Siena is the Gothic masterpiece of sunny Tuscany. Come for the impressive Duomo cathedral and medieval museums, stay for cheerful gelato shops, quiet botanical gardens, and a leisurely glass of Chianti (or two) with a view of famous Piazza del Campo. Find out what to do, where to stay, and what to eat with this ultimate guide to the city.
Best of Siena
Some kimkim travelers opt to stop in at The Tuscan Wine School for an introduction to the regional varietals to set out on wine tours with an expert eye. Then glide on an e-bike through San Gimignano and Chianti or take a private tour through the vineyards of Val D’Orcia, home of Brunello di Montalcino and Vino Nobile di Montepulciano.
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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."
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.
From Ancient Rome to the Middle Ages to the World Wars, Italy is steeped in fascinating history. Whether you're exploring historical Verona in the north, medieval Tuscany and the catacombs of Rome in central Italy, or the archeological ruins of Pompeii to the south, you can walk through the centuries. Discover the Colosseum and Roman Forum, stroll the cobbled streets of Siena, and discover the secrets of St. Mark's Basilica and Doge's Palace in Venice.
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.
Discover Tuscany's resplendent art, history, and landscapes on this weeklong jaunt that starts in Florence and ends in charming Lucca. See world-famous works by Michelangelo and da Vinci in the Uffizi Gallery, climb Pisa's iconic Leaning Tower, and relax over aperitivo in Siena's Piazza del Campo. Experience La Dolce Vita with trips to the hilltop towns of Pienza and Montepulciano to sip fine wines and stroll cobbled backstreets before finishing your trip with a pasta masterclass.
Wind your way through the hill towns and vineyards of the Tuscan countryside on this weeklong exploration of Italy's most famous wine country. Arrive in Florence and kick things off with a guided walking tour in the birthplace of the Renaissance. Then it's time to hit the road to Siena, San Gimignano, and Montepulciano, where medieval architecture and plenty of wine-tasting experiences await.
Spend a week exploring the best of Tuscany on this weeklong road trip! You'll begin in Florence, touring the city's historic center with an expert guide before picking up your rental car and venturing into the Tuscan countryside. Stop to see the Leaning Tower of Pisa, then take a full day to experience the pleasures of the Cinque Terre, hiking between quaint villages by the sea. Finish the itinerary in Siena, strolling around the historic center and day-tripping to the Chianti Classico region for a wine tasting.
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.
The vineyards of Chianti, the quaint seaside villages of the Cinque Terre, and the iconic Leaning Tower of Pisa await on this colorful eight-day road trip through Tuscany. Start in Florence, where you'll see Michelangelo's world-famous "David" sculpture, then drive to Pisa, where you'll base yourself while day-tripping to Lucca and the Cinque Terre. Continue to picturesque San Gimignano and historic Siena, finishing the trip with a wine tasting amid the vineyards in the Chianti Classico region.
This packed eight-day itinerary is perfect for travelers on a time crunch. Begin your trip in Florence to see top Renaissance works by Michelangelo da Vinci, tour the iconic Duomo, and go shopping on the Ponte Vecchio Bridge. Climb the Leaning Tower of Pisa and see the 12th-century Monumental Cemetery, then head to the countryside for wine tasting and afternoon coffee in medieval village piazzas. End in Lucca, where you'll tour the 11th-century Duomo di San Martino, then make—and eat!—the perfect bowl of pasta.
This sophisticated 10-day trip is ideal for travelers looking to experience art, culture, food, and wine—all things that make Tuscany one of Italy's most sought-after regions. Start in Florence, the birthplace of Renaissance art and architecture, to experience the city's rich history and walkable center. Then begin a self-guided road trip around Tuscany, visiting UNESCO-listed monuments, picturesque hill towns, and notable vineyards, including a memorable sit-down lunch and wine pairing in Montepulciano.
Your whole family can fully engage with Italy on this adventurous itinerary, ideally suited for teens with energy to spare. You'll begin in Venice, where you'll craft Carnival masks and explore the secret passages of the city's famous landmarks. After a stop to wander the streets of Verona, you'll head to the park-lined shores of Lake Garda, filled with attractions for all ages. Finish the tour in the Tuscan city of Siena, your base for hot air balloon rides, hikes, and more.
Off-the-Beaten-Path Greece & Italy Road Trip: Lake Garda, Bologna, Tuscany, Olympia, Nafplio, & More - 21 Days
Explore the back roads and small villages that characterize the countrysides of both Italy and Greece on this three-week road trip. You'll visit well-known highlights, like Florence, charming Tuscan hill towns, and the first Olympic site in Olympia, as well as some places a bit off the beaten path: Romeo and Juliet's Verona, the medieval villages of the Peloponnese, the wineries of Nemea, and more. With full control of the daily driving schedule, you'll have time to plan for spontaneous stops for coffee, for shopping at roadside markets, and for late-afternoon beach breaks.
Combine historic hill towns, fine wines, and the Tuscan countryside for an Italian eight-day road trip to remember. Get your bearings amid the Renaissance splendor of Florence, then set out into the surrounding landscapes—basing yourself first in Siena and then in Montepulciano. Along the way, you'll experience wine tastings and workshops focused on local Chianti vintages and set off on day trips to hilltop villages like San Gimignano, Monteriggioni, and Cortona.
Hit the road for a nine-day self-drive adventure through Tuscany! Start in Florence, exploring the historic center and learning to make pasta in a cooking class. Then pick up a rental car and drive to Pisa, where you'll see the famed Leaning Tower and sleep in lodgings in the countryside. Continue to the villages of the Cinque Terre, take a day trip to medieval Lucca, and finish the itinerary in picturesque Siena. You'll enjoy a wine tasting in the Chianti Classico region before heading back to Florence.
With 7 UNESCO designated sites (as many as Egypt!), Tuscany's rich historic background is matched only by its wine and food traditions. Explore all this and more on this 13-day itinerary, starting in Florence to see world-famous Renaissance art by Michelangelo and Da Vinci. Take in the views from the top of Pisa's leaning tower, explore Siena's 13th-century streets, and discover the rambling country roads of the Val d'Orcia region. End your trip with a pasta-making class and a full-day hike connecting historic fishing villages on the Mediterranean coast.
Embark on a scenic portion of the Via Francigena, once a path for religious pilgrims from Canterbury to Rome and today one of Italy's most magnificent long-distance walks. This five-day itinerary focuses on a short but spectacular section of the route that winds past quintessential Tuscan countryside, cypress avenues, and medieval fortresses. Along the way, you'll soak in ancient thermal baths, explore fortified castles, and spend your evenings in comfort in some of Tuscany's loveliest hill towns.
This road trip around Tuscany is perfect for those looking to delve into Italian wine culture. Start in Florence, the birthplace of the Renaissance, stroll around its medieval plazas and cathedrals, and see for yourself the history that permeates the city. Visit picturesque Tuscan villages and local wineries, getting a taste for local life and in some incredible surroundings.
Families with teens who want to get out and explore (and find the perfect backdrop for their photos) should give this two-week itinerary through the Veneto and Tuscany a try. You'll start in Venice, where you can explore secret passages, craft your own masks, and paddle a gondola. Then head to Verona and Lake Garda, biking through both urban and natural attractions. Wrap up in the Tuscan cities of Siena and Florence with a hot air balloon ride, gelato-making, and more.
Tuscany is famous for its beautiful landscapes, vineyards, cypress trees, farms, and medieval hill towns. What better way to experience some of the best views in Italy than by bike? With this brief but immersive five-day itinerary, you'll explore the hills and towers of San Gimignano, have a chance to taste Brunello wines in Montalcino, and learn about the history and architecture of Siena.
This 12-day trip through Italy is perfect for travelers who want to see the highlights. Starting in Venice, you'll walk along the bridges and ride a gondola through the famed Grand Canal. Then hop on a train to Florence to see world-class cathedrals and Renaissance masterpieces. From here, pick up your car and start a self-drive adventure, exploring the stunning region of Tuscany (and its wineries) before ending in Rome, where ancient history, eclectic neighborhoods, and a vibrant food scene await.
Indulge in the best of the Mediterranean region's food and wine on this comprehensive three-week getaway. Start the trip in Athens, home to both the famed Acropolis and the bustling Varvakios Market. Spend a few days island-hopping for winery tours and some of the world's best olive oil, before catching a flight to the south of Italy. Enjoy the best of Italy's cuisine, from pizza in Naples to parmesan in Bologna as you eat and drink your way through the country.
This 13-day trip explores Italy's three famous cities with plenty of guided excursions. Kick off in Venice to stroll across romantic bridges and glide along charming canals. From here, take a train to Florence, where you'll see its famous Renaissance masterpieces and learn how to make pasta. Then it's time to pick up a rental car for the ultimate Tuscan road trip with stops in Pisa, Siena, and Cinque Terre, before finishing in Rome for three days of sightseeing in the Eternal City.
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.
Travelers with two weeks to spare will love this Italy tour, which offers a mix of guided excursions and free time. The adventure starts in Venice, where you'll glide through charming canals and sail to lesser-known islands before taking a train to Florence. After a few days of Renaissance culture, pick up your car for a Tuscan road trip through wineries, hill towns, and beaches in Cinque Terre. Finish in Rome, where you'll see the classic sites, as well as hip neighborhoods like Trastevere.
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.
Explore the magnificent natural beauty of the Val d'Orcia region in Tuscany, walking through cypress-lined hills and vineyards, with time for tasting the wine, cheese, honey, and other culinary delights that the area is known for. Your adventure will take you through the wine-growing town of Montepulciano, then to Pienza where you can taste its distinctive Pecorino cheese, and finally to the medieval Tuscan powerhouse of Siena.
Travel by boat, train, and rental car on this exciting 15-day tour of Italy. It all starts in Venice, where you'll glide through charming canals and visit nearby islands. Next is the walkable city of Florence for incredible art and culture (and, yes, pasta). Pick up your rental car from here and explore Tuscan hill towns, Mediterranean beaches, and vineyards in Chianti before heading south. Drop your car in Rome and spend the last few days touring the Eternal City's ancient sites and famous fountains on foot.
This 16-day tour of Italy combines classic highlights and lesser-known surprises. Start in Venice, where you'll relax on a gondola and visit islands on the Adriatic. Then train to Florence to walk among Renaissance art and discover your pasta-making skills. From here, drive through Tuscany, stopping at medieval hill towns, Mediterranean beaches, and wineries. Finish in Rome to see the big hitters, followed by dinners in Monti and Trastevere—two neighborhoods filled with trendy locals.
Make your way to three of Italy's most famous cities by train and rental car on this 11-day adventure. You'll land in Venice, the "Floating City," with time to wander through its network of 150 canals. Then take a train to Florence to see Renaissance masterpieces and elegant gardens. This is where you'll begin your road trip through Tuscany, visiting hill towns, wineries, and villages on the Mediterranean. Continue the journey to Rome, where ancient history and eclectic neighborhoods await.
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.
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.
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.
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.
Explore Mediterranean beaches, Renaissance capitals, and medieval hill towns on this delightful 13-day tour through the Italian regions of Liguria and Tuscany. Start your adventure on the west coast, where you'll discover the quaint villages, rugged shorelines, and breathtaking scenery of the Cinque Terre. Head inland to spend a day wandering through history in Pisa, before journeying west to soak up the Renaissance splendor of Florence. The final five days take you deep into the Tuscan countryside, where you'll stay at a rural agriturismo villa and immerse yourself in the culture and landscape of the Val d'Orcia—wine tasting and truffle hunting around picturesque hill towns.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Embark on the ultimate Italian food and wine tour as you uncover the secrets to delicious pesto in Genoa, sample the best of Emilia-Romagna's pasta, and savor artisanal cheeses and prosciutto in Bologna. Tour medieval Siena's foodie hotspots and wine taste your way through the hills of Chianti and Val d'Orcia, then save room for some southern Italian cuisine as you master the art of pizza making in Naples.
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