Italy 2026
Proposed Itinerary Italy 2026
19 Days 30th May - 17th June
Please email me for a tour price. Athough we have maintained the tour prices from 2025. The Zealand exchange rate has made a significant diiference.
We can only hope it will improve in the next 6 months
My tours are all inclusive:
• 19 nights hotel accommodation in Boutique Hotels and the exceptional Maseria Pistola
•Daily breakfast
• I have allocated a dinner or lunch each day, inclusive of beverages and wine. Including pre-dinner drinks at the Masseria.
• Visits and guided tours all included
• Tipping is included
*Airfares are not included in this price
*All other meals will be at your own expense
The Italian tour is one day longer :
1 night south of Rome near Cassino
7 nights Masseria Pistola – Puglia
2 nights Abruzzo - Santo Stefano Sessanio
4 nights - Palazzo Bontadossi - Montefalco – Umbria
4 nights Hotel Touring – Bologna
Total 19 nights
Philip and I completed this tour of Umbria, Puglia and Abruzzo in 2025 and were delighted with everything. In 2026 we are doing the tour in a different order and including Bologna. I am helped by guides in each region, especially Michele in Puglia, who assisted me to create a wonderful itinerary for our 7 days and plus, he made sure we saw it from a local’s perspective. I was excited and thrilled that I booked the fabulous Masseria Pistola for the 7 days in Puglia and I am even more delighted that we have secured it for 2026.
The 2026 itinerary does have some changes. We are starting in Puglia, where we spend 7 nights in Masseria Pistola, travel to Abruzzo for two nights . Onto Umbria for 4 nights and will complete this tour with 4 nights in Emilia Romagna, where we will get to understand the production of Parmigiana Reggiano, Balsamico Traditional and Prosciutto.
We will begin the tour by meeting at Fiumicino airport by 14.30 on the 30th May. Many will fly in on the Emirates flight that lands at 13.30. or if you arrive a few days earlier you can catch a train or taxi to meet me.
We will drive 1/1 2 – 2 hours towards Cassino and spend our first night together.
Staying in a Masseria provides a different experience – we are the only group and have the private environs to ourselves. We will have time to enjoy its marvellous surroundings and everything that it has to offer, including the exceptional gardens, beautiful pool and the many dining areas.
The Masseria has its own chef and we are spoilt for staff.
https://www.gardensillustrated.com/gardens/international/italian-pistola-urquhart
Choosing accommodation is very important to us and I go out of my way to make sure they are different from each other.
None more different than the Hotel in Abruzzo – This is a region not frequented by hordes of tourists, but which has so much to offer.
For 2 nights we are having another exceptional experience and we will be staying in the mountains in:
Sextantio Santo Stefano di Sessanio
Santo Stefano di Sessanio is a fortified medieval village. It is located in the mountains of Abruzzo at 1250 meters above sea level, inside the Gran Sasso and Monti della Laga national park. The village is a classic example of an Italian medieval hill town, with perimeter walls encircling houses and squares.
This is experience is like no other. The small village has been restored by a developer and they have created a beautiful hotel within the village in a style that enhances the medieval lifestyle. Your rooms will be throughout the village. Expect rough stone alleyways, stairs and unique décor which enhances the objectives of the hotel. Dinners are breakfasts and served in the dining room. I loved this experience, But, I know some on tour found it quite confronting.
4 nights in Umbria follows and the accommodation couldn’t be more different Palazzo Bontadosi in Montefalco is stylish with unique rooms that reflect the region.
Montefalco is our base to explore Umbria, taste its wine, visit its gorgeous villages and absorb the history.
However, before reaching Montefalco we will drive through the wild flowering fields of Castelluccio before visiting Norcia – famous for its pork products. It is a fascinating stop and we can see the effects of the massive earthquake that basically destroyed the town in October 2016.
Our final 4 days will be in Emilia-Romagna. I have confirmed a city stay in Bologna.
Here, we will it use it as a base to explore the famous food products of the region. It’s a very foody town with lots of options. https://www.hoteltouring.it/en/
On the 17th June you have the choice to fly out of Bologna or maybe choose to spend more time in Italy. The bus will be going back to Venice and you might like a few days there.
Philip and I have just returned from our European tours and trip to Spain. Although I have booked the accommodation, this itinerary needs padding out in places.
1. Saturday 30th May - Rome / Frascati
Arrival Day:
We will begin the tour by meeting at Fiumicino airport by 14.30 on the 30th May. Many will fly in on the Emirates flight that lands at 13.30. or if you arrive a few days earlier you can catch a train or taxi to meet me.
Picked up by Daniele - we will have a nice relaxed drive out of Rome to the Countryside
Masseria Pistola
2. Sunday 31st May - Puglia
We have a longish drive today before arriving at Masseria Pistola.
We will have time to stop at Cassino which is an important and meaningful visit for many New Zealanders.
On arrival at the masseria we will be met, shown around and provided with bedrooms.
We have our own chef at the villa and after pre-dinner drinks, we will enjoy our first night in these rather fabulous surroundings.
Masseria Pistola
3. Monday 1st th June - Puglia
Alberobello
UNESCO-listed Alberobello is the birthplace of Trulli houses. They are characterised by white-washed conical-roofed dwellings and are a statement all over Puglia. Even in our frenetic world of an ancestral rural civilisation, these have never disappeared in this enchanting place.
After the town visit, we'll drive to a nearby dairy farm for a Burrata masterclass that will teach you all the secrets of this worldwide famous Apulian specialty.
We'll visit the farm, see and meet the cows and then be welcomed in the cozy house of the owner for a light lunch where you'll taste a selection of cold cuts, cheeses, mozzarella, burrata and "frise".
In the afternoon we are going to soak up the atmosphere at the seaside town of Monopoli. It makes a splash with medieval churches and castles jutting above the Adriatic. It's also a painter's dream, with bright blue fishing boats adding a pop of colour against whitewashed harbour walls.
Masseria Pistola
4. Tuesday 2nd June - Puglia Matera
Matera is one of the oldest and most unique destinations in Italy, with its sassi (cave dwellings) dating back to pre-Neolithic times. We will learn about this unique UNESCO World Heritage Site- its history, culture, its unique sassi cave dwellings and stunning natural beauty.
This ancient city will capture your soul with its pure charm. Its light, its colours, its views, and its history make it a place like no other. Michele will guide us through its past, its present, its evolution, its culinary traditions, the hospitality of its people and much more!
Masseria Pistola
5. Wednesday 3rd June - Puglia
Our Morning today will be at the Masseria where you can relax and enjoy the garden before enjoying lunch outside.
Olive Oil Visit :
In the afternoon we will visit an ancient fortified Masseria (historical farmhouse) surrounded by a magnificent olive grove dating back to Roman times. At the end of the estate, tour, we will experience a professional EVO oil tasting.
Who doesn’t love Ostuni: Its stunning white-painted architecture, its olive oil and wine production. Its history of Norman, Renaissance and Turkish influences and its sheer beauty.
The “white town", is one of the most iconic whitewashed hilltop towns in the region, with gorgeous Eastern Mediterranean charm. Michele will guide us through the narrow, enchanting alleys, reliving its history and pointing out the most interesting sites of this marvellous town
Tonight we will eat in Ostuni, looking over the beautiful white city and watching the sun go down.
Masseria Pistola
6. Thursday 4th June - Puglia
This morning, we will drive to Brindisi. This town is often overlooked but,we are going to spend some time here. This is the end of the Roman road from Rome and sits on a beautiful harbour. It has some great seafood restaurants and we are going to have lunch at one of them. Philip and I stayed in the old town this year and fell in love with the narrow streets, good shopping and atmosphere.
You will have your own time to shop before they close at 1pm, before heading to the seafood restaurants by the harbour and you can choose one that suits you. Michele will then give us a short walk back to the bus making sure we have all the history in place.
Masseria Pistola
7. Friday 5th June Puglia
We will discover Lecce today , nicknamed the Florence of the South, a hidden gem of baroque architecture and undoubtedly the most elegant city in Puglia. Our walking guide Michele, will help us to be impressed by the aristocratic old town characterized by impressive Roman ruins, scenographic squares, magnificent baroque churches and palaces.
Near Lecce, we will be visiting a beautiful Masseria for a wine tour to introduce you to the Indigenous varieties of grapes, particularly negroamaro and primitivo.
Salento is famous also for its extensive vineyards kissed by the sun and caressed by the wind, producing some of Puglia's most-awarded wineries.
Masseria Pistola
8. Saturday 6th June - Puglia
Ceglie Messapica is one of the most picturesque and authentic towns of Valle d'Itria, with beautiful hill country dotted by trulli houses, making it one of Puglia's most iconic territories.
This town has very ancient and proud origins and is also recognised as the "gastronomic capital of Puglia", so the best way to discover this hidden gem is by tasting local delicacies such as "panino cegliese" and "biscotto cegliese".
We are going to do a food tour that will not only be fun but a chance to admire the pristine old town, dominated by the massive medieval castle and the elegant mother church, touring selected charcuteries, bakeries and cafes as a local!
Our last afternoon will be back at the Masseria. Our last chance to take in the garden and maybe a late afternoon wine in their garden bar.
Masseria Pistola
9. Sunday 7th June - Puglia
Travel Day - Driving up the Adriatic Coast we will stop at the famous Trobocchi - ancient fishing stands which today are mainly restauarnats.
Trobocchi Coastline / San Vito Chietino
Just to give you an idea where we are staying in the hills of Abruzzo. This will be a rather different experience.
https://www.sextantio.it/en/santostefano/abruzzo/
Stefano is one of several so-called “diffuse hotels” that certainly ignore the usual hotel model of grouping rooms and facilities under one roof. Instead, Sextantio’s rooms, spa, wine bar, restaurant and reception are scattered in separate buildings formerly used as barns, stables, pigsties, wine cellars and farmers’ or shepherds’ lodgings. Wood and stone cottages have been restyled as suites, the village dungeons serve as a wedding room and a former witch’s lair now hosts business meetings. We will have a lot to explore on our first night and enjoy dinner in a very different environment.
10. Monday 8th June – Abruzzo
Santo Stefano di Sessanio. We have an orientation walk in the Village at the beginning of the day before a busy schedule:
I have a loop route planned that will have us see :
· The Castle of Rocca Calascio - a mountaintop fortress.
· Bominaco, a small village with a rich history and a stunning frescoed chapel, often called Abruzzo's Sistine Chapel.
Afternoon in L’Aquila, the site of the devastating Earthquake in 2009 – a walk in the beautifully restored streets.
Palazzo Bontadosi – Montefalco
11. Tuesday 9th June - Montefalco
From Santo Stefano we will drive up to the fields of Castelluccio where hopefully we will be immersed in the colours of the wildflowers which cover the surrounding farmland. Before heading down on a spectacular drive to Norcia where there is an overwhelming presence of the so-called norcinerie, butcheries specialised in the production and sale of local produce.
We will notice the changes after the devasting earthquake of 2016 that changed the village drastically.
Montefalco’s historic centre, where we are staying, is characterised by medieval walls and narrow winding streets. The town exudes medieval charm with well-preserved buildings, stone houses and picturesque squares. The local enoteca and bars are known for serving traditional Umbrian dishes, including truffles, cured meats and homemade pasta.
Dinner Montefalco
Palazzo Bontadosi – Montefalco
12. Wednesday 10h June - Umbria / Montefalco
We are going to start with a visit to Carapace. This unique winery was designed by Arnaldo Pomodoro to resemble the shape of a turtle. The building is distinctive and features curved and overlapping metal panels, creating a sculptural and shell-like appearance. Carapace will help us discover Sagrantino wines, a grape variety indigenous to the Montefalco area.
We will head to the birthplace of Saint Francis - Assisi in the afternoon. Have time to visit the Basilica with its stunning Giotto frescoes and enjoy a walk through the charming medieval town.
Dinner Montefalco
Palazzo Bontadosi – Montefalco
13. Thursday 11th June
Umbria / Montefalco
Two of my favourite hill villages in Umbria are Spello and Spoleto. With a stunning view we will have a lunch together in Spello before walking up through Spoleto in the afternoon.
Dinner Montefalco
Palazzo Bontadosi – Montefalco
14. Friday 12thJune - Umbria / Montefalco
Travelling around Lake Trasimeno we will take a morning coffee stop at Deruta where the stunning ceramics are made, then onto Gubbio. A town often left out but with an amazing historical centre
Dinner Montefalco
Palazzo Bontadosi – Montefalco
15. Saturday 13th June
Our drive to North today will have a stop at Ravenna.
The mosaic tiles of Ravenna are among the most extraordinary treasures of early Christian and Byzantine art in Europe. Ravenna, a city in Emilia-Romagna was once the capital of the Western Roman Empire (402–476 AD) and later the seat of Byzantine governors.
Its rich history, is preserved with some of the finest mosaics in the world — so much so that eight of its early Christian monuments are UNESCO World Heritage sites.
We will have a guide and view these stunning mosaics in a few of the buildings
Emilia-Romagna is often called Italy’s food capital, and Bologna is its beating heart. Regularly known as : La Grassa – The Fat, and world-famous for its culinary tradition
Signature foods include:
Tagliatelle al ragù (often misnamed "spaghetti Bolognese" abroad)
Tortellini in brodo (stuffed pasta in broth)
Mortadella (the original inspiration for “bologna” cold cuts)
Rich cheeses like Parmigiano Reggiano and Grana Padano nearby
Hotel Touring Bologna
16.Sunday 14th June
We need to do a walking tour here to find out about the food traditions, history and layout of the city.
After a morning walk there will be time for lunch and later in the day we will visit the gallery of
Giorgio Morandi (1890–1964). He was one of the most important Italian artists of the 20th century and is celebrated worldwide for his subtle, contemplative paintings of everyday objects.
Hotel Touring Bologna
17. Wednesday 15th / Thursday 16th
In no particular order, over the next two days, I will be organising visits to the big food items from the Emilia Romagna region
Parmigiano Regiano, Balsamico Tradizonale and Prosciutto
Included will be a visit to Modena. It is a beautiful and culturally rich city in Emilia-Romagna, famous for its food, fast cars, and historic art treasures. It’s a smaller, elegant city that blends medieval charm with world-class gastronomy and industry.
I know Daniele is keen to visit the home of Ferrari cars, so bring your driver’s licence !!
Hotel Touring Bologna
19 Depart 17th
Tour inclusions:
· Accommodation for 19 nights (4 star and special category Masseria )
· All breakfasts included along with either a Dinner or Lunch each day including wine
· Tips accounted for
Travel is to be organised by you.
Philip and I will already be in Europe and will meet you in Lyon
I deal with Kay Dunn: kayd@travelmanagers.co.nz | 0275222389
She knows all my tours and is amazing
I am more than happy to have a chat on the phone and go over any queries you may have - 021735617
Let me know if you would like a booking form
