Tuscany Staycation

TUSCANY STAYCATION

November 10-16, 2025 with Roberto

$3100 (no single supplement)

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Tuscany is justifiably famous for scenery and food, but also for tourist crowds. In this tour, we will find unknown villages and sample local specialties that few travelers come across. You’ll get to be a temporary part of a Tuscan/American family, staying at the home of our local guide, Roberto Bechi and his American wife, Patti on this Tuscany staycation.

We have enjoyed our small groups so much that we will continue to keep numbers low and personal attention high. This tour will have a maximum of 8 guests.

ADDITIONAL INFO
INQUIRIES

Day 1

Overnight: Casalciccia

Welcome to Off the Beaten Path Tuscany

After meeting in Florence, we will drive to Siena for a walking tour of the city and its Cathedral. Then, we visit Madonna Bella Farm, where we will have a delightful late lunch of farm-to-table local food and their own wines. We will make our way to Podere Casalciccia, your Tuscany staycation home for the next few nights, where we will have a light dinner (buffet of antipasti and spritzes).

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Day 2

Overnight: Casalciccia

Chianciano and Monticchiello

Tour of the Etruscan museum located inside a former granary near the historic center of Chianciano followed by lunch in the medieval village of Chianciano. Afterwards, we visit Monticchiello, located in the heart of the Val d’Orcia, before we return to Casalciccia around 4 pm. A painting class will be offered before dinner in Arbia.

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Day 3

Overnight: Casalciccia

Asciano

Half day visit to a local monastery and village of Asciano, where we will have lunch. In the afternoon, there will be time for dog-walking with Patti and/or Yoga. Dinner at Podere Casalciccia.

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Day 4

Overnight: Casalciccia

Hot Springs

We spend the day at the hot springs pool in Rapolano Terme. Pool entry is covered and spa treatments can be reserved. We’ll have a light lunch at the hot springs before returning to Casalciccia mid-afternoon. For those interested, a cooking class will be offered at Casalciccia, followed by dinner for everyone.

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Day 5

Overnight: Casalciccia

Etruscan Villages

Today we drive to the Maremma area to visit the half-abandoned town of Sorano, surrounded by a gorge in which the holes of ancient tombs can still be seen. Lunch in Sorano before we visit another tiny Etruscan town perched high on the Tufa clay, with narrow streets and memorable vistas. Return to Casalciccia around 6pm where we’ll kick back with some wine and eat a pick-up restaurant dinner.

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Day 6

Overnight: Casalciccia

Tuscan Hilltowns

Today we’ll tour Val D’Orcia, including visits to the famous hilltowns of Pienza and Montepulciano. Lunch in Montepulciano. Farewell pizza dinner in Arbia.

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Day 7

OVERNIGHT: N/A

Medieval Tuscany and Farewell Lunch

On our way back to Florence, we’ll visit some off the beaten path medieval hamlets like Vertine and San Donato in Poggio, and Colle Valle D’Elsa. We will stop for a farewell lunch at medieval village, and then head to the end of the tour in Florence to drop off at the airport or the city center. If you’re departing today, choose an evening flight.

ADDITIONAL INFORMATION

Price: $3100 (Air not included) per person for a double occupancy room. Due to lack of rooms at the farmhouse, single supplement may not be available. We are happy to pair solo travelers to share a room.

What’s included: 6 dinners (wine included) and 7 lunches, 6 nights lodging in a clean, comfortable and family-run farmhouse in the gorgeous Tuscan countryside. All tastings and entrance fees per itinerary above. Local guide, driver, ground transport and transfer to/from FLORENCE airport (FLR).

Deposit Policy: we require a $600 non-refundable deposit at the time of booking. If your plans change, you may transfer this deposit to any of our other tours.

Tour begins and ends in Florence. International airport there is FLR. Everyone should meet at FLORENCE AIRPORT ARRIVALS at 10:00 am (time subject to change based on arrivals). Photos and gps location of the pick-up spot will be communicated beforehand via Whatsapp.

If you would like to book this Tuscany staycation tour just for your own group of friends or family (6-8 people), we can offer a private tour with dates to suit your travel needs.

If you have additional questions please email us at info@adventureswithsarah.net

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”I rate the trip a 4+. We had a very good time, overall. Obviously, the whole purpose of the trip was the Palio. Ms. Anna was terrific and put everything into perspective. Food/meals were excellent. (Thanks for not chiseling us on the drinks with the meals.) Accommodations were very good. Cooking school was terrific and a fun activity. I still prefer to buy my pasta. The carnival museum / workshop tour was fabulous. The trip to Carrara was very interesting. Unfortunately, it was marred by the jerks who drove the 4x4s. It's as if the drivers had a competition among themselves to see how many passengers they could make dizzy or nauseous. I felt like a gallon of paint in a shaker machine. Since we are not pool or beach people, it would have been nice to have other options. I will recommend this trip to others if Sarah makes it a permanent tour.

RICHARD CPalio and Tuscany Deluxe

”Overall we had a great trip! Wonderful countries with beautiful people, food and unique experiences. Tomaz did a great job as our guide and Brancko was a wonderful driver. The cities we visited and experiences were wonderful and we did things that we would not have been able to plan on our own which made it great! Tomaz did a great job along the way and all of the local guides were wonderful! As this was our first trip there were some details that would have been nice to provide before the trip. Numerous dinners were not planned and leaving us to find restaurants which at times was a challenge as many were closing as the tourist season was coming to an end. This also added expense to our trip that we did not anticipate. One example is that 3 nights on Brac Island was too much given that most restaurants were closed and no dinners were pre-planned for our stay. Thankfully Tomaz found a restaurant that was still open our first night. The food that was preplanned was good overall but a bit more variety would be nice - we had three meals that were basically the same - chicken and veal with vegetables. The hotel accomodations were overall good but we had issues with access to several of them due to construction . The street in front of Hotel Lapad was not accessible by bus and we had to take our luggage down a series of steps and then across mud and dirt to get to the hotel - This was not the way we wanted to start the trip. In Trogir, Villa Sv Petar had their sidewalks totally jackhammered and lots of mud and dirt to navigate. The Villa staff were very accommodating to help us get our luggage and were very apologetic. Lastly on our final night the Kairos Winery was at the top of a mountain and was only accessible via a rough dirt road. The bus driver was not able to take us all the way to the winery and as such many of our group had to walk up the dirt road!! The winery manager came down and offered rides in his small car which was quite an experience!! At least the view and experience at the winery was a highlight!! The comments are meant to improve future travel for your clients. We had a wonderful trip!!!

Margaret TStayCation Tuscany November 2023

”I had a great time. Group size (6) was optimal. There was a good mix between popular tourist sites, such as Florence and Siena, and much less frequently touristed areas. Even though I had been in Europe many times before and had visited several sites before, I always learned something new and interesting. Roberto has an exhaustive source of information and an engaging way to deliver it to his clients. Roberto's son, Mike, gave us a great cooking class and an equally entertaining class on mixing Italian aperitivi. Accommodations at Roberto and Patti's house were great, with large rooms and bathrooms and a comfortable kitchen and lounge area. Food was always great, whether at one of several restaurants we visited, at Roberto's winery or at his home. I highly recommend this tour. You won't be disappointed

Patricia LStayCation Tuscany November 2023

”Excellent trip with great guide. We thoroughly enjoyed our experience.

Dorothy SStayCation Tuscany November 2023

”My time in Tuscany with Roberto and family was the best! Driving through the beautiful countryside, medieval villages, and so much amazing food were obvious pleasures. But add to that the serene time at Casalciccia and meals with Roberto and his wonderful family made for a truly unique experience for me. Roberto added so many personal touches to the days in Tuscany, which set this tour apart from any other. Thank you Roberto!

Cheryl KStayCation Tuscany October 2023

”Anna is a prize! She knows and shares so much about the local events, culture, and art. She and Sarah led us to fantastic viewing sites for the practices, the race itself, and other related events. The group were all good travelers and fine companions, and it was delightfully small. We have heard about (and seen videos of) the Palio for decades and it was a bucket list experience for us to be there. Even the weather stayed cool for us. Food and hotels were excellent. Thank you Sarah and Anna for making this trip possible and for teaching us so much about the local culture. Sarah, please keep finding special and unusual trips and events for us to enjoy! Regards, Ben and Linda Shuler

Ben SPalio and Tuscany Deluxe

”This was a wonderful trip. Our guide, Roberto and his family were the best. Food and accommodations were great. I did not give the trip 5 stars for two reasons: the trip was mishandled administratively and I thought there was too much driving involved.

Susan GStayCation Tuscany October 2023

”Fantastic experience. The tour was exceptionally well organized and expertly led by Anna Piperato. Her knowledge of Italy, Florence, and art history and her engaging personality made the tour extremely enjoyable and enriching. She looked after the needs of the tour participants exceptionally well. The hotel was comfortable and well-located. The mix of activities was just right. The food tour of Florence markets was a distinct highlight. We highly recommend this tour.

Michael Carlsonfor StayCation Florence on Sep 29, 2022

”We had such a great time. Anna was the perfect host, sharing her knowledge and enthusiasm for Italy and its history and art. The excursions both in Florence and the surrounding countryside were wonderful and we learned so much from the local guides. The small group size made it easy to get to know everyone and, as much as I enjoyed the group activities, I also appreciated the opportunities to explore on our own. This tour is perfect whether it's your first visit to Florence or you have been there many times. I learned new things about familiar places and saw many things that I had never seen or just passed by without appreciating before. I highly recommend this tour.

Janet Suttonfor StayCation Florence on Sep 24, 2022

”Anna is a prize! She knows and shares so much about the local events, culture, and art. She and Sarah led us to fantastic viewing sites for the practices, the race itself, and other related events. The group were all good travelers and fine companions, and it was delightfully small. We have heard about (and seen videos of) the Palio for decades and it was a bucket list experience for us to be there. Even the weather stayed cool for us. Food and hotels were excellent. Thank you Sarah and Anna for making this trip possible and for teaching us so much about the local culture. Sarah, please keep finding special and unusual trips and events for us to enjoy! Regards, Ben and Linda Shuler.

Richard Corbinfor Palio and Tuscany Deluxe on Jul 17, 2023

”Sarah is a wonderful, flexible, experienced guide - our previous experience with her in Sicily is part of what drew us to this trip. Her ability to talk about nearly anything we saw in a way that is engaging and informative, and her way of seamlessly integrating information about art and architecture with history and what we're seeing in the present moment helped to make this a great week. She made Florence manageable (no small feat given the crowds, even in October), and by the time we left we felt we'd had a solid introduction to this amazing city. There was a good balance of structured activities and free time, which allowed for exploration (and naps!).

Ann Rfor StayCation Florence October 2023 on Oct 22, 2023

“Overall we had a great trip! Wonderful countries with beautiful people, food and unique experiences. Tomaz did a great job as our guide and Brancko was a wonderful driver. The cities we visited and experiences were wonderful and we did things that we would not have been able to plan on our own which made it great! Tomaz did a great job along the way and all of the local guides were wonderful! As this was our first trip there were some details that would have been nice to provide before the trip. Numerous dinners were not planned and leaving us to find restaurants which at times was a challenge as many were closing as the tourist season was coming to an end. This also added expense to our trip that we did not anticipate. One example is that 3 nights on Brac Island was too much given that most restaurants were closed and no dinners were pre-planned for our stay. Thankfully Tomaz found a restaurant that was still open our first night. The food that was preplanned was good overall but a bit more variety would be nice - we had three meals that were basically the same - chicken and veal with vegetables. The hotel accomodations were overall good but we had issues with access to several of them due to construction . The street in front of Hotel Lapad was not accessible by bus and we had to take our luggage down a series of steps and then across mud and dirt to get to the hotel - This was not the way we wanted to start the trip. In Trogir, Villa Sv Petar had their sidewalks totally jackhammered and lots of mud and dirt to navigate. The Villa staff were very accommodating to help us get our luggage and were very apologetic. Lastly on our final night the Kairos Winery was at the top of a mountain and was only accessible via a rough dirt road. The bus driver was not able to take us all the way to the winery and as such many of our group had to walk up the dirt road!! The winery manager came down and offered rides in his small car which was quite an experience!! At least the view and experience at the winery was a highlight!! The comments are meant to improve future travel for your clients. We had a wonderful trip!!!”

Margaret TStayCation Tuscany November 2023

“I had a great time. Group size (6) was optimal. There was a good mix between popular tourist sites, such as Florence and Siena, and much less frequently touristed areas. Even though I had been in Europe many times before and had visited several sites before, I always learned something new and interesting. Roberto has an exhaustive source of information and an engaging way to deliver it to his clients. Roberto's son, Mike, gave us a great cooking class and an equally entertaining class on mixing Italian aperitivi. Accommodations at Roberto and Patti's house were great, with large rooms and bathrooms and a comfortable kitchen and lounge area. Food was always great, whether at one of several restaurants we visited, at Roberto's winery or at his home. I highly recommend this tour. You won't be disappointed”

Patricia LStayCation Tuscany November 2023

“Excellent trip with great guide. We thoroughly enjoyed our experience.”

Dorothy SStayCation Tuscany November 2023

“My time in Tuscany with Roberto and family was the best! Driving through the beautiful countryside, medieval villages, and so much amazing food were obvious pleasures. But add to that the serene time at Casalciccia and meals with Roberto and his wonderful family made for a truly unique experience for me. Roberto added so many personal touches to the days in Tuscany, which set this tour apart from any other. Thank you Roberto!”

Cheryl KStayCation Tuscany October 2023

“This was a wonderful trip. Our guide, Roberto and his family were the best. Food and accommodations were great. I did not give the trip 5 stars for two reasons: the trip was mishandled administratively and I thought there was too much driving involved.”

Susan GStayCation Tuscany October 2023

“I rate the trip a 4+. We had a very good time, overall. Obviously, the whole purpose of the trip was the Palio. Ms. Anna was terrific and put everything into perspective. Food/meals were excellent. (Thanks for not chiseling us on the drinks with the meals.) Accommodations were very good. Cooking school was terrific and a fun activity. I still prefer to buy my pasta. The carnival museum / workshop tour was fabulous. The trip to Carrara was very interesting. Unfortunately, it was marred by the jerks who drove the 4x4s. It's as if the drivers had a competition among themselves to see how many passengers they could make dizzy or nauseous. I felt like a gallon of paint in a shaker machine. Since we are not pool or beach people, it would have been nice to have other options. I will recommend this trip to others if Sarah makes it a permanent tour.”

RICHARD CPalio and Tuscany Deluxe

“Anna is a prize! She knows and shares so much about the local events, culture, and art. She and Sarah led us to fantastic viewing sites for the practices, the race itself, and other related events. The group were all good travelers and fine companions, and it was delightfully small. We have heard about (and seen videos of) the Palio for decades and it was a bucket list experience for us to be there. Even the weather stayed cool for us. Food and hotels were excellent. Thank you Sarah and Anna for making this trip possible and for teaching us so much about the local culture. Sarah, please keep finding special and unusual trips and events for us to enjoy! Regards, Ben and Linda Shuler”

Ben SPalio and Tuscany Deluxe

“Fantastic experience. The tour was exceptionally well organized and expertly led by Anna Piperato. Her knowledge of Italy, Florence, and art history and her engaging personality made the tour extremely enjoyable and enriching. She looked after the needs of the tour participants exceptionally well. The hotel was comfortable and well-located. The mix of activities was just right. The food tour of Florence markets was a distinct highlight. We highly recommend this tour.”

Michael Carlsonfor StayCation Florence on Sep 29, 2022

“We had such a great time. Anna was the perfect host, sharing her knowledge and enthusiasm for Italy and its history and art. The excursions both in Florence and the surrounding countryside were wonderful and we learned so much from the local guides. The small group size made it easy to get to know everyone and, as much as I enjoyed the group activities, I also appreciated the opportunities to explore on our own. This tour is perfect whether it's your first visit to Florence or you have been there many times. I learned new things about familiar places and saw many things that I had never seen or just passed by without appreciating before. I highly recommend this tour.”

Janet Suttonfor StayCation Florence on Sep 24, 2022

“Anna is a prize! She knows and shares so much about the local events, culture, and art. She and Sarah led us to fantastic viewing sites for the practices, the race itself, and other related events. The group were all good travelers and fine companions, and it was delightfully small. We have heard about (and seen videos of) the Palio for decades and it was a bucket list experience for us to be there. Even the weather stayed cool for us. Food and hotels were excellent. Thank you Sarah and Anna for making this trip possible and for teaching us so much about the local culture. Sarah, please keep finding special and unusual trips and events for us to enjoy! Regards, Ben and Linda Shuler.”

Richard Corbinfor Palio and Tuscany Deluxe on Jul 17, 2023

“Sarah is a wonderful, flexible, experienced guide - our previous experience with her in Sicily is part of what drew us to this trip. Her ability to talk about nearly anything we saw in a way that is engaging and informative, and her way of seamlessly integrating information about art and architecture with history and what we're seeing in the present moment helped to make this a great week. She made Florence manageable (no small feat given the crowds, even in October), and by the time we left we felt we'd had a solid introduction to this amazing city. There was a good balance of structured activities and free time, which allowed for exploration (and naps!).
”

Ann Rfor StayCation Florence October 2023 on Oct 22, 2023