Are you dreaming of Tuscany? Medieval hilltop villages and iconic landscapes that have inspired artists for centuries. Experience the tranquility of the rolling vineyards, country roads dotted with Cypress trees and a quiet pace that exists outside of the bustling cities.
This relaxed escape allows you to immerse yourself in the peaceful and picturesque surroundings. Tuscany offers the quintessential Italian experience featuring Chianti Classico, Brunello di Montalcino and UNESCO world heritage Tuscan cuisine.
Your hosts, Susan and Cameron curate authentic experiences allowing a deeper cultural immersion and personalized attention that
larger tours are unable to offer.
Photos above from left to right are San Biagio, Montepulciano and views from our home for 8 days. Hike the rolling countryside, cooking class at the agriturismo and picnicking at the most sublime cheese farm in the countryside around Montepulciano.
Cameron & Susan will meet you at the Roma Termini in the centre of Rome and together we will board the train to Tuscany. Relax and settle in for the week at a charming, multi-generational agriturismo. This is a working farm surrounded by vineyards, olives groves, gardens,animals and the most spectacular views of the Tuscan countryside. 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.
After a hearty breakfast we”ll embark on daily excursions to medieval hilltop towns and family owned culinary expereinces. Immerse yourself in local culture with ample time to do some shopping or relax with a cold drink at a trattoria and people-watch.
September is 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.
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
Group size ~ 14 guests
Sunday
- Susan and Cameron will meet you at the Roma Termini which is the train station in the centre of Rome on Sunday afternoon. If you require any assistance we are here to help.
- 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 with wine tasting tips
- 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.
- Farm to Table Breakfast
- Private Transfer to Montepulciano
- Tour of the Cathedral and caves at De’Ricci Winery followed by a Wine Tasting
- Free time to explore the town and enjoy some shopping. Vans will transport you to the Cheese Farm
- Or optional 4 km hike through magnificent countryside to the Cheese Farm.
- Picnic at the Pecorino Cheese Farm with organic, handmade cheese, house made charcuterie, salad and breads
- Transport back to the agriturismo for free time to relax or go for a swim
- 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.
- 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.
- 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 produce their own cheeses, cured meats, lardo & wine
Thursday ~ Siena ~ Stunning medieval city ~ famous for shell-shaped Piazza del Campo.
- Farm to Table Breakfast
- Private Transport to Siena
- Private Food tour of Siena with a local guide featuring traditional Sienese Street Food
- Chianti Classico Tasting with a local wine merchant on terrazza next to the Duomo in Siena
- 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.
- 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
- 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/ person. Single Occupancy $3899
Inclusive in the Tour :
- Train from Rome to Tuscany
- 7 Nights Accommodation at a charming Agriturismo
- 6 Four Course, Locally Sourced Dinners at the Agriturismo
- 1 Evening of Tuscan Sharing Boards at Local Wine Bar
- 7 Farm to Table Breakfast
- 2 Lunches
- 1 Picnic
- 1 Food Tour
- 1 Cooking Class with Chef Stefano
- 7 Guided Wine Tastings
- 3 Walking Tours in Medieval Hill-towns with a Local Guide
- Transportation for the group for Daily Excursions
- Transportation to and From the Train Station
- Tax as well as gratuities for drivers & guides is included.
Not Inclusive in the Tour:
- Flights
- Travel Insurance
- Optional Activities such as: Visit to Thermal Spa, Horseback Riding, Mountain Biking
- Return train ticket
- Gratuity for staff at Agriturismo
$500 non-refundable deposit per guest is required to secure your reservation.
Double Occupancy $3299 per/ person
Single Occupancy $3899 per/person
If you are interested in joining the tour or would like more information please contact Susan susan@pleasantstliving.com
Grazie Mille! We look forward to hosting you in Tuscany.
Susan and Cameron