Tuscany Tours & Vacations

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How Zicasso WorksCustom Tuscany Tours

  1. Describe your dream trip to Tuscany.

  2. We match you with up to 3 top travel specialists. They compete to plan your trip and tour.

  3. Book the trip when you are satisfied.

The emerald rolling hills and expansive rustic landscapes of Tuscany have captured and inspired imaginations for millennia. Discover grandiose castles and medieval abbeys nestled in the hidden countryside. Explore the timeless and classic influences of the Renaissance, which sparked a cultural movement that forever changed the world.

Sample Itineraries

Get inspired with our sample trips below. You can have any trip tailor made for your private travel. Any number of days.
Any departure date. Any experience you want.

Extraordinary Tuscany Vacation: Countryside, Riviera & More

Extraordinary Tuscany Vacation: Countryside, Riviera...

8 Day Custom Tour

From $2,195

Come see extraordinary Tuscany on this 8-day tour through famous hillsides to vivacious coastlines. Explore Renaissance art and modern marble. This journey through Tuscany will have you watching the sapphire Ligurian Sea and sitting in a 17th century palace looking over the valley at sunset. Walk along medieval fortified walls and hold the Leaning Tower of Pisa in the palm of your hand. From Michelangelo’s David to the music of Puccini, Etruscan ruins to serene lakes, there is no end to the extraordinary sights of Tuscany and beyond. 

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A Perfect Private Tour of Tuscany in 2 Weeks

A Perfect Private Tour of Tuscany in 2 Weeks

14 Day Custom Tour

From $8,395

When every day is personalized to your preferences, you can be certain that each moment will be captivating. Stand in front of Botticelli’s Birth of Venus on a private tour of the Uffizi Gallery. Stroll along cavernous halls in labyrinthine abbeys with views out to vast valleys. Sip wine in a private villa with a boutique vineyard and discover tiny towns untouched by time with locals who welcome you like beloved family. Your 2 weeks in Tuscany tour provides you with a unique view of Tuscany, tailored by our Tuscany travel agents, to ensure that every day is made specifically for you.

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A Foodie's Slow Tour of Tuscany

A Foodie's Slow Tour of Tuscany

8 Day Custom Tour

From $2,195

Cuisine runs deep in Italy, connecting families and reflecting the soul of the chef, whether cooking rustic pasta at home or preparing gourmet dishes in a restaurant. The scent of celebrated confections emanates from display windows along the main avenues. Luscious cheeses maintain complex flavors, offering insight into the care taken during their production. Ruby-tinted wines glow against the verdant hills and cypress trees. Your 8-day foodie tour of Tuscany takes you deep into local tradition by highlighting cuisines and methods of creation, from the farm and vineyard to the table, showcasing the labors of love with every sumptuous bite you take.

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Tuscany & Cinque Terre Tour

Tuscany & Cinque Terre Tour

13 Day Custom Tour

From $3,570

From the lush green of Tuscany’s hills to the pearl blue water of Cinque Terre’s coastline, experience why Italy is one of the world’s top destinations. Tuscany and Cinque Terre are works of art that everyone can enjoy. In Tuscany and Cinque Terre you do not just view the art, you become a part of it. Find out for yourself what all the great reviews are about!

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Castle of Spoleto in Umbria.

10-Day Umbria and Tuscany Exploration Tour

10-Day Umbria and Tuscany Exploration Tour

10 Day Custom Tour

From $4,245

Immerse yourself in the iconic landscape of rolling hills, terraced vineyards, and hidden medieval towns of Umbria and Tuscany during this 10-day Italy tour. Sip celebrated wines, indulge in the rich flavors of local cuisine, climb ancient towers, and discover the charms of cobblestone lanes. Embrace Italy’s relaxed pace and bask in endless beauty from Renaissance art to exquisite scenery while experiencing the vacation of a lifetime.

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Tuscany Tour for Lovers: Siena, Cortona, Volterra, San Gimignano and Certaldo

Tuscany Tour for Lovers: Siena, Cortona, Volterra,...

8 Day Custom Tour

From $2,195

Medieval city walls and historic towers make each town in the Tuscan countryside feel like a fairytale, and you will feel like royalty. On your custom tailored Tuscany tour for lovers, each day takes you to the intimate villages and enchanting landscapes, from lush valleys to glistening seaside. Taste the traditions of elegant, regional cuisine and savor the treasured company of your partner. You will find the charms of history and the enchantment of sunsets over castle walls, sipping wine in a piazza, sharing gelato, and discovering all the different ways that Tuscany is for lovers.

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Culture of Tuscan Wine & Cuisine Tour

Culture of Tuscan Wine & Cuisine Tour

9 Day Custom Tour

From $2,470

The red hue of a perfect bottle of wine shines like a ruby. The scent of freshly made pasta emanates from a restaurant located in a historic cellar. Chestnut trees and olive groves fill the open Tuscan valleys, leading you to far-reaching vineyards and medieval hilltop towns. Your custom tailored food and wine tour of Tuscany takes you on a unique blend of wine and culinary experiences set in the world-renowned countryside of Tuscany. Tuscany is where the cuisine is as artful as the region’s Renaissance paintings, the wine is as important as the medieval architecture, and the culture is rooted in the landscape.

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An Italian Wine Tasting Journey: From Piedmont to Tuscany Wine Tour

An Italian Wine Tasting Journey: From Piedmont to Tuscany...

9 Day Custom Tour

From $2,470

Italy should be devoured! Piedmont with its mountains and Tuscany with its hills: fill your senses with tastes from award-winning vintners, wines that range from robust to comforting, old to young, and food that sings and melts in your mouth, all with medieval towns at your fingertips. Italy allows you to slow down, smell the grass, smell the food, smell the wine, see the land, touch history, and devour it all.

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Tuscany Tour of Medieval Cities & Renaissance Preserves

Tuscany Tour of Medieval Cities & Renaissance Preserves...

8 Day Custom Tour

From $2,195

When you think of Tuscany, you can already imagine the green hills and practically taste the lingering pleasures of Chianti wine. Your custom tailored Tuscany tour of Medieval cities shows you the celebrated Italian province by taking you deeper into the cities you already know, and into the countryside towns protected from the toils of time like a secret. Let your private guide lead you to Renaissance artwork and down preserved streets of medieval villages holding close to heritage and tradition. Taste award-winning local cheese and revel in a perfect view of Tuscany from atop a medieval tower.

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The ruins of the Roman Forum, Rome, Italy.

Tour of Italy: Milan, Lake Como, Venice, Tuscany & Rome

Tour of Italy: Milan, Lake Como, Venice, Tuscany &...

16 Day Custom Tour

From $4,395

The birthplace of Michelangelo and Leonardo da Vinci. The civilization that built the Pantheon and the Sistine Chapel. The destination of fashion enthusiasts and religious pilgrims alike. Italy’s history and beauty is endlessly inspiring to every visitor. From the ancient ruins of Rome to the magnificent Renaissance in Florence and surreal decadence in Venice, this tour of Italy promises to astound you.

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Finest Wines of Tuscany & Central Italy Tour

Finest Wines of Tuscany & Central Italy Tour

10 Day Custom Tour

From $2,745

On this 10-day tour of Tuscany and Central Italy, immerse yourself in the encompassing culture of Italy and enjoy the sumptuous luxuries that the country has to offer. Taste wine from boutique wineries that have mastered the craft over centuries. The authentic Tuscan culture, the appetizing food, and the delectable wine are all within arms reach in this luxury Tuscany vacation.

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Medieval town of San Gimignano in Italy.

Rolling Tuscan Countryside Tour 2021-2022

Rolling Tuscan Countryside Tour 2021-2022

7 Day Custom Tour

From $1,920

Italy’s countryside is teeming with hilltop towns that are speckled across the breathtaking region of Tuscany, which you will explore on this handcrafted 7-day tour. Under the Tuscan Sun, you will appreciate the endless beauty of the emerald hills that roll from Montepulciano in addition to admiring the ancient architecture of the cultural heritage sites in San Gimignano. From town to town, you can find beauty in every charming destination against the beautiful countryside backdrop.

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Explore Tuscany Tour: Ancient Towns, Coastlines, Snorkeling & Trekking

Explore Tuscany Tour: Ancient Towns, Coastlines, Snorkeling...

8 Day Custom Tour

From $2,195

Step off the beaten path on your custom-tailored luxury vacation for a view of the unparalleled charms of Tuscany. From undulating open valleys to treasured shores, experience an unforgettable journey through the uncharted and overlooked splendors of Elba, Florence, and the surrounding beauty of Tuscany. The Mediterranean sun spreads over the rugged and lush niches of the Island of Elba. Emerald hills and cypress trees expand across the lengths of the horizon. Museums display breathtaking artwork. Ancient villages display remnants of their heritage along cobbled lanes and antique walls.

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Classic Tuscany Itinerary

Classic Tuscany Itinerary

8 Day Custom Tour

From $2,195

Classic is another word for quality and charm, words that describe the splendor around you. Cafes set out tables alongside streets offering you a moment to yourself surrounded by indescribable history. Standing in front of Michelangelo’s David teaches you how to treasure a moment. Listening to the quiet passing of the Arno River provides a soundtrack to unforgettable memories. Your custom tailored 2020 Tuscan tour offers you the true meaning of classic, where no single image creates the wonders of the region. Instead, you find a unique combination of Tuscan experiences that shows why the word “classic” is synonymous with timelessness.

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Art Capitals of Italy Tour

Art Capitals of Italy Tour

8 Day Custom Tour

From $2,195

The immaculate statues of Michelangelo and the soaring grandeur of the Duomo of Florence. The gorgeous scenery and grand basilica at Assisi and the charming streets of Padua leading to the dramatic memorial to the city’s patron saint. The graceful domes of Saint Mark’s Basilica, the intricate glasswork of Murano and the inestimable beauty of the sunset over the Venetian lagoon. From shore to shore, Italy is a country filled with masterpieces just waiting to be discovered.

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Wonders of the Italian Renaissance Tour: Past & Present

Wonders of the Italian Renaissance Tour: Past &...

8 Day Custom Tour

From $2,195

When imagining Tuscany, you can easily conjure up medieval towers and historic walls, undulating hills and vibrant sunflowers. Cities radiate historic artwork and the countryside bursts with vineyards. Step beyond the imagined, venturing past the veil of your imagination and into the true grandeur of history. Your custom tailored tour immerses you in the splendor of Tuscany and lets you experience the beatitudes of alpine foothills, overlooked Renaissance towns, and even poetic vendors, allowing you the chance to discover the character of life in every day Tuscany.

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An In-Depth Tour of Tuscan Gourmet Cuisine

An In-Depth Tour of Tuscan Gourmet Cuisine

8 Day Custom Tour

From $2,195

In Tuscany, eating is more than sustenance. You do not eat to live,  but you truly live to eat. Home cooks understand the reason for pairing types of pastas with different types of sauce. A local butcher is happy to share home recipes. Chefs cook with their hearts, basing their recipes on traditional flavors with modern twists. Your custom tailored tour of Tuscan Gourmet Cuisine leads you through seven Tuscan destinations known for specific types of cuisine, ensuring your immersion into the soul of the province, and showcasing the uniqueness of each personal recipe, in each town, and in each region of Tuscany.  

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Via Francigena Tour: Pilgrims Route of Tuscany

Via Francigena Tour: Pilgrims Route of Tuscany

12 Day Custom Tour

From $3,295

The road to Rome remains unchanged in parts of Tuscany, leading across the unspoiled landscape. Vineyards decorate hillsides. Cypress trees shade unpaved country lanes. Medieval towns that were built around historic churches maintain strong connections to their roots. Your custom tailored Tuscany tour takes you on the route of pilgrims known as Via Francigena. Stroll alongside historic walls; meander around ancient burial grounds; discover the antique abbeys that once connected the Western World. Slow down, take a look around, and know that each step brings you closer to another inspiring moment, whether in the countryside or an ancient Tuscan village.

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A Unique In-Depth Tour of Florence

A Unique In-Depth Tour of Florence

8 Day Custom Tour

From $2,195

Tuscany is not just a region in Italy; it is a state of being. The landscape rolls along the horizon. Unforgettable wine accompanies even more memorable cuisines. Restaurants fill historic cellars, and castles decorate the skyline with bell towers. Treasured artwork fills churches. Designer stores fill ancient buildings. The true essence of Tuscany is captured and expressed along the Renaissance streets of Florence. On this 8-day in-depth tour of Florence, you will settle in like a local and find that when in Florence the rest of Italy disappears behind the city that has it all.

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The Great Escape to Tuscany Tour

The Great Escape to Tuscany Tour

8 Day Custom Tour

From $2,195

This is a land of gentle rises and fecund meadows, where grapes grow fat in the summer sun and Italian nobles retire to enjoy the countryside. It’s a place of fine art and delectable food, cosmopolitan cities and entrancing towns, timeless history and endless culture. It’s a region of untrammeled natural beauty and unbounded imagination, the home to some of the great minds and great landscapes in the world. This is Tuscany, and there’s nowhere else quite like it.

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Unbeaten Path Tour of Tuscany: Florence, Mugello, Borgo San Lorenzo

Unbeaten Path Tour of Tuscany: Florence, Mugello, Borgo...

8 Day Custom Tour

From $2,195

Step into the hidden towns of Tuscany tucked away along the northern border of the province. The imagery leaps out of a storybook, filled with rolling hills, towering mountains, cool streams, and quaint villages. Palaces perch on a hilltop overlooking the valleys below. Traditions persevere in culture and cuisine, adding layers of flavor to every dish. Your custom tailored tour of Tuscany takes you into the lesser-traveled region of Mugello, where the wonders of the past are real, and the treasures of homemade cooking loom large.

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Italian Jewels: Rome, Florence, Tuscany & Venice Tour

Italian Jewels: Rome, Florence, Tuscany & Venice...

11 Day Custom Tour

From $3,020

The rolling meadows of the Tuscan countryside and the famed Seven Hills of Rome. The soaring dome of the Duomo in Florence and the floating marvel of San Giorgio Maggiore in Venice. With the bucolic countryside and the bustling cityscape, the allures of fine food and the inspiration of fine art, this is the tour that will show you it all, offering an unmatched glimpse into the incomparable jewels of Italy.

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An Unforgettable Honeymoon in Italy

An Unforgettable Honeymoon in Italy

14 Day Custom Tour

From $3,845

Your first trip as a married couple should be remarkable. It should be filled with fine food and fun times, dictated by nothing but the slow circuit of the sun across a cloudless blue sky. It should be notable for its uniqueness, taking you to places you’ve never heard of and showing you things you could have never imagined. It should be as bold and as boundless as your love for each other, which means it can only be done in inimitable Italy.

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Custom Cultural Italy Tour in 2 Weeks

Custom Cultural Italy Tour in 2 Weeks

14 Day Custom Tour

From $3,845

Italy is like a great masterpiece waiting to dazzle the viewer. On first impression, she amazes you with her beauty. Upon a closer look, her details and history enrapture you—as you’re awestruck by the ruins of Rome, the majesty of the Vatican and the surreal waterways in Venice. Finally, you leave changed forever by the magic of this incomparable place. We invite you to indulge in the enchanting experiences that await you in this itinerary as well as our carefully selected collection of Italy tours on Zicasso.

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Reviews of Zicasso's Referral Service

4.91 stars based on 1496 reviews. See all our reviews.

Italy Travel Review: Venice, Florence, Tuscany, Cinque Terre,...
"Our tour guides in each city were extremely knowledgeable,

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Reviewed By Ashley P.

Travel Review: Italy & Portugal 2-Week Anniversary Trip,...
"Our trip was simply magical...and it was everything my

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Reviewed By Randolph W.

Italy Tour Review, Cinque Terre, Italian Riviera, Private...
"The bottom line is that everything [our trip planner] set

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Reviewed By David S.

10-Day Italy Vacation Review: Venice, Burano, Florence,...
"The itinerary was easy to follow and very professionally

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Reviewed By Clay Y.

Italy Sisters Travel: Tuscany Countryside, Tours of Balsamic...
"...absolutely loved our excursions out of the city and

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Reviewed By Chelsey A.

Honeymoon to Italy Review: Positano Private Sunset Coastal...
"This company truly works with the best vendors and we couldn't

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Reviewed By Megan H.