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Italy - Food, Wine & Culture | Well Arranged Travel
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Group Tours


Italy Small Group Tour in Tuscany & Umbria
A gourmet tour in Italy through picturesque and historic Tuscany & Umbria

You may book this Italy tour as a private tour for your group, large or small. Travel Anytime. Inquire.


Tour Cost & DatesItinerary Information Request FormI Reservation Form



Italy’s historic Tuscany & Umbria + exploration of the food and wine of the two regions. A Culinary Adventure.

Group Size: 8 to 12 people This unique tour of Italy is also available for private groups, any size, any travel dates.

Touring: San Gimignano, Chianti, Bolgheri, Panzano, Greve, Montepulciano & Montalcino, Pienza, Volterra, Norcia, Todi, Bevagna, Borgo San Gemini, Montefalco & Spello, Arezzo


To really experience Italy’s authentic food, wine and culture, you must visit the countryside. On this upscale small group tour of Italy, we’ll visit charming, historic yet often overlooked small towns and villages like Volterrra in Northern Tuscany known for alabaster, and Bolgheri in Tuscany and Norcia in Umbria for their fine local wines, cured meats, and other products straight from the source.

On this culinary adventure, we will tour Italy’s two diverse regions – Tuscany and Umbria – each with their own unique flavors and specialties. We’ll experience the great diversity of regional food and wine – from truffles and olive oil to fantastic cheeses like Pecorino. We will also visit several wine producers, refining our palates as we discover the subtle differences in Tuscan & Umbrian wines from San Gimignano, Chianti, Bolgheri, Montalcino, Montepulciano and Montefalco. Along the way, we’ll go truffle hunting, take a cooking class at a farm, visit olive oil producers, lunch at our friends’ home in Umbria, drop in on an annual village festival and more. A unique touring experience awaits you in Italy.

Possible tour extensions:

The possibilities are endless. Inquire.

3-day trip to Rome before the tour

2-day trip to Venice after the tour Additional days in Florence before or after the tour

3-day trip to Lake Como & Milan before or after the tour

3-day trip to Paris, France

3-day trip in Nice, France

Arrival Airport: Florence Arrive by 10:30am

Departure Airport: Florence

VIEW Rates & Dates »



Italy Tour Package Includes:

  • Eleven days land tour
  • Comfortable, charming and elegant accommodations in centrally located hotels (country inn, 4 Star hotels)
  • Three dinners and four lunches with wine
  • Breakfast daily
  • Walking tours with local tour guides to Volterra, Arezzo, Todi, Bevagna
  • Gratuities to expert guides and drivers
  • Winery tour and wine tasting in Montalcino, Montepulciano, San Gimignano, Chianti, Bolgheri, Montefalco
  • Cooking Class
  • Cheese tasting
  • Farm visits in San Gimignano and Pienza
  • Olive oil mill visit with tasting
  • Truffle hunting
  • Special visit and lunch at Raffaele’s family
  • Medieval Festival (with dinner)
  • Services of your Tour Manager throughout the tour
  • Airport transfer on arrival day
  • Transportation to all planned activities
  • Entrance fees to all scheduled museums and sites

Not included:

  • Gratuity to your Tour Manager
  • Airport Transfer on departure day.
  • Gratuity to drivers for airport transfers

Optional 3-Day Venice Tour


  • Accommodations at a 4 Star hotels

  • Breakfast Daily

  • Private Transfer from hotel in Florence to Florence Train Station
  • Guided Walking Tour of Venice

  • Private Transfer (boat) from Venice Train Station to Hotel in Venice
  • Escort Service from Venice train station to the Venice hotel

  • First Class train ticket from Florence to Venice
  • Entrance Tickets to Doge’s Palace and St. Mark’s Cathedral
  • Gratuities to boat driver, local guide

Not Included:

  • Gratuities to Tour Escort/Manager
  • Airport Transfer on departure day

Optional 3-Day Rome Tour


  • Accommodations at a 4-Star Hotel, 2 nights
  • Breakfast Daily

  • Private Transfer from Rome Hotel to Rome Train Station

  • First Class train ticket from Rome to Florence

  • Guided Tour of Vatican Museum, Sistine Chapel and St. Peter’s Basilica

  • Guided Tour of Ancient Rome
  • Entrance tickets Colosseum and Forum
  • Entrance tickets with reservations to Vatican museum

Not Included:

  • Gratuities to local guides and drivers
  • Service of Tour Escort


An Escorted Italy Small Group Tour

paris, franceNote: Activities or order of activities are subject to change due to unforeseen closures, schedule changes, etc. We reserve the right to replace an activity.

(B = Breakfast, L = Lunch, D = Dinner)


Itineraries for the Optional Rome & Venice Tour are found at the end of the itinerary below. Inquire about other optional tour itineraries.

DAY 1:
Arrival in Florence, Orientation Tour of San Gimignano, Welcome Dinner, Overnight in San Gimignano

Today we will meet you in Florence and transfer to the beautiful hilltop town of San Gimignano. Depending on your arrival time in Florence, we may take a detour to Fiesole. This beautiful area above Florence offers a great bird’s eye view of Florence, ancient ruins and a small but interesting museum. You’ll have free time after orientation stroll with your tour manager to explore San Gimignano, which is peaceful and beautiful at night.

In the evening, we will visit our friend, Sarah and her family farm that not only grows saffron, olives, and grapes but also raises Chianina cattle for the perfect bistecca fiorentina (Tuscan Porterhouse). Sarah has done an amazing job in introducing their wine their in the US and European market. You’ll have a chance to sample the many fine products of the farm, to include cheeses, cured meats, olive oil and an excellent white wine called Vernaccia. We’ll tour the grounds before a group farm feast. (D)

Day 2:

Volterra, Bolgheri With Wine Tasting, Overnight in San Gimignano
Today we will explore Volterra, an ancient Etruscan town enclosed by intact 12th-century walls, with remnants of its defensive walls and Porta All’Arco gate dating back to 7th century BC. We will have a guided tour of Volterra with a local guide, who will take us to see the local alabaster artists at work and shop for souvenirs.

You’ll have free time to explore this fantastic city and have lunch on your own. You may choose visit the Etruscan Guarnaci museum, one of the earliest public museums in Europe, which houses some of the most important collections of Etruscan antiquities. You may also choose to visit the Alabaster Museum, which displays more than 300 alabaster sculptures from three centuries past, among other fine works of art.

After your free time, we will visit a prestigious wine producer in Bolgheri to sample some Tuscan wine. Bolgheri has received much attention for its special reds, which blend Cabernet Franc, Sangiovese, Syrah, Merlot and/or Cabernet Sauvignon to wonderful effect.
You’ll have more free time in the evening after your return from the day trip. Your tour manager is available, if you want company for dinner. (B)

Day 3:

Day Trip to Volpaia With Wine Tasting, Overnight in Pienza

Today we will enjoy one of the most picturesque areas of Tuscany, the scenic wine-making Chianti region. We will spend the day in Volpaia, a 12th century village dedicated to the production of wine. In the 1970s, Volpaia’s former homes, churches and underground passages were converted into wine cellars and olive oil presses, connected through an underground “wineduct.” You’ll have an opportunity to tour the town’s namesake castle and winery, Castello di Volpaia, and taste the Chianti Classico produced here. Volpaia’s wines are all made strictly using organic production methods. Your guide will introduce you to the town’s rich history, such as the della Volpaia family. This family made their fortune as master clock and instrument makers and counted Leonardo di Vinci among their closest friends.

We will enjoy a tour of this fantastic village followed by tastings of their fine wine with pecorino and bruschetta. The group will have lunch at a wine bar after. You’ll enjoy the panoramic views over the surrounding vineyards as we make our way back to Pienza for the night.

(B, L)

Day 4:

Wine Tasting in Montepulciano & Montalcino, Orientation Tour of Pienza, Overnight in Pienzaparis, france
Today we will enjoy two towns known for wine. Our fist destination is the charming village of Montepulciano. It is one of the highest of Tuscan hill towns, built along a narrow tufa ridge, with a long main street and alleys that drop away to the walls. We will enjoy a tour of a fine wine producer with a historic wine cellar, and then give you free time to shop, have lunch and explore the town.

Next we’ll stop in Montalcino, the proud home of one of the finest wines of Italy, the Brunello di Montalcino. You can pick up a few bottles of this fabulous red at Croce di Mezzo, a family-run winery where we will have a private wine tasting tour.

You are on your own this evening. (B)

Day 5:

Farm Visit: Cooking Class, Pecorino Cheese Tasting, Overnight in Pienza
This morning, you will have time to explore the romantic streets of Pienza, a UNESCO World Heritage Site. Pope Pius II conceived Pienza, his birthplace, as a Utopian “new town.” The beautiful Via del Casello offers a spectacular panoramic view of the Orcia Valley, and there are several beautiful plazas and palaces for you to stroll. You may also enjoy the great shopping in Corso Rossellino, or visit the beautiful cathedral and the Pope Palace.

We’ll take a late morning trek to a nearby farm for a cooking class, lunch and tasting of the flavorful Pecorino cheese Pienza is known for.
You’ll have free time in the afternoon and evening to enjoy peaceful Pienza on your own. (B, L)

Day 6:

Montefalco & Spello, Cellar Visit & Wine Tasting, Olive Press, Overnight in Bevagna
This morning we will travel directly to Bevagna, our base for the next 4 nights. This walled city has its origins deep in ancient history. There are many historic sights of interest here, including the church of the Madonna of the Snow, built on the ruins of a Roman temple, and an ancient Roman bathhouse featuring mosaics depicting assorted sea creatures.

After we check-in we will go spend some time in town for a guided tour of this beautiful town and for some free time for lunch. In the afternoon, we will drive a short distance to Montefalco, known for fine red wines such as the Sagrantino. We will visit a great wine producer for a tour and tasting, and have the opportunity to buy some of their well-known vintages. We may also tour one of Montefalco’s beautiful churches, which cover the Romanesque, Gothic and Renaissance styles. The beautifully frescoed church of San Francesco has been converted to the town’s museum, offering an extensive collection of art and artifacts from Umbria.

Next we will stop to visit an extra-virgin olive oil producer between Spello and Trevi. This area is known for the best olive oil in Umbria. You will get to see the olive mill and cold pressing machine in action, then taste the oil with some freshly baked Umbrian bread. After, we will have a short visit of steep and ancient Spello with its Porta di Venere, a gate from 1st century B.C.

You are on your own this evening. (B)

Day 7:

Norcia, Truffle Hunting, Overnight in Bevagna

Our activities today include truffle hunting -black truffles. We will have the aid of a special local guide, a truffle-hunting dog, who will help us find these rare treasures of the forest floor. Following our truffle hunt is a cooking class and lunch with a dish featuring truffles.

Today we will also visit Norcia, the birthplace of St. Benedict, the patron saint of Europe. Norcia’s basilica is dedicated to St. Benedict, still attached to a functioning Benedictine monastery. Norcia is also the birthplace of several culinary specialties. The wilderness around Norcia is known for mountaineering and hunting, especially wild boar, which are often made into sausages and ham known in Italian as norcineria.

Return to Bevagna in mid-afternoon for some free time. (B, L)

Day 8:

Leisurely Day in Borgo San Gemini, Festival, Visit to Local Family Home & Garden with Lunch, Overnight in Bevagna
Today, Raffaele, your tour manager, will take you on a walking tour of his native village, Borgo San Gemini. We’ll time our visit with a local festival celebrating San Gemini’s medieval past, with the town’s historic center decorated with flags, candles and other special touches.
After enjoying the festivities, you will visit Raffaele’s grandpa’s vegetable and herb garden, learning about some of the key ingredients in the local specialties you will sample for lunch. You will then proceed to Raffaele’s mom’s house, where his mother and aunt will have a home-cooked meal waiting for you.

After lunch, we will go back into town, where the festivities will be in full swing, enjoying a colorful parade with townspeople in medieval costume. We will work on having our group dinner in town to join the locals in their festivities. (B, L, D)

Day 9:

Todi, Overnight in Bevagna
Today we will visit Todi, a lovely medieval hilltop town overlooking the Tiber River. Todi’s central piazza, originally the Roman forum, has several beautiful medieval buildings for you to explore.

You are free to have dinner on your own tonight, but as always, the tour manager is happy to make recommendations or accompany you. (B)paris, france

Day 10:

Arezzo, Florence, Farewell Dinner, Overnight in Florence
On our last day of the tour, we will finish in Florence, stopping en route in Arezzo, an important Etruscan town, for a guided tour of this interesting city. Arezzo is known for its antiques market and shops; we’ll stop for a guided tour and some free timet for you to explore, have lunch, perhaps tasting Arezzo’s famous Acquacotta, a bread soup made with porcini mushrooms.

We will arrive in Florence in the late afternoon, when you will have some time to explore the city before our farewell dinner together.

(B, D)

paris, france

Day 11:

Departure for Home
Today, you will prepare for your departure home, or for an optional extended tour in Florence, the birthplace of the Renaissance and home to Italy’s finest art and architecture. (B)




Day 1

Arrival in Rome, Ancient Rome Tour, Overnight in Rome

Our driver guide will meet you at the airport upon arrival and take you to your hotel in Rome. After you check in and have lunch, you will have a guided tour of Rome. Rome’s fascinating history will come alive as our excellent tour guide shows Rome’s Colosseum, forum, arch of Constantine and more. (If your flight does not allow you do this guided tour on your arrival day, this tour can be scheduled on Day 2)

A short walk from your hotel are some of Rome’s most beautful squares: Piazza Navona, Pantheon and Campo dei Fiori. Have lunch in Campo dei Fiori, either at a take-out place called Forno for slices of pizza and such or at a restaurant called La Carbonara for a great selection of pastas. The end of your guided tour will leave you in the Pantheon square, where you may sit at one of the cafes facing what some of us believe is the most beautiful ancient structure in Rome.

Day 2

Private Tour of Vatican With Expert Tour Guide, Overnight in Rome

Our tour guide in Rome will pick you up at the hotel early in the morning for your guided tour of the Vatican museum, Sistine Chapel and St. Peter’s Basilica. At the end of the Vatican tour your guide will take you to Trevi fountain for a photo op and continue onto your final destination, The Spanish Steps, where our guide will leave you. Consider lunch at Ristorant Alla Rampa, on Piazza MIgnarelli, around the corner from the Spanish Steps. Taxi stand is by the obelisk should you decide not to walk back to your hotel.

Day 3

Last Day in Rome

Explore on your own and prepare to depart for your next destination.


Day 1

Arrival in Venice, Venice Walking Tour: St. Mark’s Square, The Duomo, Doge’s Palace, Bridge of Sighs and More, Doge’s Palace, Overnight in Venice

You will take the train from Florence to Venice. Our tour escort will meet you at the airport and take you to your charming hotel in Venice via a private boat. After you check in and lunch, you will have a guided tour of Venice’s St. Mark’s Square, the Basilica and Doge’s Palace. See the ancient political and administrative center of the Republic of Venice, the Doge’s Palace -the seat of the government including the prison and the famous Bridge of Sighs and St. Mark’s Basilica with its gold mosaics.

Day 2

Leisure Day, Overnight in Venice

You are free to explore Venice on your own. Explolre without any specific destination in Venice can be very rewarding. You’ll experience many different neighborhoods, see how people live and come across great restaurants outside the tourist track. We suggest a quick visit to Peggy Guggenheim museum. The museum is in a mansion, her old home on the Grand Canal. It is located in a nice and quieter part of Venice.

NOTE: Request a private water taxi from your hotel concierge for your flight tomorrow. It is best to inquire/reserve particularly if your flight is very early in the morning.. (B)

Day 3

Last Day in Venice, Prepare for Your Flight Home

Have breakfast and enjoy Venice one last time. (B)


“Ning, we really enjoyed our second trip with your company. The trip is well planned, from delicious meals to nice, well-run hotels with attentive service. Our group was delightful. Everyone was glad to take a suggestion and go with it. We thoroughly enjoyed each other’s company and even scheduled dinners together when they were not planned.

Raffaele, our guide, did a wonderful job at shepherding us through cities, towns, villages and countryside. Raffaele is quite knowledgeable and truly enjoys talking to people. He has a great sense of humor and shared his relationship with his family, which gave us a insight into the Italian family life. He also kept us moving and so we never were bored.

We all loved having beautiful and lively Lucca as a home base for three days. It is beautiful and has an active night life. Our visit to the small village of Pienza was also a nice change of pace from busy Lucca and the other cities we visited. The visit to the winery there was great…we ate fresh figs off their tree, tasted wine and bought some for home. York, our guide from the vineyard, was knowledgeable and pleasant. He helped us appreciate the challenges of wine making. Thanks for a great trip.” — Brad and Louise Eisenbrey, Tuscany and Umbria Group Tour

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