We all dream of Tuscany. Medieval hilltop villages and iconic landscapes that have inspired countless artists and filmmakers. The wine, food, friendly people and quiet that exists outside of the bustling cities of Rome and Florence. It’s la Dolce Vita! Experience authentic Tuscany with your hosts, Susan Lane and Cameron Dexter. We ensure attention to detail with all of our energies focused on your enjoyment in Tuscany. We create memorable experiences that aren’t available from other tours. Photos above from left to right are San Biagio, Montepulciano, a view from our agriturismo and the 2025 group in Siena. Below are photos of Cameron & Susan hiking the hills around Montepulciano, cooking class at the agriturismo and picnicking at the most sublime cheese farm after hiking in the countryside.
We will meet you at the Train Station in Rome and together we will board the train to Tuscany for a week of food and wine adventures. Each day enjoy thoughtfully curated, private food & wine experiences. You will have time to explore the picturesque medieval villages, do some shopping or relax with a cold drink at a trattoria and people watch.
September is even more breathtaking in Tuscany & Umbria as the vineyards get ready for the harvest. Susan, a certified sommelier, will host an introduction to Tuscan wines before dinner on our first night . This fun & informal tasting will give you the confidence to taste wine like a pro.
Our home for 7 nights will be a multi-generational agriturismo. This is a working farm surrounded by vineyards, olives trees, gardens and animals. Our host Stefano follows the philosophy of the Slow Food movement. “Take pleasure in food and enjoy the freshest, local ingredients. Eat with the seasons” Italian cuisine recently became the world’s first to be awarded UNESCO status.
In the itinerary below we mention the amount of walking to be expected daily on the tour. Hikes are optional and we will do our best to accommodate. We recommend good walking shoes as the medieval towns have uneven cobblestones and the hiking trails are mostly gravel paths
Below pictured is our host/chef Stefano, vineyard in Montalcino, an unforgettable lunch in Orvieto’s Piazza del Duomo, private transportation for comfortable excursions and the breathtaking countryside of Val D’Orcia that surrounds us.
Pleasant Street Tours 8 day Itinerary for September 6-13 and September 13-20
Group size ~ 14 guests
Each day we estimate the amount of walking we’ll be doing. This is an estimate for the entire day. All hikes are optional and we will do our best to accommodate those with limited mobility.
Sunday ~ We will meet you at Roma Termini
- Cameron and Susan will meet you at the Rome Train station.
- We’ll board a first class car from Rome to Tuscany where we’ll be met at the station and
- private transportation takes us to your home for the week.
- Upon arrival at the Agriturismo, you will be welcomed by your host, chef Stefano and his team.
- Aperitivo time on the terrace.
- Wine Tasting on the Terrace ~ Susan will host a fun & informal introduction to Tuscan wines
- Locally sourced four course Dinner served at the farm by Chef Stefano and his team
Monday ~ Montepulciano ~ Medieval hilltop town famous for Nobile de Montepulciano Wines. Expect 3-6 kms of walking throughout the day
- Farm to Table Breakfast
- Private Transfer to Montepulciano
- Private tour of the Cathedral and caves at De’Ricci Winery followed by a Wine Tasting
- Free time to explore the town, visit the shops, climb the Torre del Pulcinella or visit the Enoliteca for the magnificent views
- of Val d’Orcia while enjoying a glass of Vino Nobile de Montepulciano. There are over 100 producers represented.
- Or optional 4 km hike through magnificent countryside to the Cheese Farm.
- Picnic at the Cheese Farm with organic, handmade cheese, house made charcuterie, salad and breads
- Free time to relax back at the agriturismo
- Locally sourced four course Dinner served at the farm by Chef Stefano and his team
Tuesday ~ Orvieto ~ Majestic Umbrian Hilltop Town famous for Subterranean World. Expect 2-4 kms of walking throughout the day
- Farm to Table Breakfast
- Private Transfer to Orvieto in the neighbouring region of Umbria
- Free time to shop, explore the Cathedral, St Patrick’s Well or Etruscan Caves
- Lunch and informal Wine Tasting presented by the family members of a restaurant in Piazza del Duomo next to the Cathedral
- Visit historic family Winery located outside the city walls of Orvieto for a private tour and wine tasting on the terrace
- Free time to relax back at the agriturismo
- Locally sourced four course Dinner served at the farm by Chef Stefano and his team
Wednesday ~ Cooking Class on the Farm ~ Walk to Chianciano ~ famous for thermal mineral spas. Expect 2-4 kms of walking throughout the day
- Farm to Table Breakfast
- Cooking class with chef Stefano followed by a lavish lunch feasting on our creations.
- Afternoon free to hike the hills, relax around the pool or visit the Etruscan museum and walk through the village
- Walk to the village for an evening of Tuscan sharing boards in a local wine bar owned by 3 brothers.
- They create their own cheeses, meats, wine and condiments.
Thursday ~ Siena ~ Stunning medieval city ~ famous for shell-shaped Piazza del Campo. Expect 2-5 kms of walking throughout the day
- Farm to Table Breakfast
- Private Transport to Siena
- Private Food tour of Siena featuring traditional Sienese Street Food
- Private Chianti Classico Tasting on terrazza next to the Duomo
- Free time for shopping, exploring the Cathedral, climbing the Torre del Mangia tower or people watching with a cold drink in
- Piazza del Campo
- Return to agriturismo for relaxation
- Locally sourced four course Dinner served at the farm by Chef Stefano and his team
Friday ~ Pienza ~ Ideal Renaissance Town and Montalcino ~ Home of Brunello di Montalcino wine. Expect 3-6 kms of walking throughout the day
- Farm to Table Breakfast
- Private transport to Pienza ~ Picture Perfect Renaissance Village and home of Pecorino cheese
- Private Walking tour of Pienza with a local guide and then some free time to shop or grab a bite. Lunch is on your own today.
- Private Transport to Montalcino ~ Magical Hilltop Village and home to Brunello di Montalcino wines
- Private Walking Tour with a local guide and then some free time to shop or grab a bite.
- Visit a legendary and historic family run winery just outside the walls of Montalcino for private tour & tasting of Brunello Wines
- Return to the agriturismo for relaxation
- Locally sourced four course Dinner served at the farm by Chef Stefano and his team
Saturday ~ A Day all for you Walking is up to you!
- Farm to Table Breakfast
- Spend your last full day as you like. Relaxing around the pool or hiking the hills around the farmhouse. We can organize a spa visit for a group wishing to experience the therapeutic mineral spas. There is horseback riding as well as mountain bikes and e-bikes that can be arranged. Chianciano Terme is a beautiful village to explore and there are several lovely restaurants. Lunch is on your own. The day is yours to enjoy.
- Olive Oil Lesson with Stefano at the farmhouse before dinner ~ understand all of the variables of this indispensable ingredient
- Locally sourced four course Dinner served at the farm by Chef Stefano and his team
Sunday ~ Separandosi in un dolore cosi dolce ~ Parting in such sweet sorrow
- Farm to Table Breakfast
- Check out & Transfer to the Train Station
Double Occupancy $3299 Single Occupancy $3899
Tax as well as gratuities for drivers & guides is included.
Not inclusive with the tour :
Flights
Travel Insurance
Optional Activities such as: Visit to Thermal Spa, Horseback Riding, Mountain Biking, Entrance fees for museums and cathedrals
Return train ticket
Gratuity for staff at Agriturismo
$500 non-refundable deposit per guest is required to secure your reservation.
If you are interested in joining a tour please contact Susan at susan@pleasantstliving.com
We will email a contract and deposit due to secure your reservation.
The balance is due on or before June 1st.
Grazie Mille! We look forward to joining you in Tuscany.
Susan and Cameron