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Spotlight on Tuscany Private Vacation Package - Well Arranged Travel
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Tuscany Private Vacation 

Destinations: Pienza, Monteriggioni, Montalcino, Monticchielo, Montepulciano, Cortona, Siena, Castellina in Chianti, Lucca and Florence, Lucca or Pisa


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Florence and Tuscany Private Vacation: 

Enjoy the breathtaking scenery as you travel the peaceful Tuscan countryside and Florence in search of world-class art, living history and fine cuisine. You’ll visit such famous places as Siena, Chianti region, Lucca and Florence while also getting off the beaten track to explore small vineyards and hilltop villages.

You will enjoy the fine food and wine of Tuscany as you explore different hill towns and villages. You will sample fine wines and the fantastic local cuisine. You will enjoy the cheeses, cured meats, handmade pastas, olive oils of Tuscany. Breathtaking views will frequently be the setting where you will enjoy the delicious meals while on this Tuscany Private Vacation.

The elegant, comfortable and centrally located accommodations in these upscale Italy vacation packages were carefully selected to give you a variety of experiences.

This Tuscany Private Vacation includes overnight stays in beautiful Florence, a perfect city to end a fabulous Tuscany tour. 


Spotlight On Tuscany Private Vacation Package in Italy:

  • 3 nights in Pienza, 4 nights in Florence
  • Beautiful, elegant, centrally located four-star hotels
  • Breakfast daily
  • Olive oil and Wine Tasting in Tuscany
  • Private transportation
  • Guided tours of Florence city tour, Accademia and Uffizi museum tours by expert local guide
  • Entrance and reservation fees to all museums and sites included in the tour itinerary
  • Train tickets to and from Lucca or Pisa
  • Private transportation from airport to hotel on arrival day and departure day

Not Included:

  • Airline tickets
  • Gratuities to guides and drivers



For Tour Package Pricing Contact Us 


ITINERARY – Florence & Tuscany Private Vacation 


DAY 1: Arrival in Florence, Pienza, Tour of Monteriggioni, Overnight in Pienza10411769_10203908181959120_2623433674933512046_n

Your guide will pick you up at the airport in Florence.  Your first stop in Tuscany is Pienza, a UNESCO World Heritage site and your base for the next three nights. En route our Tuscany group tour will take us to sleepy Monteriggioni, once a fortress and now a walled medieval village.

Finally, you arrive in Pienza where you will stay for 3 nights. Pienza overlooks the Orcia Valley, arguably the most scenic and definitely most photographed area of in all of Tuscany. Pienza is the birthplace of Pope Pius II, who ordered the town to be redesigned into a masterpiece Renaissance city. Charming Pienza has several specialty stores, including food shops where you can sample pecorino cheese, one of the locally produced delicacies. Welcome Dinner is planned to celebrate the start of our tour. 


DAY 2: Montalcino, Monticchiello, Wine Tasting & Lunch, Sant’Antimo Abbey, Overnight in Pienza
This morning your Tuscany private tour takes you through the scenic Tuscan countryside. You will stop in one of Tuscany’s jewel, the lovely tiny town of Monticchiello. The site here is the town itself, picture-perfect town as you would expect to find in Tuscany.

You will continue traveling Tuscany’s backroads and will quickly reach the Romanesque Abbey of Sant’Antimo, an unforgettable 9th-century Benedictine monastery. It is a simple yet magnificent stone church, set amongst the field of olive trees. You will have time to take photos, have a quick look before you continue onto charming Montalcino, whose acclaimed vineyards produce Brunello di Montalcino. We will have lunch in town followed by wine tasting of several Tuscan wines.

Free evening once get back to our hotel.

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DAY 3: Montepulciano, Cortona, Le Celle, Overnight in Pienza

Today, your Tuscany tour takes you to Cortona, one of the oldest hill towns and best-preserved Etruscan cities in Tuscany. Our first stop is Le Celle, a hilltop monastery founded by St. Francis of Assisi in the early 1300s. It is a beautiful spiritual place built in the foothills of Monte Sant’Edigio in a natural gorge carved out by a stream. It is believe that this is where the saint dictated his will. You will explore the town’s charming medieval streets and squares with cafes, restaurants and shops. As you follow Cortona’s meandering medieval walls, you will be treated to magnificent views of vineyards, olive groves and Lake Trasimeno.10153708_10203908181439107_447817114723696793_n

On your free time, you may consider visiting Museo dell’Accademia Etrusca, an Etruscan museum housed in a 13th century palazzo. The museum contains important Etruscan artifacts, such as a 4th century lamp and jewelry found in ancient tombs. The museum also houses an important Egyptian collection as well as paintings from up to the 20th century. Free time after your visit.

After lunch, you will tour 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. It’s a stunning town, endowed with dozens of Renaissance palaces and churches, and full of beautiful vistas and odd little corners to discover, artisan shops and a winery.  You will explore the town leisurely and also have time on your own.

The rest of the day is on your own. 


DAY 4: Siena, Chianti: Castellina-in-Chianti, Overnight in Florence

This morning you will make your way to the romantic city of Florence, which will be your next home base till the end of your Tuscany tour. You will travel through the Tuscan countryside and stop in the historic city of Siena. Built on three hills in the middle of the Via Francigena (pilgrimage road), Siena is one of Tuscany’s crown jewels. It has an outstanding Gothic Duomo and another important church, San Domenico, which claims the skull of St. Catherine. Siena also has one of the most beautiful squares in Italy, il Campo, where the famous Palio horse race is held twice a year. See the city’s most important neighborhoods, squares and churches, before giving you some time to explore them on your own.


Your Tuscany tour also takes you to a jewel in Chianti, Castellina, a small town with lovely squares, homes, tiny charming streets and a sprinkling of small cafes, shops and restaurants. A picture-perfect Tuscan town.

We are excited to offer this tour with a three-night stay in the most important city in all of Tuscany – Florence. You will arrive in Florence late afternoon.  


DAY 5: Walking Tour of Florence with The Accademia Museum, Afternoon at the Uffizi Museum, Overnight in Florence

You will have an early morning walking tour of Florence with a licensed local guide covering some of the city’s history and architectural treasures including the beautiful Piazza della Signoria, the Duomo, Ponte Vecchio, Piazza Santa Croce and more. You will also visit the Accademia museum where you will view some of Michelangelo’s works, including the famous Statue of David.

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DAY 6: Morning Tour of Lucca OR Pisa,  Overnight in Florence10563195_10203908203519659_3407086977159749736_n

 This morning, you will continue your exploration of Tuscany and travel by train to Lucca, an elegant city that is rich in history and is the birthplace of composer Giacomo Puccini. Lucca has sites that depict its Etruscan and Roman rule, and much later by Napoleon and his sister, Elisa. This ancient Tuscan city is completely enclosed by a massive well-preserved wall (60 ft. wide x 40 ft. high) – wide enough to hold small parks and a pedestrian path along the top. You will enjoy Lucca’s ancient and charming squares, medieval streets, elegant shops and palaces.  

NOTE: Instead of touring Lucca, you can opt to go to Pisa to see the famous Leaning Tower.  Return to Florence by lunch time. (B)


DAY 7: Leisure Day, Overnight in Florence

By this time you will be very comfortable in exploring Florence on your own.  Enjoy Florence one last time.  Consider a visit to the Bargello museum or the Pitti Palace or simply enjoy the city as you wander through its old streets, beautiful squares and markets. 

Italy Vacation Package - Tuscany Women's Tours by Well Arranged Travel



DAY 8: Departure Day

Prepare for your flight home. You will be picked up at the hotel and taken to the airport. 


NOTE: This Florence & Tuscany private tour can be privatized for your own group – any size.  You can customized this to include your desired destinations and activities or you may design your own Italy vacation package. Inquire.