Tuscany and Florence

  1. The Color of Fall in the Vineyards
    The Color of Fall in the Vineyards
  2. One Never Tires of the Views
    One Never Tires of the Views
  3. The Ponte Vecchio at Night
    The Ponte Vecchio at Night
  4. Winding Roads
    Winding Roads
  5. Views from Panzano in Chianti
    Views from Panzano in Chianti
  6. Montepulciano
  7. Greve in Chianti
    Greve in Chianti
  8. Famous Pecorino Cheeses
    Famous Pecorino Cheeses
  9. Panzano in Chianti
    Panzano in Chianti
  10. The Ponte Vecchio
    The Ponte Vecchio
  11. The Doors of the Baptistry
    The Doors of the Baptistry
  12. The Blessing of the Wine Festival
    The Blessing of the Wine Festival
  13. Santo Spirito Church
    Santo Spirito Church

Cost from
per person
double occupancy

11 Days
7 Days - Tuscany
4 Days - Florence

Sept. 21 - Oct. 2, 2019

Shared Premium Vehicles in Tuscany


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​​Trip Details and Highlights

Towns Visited:
Greve, Siena, Montefioralle, Monteriggioni, Panzano, Montepulciano, Volpaia, Impruneta, San Gimignano, Pienza, Castellina, Volterre and Florence

Trip Dates:
Arrive in Florence, Italy on September 21, 2019 and depart from Florence, Italy on October 2, 2019

7 Nights in a luxury villa in the Chianti area with stunning panoramic views of its rolling hills and patchwork landscapes. 

4 Nights in a luxury boutique hotel in the historic center of Florence within walking distance to the famous sites.

What's not to love about Tuscany? Tuscany has it all; from its timeless landscapes, traditions rich in history, Renaissance art, architecture, ornate churches, incredible food, superb wines and local artisans.  You'll not only spend time in Siena and Florence but you will also visit the smaller, quaint villages.  Tuscany in the fall is a magical time with the everchanging landscape of colors and cooler days.  Seven days in the wine region of Tuscany allows you to truly indulge and connect with this beautiful region in a special way. The itinerary allows plenty of time to explore the landscapes, medieval villages, ancient architecture and incomparable art and shops as desired. Remember, you have the opportunity to do as much or as little as you choose. 

It's the lesser known villages where you will find the local artisans, farmers, craftsmen, and their families whose skills have been honed over the centuries. This is the perfect vacation for anyone wanting to focus on the best of Tuscany: hilltop villages, driving the scenic backroads, leisurely lunches with amazing views, and admiring the works of the local artisans.  

Prior to the trip rely on us to handle reservations for museums, restaurants, or a personal tour guide. 

Tuscany and Florence Trip Highlights and Experiences:
  • Stay in a luxurious villa complete with ensuite bath and plenty of room for relaxing
  • Your choice of of hands-on cooking class in a local Tuscan kitchen learning to prepare a 4-course meal from scratch or enjoy a romantic dinner at a local restaurant complete with wine at a local restaurant
  • Visit some phenomenal wineries and underground cellars followed by a few tastings of excellent wines produced from both small family wineries and the historic wineries you've dreamed of visiting
  • Visit the town of San Gimignano famous for it's towers and have lunch with a view of the Tuscan hills
  • Spend the day in Siena, tour the church, climb the bell tower, eat gelato, and sit in the famous piazza after walking the neighborhood streets full of shops and restaurants
  • Chef prepared welcome dinner at the villa on the night of your arrival
  • Farewell dinner at the villa

Transportation in Tuscany:
Tuscany is best viewed with a vehicle as it is difficult to get from place to place otherwise. Guests have the choice of having a driver in a luxury Mercedes van or touring with premium vehicles (Mercedes, Audi, BMW or similar) shared between 4 people and driving the scenic backroads whenever possible. Each car comes pre-loaded with a GPS with all of our favorite places: wineries, restaurants, and town centers. Better yet, it is preloaded with the day-to-day itinerary, you simply hit the start button and you are on your way. With a shared vehicle, guests have more flexibility in getting around. 

Have a question? Feel free to give us a call at 800-929-1078 or email us.  

Your Day to Day Itinerary
Arrival day in Tuscany, Greve in Chianti
Accommodations, Lite Lunch with Wine Tasting,
Welcome Gift, Reception and Dinner
Plan to arrive in Florence at the airport no later than 1:00 pm where you will be met by Anne or Dennis. From there we will pick up our rental cars. Note: For those who were in the Cinque Terre area as a pre-trip, we will meet you at a predetermined location. For lunch there will be a wine tasting and light lunch in Greve in Chianti. Under the porticoes in Greve, there are plenty of shops selling local specialties. In the afternoon, you can settle into your room at the villa. A welcome reception and dinner is planned at the villa.
Day 2

Panzano and Winery Visit
Accommodations with Breakfast, Wine Tasting,
Pizza Party on the Terrace
This morning you will visit the small town of Panzano. Sunday morning is market day in Panzano with vendors selling crafts and foods such as honey, olive oil, and pecorino cheese. Everyone is on their own for lunch in this charming medieval village. After Panzano, we will drive some of the winding and picturesque roads before stopping at a local winery for a tasting that has been producing wines for the past 350 years. Tonight we will have a wood-fired pizza party on the terrace (weather permitting) with local Chianti wines.
San Gimignano and Volterre
Accommodations with Breakfast
Centered around two piazzas is the town of San Gimignano that dates back to the 10th century. At one time there were over 70 towers of which 13 remain today. Medieval architecture is abundantly represented and one of its main attractions. A short distance from San Gimignano is the fortified town of Volterre. On the edge of town in Volterre, a Roman amphitheater and the Rocca (the fortress), gives the impression that they meant business when it came to keeping their town safe. This town is known for its alabaster artisans and workshops. The artisans are distant descendants of the Etruscan alabaster craftsmen whose designs, on display, still inspire the local art. 
 Siena and Monterrigioni
Accommodations with Breakfast
A trip to Tuscany wouldn't be complete without a visit to Siena, whose ochre-colored buildings and ancient ramparts evoke the city's medieval past. Siena looks much like it did in the 16th century except for the selfie-taking tourists. Siena is surrounded by four and a half miles of medieval walls today. The Cathedral of Santa Maria Assunta is beautiful on the inside as it is on the exterior. Inside, the Cathedral contains original artwork by Bernini, Donatello, and Michelangelo. The city's narrow streets and sun-filled squares are full with artistic treasures in the form of paintings and sculptures. After Siena, we will stop in the nearby town of Monterrigioni. This circular hilltop village is perched high up on a natural hill above the olive trees, the ideal spot for building its defensive walls. The 13th century towers in the wall have remained unchanged since the Middle Ages. 

Day 5

Montepulciano and Pienza
Accommodations with Breakfast

After entering the town gates of Montepulciano on Corso Street, you'll pass Renaissance palaces before arriving at the Piazza Grande. The views from the top are simply spectacular. This lovely hilltop town is rich in church architecture. One of the best reasons to visit is to try the great Brunello wines. Next, is the lovely town of Pienza and a UNESCO World Heritage Site that was transformed by Pope Pius II into the "Ideal City of the Renaissance" with its delightful street names that reflect peace rather than war. Stroll down Via della Fortuna (Fortune), Via dell'Amore (love) and Via del Bacio (Kiss). This town is so picturesque that Romeo and Juliet and The English Patient were filmed here. Pienza is known for its gourmet shops displaying foods of the region especially the pecorino cheese. 
Day 6

Impruneta and San Casciano
Accommodations with Breakfast, Cooking Class with Dinner
Impruneta is famous throughout the world for terracotta pots. We will visit a small factory with an antique kiln known for making large pots and statues formed by hand from the ground up. The techniques used today are the same as those used during Roman times. Afterwards, in San Casciano, we will stop by a family farm that is famous for its cheeses, olive oils, and honey. We will have lunch overlooking the vineyards (weather permitting). This afternoon, Chef Stefania holds cooking classes in her welcoming Tuscan kitchen. She will share her family recipes learned from her mother and grandmother then add her own twist with unexpected flavors and combinations of ingredients. Most of the ingredients used are grown organically from her own garden. Participants will make a complete 4-course meal including made from scratch pasta. Once the meal is complete everyone will enjoy the fruits of their labor and wine.  For those who are not into cooking classes, they will enjoy a lovely dinner with wine at one of our favorite restaurants near the villa.
Day 7

Volpaia and Castellina
Accommodations with Breakfast, Wine Tasting
Today we take another beautiful drive up in the hills to another picture perfect village. The medieval village of Volpaia is owned by the Stinti family and they turned the entire town into their winery where we will have a wine tasting and a tour of the cellars. After lunch, we will visit the Etruscan town of Castellina driving through gorgeous countryside, rolling hills ,and picture perfect towns. The buildings are from the 15th century including the ancient fortress that dominates its skyline, the Rocca Comunale. Castellina offers amazing views, nice shops and my favorite gelato in all of Italy.   This evening we will have a special farewell dinner at the villa.
Accommodations with Breakfast, Transfer to Florence,
Walking Tour of Florence (private for our group only)
Day 8

We leave the countryside this morning after breakfast for Florence. We return our rental cars and go by private transfer to our luxury boutique hotel. Everyone is on their own for lunch and then in the afternoon we will have a private 3 hour walking tour of Florence. The remainder of the afternoon and evening is at your leisure.  (Guests will have a choice tours: an orientation tour of the city, a tour of the Olrarno area known for the artisans and locals way of life, or a sunset promenade walking tour of the highlights.)
Day 9

Accommodations with Breakfast
Accommodations with Breakfast
Accommodations with Breakfast
Breakfast, Transfer to Florence Airport
Day 12

Today is the end of our eleven days in Tuscany. Arrangements will be made for those needing transportation back to the Florence airport.  For those staying longer in this beautiful country, enjoy the remainder of your stay in Italy. Until next time, Ciao!

For those who aren't ready to return home; ask us about our post trips.
Day 1

Day 3

Day 4

Enjoy a day of total freedom in one of the world's most beautiful cities. We are happy to assist you in making reservations to see museums if needed. For those who have not visited the Galleria dell'Accademia to see Michelangelo's David, it highly recommended and so is the Uffizi Gallery. You are at your leisure to shop the many stores, visit the churches, or simply sit in one of the many piazzas and watch the people.
Day 10

Many of the popular museums are closed on Mondays, but there is still plenty to do. The Medici Chapels, the Duomo and the Basilica of Santa Croce are both open on Monday's. Behind the Basilica there is the historic leather school where you can watch firsthand the work of its fine craftspeople and purchase one-of-a-kind leather products. You might also consider Dante's House, in the city center or visit the incredible Mercato Centrale.
Day 11

A visit to the Oltrarno section of Florence is a nice option for today. The Oltrarno district is known for its artisans who carry on the traditions passed down through the centuries. Wandering its narrow streets you'll find many talented craftsmen just as they have done for centuries in this area. This area has many great restaurants, beautiful churches and is much calmer than the other side of the Arno.
What's Included in the Trip Price 
  • Assistance with travel planning before and during the trip such as airline tickets, museum tickets, private tour guides and concierge services
  • 7 Nights in a luxury villa in the Chianti region of Tuscany.
  • 4 Nights in a boutique or luxury hotel in Florence
  • Daily breakfast
  • Light lunch and wine tasting on the day of arrival
  • Welcome reception with dinner on the evening of arrival
  • Wood-fired pizza dinner on the terrace  at the villa one evening (in the dining room if inclement weather)
  • Farewell dinner with wine prepared by a private chef
  • Two wine tastings and light lunches
  • Gratuities for all included meals 
  • A choice of: Hands-on cooking class including wine and a meal with the foods prepared in class
         OR a gourmet Tuscan dinner at one of our favorite local restaurants
  • Shared car rental for 7 days while we are at the villa complete with preloaded GPS, fuel and insurance (A valid U.S. driver's license and major credit card required for all drivers). Fuel is provided for areas included in the itinerary. (If you are not confident with a shared vehicle, a driver with a Mercedes vehicle will be provided.
  • Private 3 hour walking tour of Florence with our small group
  • Choice of a small group tour in Florence that is meaningful to you: In-depth tour of the Duomo,  Oltrarno Artisans Tour, Ufizzi or the Academia Museum, Florence Food Tour, or any other tour that interests you. Tours are limited to 6 guests.
  • ​Tourism fee of 4 euros per day per person
  • Transportation from the villa to Florence, gratuities included
  • Return transportation to Florence airport for those returning home today
What's Not Included in the Trip Price
  • Airfare and airport taxes
  • All transportation not expressed as included is not included
  • Cab fare(s)
  • Excess baggage, baggage loss and/or forwarding of baggage
  • Travel insurance  
  • Tickets and fines for moving and parking violations or unpaid tolls
  • Gratuities other than what is specifically mentioned as being included
  • Entry fees to museums/galleries and other places wherever entry fees apply
  • Beverages and meals other than what is not specifically mentioned as included in the price
  • Medical expenses
  • All personal expenditures
  • Extra charges at the villa or hotel such as  wine that is not included, bottled water, laundry, or other incidental charges
  • Additional linen or towel changes other than what is provided in the weekly rental fee
  • Additional beverages or groceries not provided by Villas and Vines
  • Expenses related to unforeseen travel conditions, weather conditions, flight delays, train delays, airport blockages, terrorism and strikes.
  • Any travel expense not specified to be included is not included
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