Best of Chianti

Top itineraries and travel advice in and around Chianti

You probably recognize this region’s name, even if it’s only from a sighting on a wine bottle. Aside from its eponymous varietal, Chianti offers a relaxed base for Tuscan explorations in the towns of Radda and Castellina and easy access to the region’s best sights. Each part of this incredible region is full of wineries, medieval towns, and winding rural roads, along with the seemingly endless stretches of vineyards. But you aren’t just here for the wine; there are standout gelaterias, the fantasy castle at Rocca di Staggia, Etruscan necropoli outside Castellina, and more.

Kimkim travelers can take in the countryside from above in a hot air balloon or hop on a wagon ride, then descend for private wine tastings. If you want to do your own piloting, we’ll map out a route for a road trip through the Chianti Valley that offers a multitude of wineries, castles, and villages to visit.

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A walking path through the Tuscan countryside

Hiking Through Tuscany: Florence, Chianti, & Siena - 8 days

Active travelers who value independence and flexibility will appreciate this self-guided tour through the Tuscan countryside. Opt for a leisurely pace, or more involved hikes, as you first see the masterworks of Florence—the birthplace of the Renaissance—and then make your way to Chianti. You won't want to miss tasting some of the region's famous vintages, with Cypress tree views all around you. End your journey with an exploration of the preserved medieval city of Siena for a trip back in time.

Active Italy: Trekking & Tuscan Heritage - 7 Days

From Florence, the symbol of the Renaissance, to the vistas of the Val d'Orcia, classified as a UNESCO World Heritage Site, this route will allow you to discover all the facets of Tuscany. You'll trek through some of Tuscany's most famous landscapes, including Chianti, Pienza, and Montepulciano, and explore Tuscany's two most famous cities, Florence and Siena.

Cycling Tuscany: Florence to Siena - 5 Days

Take a quick spin through the birthplace of the Italian Renaissance with this five-day Tuscan cycling tour. This challenging bike route will take you through the medieval villages and cypress-spotted hills of the Tuscan wine region . Go from Florence to Siena as you take in the region's food, historic castles, and sun-kissed landscapes, accompanied, of course, by a good glass or two.

Getaway to Tuscany & Rome - 6 Days

Spend six days visiting historical sites, eating delicious food, and relaxing in Italy. Start in Tuscany for a wine tour of the Chianti region and admire the beautiful villages of the Italian countryside. Catch a high-speed train to Rome and explore the Eternal City with visits to the Vatican City and Colosseum, then round out your trip with a food tour of the city's famous markets and gelaterias.

Casale Marittimo village vineyards in Tuscany

Riding the Eroica Among Famous Vineyards in Tuscany - 7 Days

Get ready, cyclists: this one's for you! The Eroica is a world-renowned vintage bike race, held annually in the hilly, vineyard-dotted region of Chianti in Tuscany. Follow the route of this legendary race, experiencing the Strade Bianche (unpaved white roads) that take you through the heart of this magnificent countryside.

Venice, Florence, Amalfi Coast & Rome - 9 Days

This 9-day itinerary is perfect for adventurous travelers who are short on time. Start in the floating city of Venice to explore city canals and tour ornate palaces, then continue to Florence to see works by da Vinci and enjoy a full-day Tuscany wine tour. After exploring the beautiful Amalfi Coast, finish in Rome where the ancient Colosseum, world-famous Vatican, and romantic streetside cafes await.

Food & Wine in Italy: Venice, Bologna, Florence, Rome, & More - 15 Days

This 15-day itinerary is our most comprehensive culinary tour through Italy, from a Venice street food excursion to wine tasting in Tuscany's medieval vineyards. You'll visit Bologna for medieval churches, aged cheese, and cured Parma ham, spend four days relaxing on the sunny Amalfi Coast, and end your trip in Rome, where the Vatican City, Colosseum, and the perfect cappuccino await.

Food & Wine in Italy: Bologna, Florence, Rome - 7 Days

Eat and drink your way through Italy's famous culinary regions —Bologna, Tuscany, and Rome—on this packed weeklong tour. Start in Bologna, Italy's food capital, to try the Parmigiano Reggiano cheese and see the University of Bologna. Continue to Florence to see works by Michelangelo and Leonardo da Vinci, then sample local Chianti in a Tuscan winery. End your trip in Rome to experience Vatican City, Roman ruins, and the perfect Italian pizza.

Cinque Terre and the Italian Riviera - 14 Days

Spend two weeks exploring the Cinque Terre to your heart's content on this packed itinerary. Start in the medieval village of Manarola where you'll learn traditional cooking from a local, then head up the coast to the beautiful town of Portofino to explore the rugged coast from the water. Continue to Genoa for medieval alleyways and a food tour, then end in Pisa to learn why, exactly, the famous tower leans.

Food & Wine in Italy: Bologna, Florence, Rome - 10 Days

Ten days may not be enough time to see all of Italy, but you should try anyway! Fuel your Colosseum-sized appetite with regional cheese & prosciutto specialties in Bologna, then head to Florence to see art by Michelangelo, Donatello, and Leonardo da Vinci. Take our word and sample the fresh-pressed olive oil and handmade chocolate focaccia, then spend a full day drinking Chinati in Tuscan vineyards and medieval courtyards. End your trip in Rome, where the Vatican City, Roman Forum, and the perfect cup of gelato await.

Food & Wine in Italy: Bologna, Florence, Amalfi Coast, & Rome - 12 Days

Is twelve days enough time to try every single gelato flavor? Likely not—but you can try your best with this food-centric tour of Italy. Start in Bologna, where artisanal cheese, cured ham, and medieval architecture dominate the scene. Then, head to Florence and visit a perfect Tuscan winery before soaking in the sunshine of the Amalfi Coast. End your trip in Rome, with nightlife, the iconic city highlights, and plenty of pizza.

Food & Wine in Italy: Venice, Bologna, Florence, Rome, & More - 14 Days

Rome wasn't built in a day, but you can spend fourteen days eating and drinking your way through Italy's top culinary destinations! Go for a gondola ride in Venice, try the decadent tiramisu, and sample the local Cicchetti. Head to Bologna to see 11th-century architecture and try the Parmeggiano, then head to Florence to see Michelangelo's David and Leonardo's top works. Pair a bottle of Tuscan Chianti with a farm-to-table charcuterie board, then head west for four days on the sunny Amalfi Coast. Explore medieval fishing villages and learn to make the perfect Neopolitan pizza before capping your trip off with visits to the Sistine Chapel, Colosseum, and local gelateria in Rome.

Venice, Florence, Amalfi Coast & Rome - 10 Days

From Venice's canals to seaside towns on the Amalfi Coast, this packed 10-day itinerary covers Italy's top sites. Tour the Doge's Palace and look out on the city from the Bridge of Sighs in Venice, then view Michelangelo's art and explore the Chianti region in Tuscany. Continue to the Amalfi Coast for cliffside villages and rocky beaches, then end in Rome to see the Vatican and Ancient Roman ruins.

Venice, Florence, Amalfi Coast & Rome - 14 Days

Spend two weeks delving into Italy's historic and cultural sites on this packed itinerary. Ride a gondola down Venice's Grand Canal and see art by Michelangelo and da Vinci in Florence. Explore Tuscany's medieval towns, then continue to the Amalfi Coast for ancient summer villas, limoncello, and seaside terraces. End in Rome to see the Vatican and explore eclectic neighborhoods.

Discover Venice, Florence & Rome - 7 Days

From Venice's Grand Canal to Tuscany's winemaking region, this 7-day itinerary is a top choice for travelers on a time crunch. See Michelangelo's 'David' sculpture in Florence, shop for carnival masks and handblown art in Venice, and explore medieval hilltop towns in the Chianti Classico Region. End in Rome, where legendary Colosseum, Sistine Chapel, and buzzing nightlife await.

Luxury Italian Highlights: Venice, Florence, Amalfi Coast, Rome, & More - 14 Days

Spend two weeks experiencing Italy's cities and Amalfi Coast in luxury. Start with a private tour of Venice to see ornate palaces and visit a traditional gondola workshop. In Florence, dine on world-class food and wine and go on a hot-air balloon ride above the Tuscan hills. Dive into history with priority access to the Vatican and a private tour of the Colosseum, then soak up the sunshine and ocean views on the gorgeous Amalfi Coast.

Discover Venice, Florence & Rome - 12 Days

From the top of the leaning tower of Pisa to the rolling hillsides of Tuscany, this 12-day itinerary is perfect for adventurous travelers. Start in Venice to explore ornate palaces and tour glassblowing workshops. Head to Florence for masterpieces by da Vinci and tour small vineyards and farms in Tuscany, then end in Rome—the world-famous home of the Vatican, bohemian neighborhoods, and a buzzing street food scene.

Food & Wine in Italy: Bologna, Florence, Rome - 9 Days

If sitting on a Tuscan hillside winery with a glass of Chianti, kneading fresh pizza dough, and seeing the Sistine Chapel sound like a good way to spend nine days—look no further, because this packed itinerary is for you. Start in Bologna to see the 11th-century university and stuff yourself full of Parmeggiano cheese, prosciutto, and Ragu alla Bolognese. Continue to Florence to see Michelangelo's 'David' in the Uffizi Gallery, then spend a day drinking Chianti like the Romans do in Tuscany. Finish in Rome to see the Galleria Borghese and Colosseum before becoming best friends with your perfectly handmade Italian pizza.

Venice, Florence, Amalfi Coast & Rome - 12 Days

If spending 12 days exploring art and history in Italy's beautiful cities sounds perfect, this itinerary is for you. Tour the exquisite San Marco Basilica and bohemian San Samuele district in Venice, see Michelangelo's 'David' and go wine tasting in Florence, then spend three days in the stunning fishing villages of the Amalfi Coast. End in Rome for ancient Roman ruins and the world-class Vatican.

Cinque Terre and the Italian Riviera - 15 Days

Explore the small villages, rugged coastline, and the incredible scenery of the Cinque Terre and the Italian Riviera on this comprehensive 15-day trip. Stay in old-world towns where you'll hike cliffside paths, visit coastal medieval fortresses, and learn to cook in a local's home. Visit Genoa for the food & old town, then end your trip in Pisa to climb the famed tower and hunt for truffles in the Tuscan countryside.

Food & Wine in Italy: Bologna, Florence, Rome - 8 Days

This 8-day trip is perfect for travelers who want a packed itinerary but don't have tons of time. Explore Bologna's culinary delights, from traditional Parmeggiano Reggiano cheese to local prosciutto, then head to Florence to see pieces by top Renaissance artists like Michelangelo, Leonardo da Vinci, and Machiavelli. In Tuscany, visit medieval villages, sip on full-bodied Chianti, and relax in sun-filled plazas overlooking rolling hills. End the trip in Rome to see the Sistine Chapel, Colosseum, and try your hand at making the perfect pizza.

Discover Venice, Florence & Rome - 8 Days

Explore Italy's top cities and winemaking regions with this whirlwind 8-day itinerary. Dive into history as you discover extravagant Venetian palaces, medieval Tuscan towns, and Rome's Vatican City. Ride a gondola on Venice's Grand Canal and taste world-famous wine in the Chianti Classico region. See masterpieces by Michelangelo and da Vinci in Florence, then end in Rome, where bohemian neighborhoods, a vibrant food scene, and the magnificent Colosseum await.

Discover Venice, Florence & Rome - 10 Days

Explore Italy's top cities and cultural sights on this 10-day trip. Start in colorful Venice to see the ornate Doge's Palace and take a ride on the Grand Canal. In Florence, see world-famous art by Renaissance masters like Michelangelo and Donatello, then go wine tasting in rural Tuscany. End your trip in Rome, where visits to the Sistine Chapel, bohemian Trastevere neighborhood, and mouth-watering pizza round out the perfect getaway.

Cinque Terre and the Italian Riviera - 13 Days

Fare tredici (Italian for 'hit the jackpot') with this amazing 13-day itinerary of the Cinque Terre coastline. Hike between small villages on a stunning coastal path, snorkel to see the incredible Christ of the Abyss statue and sunbathe on rocky beaches in Portofino. Explore Genoa's maritime history & medieval downtown, then end in Pisa to climb the famous leaning tower and go wine tasting in the Tuscan countryside.

Discover Venice, Florence & Rome - 14 Days

Spend two weeks visiting Italy's top cities and world-famous winemaking regions. See ornate palaces and colorful bohemian islands in Venice, tour the Uffizi Gallery to see da Vinci's work in Florence, and climb the leaning tower in Pisa. Spend a day touring vineyards and small farms in Tuscany, then make—and eat!—the perfect pasta dish. Round out your trip in Rome for a visit of the Sistine Chapel and buzzing neighborhood wine bar.

Venice, Florence, Amalfi Coast & Rome - 15 Days

Head to Itay for 15 days of adventure and relaxation. Visit world-famous art museums and historic palaces, take a gondola ride in Venice, and explore Tuscany's Chianti wine region. From the cliffside villages and rocky beaches of the Amalfi Coast to the ancient Colosseum in Rome, this itinerary offers the best of Italy's culture for every type of traveler.

Discover Venice, Florence & Rome - 15 Days

Spend 15 days discovering Italy's art, culture, and cuisine with this comprehensive trip. Ride a gondola in Venice, climb Pisa's famous tower, and see Michelangelo's 'David' sculpture in Florence. Enjoy wine tasting in Tuscany and learn to make the perfect pasta dish. Round out the trip with 5 days in Rome, where world-famous Vatican City and a relaxing visit to Castelli Romani summer estates await.

Cinque Terre and the Italian Riviera - 11 Days

Spend eleven days hiking between small fishing villages and exploring Pisa on this getaway adventure. Start in the tight-knit community of Manarola, one of the Cinque Terre's many towns, to explore 1,000-year-old fortresses and rocky beaches. Continue to Portofino where elegant summer villas dot the steep hills to explore the coastline from the water, then end your trip in Pisa to climb the famous leaning tower.

Venice, Florence, Amalfi Coast & Rome - 13 Days

Immerse yourself in the richness of Italian culture and Renaissance art on this 13-day itinerary. View ornate palaces in Venice, go wine tasting in Tuscany, and enjoy rocky beaches and summer villas on the Amalfi Coast. End in Rome, where bohemian city neighborhoods, world-famous Sistine Chapel, and ancient Roman ruins await your exploration.

Food & Wine in Italy: Bologna, Florence, Rome - 11 Days

Eat like royalty, drink like a Roman, and explore Italy's top cultural and historic sites on this packed 11-day trip. Start in Bologna and explore the 11th-century university and the covered porticos which line the streets. Indulge your taste buds with the local Parmigiano Reggiano and mortadella, then continue to Florence to see the iconic Duomo and Galleria dell'Accademia, which houses Michelangelo's 'David'. Pair handmade chocolate Foccacia with a glass of chilled Prosecco and the rolling Tuscan countryside for a perfect afternoon delight. End in Rome to see the Galleria Borghese & Sistine Chapel and spend lazy afternoons trying every single flavor of gelato.

Gondolas near Piazza San Marco in Venice

Venice, Florence, Amalfi Coast & Rome - 21 Days

Dive deep into Italian life and culture on this immersive 21-day highlights itinerary. Sample the chocolate focaccia and go wine tasting in Florence, tour ornate palaces and glass-making workshops in Venice, and relax on the sunny beaches of the Amalfi Coast. End your trip in Rome, where the world-famous Sistine Chapel, bohemian neighborhoods, and Ancient Roman ruins await.

Food & Wine in Italy: Bologna, Florence, Amalfi Coast, & Rome - 13 Days

If you like eating and think thirteen is a lucky number, then we've got the trip for you! Start in Venice, the "City of Water", and explore the Grand Canal with a ride on a gondola. Sample Parmigiano-Reggiano, local prosciutto, and explore medieval architecture in Bologna, then head to Tuscany to see Renaissance-era art in Florence and spend a sunny afternoon with a glass of local Chianti. Explore the steep cliffside wineries, turquoise water, and lemon groves of the Amalfi Coast before ending your trip in metropolitan Rome at the Galleria Borghese & Sistine Chapel, and exploring bohemian Trastevere in a full-day food & wine tour.

Venice, Florence, Amalfi Coast & Rome - 16 Days

Spend sixteen days visiting Italy's incredible cities and explore the sunny Amalfi Coast on this getaway trip. Visit ornate palaces and art galleries in Venice and Florence, go wine tasting in Tuscany, and slow down to a quieter pace of life on the Amalfi Coast. Spend the last four days in the capital city of Rome where ancient ruins and a buzzing nightlife meet for a modern vibe.

Venice, Florence, Amalfi Coast & Rome - 11 Days

Experience La Dolce Vita on this packed 11-day itinerary of Italy's favorite cities. Start in Venice to see the Grand Canal, then head to Florence for a tour of the Uffizi Gallery and a day in Tuscany. Continue to the Amalfi Coast for rocky beaches and summer villas, then end in Rome where the Sistine Chapel, Galleria Borghese, and bohemian Trastevere await.

Cinque Terre and the Italian Riviera - 12 Days

If spending 12 days exploring the rugged scenery and medieval fishing villages of the Cinque Terre sounds good, this trip is perfect for you. Start in Manarola, a small community with a big heart, for coastal hikes & a chance to learn traditional cooking from a local. Continue to Portofino for medieval fortresses and sunset kayaking, then end your trip in Pisa to see world-famous architecture and the Tuscan countryside.

Gondolas in front of Venice's Grand Canal

Venice, Florence, Amalfi Coast & Rome - 17 Days

Discover Italy's incredible history and beautiful cities on this whirlwind 17-day trip. Explore Venice on foot, try Tuscany's famous gelato and visit art museums in Florence, then check out the turquoise sea and old-timey fishing villages of the Amalfi Coast. Your trip ends in Rome where the ancient Roman Colosseum, world-famous Vatican, and the perfect slice of pizza await.

Discover Venice, Florence & Rome - 9 Days

From the Sistine Chapel in Rome to eclectic artist neighborhoods in Venice, this 9-day trip is perfect for travelers who want to see Italy's top sights at a relaxed pace. Start in Venice to see the Grand Canal, then head to Florence to see Michelangelo's 'David' sculpture and taste Chianti wine in Tuscany. End your trip with three days in Rome for trendy wine bars, nighttime foodie crawls, and an exclusive tour of the Vatican City.

Luxury Italian Highlights: Venice, Florence, Amalfi Coast, Rome, & More - 12 Days

Spend 12 days indulging in Italy's finest artwork, cuisine, and scenery on this luxurious itinerary. Explore Venice on a private guided gondola tour, dine at 3-star Michelin restaurant in Florence, and go wine tasting in the scenic hills of Tuscany. Travel to Rome to see the Sistine Chapel before the crowds arrive then head to the Amalfi Coast for old-world fishing villages and a luxury yacht trip to the famed island of Capri.

Luxury Italian Highlights: Venice, Florence, Amalfi Coast, Rome, & More - 15 Days

From metropolitan Rome to small-town Amalfi, explore Italy's cities and coast on this luxurious 15-day comprehensive itinerary. Start in Venice to tour grand palaces and dine on fresh seafood, then head to Florence for world-famous art museums and famous Tuscan wine. End the trip with exclusive access to Vatican City and three days on the Amalfi Coast for luxury yacht tours and a helicopter flight over Pompeii.

Luxury Italian Highlights: Venice, Florence, Amalfi Coast, Rome, & More - 13 Days

Explore the best of Italy's culture and history on this luxurious 13-day trip. Begin with the City of Water to dine on famously fresh seafood and visit a gondola workshop, then head to Tuscany for world-famous artwork and a stay in a luxurious countryside Relais. Tour Rome on a private city tour and dive into ancient history at the Colosseum, then end on the Amalfi Coast for old-world fishing villages and a helicopter flight over Pompeii.

Discover Venice, Florence & Rome - 11 Days

Spend eleven days visiting historical sites, eating delicious food, and enjoying yourself in Italy. Start in Venice, where romantic canals, Italo-Byzantine architecture, and exquisite hand-blown glass beckon. Tour the Uffizi Gallery in Florence, then spend a day visiting vineyards and medieval fortresses in Tuscany. Finish the trip in Rome, where you'll dive into history at the Colosseum and Sistine Chapel, then enjoy the buzzing nightlife.

Venice, Florence, Amalfi Coast & Rome - 18 Days

Explore world-famous art and discover Italy's incredible food on this packed 18-day itinerary. Visit ornate palaces and go on a food tour in Venice, check out Tuscany's hilltop villages and learn to cook in Florence, then relax on the rocky beaches of the Amalfi Coast. End your trip in Rome to see 2nd-century Roman catacombs and view the world-famous Sistine Chapel.

Discover Venice, Florence & Rome - 13 Days

Explore Renaissance masterpieces and modern culture in this 13-day packed Italy trip. See the Grand Canal in Venice, visit colorful Murano island, and tour the gothic Doge's Palace. Head to Florence for Michelangelo's 'David' and a visit to Pisa's famous tower, then spend a day in rural Tuscany. End in Rome, where Vatican City, trendy restaurants, and a visit to the serene Castelli Romani estates await.

Venice, Florence, Amalfi Coast & Rome - 20 Days

From the sunny Amalfi Coast to Rome's buzzing nightlife, this incredible 20-day highlights trip through Italy is perfect for travelers who want to see it all. Start in Venice to see the famed Grand Canal, then head to Florence for Tuscan wines and da Vinci's art. Round out your trip with a stay in the small coastal town of Amalfi before ending in Rome, where ancient history, eclectic neighborhoods, and a vibrant food scene await.

Highlights of Rome and Florence - 7 Days

Your trip to Rome and Florence starts with guided tours through Rome's historical core, Vatican City, and the Roman Forum, with walks through the Colosseum and to the top of Palatine Hill. Head to Florence to experience its historic squares, cathedrals, and museums, plus an Italian cooking class to learn how to make traditional pasta and dessert. End your trip in the Tuscan countryside with visits to Siena and San Gimignano, complete with walking tours and a wine tasting.

Vatican through the Aventine Hill keyhole

Venice, Florence, Amalfi Coast & Rome - 19 Days

Get to know Italy on this comprehensive 19-day city highlights itinerary. View world-famous art by Michelangelo and da Vinci, explore medieval piazzas, and spend a day on a wine tour of Tuscany. Relax in the old-timey fishing villages of the Amalfi Coast and see how Roman emperors spent their summers, then head to Rome for a visit to the Vatican and ancient Colosseum.

Other popular travel destinations in Italy
Tuscany · Rome · Florence · Venice · Amalfi Coast · Sicily · Naples · Milan · Siena · Capri · San Gimignano · Verona · Lakes District · Cinque Terre · Lake Garda · Lake Como · Italian Riviera · Emilia Romagna · Piedmont · Bologna · Sorrento · Umbria · Puglia · Dolomites · Aeolian Islands · Montepulciano · Sardinia

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