San Gimignano in Tuscany, Italy
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Tuscany and Cinque Terre Itineraries & Tours

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From rolling hills to seaside villages, an Italian getaway has everything to desire in a vacation. Visit the iconic Tuscan countryside and the famed city of Florence, explore fascinating museums and distinct wines, and indulge in the romantic ambiance of the coast. Your Tuscany and Cinque Terre itinerary from Zicasso will be a dream vacation.

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    Describe your dream tour.

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Tailor Made Itineraries

Get inspired with our sample trips below. Let our travel specialists customize a trip just for you.

Mom and daughter admire the view of Florence from Piazzale Michelangelo
One Week Family Vacation to Tuscany and Cinque Terre

7 Day Custom Tour

Dynamic pricing from $2,501

The rolling hills of Tuscany and unrivaled landscapes of Cinque Terre provide the perfect backdrop for this memorable 7-day family vacation. Enjoy exclusive experiences and private tours, such as a pizza-making course, a family bike ride, and a gelato tasting, while you bask in the Tuscan sun and create lifelong memories. Immerse yourself in the beauty, history, and delicious cuisine of Tuscany and Cinque Terre during this unforgettable family vacation.

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Couple relaxing and enjoying the view of the Tuscany countryside in Italy
Immersive Couple’s Tour of Tuscany and Cinque Terre

9 Day Custom Tour

Dynamic pricing from $3,217

This 9-day couples trip to Italy’s Tuscany and Cinque Terre regions is a discovery of rich history and natural beauty. Experience the culture, history, and cuisine of Italy in addition to the iconic la dolce vita during this unforgettable couple’s vacation. Indulge in a private wine tasting in the Chianti region, explore the idyllic haven of Cinque Terre, and enjoy private time on some of Italy’s most pristine beaches.

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Pathway thru vineyards above Manarola in the Cinque Terre, Italy.
Indulgent Food and Wine Tour of Tuscany and Cinque Terre

8 Day Custom Tour

Dynamic pricing from $2,859

Indulge in the delicious food and wine of Tuscany and Cinque Terre during this 8-day journey. Uncover the beauty and history of the region as you taste your way from scenic cities to historical landmarks. From the Leaning Tower of Pisa to the Renaissance art of Florence, discover all Tuscany has to offer. Savor the renowned wine of the area, indulge in private cooking classes, and visit the seaside haven of Cinque Terre.

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Riomaggiore, the southernmost town of the Cinque Terre
7-Day Senior’s Tour of Tuscany and Cinque Terre

7 Day Custom Tour

Dynamic pricing from $2,501

Designed especially for seniors travelers, this incredible 7-day trip allows you to experience the unrivaled beauty and rich history of Tuscany and Cinque Terre. From the art masterpieces in Florence to the famous Leaning Tower in Pisa, discover the best locations in Tuscany before exploring the gorgeous Cinque Terre area. Private tours and experiences in each stunning town immerse you in the fabled lifestyle and culture of this idyllic destination.

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San Gimignano surrounded by the green rolling hills and vineyards of Tuscany, Italy
The Best of Tuscany and Cinque Terre in 8 Days

8 Day Custom Tour

Dynamic pricing from $2,859

Discover the beauty, history, and idyllic atmosphere of Tuscany and Cinque Terre during this immersive 8-day vacation. From Renaissance art to medieval towns and Italy’s mouthwatering cuisine, indulge in all this amazing area has to offer. Journey through the medieval town center of San Gimignano, explore the enchanting town of Pisa, and uncover the history of Siena.

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Florence Cathedral, Duomo di Firenze, in Florence, Italy

On this 12-day trip to Italy, you will experience the awe-inspiring landscape of Tuscany, and enjoy sumptuous and delicate wines from the heart of Chianti. Stand in awe of the soaring dome of the Duomo, and enjoy the magnificent achievements of artistic expression that fill the Uffizi. You will tour the Vatican and learn the inimitable history that fills the Roman Forum.  On the coast, you may want to walk along the stunning cliffs near Cinque Terre on the Italian Riviera. This is a vacation dedicated to all of Italy, and it’s sure to take your breath away.

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Benefits of Using Zicasso

Plan Your Trip with
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More About Tuscany & Cinque Terre Itineraries

Italy Travel Guide
Florence, Italy
Italy Travel Guide

From Roman ruins to the Tuscan countryside, there is something for every traveler in Italy.

Our Italy Travel Guide provides helpful tips and inspiration from must-see destinations and top activities to the best time to visit. Discover traditional food and wine, inspirational culture, and amazing cities on a personalized vacation.

For more information on how to make your dream journey a reality, get connected with a top travel specialist by filling out a Trip Request.

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Best Time to Visit Italy
Summer Tuscany scenery with red poppy flowers and grain fields surrounding cute Vitaleta chapel and Pienza on the hill in Italy
Best Time to Visit Italy

The best time to visit Italy is in the spring and early summer months, from March through June. During this time, the weather is great for the beaches, sightseeing, wine tasting, food tours, and more. Fall, particularly September and October, are also lovely times, when Italy is quieter and the fall colors are on show.

Your ideal experiences also affect the best time of the year to visit Italy for your vacation. Skiing in the Dolomites is exceptional in December, while enjoying the sun-washed beaches of Sicily is best in May. Rome is brilliant in April, while Florence is stunning in September.

From wine tasting to Roman-ruin exploration and coastal sightseeing, find the best time for your experience. As a family, couple, senior, or adventure traveler, we share ideas to help ...

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How to Plan a Trip to Italy: Frequently Asked Questions
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How to Plan a Trip to Italy: Frequently Asked Questions

As you plan your trip to Italy, consider our tips with the following answers to the most frequently asked questions.

From dreaming of the sunflower fields in Tuscany to searching the ruins of Rome for ancient treasures, you can book a vacation in Italy using our ideas as inspiration. Enjoy the pleasures of La Dolce Vita or alpine panoramas, lounging on golden beaches, or embracing rolling vineyards. It is all about finding the information you need to plan the right trip for you.

Whether you are designing a first-time Italian vacation as a couple or returning to the Mediterranean jewel with family, we share how to plan a stress-free trip.

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Tuscany Travel Guide
Rolling hills in Tuscany, Italy
Tuscany Travel Guide

Picturesque rolling hills, terraced vineyards, and pebbled streets lined with cypress trees create the celebrated image of Tuscany. Medieval towns with soaring towers and cobblestone streets crown the bluffs, while beautiful estates offer samples of historic wines and luscious olive oils. The Renaissance takes on life among the museum galleries and preserved palaces, while hidden corners of the region retain their beauty through national parks and Unesco statuses. Our Tuscany Travel Guide has more information on how to enjoy the combination of expected wonders and surprising treasures during your trip.

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How To Spend 2, 5, or 7 Days in Cinque Terre
Manarola village in Conque Terre, Italy
How To Spend 2, 5, or 7 Days in Cinque Terre

Set along Italy’s northwest coast, and comprising a handful of picturesque cliffs and stunning villages, the following information is a guide to how you can explore Cinque Terre over two, five, or seven days.

The location, a UNESCO World Heritage Site along the pristine Ligurian coast, provides endless views and vibrant sunsets. Built among the rocks, with unique layouts etched into the contours of the cliffs, discovering any of the five towns of the Cinque Terre will leave you with incredible memories.

Discover the best experiences for your trip to make the most of your adventures in this gorgeous, charismatic corner of Italy.

Read More    >

Reviews of Zicasso's Referral Service

4.9 stars based on 196 reviews.

Italy Travel Review: Tuscany, Cinque Terre, Lake Como, Private...
"Giulio at this travel company did an exceptional job arranging...

Reviewed By Irene P.

Italy & France Trip Review: Rome, Florence, Venice,...
"[Our travel agent] and his staff were excellent about communication...

Reviewed By Deryl H.

Girls' Trip to Italy Vacation Review: Hiking Cinque Terre,...
"[The travel designer] planned this trip perfectly for us...

Reviewed By Erin E.

Luxury Italy Vacation Review: Tuscany, Florence, Santa Margherita...
"It was our first time in Italy and Marcello planned the...

Reviewed By Jennifer R.

Northern Italy Vacation Review: Tuscany, Lucca, Cinque Terre,...
"Highly recommended."

Reviewed By Manoj U.

Italy Trip Review: Rome, Sorrento, Chianti, Tuscany, Capri,...
"Susanna worked with us to provide a wonderful balance of...

Reviewed By Angela H.