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Wine Tastings, a Cooking Class and a Bike Tour: Francis C.'s Trip to Siena, Assisi and Rome

The first time Francis C. and his wife used a travel agent, they gave a list of what they wanted to do, and a private trip through Siena, Assisi and Rome was built around it.

The trip in briefFrancis C. and his wife, using a travel agent for the first time, explored Siena, Assisi and Rome with Thrill of Italy. They asked for wine tastings, a cooking class, a guided bike tour, drivers, guides and free time. He singled out the daily texts during the trip and the quick changes to the next day's plan when they asked.

Trip story based on Francis C.’s Google review · Read the review on Google

The trip at a glance
TravellersFrancis C. and his wife
PlacesSiena, Assisi and Rome
Asked forWine tastings, a cooking class, a guided bike tour, unique places, drivers, guides and time to explore alone
During the tripDaily texts with the day's events and the next day's plan
ChangesNext-day itinerary changes made on request

What is it like to hand over the planning of an Italy trip?

For Francis C. and his wife, who had never used a travel agent before, it meant sending a list of what they wanted and leaving the logistics to Thrill of Italy. He wrote that “We always felt like we were in safe hands” and called their “own curated tour” “so thoughtfully planned and executed”.

For Francis, travel is about having different experiences. He wrote that “With a name like “Thrill of Italy” we assumed they knew their stuff”, and added: “From our experience, they lived up to their namesake and then some.”

Every Thrill of Italy trip is fully private: private drivers, local guides, selected hotels, entrance tickets and a day-by-day itinerary. Flights are not included, and there are no published prices, because each trip is quoted on its own.

Can wine, cooking and cycling fit into one trip to Siena, Assisi and Rome?

Yes. Francis C. and his wife specifically asked for wine tastings, a cooking class and a guided bike tour, plus unique places they would not have found on their own. Their trip took in Siena in Tuscany, Assisi in Umbria and Rome, with drivers to take them there and guides to explain the churches, museums and towns.

The review does not say where each activity took place.

If food and wine are the reason you travel, our page on private food and wine tours in Italy shows how tastings and cooking days fit into a longer trip, and the Super Tuscan wine tour with a medieval village lunch and cooking experience combines both in a single day. For the regions themselves, see private Tuscany tours and private Umbria tours.

Some background on the places: Siena is a medieval hill town in Tuscany, known for its shell-shaped Piazza del Campo. Assisi, in neighbouring Umbria, is the home town of St Francis and the site of the Basilica of San Francesco. Both sit in farming country where wine and food are central to local life.

What happens if you want to change the next day's plan?

For Francis C. and his wife, asking was enough: the few times they requested a change to the next day’s itinerary, Thrill of Italy pivoted immediately, and “No problem” was always the response. “What a comfort!” he wrote. He also praised the communication both in the planning stages and during each day of the trip.

They had also asked for time to explore on their own, and Francis wrote that “In every way you hit a home run!”

As a general rule, travellers have a 24/7 WhatsApp concierge while they are in Italy. The company’s trip designers are based in Florence, Umbria and Rome.

What did Francis C. write after Siena, Assisi and Rome?

Francis C., who travelled to Siena, Assisi and Rome with his wife, left a five-star review on Google calling it the best vacation they ever had. He praised the planning, the daily texts and the quick changes to next-day plans, and said they always felt in safe hands. His full review is below, unedited, with his original spelling.

The Thrill of Italy team replied to thank him for his trust and said they looked forward to welcoming the couple back to Italy.

Wow! What a wonderful trip we had exploring Sienna, Assisi and Rome! This was the first time my wife and I used a travel agent. At the heart of traveling, is having different experiences. We specifically asked for wine tastings, a cooking class, a guided bike tour, visiting unique places that we would not on our own know about, drivers who would take us there and guides to explain the churches, museums and towns. And yet have time to explore on our own. In every way you hit a home run! Our own curated tour was so thoughtfully planned and executed. I cannot say enough about their excellent communication with us not only in the planning stages but especially during each day of the trip when they texted us and reminded us not only about the day’s events but also what tomorrow’s plan was. We always felt like we were in safe hands. To their credit, they were also able to immediately pivot the few times we threw a curve ball at them and requested a change in the next day’s itinerary. “No problem” was always the response. What a comfort! With a name like “Thrill of Italy” we assumed they knew their stuff. From our experience, they lived up to their namesake and then some. It was obvious to us the effort and care they put into planning and executing the best vacation we ever had!

Francis C., Google review

What should you put on your list before you contact a trip designer?

Write down what you want to do, not only where you want to go. Francis C. and his wife listed wine tastings, a cooking class, a guided bike tour, unique places they would not find alone, drivers, guides and time on their own. A trip designer then plans the days around a list like that.

Want a trip like this?

Tell us your dates and what you love. A member of the team replies personally.

Photos from the trip

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Questions about a trip like this

Something else on your mind? A member of the team replies personally.

That was Francis C.’s experience. He wrote that during each day of the trip the team texted him and his wife about that day’s events and what the next day’s plan was.

Francis C. thought so. He wrote that it was “the first time my wife and I used a travel agent”, and that “Our own curated tour was so thoughtfully planned and executed.” Every Thrill of Italy trip is private and planned around what you ask for.

Yes. Francis C. and his wife asked for wine tastings, a cooking class, a guided bike tour and unique places they would not have known about, and their private trip to Siena, Assisi and Rome was planned around that list. He called it “Our own curated tour”.

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