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Private · Florence

Florence, Tuscany and the Italian Riviera

10 Days Tuscany · Liguria

The Overview

Overview

We will meet you at Florence airport and transport you straightaway to the lush green of the Chianti countryside, where you will spend 3 days exploring the Renaissance towns, UNESCO sites and wine-producers of Tuscany.  

At its height, San Gimignano could boast 72 towers, symbols of the wealth and power of the Medieval families who lived here.  Today, even with just 14 surviving, San Gimignano is recognized for its unique characteristics.  You will have time to visit the town and the option to climb one of the towers to enjoy sweeping views across the countryside below.  There's a reason that Siena is one of the most visited towns in Italy, with its rich history and clean, pedestrianized center it makes for a perfect afternoon stroll, not to mention the chance to visit the famous, striped duomo and taste the delicious local sweets.

Val d'Orcia is so picturesque that the entire area has been named a World Heritage site!  Our tour will take us to just 3 of the delightful towns that scatter the countryside: firstly, the hilltop town of Montalcino, surrounded by vineyards growing the Sangiovese grapes that are used to make the famous Brunello di Montalcino.  Of course, there will be the opportunity to taste examples of this wine in a very special enoteca.  Next we will go to Pienza, the Renaissance utopia and producer of pecorino di pienza.  Finally, Montepulciano, home to another famous Tuscan wine.

On our way to Cinque Terre, we will stop in Pisa to visit the Leaning Tower and the town of Lucca for lunch before ending the day in Monterosso a Mare.  You'll get the chance to hike the famous trails between the 5 fishing villages as well as visiting them from the tranquility of a boat.  To round off the tour will head to Portovenere for a wonderful dinner in the Palmaria Restuarant.

The final stop of our tour will be 2 nights in the heart of Tuscany, in Florence, cradle of the Renaissance.  Here you will be introduced to the history of the city and the men who brought it to prominence as we tour the streets and visit the 2 most famous galleries. You will also have plenty of free time to explore the compact city-center on your own, try the famous bistecca alla fiorentina, explore the leather market and shopping streets and wander the banks of the river with an ice-cream as the locals do!

As our tour comes to end, our drivers will take you back to Florence to fly home.  If you are interested in extending your Italian vacation, speak to one of our Italian experts who will be happy to help you.

Duration

10 days

9 nights

Starting From

EUR 5,450

Per person for two travelers

Tailored to your departure and group.

A classic introduction to the must-see sites of Tuscany and Cinque Terre. From the wine-growing lands of Chianti and Val d'Orcia to the Renaissance splendour and the museums of Florence, the tour ends in the incredible natural beauty of the Italian Riviera.

Regions
Tuscany · Liguria
Tour Style
Private
Departs From
Florence
Meeting Point
Florence Airport
Included Meals
Daily breakfast · 2 wine tastings · 1 lunch · 1 cooking class
Day by day

Itinerary

Follow the route as you read. The map traces each day of the journey, moving with you from place to place.

Tuscany

Chapter 1 · Days 1–7

Welcome to Tuscany

Tuscany is among the most beautiful regions of Italy. The gentle curves and slopes of the land will enchant you. Tuscany is as famous for its wine and cuisine as it is for its landscapes. Wine production focuses on red wines like Chianti, San Giovese, Rosso di Montalcino, Rosso di Montepulciano, Bolgheri, and others. Food is prepared with seasonal…

Explore Tuscany
Day 1

Tuscany, Florence Tuscany, Chianti

Arrival at Florence airport

Arrival at Florence airport — photo 1 Arrival at Florence airport — photo 2 Arrival at Florence airport — photo 3 Arrival at Florence airport — photo 4 Arrival at Florence airport — photo 5

When you arrive at Florence airport, you will be met by one of our drivers and taken to the lovely Hotel Cisterna located in the old town of San Gimignano with sweeping views of the Tuscan countryside. 

Spend the rest of the day relaxing from your flight, with the option to enjoy the town, incredible shops and one of the very best Gelato stops in Italy! 

In the evening, you will enjoy your first taste of Tuscan life before turning in for the night in the peace of the countryside.

Overnight at Hotel Cisterna. 

 

Where we meet Florence Airport
Day 2

Tuscany, Siena Tuscany, San Gimignano

The Chianti Region: Siena & San Gimignano

  • Breakfast
  • Wine Tasting
The Chianti Region: Siena & San Gimignano — photo 1 The Chianti Region: Siena & San Gimignano — photo 2 The Chianti Region: Siena & San Gimignano — photo 3 The Chianti Region: Siena & San Gimignano — photo 4 The Chianti Region: Siena & San Gimignano — photo 5

After breakfast, our driver will meet you at the hotel and take you around San Gimignano; you will have time to explore the town on your own and climb one of its famous towers.

For lunch, we will stop at a local winery, enjoy some local produce and sample both the famous Chianti reds and Vernaccia, one of Italy's finest white wines, which is produced in vineyards around San Gimignano.

The afternoon will be spent in the delightful provincial capital of Siena.  Here you will meet a local guide, who will  walk you through the lovely, traffic-free Renaissance center, the Piazza del Campo, one of the loveliest squares in Italy where the Palio takes place twice a year and the famous black and white duomo.  The day will end back at the hotel.

Overnight at the Hotel Cisterna 

Day 3

Tuscany, Montalcino Tuscany, Pienza

Val d'Orcia: Montalcino & Pienza

  • Breakfast
  • Wine Tasting
Val d'Orcia: Montalcino & Pienza — photo 1 Val d'Orcia: Montalcino & Pienza — photo 2 Val d'Orcia: Montalcino & Pienza — photo 3 Val d'Orcia: Montalcino & Pienza — photo 4 Val d'Orcia: Montalcino & Pienza — photo 5

This morning, following breakfast, your driver will take you to the southern part of Tuscany and the beautiful Val d'Orcia.  This is the Tuscan countryside you are used to seeing in photos: miles of vineyards and cornfields, isolated hilltop farmhouses and roads lined with poplar trees.

The first stop of the day will be the town of Montalcino.  We suggest you pop into the wonderful enoteca inside a majestic 12th century fortress that was once part of the town's defenses.  Here we can enjoy a tasting of local wines, including Brunello di Montalcino served with local cheese and cold cuts to keep you going till lunch! 

The next town as you make your way through the valley is Pienza, where you will have free time to sit down for lunch or to grab a snack and explore the town.  Pienza is known as the 'ideal city of the Renaissance', thanks to the patronage of Pope Pius II, who wanted to change his humble birthplace into a utopia.  

The final stop of the day will be Montepulciano, a name associated the world over with the rich red wine produced here.  Wander through the town, enjoying the stunning views across the Orcia Valley, before stopping for a tour of a famous wine cellar, where you will be able to taste more local wines.

Back to the villa for dinner and some well-deserved relaxation.

NB: uphill walking is unavoidable in the towns.

Return in the early evening to San Gimignano for dinner at leisure and Overnight at the Hotel Cisterna 

Day 4

Tuscany, Chianti Tuscany, Florence

Cooking class and Transfer to Florence

  • Breakfast
  • Lunch
  • Cooking Class
Cooking class and Transfer to Florence — photo 1 Cooking class and Transfer to Florence — photo 2 Cooking class and Transfer to Florence — photo 3 Cooking class and Transfer to Florence — photo 4 Cooking class and Transfer to Florence — photo 5

This morning you will learn a little about Tuscan cooking in the kitchen of the Tenuta Torciano and develop some culinary skills to take home with you!  Try your hand at making pasta, then enjoy eating the fruits of your labors with a truly homemade lunch.

In the afternoon, it is time to say goodbye to the green hills of the Tuscan countryside.  Your driver will meet you at the hotel to drive you to the Renaissance splendor of Florence and the lovely Hotel Berchielli centrally located on the banks of the Arno River, right by Ponte Vecchio in central Florence.

You will have the rest of the day to relax, enjoy a leisurely dinner and an evening walk along the banks of the Arno.

Overnight at Hotel Berchielli. 

Day 5

Tuscany, Florence

Florence and the Accademia

  • Breakfast
Florence and the Accademia — photo 1 Florence and the Accademia — photo 2 Florence and the Accademia — photo 3 Florence and the Accademia — photo 4 Florence and the Accademia — photo 5

Following breakfast, your guide will meet you at the hotel and take you through the Renaissance streets of Florence, passing some of the city’s best-known sites including Palazzo Vecchio, Ponte Vecchio, Palazzo Pitti and the duomo.  Discover the history of the powerful Medici family who at one time ruled great parts of Tuscany and whose influence of Florence can still be seen today.  Their patronage of young artists gave rise to some of the greatest talents of their day, including Michelangelo.  Your tour will include a visit to the Accademia Gallery, which houses one of his finest sculptures: the monumental statue of David.

Afterwards, you will have the rest of the day free to enjoy the city at your leisure.

Overnight in Florence.

Day 6

Tuscany, Florence

Florence: The Uffizi

  • Breakfast
Florence: The Uffizi — photo 1 Florence: The Uffizi — photo 2 Florence: The Uffizi — photo 3 Florence: The Uffizi — photo 4 Florence: The Uffizi — photo 5

Your guide will meet you at the hotel and accompany you down the street to Italy's most visited museum.  Here you will spend the morning discovering the paintings, sculptures and drawings of the Masters of the Italian Renaissance, including Giotti, Botticelli, Leonardo da Vinci, Michelangelo, Caravaggio and many others.

After the tour, you will have the rest of the day free.

Overnight in Florence.

Day 7

Tuscany, Pisa Tuscany, Lucca Liguria, Cinque Terre, Monterosso Al Mare

Depart Florence via Pisa and Lucca

  • Breakfast
Depart Florence via Pisa and Lucca — photo 1 Depart Florence via Pisa and Lucca — photo 2 Depart Florence via Pisa and Lucca — photo 3 Depart Florence via Pisa and Lucca — photo 4 Depart Florence via Pisa and Lucca — photo 5

Leaving Florence after breakfast, you will have the chance to visit 2 more famous Tuscan towns on route to Cinque Terre.

In Pisa you will have time to walk around the 'Field of Miracles', climb the famous tower and visit the cathedral before moving onto Lucca.  This lovely Renaissance town is centered around a 'square' that was built over a Roman amphitheater.  You will also be able to get lunch here, before continuing your journey north.

In the afternoon, we will arrive in Monterosso where we will be staying at  Margherita which is few minutes walking to the seafront.  You will now have the evening to relax, stroll on the beach and enjoy dinner in the town.

Overnight in Monterosso.

Liguria

Chapter 2 · Days 8–10

Welcome to Liguria

 Liguria, whose history and destiny are closely tied to the sea, is home of the Italian Riviera; sandwiched between the French Riviera and the Tuscan coast, bounded to the north by the Piemontese Alps. This magnificent coastal area, is best known for its string of glamorous resorts like San Malo, Portofino, and  Cinque Terre) and picturesque fishing…

Explore Liguria
Day 8

Liguria, Cinque Terre

Hiking in Cinque Terre

  • Breakfast
Hiking in Cinque Terre — photo 1 Hiking in Cinque Terre — photo 2 Hiking in Cinque Terre — photo 3 Hiking in Cinque Terre — photo 4 Hiking in Cinque Terre — photo 5

Today will be completely free for you to explore as much, or as little of the five villages as you wish.  

If you are feeling energetic, hike between them enjoying the wonderful views as you go.  Alternatively, you can take the train or ferry which stop in each of the villages for a more relaxed experience.

Overnight in Monterosso.

Day 9

Liguria, Cinque Terre

Hiking and Farewell Dinner

  • Breakfast
Hiking and Farewell Dinner — photo 1 Hiking and Farewell Dinner — photo 2 Hiking and Farewell Dinner — photo 3 Hiking and Farewell Dinner — photo 4 Hiking and Farewell Dinner — photo 5

Continue exploring the villages, or take the ferry to Portovenere and Palmaria island for wonderful views over the Gulf of Poets.

Overnight in Monterosso.

The details

Inclusions & Exclusions

What's Included

  • All hotel taxes and service charges
  • All transfers
  • Cellar Tour
  • Cooking class
  • Daily Buffet Breakfast
  • English speaking tour escort for the duration of the tour
  • Entrance Ticket to Leaning Tower
  • Florence: Guided visit of the most important monuments including the inside visit of the Academia museum with its Michelangelo statue
  • Free Time For Lunch
  • Fuel
  • Road Tolls
  • Service Charges and Taxes
  • Siena and San Gimignano
  • Small Group Sizes
  • Wine Tastings
  • Winery Visits
Your rooms

Where You'll Stay

Hotels are subject to availability and may be replaced with a property of similar standard.

Hotel Berchielli

Hotel Berchielli

Tuscany, Florence

Hotel Berchielli is a luxurious 4-star establishment nestled in the heart of Florence. Situated on the picturesque riverfront, the hotel boasts breath...

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Hotel Margherita Monterosso Al Mare

Hotel Margherita Monterosso Al Mare

Italy

Hotel margherita is situated in the old part of Monterosso just a few steps away from the beaches, touristic port, trails, local shops and many restau...

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Hotel Plaza Lucchesi Florence

Hotel Plaza Lucchesi Florence

Tuscany, Florence

Plaza Hotel Lucchesi is located right on the bank of the Arno River, just 10 minutes' walk from Piazza della Signoria. The hotel features air-conditio...

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Hotel Sovestro

Hotel Sovestro

Siena, San Gimignano

This hotel is situated in a delightful position just 2 km from the towers of the historical town of San Gimignano, the HOTEL SOVESTRO complex stretche...

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La Cisterna Hotel San Gimignano

La Cisterna Hotel San Gimignano

Tuscany, San Gimignano

La Cisterna is located on a gorgeous, named piazza in the centre of San Gimignano and is housed in an excellent 14th-century building. Air conditionin...

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In their words

Traveler Reviews

Emily and David Davison Travelled with us

My husband and I just took a two week trip to Italy that was planned for us by Eleanor Kinchin-Smith. It was a fantastic trip and we could not have been more thrilled. We worked together with Ele to let her know about our interests and our style of travel. She planned the perfect trip with excellent private guides at all of our sites, professional drivers and lovely hotels. We arrived in Italy with all of our train and ferry reservations made by Ele, with tickets in hand. She was in touch with us daily throughout our trip to make sure that things were going smoothly. She was able to make a few changes to our itinerary as needed. We look forward to working with Ele again on our next trip and have put her in touch with another family member to help plan their trip as well.

Ron and Deb Crosby Travelled with us

Dear Guiseppe and Jesse,

We just returned from our most wonderful vacation to Italy and wanted to first thank you for putting together such a wonderful trip, and second to provide some feedback for the future.

Hotels

1. Hotel Sovestro in San Gimignano was wonderful. The staff were very friendly and helpful and made the first portion of our journey very stress free. They made us feel like we were part of their family. I would recommend it to anyone and would specifically ask for it if we were to make a return visit.

2. Hotel La Baia in Monterosso was nice and it's location was very good especially for us older folks humping luggage from/to the train station.

3. Hotel Lucchesi in Florence- what can I say expect FANTASTIC. The rooftop view at sunset is well worth it. Again very friendly and helpful staff. Would recommend it to everyone.

Wine Tour

Money well spent. We had a great time overall. The driver Mario was OUTSTANDING. He had lots of local knowledge as well as about winemaking. USE HIM AGAIN!!!

The various wineries we visited on tour:

Altesino- fantastic and they were not cheap on their pouring. Great experience.

Azienda Agricola Patrizia Cencion Sloaria- Again a great tour by one of the owner's daughters. We felt like we were the only thing on their mind although there were other customers there. A great way to complete the day.

Again we had a fantastic time and are very appreciative of everything you booked for us. We wish you continued success and if our travels should bring us back to Italy, we know who to call.

Leon and Michele Travelled with us

The trip was great we appreciate all the hard work you and your team invested to make our experience a once in a lifetime trip. We appreciate all the attention to the details in particular Giuseppe spending the time and the focus with us on the road and as we were exploring your great country.

Bob & Sandy Travelled with us

Jesse & Giuseppe,

Sandy and I have been looking through my slides of our trip to Southern Italy. We had such a good time with you and Giuseppe that we wanted to let you know again. You were the best guides ever.

Where you are

Location

Italy Florence

Florence and beyond

10 days through Italy, with every stop chosen by the people who live here.

Where we meet

Florence Airport

Where it starts

Florence

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Good to know

Frequently Asked Questions

Is this a private tour, or will we join a group?

Private. You travel with your own guide and driver, and the only people on the itinerary are the ones you bring with you. Nothing is shared with strangers, and the pace of each day is yours to set.

Can the itinerary be changed to suit us?

Yes. What you see here is a starting point, not a fixed departure. Tell us how long you have, what you love and what you would rather skip, and we will reshape it around you. A slower morning, an extra night somewhere you fell for, a different region entirely.

How do we start planning?

Send us a note using the form on this page, or call us on 1-866-779-2565. A travel specialist replies within one business day, usually with a few questions of their own. There is no cost and no obligation in asking.

Are the hotels shown the ones we will stay in?

Usually, yes. Hotels are subject to availability, and if one is full on your dates we will replace it with a property of a similar standard and tell you before you book. Never a surprise on arrival.

When should we book?

The earlier the better, particularly for travel between May and September, when the best small hotels and the guides worth having are taken first. That said, we have put together beautiful trips at short notice, so ask and we will tell you honestly what is still possible for your dates.

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