Tuscany Small Group Tours

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Private Guided Tours of Tuscany

The cities of the Tuscany region are as diverse as its people. Each offers its own unique culture, cuisine and style. Why such a diverse offering within one region you can drive across in just a few hours. Until the 1600’s Italy was divided and each city was basically its own country complete with its own government, rules, traditions, dialects and even their own money.

Once Italy was unified between 1815–1871 it created a singular country but within it had a very diverse and multi-directional culture separated by the boundaries of each region and city.

Today Tuscany offers the traveler a plethora of choices from grand Florence, historic Siena, sleepy Tuscany countryside towns or the coastal villages of the Mediterranean Sea. Here are just a few of our favorite unique experiences that we cover with our Tuscany escorted tours.

Couple researching their Italian roots with a family tree chart, local guide showing a map in an Italian village, and on-site document research inside a historic church — examples of genealogy and ancestral tours in Italy.

Genealogy & Ancestral Roots Tours in Italy

Customized Pricing

All Year - you pick your own dates

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castle tower at sunset with pool in front

6-Day Private Castles & Chianti Tour: Discovering Italy’s Heartland

Customized Pricing

April to October - Pick your own dates

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lake maggiore garden and castle

13 Day Primo Italiano Luxury Small Group Tour of Italy

$5,999 (USD)

September 1-13

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Florence panoramic view

9-Day Rome, Florence, Venice: The Big 3 Small Group Tour

Small Group FROM €3275 pp
(from pricing reflects double occupancy/low season)
See the schedule below for complete dates & pricing

Small Group
April - November
or Customizable = Pick your own dates
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Venice Food Tour

10-Day Italy on a Budget: Milan, Venice, Florence & More

From €2,999 per person.

All Year

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Siena skyline

8-Day Tuscan Elegance: An Immersive Journey

Customized Pricing

Pick your own date

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The Amalfi Coas

10-Day Italian Journey by Train: Discover Italy with Italy4Real

From €4,249 per person.

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April to October

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Helicopter on grass with tree in the background

Helicopter Wine Adventure from Rome: Truffle Hunting and Gourmet Lunch Experience

Must be part of an existing luxury package.
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March to October
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7-Day Odyssey by High-Speed Train

From €2,299 per person.
(triple occupancy)
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January to November
- Monday
-Wednesday
-Thursday
-Friday
-Sunday

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helicopter-flying-over-a-lush-Tuscan-vineyard.-

Tuscany Brunello Wine Tour by Helicopter from Florence

Must be part of an existing luxury package.
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March to October
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15-Day Rome Tuscany, Amalfi Coast Cinque Terre and Italy’s Boot

Customized Pricing

Choose your Departure
April – Dec
or pick your own dates

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7-Day Tuscan Villa Cycling Retreat: Authentic Exploration and Serenity

Price Euro 3,298
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March to October
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Ugolino Golf Club green

6 Day Golf Tour: Tuscany Tee & Wine Time: Your Chill Golf Getaway

Customized Pricing - Email us for a quote today!
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Spring to Fall
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biker in countryside with tree and sun

Tuscany E-Bike Adventure: Montalcino & Brunello Wine 🚴‍♂️🍇

Must be part of an existing Italy4Real package
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March to October
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Tuscany cooking class and Winery Visit

This must be part of an existing Italy4Real Package
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All Year
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🍇 Tuscany Winery Visit with Organic Lunch 🍷

Must be part of an existing Italy4Real package
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All year
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9-Day Golfing in Italy Tuscany & Rome’s Ryder Cup Course

Customized Pricing
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Spring through Fall
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Cinque Terre Many Colours

8-Day Rome, Florence & Cinque Terre Italian Tapestry

Price From Euro 2,940
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March to October
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Milanese sights

12-Day Italian Odyssey by Train North to South Through Culture, Culinary and Coastlines

Price From Euro €3,590 per person
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April - October
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An Evening Electric Bike Ride Through Tuscany

UPON REQUEST

APRIL – OCTOBER

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The Best of Italy and Paris Custom Tour

Customized Pricing

All year

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Florence bridge at night

A Discovery of Florence by Foot

UPON REQUEST

ALL YEAR

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Day Trip To Pisa Tour From Tuscany: A Journey

PRICING UPON REQUEST

ALL YEAR

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8-Day Tuscany Wine Tour for wine lovers

From € 3,981 per person
Customize this tour

Multiple Departures
Apr – Oct
Or Pick your own dates

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8-Day Customized Rome, Florence & Venice

Customized Pricing

Multiple Departures
pick your own dates

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7-Day Wine Food Tour of Tuscany from Rome

Customized Pricing

Multiple Departures
April – Oct

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7-Day Tuscany Tour

From € 3,971 per person

All Year

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7-Day Back Roads of Northern Italy

From € 2,371 per person

Multiple Departures
April – Nov
or pick your own dates

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6-Day Best of Rome & Florence (Add-On)

From € 1,321

Multiple Departures
Jan – Dec

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15-Day Magnificent Tour of Italy

From € 3,850

Multiple Departures, pick your own date
April – Nov 2024

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What to See In Tuscany

Tuscany’s highlights are endless. No matter if you are visiting the major towns of Florence and Siena or going to smaller cities like San Gimignano, Montepulciano or Volterra our staff can show you the proper way to explore this region that makes sense and is enjoyable for your entire Family. Tuscany has the famous wine roads that offer you a wonderful experience tasting some of the worlds most famous wines. The region offers you the chance to travel from town to town tasting, eating and enjoying all that this amazing area has to offer.

The Chianti Wine Region

The area of the chianti Classico D.O.C. wine, in the Florentine country include the territory of Barberino Val d´Elsa, Grevew, S. Casciano e Tavarnelle Val di Pesa. The name has its origins in the “Leauge of the Chianti”, established from the Florentine Republic in the XVIth century. The great reputation of Chianti Wine; a brilliant red-colored wine from an intense bouquet can be traced back to the 15th century. A great way to explore Tuscany is to visit one of the many wineries to enjoy a lunch and wine tasting.

Private Guided Tours Tuscany

One of the great things to do in the area are Tuscany guided tours and town hop, exploring off the track hidden gems. This is when you get a rental car and travel the winding country roads; through the Tuscan wine country stopping along the way at some veray interesting Tuscan hill towns.

Small Private San Gimignano Tours

San Gimignano

Called the Manhattan of Tuscany because of its ancient towers, this castle hill town offers quaint small village feel with a selection of small hotels and local restaurants.

Siena

One of Tuscany’s main towns outside of Florence; Siena is the home of the Palio di Siena horse race that happens twice a year in July and August. Siena also has the Duomo di Siena with its characteristic black and white marble.

Florence

A city in Tuscany and one of the most famous cities in all of Italy. When you are planning a trip to Tuscany you must visit Florence to see Michelangelo’s masterpiece; David. The sculpture was created around 1501 and you can purchase skip the line tickets to see David in Florence from your travel specialist.

Tours of Tuscany

Tuscany is one of the most popular regions in the world. This can be a good thing or a bad thing.. Good because it contains some of the most iconic cities and towns such as Florence and Siena; bad because it can be crowded and full of tourists if you don’t know how to plan accordingly. Our expert travel guides can help you design a custom tour through Tuscany that will take you to the major towns and show you them in a way only a local would know. We can also show you how to stay in a villa in the countryside and use it as base location to go out and experience some of the amazing wine country, castle hill towns and iconic cities in a comfortable, organized and enjoyable way. We have created some wonderful tours of Tuscany to give you an idea of what we can offer you; but many of our experiences are fully customized to fit your likes and budget; so submit your request today to get your complementary route and ideas for how to visit Tuscany properly.

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