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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Chianti Essentials

Cafes and Tasty Meals in Rome
Top Culinary Experiences in Italy

Italy is a food haven with some of the world's favorite dishes, like the signature Neapolitan pizza, fresh pesto pasta from the Italian Riviera, lemon-infused delicacies of Sorrento, and various seafood dishes in the south. And no trip to Italy is complete without tasting wine and gelato! Enjoy perusing through local markets, attending culinary workshops, partaking in traditions like evening Apertivos, and exploring the country's famous "Food Valley."

The Idyllic Landscape of Tuscany
Top Experiences in Tuscany

A trip to Tuscany is truly unforgettable, with its landscape of endless vineyards and hills dotted with medieval villages and castles. Explore the historical centers of Florence, Siena, and San Gimignano and taste the region's famed wine at picturesque vineyards, estates, and bars. Savor the views with unique experiences, like ballooning over Chianti or walking along an ancient pilgrim path. Enjoy sunset-filled dinners, delicious cuisines, and some of Italy's most important history, architecture, and art.

Swimming and Snorkeling in Italy
Top Active Experiences in Italy

Being active in Italy is easy, and it's a great way to dive a bit deeper into the cultural essence of the country. You can hike and explore lakes in the north, walk the cliffs of Cinque Terre, the Italian Riviera, and the Amalfi Coast, and take full advantage of the warm, crystalline waters with swimming, snorkeling, and kayaking excursions. With so much diversity, you can quickly build an adventurous dream trip for any interest or ability!

Chianti Itineraries

A walking path through the Tuscan countryside
Map of Hiking Through Tuscany: Florence, Chianti, & Siena - 8 days
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.

Radda in the Chianti countryside
Map of Getaway to Tuscany & Rome - 6 Days
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.

Hike along the famous "white roads" of the Val D'Orcia landscape
Map of Active Italy: Trekking & Tuscan Heritage - 7 Days
Active Italy: Trekking & Tuscan Heritage - 7 Days

From the Renaissance jewel of Florence to the vistas of the UNESCO-listed Val d'Orcia, spend a week discovering central Italy's medieval hilltop towns and vineyard-strewn landscapes with this gentle Tuscan walking tour. Hike through undulating hills dotted with cypress trees to some of the area's iconic towns, including Radda in Chianti and Pienza, before finishing with a well-deserved glass of wine in beautiful Montepulciano.

Bicycles are a great way to get around Florence and the surrounding region
Map of Cycling Tuscany: Florence to Siena - 5 Days
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.

Florence from San Miniato al Monte Church
Map of Northern Italy Family Road Trip: Florence, Chianti, Italian Riviera, Lake Como & Lake Garda - 10 Days
Northern Italy Family Road Trip: Florence, Chianti, Italian Riviera, Lake Como & Lake Garda - 10 Days

Wheel your way through northern Italy on this road trip with stops that school-aged children and parents can enjoy, with timing adjustable to your own preferences. You'll start amid the Renaissance influences of Florence, then set out into the Tuscan countryside and Chianti Valley on winding olive- and vineyard-lined roads. From there, head to the coast to wander the beaches of the Italian Riviera and then up to Lake Como to explore its luxurious shores. Wrap up your Italian sojourn on the playful shores of Lake Garda before you return to Florence.

Friends cycling along the famous L'Eroica
Map of Cycle the Eroica Among Tuscany's Famous Vineyards - 7 Days
Cycle the Eroica Among Tuscany's Famous Vineyards - 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. With a week to spare, you can follow the route of this legendary race, experiencing the "strade bianche" (unpaved white roads) that take you through the heart of this magnificent countryside. Between epic rides, you'll spend your free time strolling through hilltop medieval villages, sampling the local wines, and relaxing at peaceful agriturismos.

Exploring Cinque Terre
Map of Family Road Trip: Northern Lakes, Tuscany & Italian Riviera - 14 Days
Family Road Trip: Northern Lakes, Tuscany & Italian Riviera - 14 Days

Spend two weeks exploring northern Italy at your own speed with this self-drive itinerary that allows you to choose the stops. You'll start off in the northern lakes, with Lake Como and Lake Garda offering boat tours past villas and amusement parks alike. Then make your way into Tuscany, where you'll ride a horse-drawn wagon through the countryside and explore the medieval walled city of Siena and famous art of Florence. Finish your trip in the Italian Riviera and colorful five villages of Cinque Terre.

Stroll the Ponte Vecchio over the Arno in Florence for a little shopping
Map of Luxury Italy: Sorrento, Naples, Rome, Tuscany, Florence & Venice  - 18 Days
Luxury Italy: Sorrento, Naples, Rome, Tuscany, Florence & Venice - 18 Days

Never feel rushed on this 18-day luxury grand tour as you're whisked to each destination by a blend of private drivers and concierge train journeys. Start in Naples to explore the clifftop villages of the Amalfi Coast, then head to Rome for ancient history and buzzing nightlife. Taste your way through Tuscany as you tour Chianti's lush countryside and discover Florence's Renaissance splendor before ending your journey of a lifetime among the palaces and canals of Venice.

Amalfi Coast
Map of Venice, Florence, Amalfi Coast & Rome - 9 Days
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.

Village of Manarola
Map of Cinque Terre and the Italian Riviera - 14 Days
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.

Lemon Stand on the Amalfi Coast
Map of Food & Wine in Italy: Bologna, Florence, Amalfi Coast, & Rome - 12 Days
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.

Faraglioni Rocks on Capri
Map of Venice, Florence, Amalfi Coast & Rome - 15 Days
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. 

The beautiful Amalfi Coast
Map of Luxury Italian Highlights: Venice, Florence, Amalfi Coast, Rome & More - 14 Days
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.

Rocco di Papa
Map of Discover Venice, Florence & Rome - 12 Days
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.

Tiramisu—The Perfect Dessert
Map of Food & Wine in Italy: Bologna, Florence, Rome - 8 Days
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. 

Florence Skyline at Sunset
Map of Luxury Italian Highlights: Venice, Florence, Amalfi Coast, Rome, & More - 12 Days
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.

Vatican City
Map of Discover Venice, Florence & Rome - 14 Days
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.

Rome's Pantheon at sunrise
Map of Venice, Florence, Amalfi Coast & Rome - 16 Days
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.

Arno River & Ponte Vecchio in Florence
Map of Venice, Florence, Amalfi Coast & Rome - 20 Days
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.

Gondolas in front of Venice's Grand Canal
Map of Venice, Florence, Amalfi Coast & Rome - 17 Days
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.

Coastal town of Rio Maggiore
Map of Cinque Terre and the Italian Riviera - 15 Days
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.

Typical Italian Pizza
Map of Food & Wine in Italy: Bologna, Florence, Rome - 9 Days
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. 

Portofino's coastline
Map of Cinque Terre and the Italian Riviera - 13 Days
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.

A gondolier steers a boat in Venice
Map of Discover Venice, Florence & Rome - 15 Days
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.

Town of Campania on the Amalfi Coast
Map of Luxury Italian Highlights: Venice, Florence, Amalfi Coast, Rome, & More - 15 Days
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.

Positano on the Amalfi Coast
Map of Venice, Florence, Amalfi Coast & Rome - 18 Days
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. 

Genoa's historic port and town center
Map of Cinque Terre and the Italian Riviera - 12 Days
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.

Parmigiano-Reggiano in Parma
Map of Food & Wine in Italy: Bologna, Florence, Rome - 11 Days
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.

Castel Gandolfo
Map of Discover Venice, Florence & Rome - 13 Days
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.

Handblown Murano glass in Venice
Map of Discover Venice, Florence & Rome - 11 Days
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.

Ripe Wine Grapes in Tuscany
Map of Food & Wine in Italy: Bologna, Florence, Amalfi Coast, & Rome - 13 Days
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.  

Piazza dei Miracoli in Pisa
Map of Cinque Terre and the Italian Riviera - 11 Days
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.

Rome Skyline at Sunrise
Map of Luxury Italian Highlights: Venice, Florence, Amalfi Coast, Rome, & More - 13 Days
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.

Vatican through the Aventine Hill keyhole
Map of Venice, Florence, Amalfi Coast & Rome - 19 Days
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.