tours provides land services in Europe. We cover most of Europe and are continually expanding. If your destination is uncommon, please contact us to confirm availability.

We offer Small Group Journeys on set departure dates (max. 10 guests for 2025 and max. 12 guests for 2026), tailored private journeys (full F.I.T. services), and booking and coordination of accommodation. From airport transfers to fully customized European travel, we cover everything, except flights

Where is Ormina Tours based, and do you serve clients worldwide?

We are an Australian company with offices in Sydney and Perth, as well as a team in Europe to ensure seamless service delivery. While based in Australia, we cater to clients globally and partner with over 250 travel agents across Australia, New Zealand, and the USA.

When is the best time to visit Europe, and do your tours operate year-round?

Europe offers charm year-round. May and September are popular for Australians, while beach destinations are busiest in August. Most Small Group Journeys run between April and October, while private journeys are available year-round. Early planning (at least 6 months) is recommended for busy regions like the Amalfi Coast.

Is travel insurance required?

Yes, we require all clients travelling to have travel insurance as this is a requirement for Tour Operators Insurances, otherwise guests must sign a release and discharge of liability waiver for us to accept the booking. If you need assistance arranging insurance, just ask.

Do you cater to travellers with mobility challenges?

We tailor all journeys to our client’s travel preferences and needs, including any mobility challenges whether it is special vehicles, travel scooters, hotel rooms with accessible showers and hoists. We also have expertise on most attractions and towns to know which are more accessible than others.

With our Small Group Journeys, any significant mobility challenge requires an accompanying minder/helper to attend on the tour as it is not always possible for our Tour Directors, drivers and guides to offer continuous care in a group environment. If you have any questions or concerns, please contact us.

What is the group size, and what happens if only two people book the tour?

Our Small Group Journeys are designed for a maximum of 10 guests (12 guests in 2026) to ensure an intimate experience. A minimum of 2 guests is required to guarantee departure (4 guests in 2026).

Should fewer than four guests be booked, you will have the exclusive opportunity to enjoy the same itinerary as a private journey at a preferential rate, giving you the confidence and certainty to book in advance. If you do not wish to undertake the small group journey itinerary as a private journey and we advised within the require deadline as disclosed, we will provide you with a full refund.

What is included and excluded in a Small Group Journey?

Our itineraries include accommodation, transportation, guided activities, and meals as marked – B (breakfast), L (lunch), or D (dinner). Exclusions typically include flights, city taxes, personal expenses, and any items not explicitly listed in the itinerary.

Do I need to tip?

Tipping is optional but appreciated for exceptional service. After booking you will be provided with some tipping guidelines should you choose to do so.

What is the luggage allowance?

Each guest can bring one standard checked bag and one carry-on. Please inform us if you need to bring extra luggage.

What is a private journey?

Private journeys (named City Breaks and Regional Discoveries) are not tours with other people. They are suggested itineraries for the city/region that can be fully customised with prearranged services, allowing independent exploration.

Can I choose my hotel?

For private itineraries, we recommend hotels in our itineraries, we can certainly work to accommodate your preferences.

Hotels are set for Small Group Journeys but you can opt to upgrade your room.

What currency are your tours priced in?

Tours (that is our Small Group Journeys) are priced in AUD for Australian residents, NZD for New Zealand residents, and USD for US residents. Other nationalities will pay in AUD unless otherwise arranged.

Prices are fixed once paid in full. In rare cases of significant currency fluctuations, unpaid bookings may be subject to price adjustments. If this occurs, we will contact you or your travel agent to advise you and you will have the option to either pay the full tour price by a certain date or accept the increase.

Do you accept credit cards?

Yes, though credit card fees may apply. Domestic wire transfers are also accepted.

What deposit is required?

Deposit amounts vary on the size of the booking and whether the booking includes tickets and admissions that maybe non-refundable or non-transferable after purchase. Full payment is due 3 months before your first service date.

Can I change or cancel my booking after making a deposit?

Changes incur a $100 fee per request unless additional services are added. Cancelling more than 50% of services is considered a cancellation, and fees will apply.
Any cancellation made by you prior to your travel (including any changes to your departure date) will result in the following cancellation fees:

Days of notice from notification to first date of service:

  • 91+ days: Loss of deposit
  • 90–75 days: Loss of Booking Deposit and 50% of the balance of the Tour Price
  • 75 days or less: Loss of Booking Deposit and 100% of the balance of the Tour Price

We always advise our clients to purchase comprehensive travel insurance to cover any unforeseen cancellations.

What are Ormina Tours’ COVID-19 guidelines?
  • Follow local laws, wear masks, and maintain social distancing as required.
  • Do not travel if you are symptomatic, recently exposed, or COVID-positive.
  • Stay updated on airline and country-specific protocols.

Have Questions? We’re Here to Help!

Reach out to our team for personalised assistance and start planning your next European adventure with Ormina Tours.