Best of San Gimignano

Top itineraries and travel advice in and around San Gimignano
San Gimignano is a quintessentially Tuscan medieval village perched atop one of the region’s iconic hills. A UNESCO World Heritage Site, it is known for its 14 towers that dominate the village skyline, which sit alongside beautiful squares, palaces, and churches. San Gimignano is one of the most visited villages in Tuscany, and staying overnight allows you to experience its charm after the day-trippers have departed, with lodgings from agriturismos to palazzos.

Take a self-drive tour to the villages of Volterra or Monteriggioni to experience them at your own pace; Volterra is known for its Etruscan ruins, while Monteriggioni and its famous still-intact medieval castle walls make an appearance in Dante’s Divine Comedy. Previous kimkim travelers have also opted to pop over to Castellina to visit the area’s Archaeological Museum or hop aboard a private wine tour through the Chianti Valley or Val D’Orcia and learn to taste like a pro. Don’t skip the local wineries in the Elsa Valley below town, home of the Vernaccia di San Gimignano vintage, or the gelaterias famous for producing some of the world’s best flavors.
Plan your trip to Italy
Customize your trip with help from a local travel specialist.
Tuscany, Italy countryside
Map of Tuscany By Bike: San Gimignano, Montalcino, Siena - 5 Days
Tuscany By Bike: San Gimignano, Montalcino, Siena - 5 Days

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. 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.

Francigena Way, Tuscany, Italy
Map of Via Francigena: San Miniato, San Gimignano, & Siena - 5 Days
Via Francigena: San Miniato, San Gimignano, & Siena - 5 Days

In 990 BCE, the Archbishop of Canterbury traveled from England to Rome to meet with the Pope. He wrote a detailed diary of the 80 stages of his journey through the United Kingdom, France, and Italy, and this path is now known at the Via Francigena (the Francigena Way), a path for religious pilgrims from Canterbury to Rome. The trail travels through Tuscany, and you can experience it on this five-day itinerary that winds through the Tuscan countryside.

Steep Buildings on the 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.

Tuscan Countryside
Map of Food & Wine in Italy: Bologna, Florence, Rome - 7 Days
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.

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.

Selection in a Local Gelateria
Map of Food & Wine in Italy: Venice, Bologna, Florence, Rome, & More - 15 Days
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.

Cafe in Bologna's Porticos
Map of Food & Wine in Italy: Bologna, Florence, Rome - 10 Days
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. 

Traditional Buranelli Cookies
Map of Food & Wine in Italy: Venice, Bologna, Florence, Rome, & More - 14 Days
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. 

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.

Colorful Carnival Masks in Venice
Map of Venice, Florence, Amalfi Coast & Rome - 10 Days
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. 

Monreale Cathedral in Palermo
Map of Venice, Florence, Amalfi Coast & Rome - 14 Days
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. 

Florence City Skyline
Map of Discover Venice, Florence & Rome - 7 Days
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.

Island of Capri on the 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.

Church interior on the Amalfi Coast
Map of Venice, Florence, Amalfi Coast & Rome - 12 Days
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.

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. 

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.

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. 

Colorful homes on Burano Island, Venice
Map of Discover Venice, Florence & Rome - 8 Days
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.

Murano Island in Venice
Map of Discover Venice, Florence & Rome - 10 Days
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.

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.

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. 

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.

Gondolas near Piazza San Marco in Venice
Map of Venice, Florence, Amalfi Coast & Rome - 21 Days
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.

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.

Capri Beach
Map of Venice, Florence, Amalfi Coast & Rome - 13 Days
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.

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.

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.

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.

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.  

Colosseum in Rome
Map of Venice, Florence, Amalfi Coast & Rome - 11 Days
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.

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.

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.

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.

Typical house facade in Venice
Map of Discover Venice, Florence & Rome - 9 Days
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.

Santa Lucia Archway in Bologna
Discover Northern Italy, From Florence to Milan - 12 Days

Discover the best of Italy's northern regions, starting in the medieval city of Florence, with guided walking tours and wine tastings in Tuscany. Make your way through San Marino and the coastal cities of Riccione and Ravena before heading into Emilia-Romagna for a culinary exploration through Bologna and Parma. Take a cooking class and learn how to identify wine with a sommelier, then enjoy exploring the extravagant shores of Lake Como and the fashion-focused streets of Milan.

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. 

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.

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.

The Cinque Terre village of Vernazza.
Map of Explore Liguria & Tuscany: Cinque Terre, Florence, Pisa & Val D'Orcia - 13 Days
Explore Liguria & Tuscany: Cinque Terre, Florence, Pisa & Val D'Orcia - 13 Days

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.

Venice
Map of Romantic Italy: Rome, Florence, and Venice by Train - 10 Days
Romantic Italy: Rome, Florence, and Venice by Train - 10 Days

On this 10-day trip, you'll travel by train to three of Italy's most popular cities, where flavors, history, archaeology, and the territory intertwine. Your journey begins in Rome with a day-long excursion to the fabled ruins of Pompeii. Next, you'll visit Florence, the city of Michelangelo, and take a day tour to the Chianti region. Your Italian adventure concludes in Venice, where you'll wander through Saint Mark's Square and travel by boat along the famous Grand Canal. After this trip, you will truly understand why Italy is called the Bel Paese!

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.

Siena's Main Square
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.

Side street of Cortona
Map of Tuscany Road Trip: Florence, Siena, & Montepulciano - 9 Days
Tuscany Road Trip: Florence, Siena, & Montepulciano - 9 Days

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.

Chianti vineyards
Map of Tuscany Road Trip: Florence, Siena, & Montepulciano - 7 Days
Tuscany Road Trip: Florence, Siena, & Montepulciano - 7 Days

This self-drive tour 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.

Medieval buildings in Siena
Map of Tuscany Self-Drive Tour - 8 Days
Tuscany Self-Drive Tour - 8 Days

Explore Tuscany's incredible art and history with this itinerary. Start your trip in Florence, where world-famous works by Michelangelo, da Vinci, and others dominate the art scene. On a self-drive tour, explore the Tuscan countryside to see 13th-century churches in Siena and try the renowned Chianti wine. Visit the leaning tower of Pisa and relax in the charming villages of the Cinque Terre before ending your trip back in Florence.

Gondola through the Venice canals
Map of Discover Venice, Tuscany, & Rome - 14 Days
Discover Venice, Tuscany, & Rome - 14 Days

From the canals of Venice to Rome's buzzing nightlife, this incredible trip through the highlights of Italy is perfect for travelers who want to see it all, making your way across the country with a mix of trains and rental car. Start in Venice to see the famed Grand Canal, then head to Florence for its famed cathedrals and da Vinci's art. From here, start the self-drive portion of your trip exploring the stunning region of Tuscany to its fullest before ending in Rome, where ancient history, eclectic neighborhoods, and a vibrant food scene await.

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.

Hillside of Montepulciano
Map of Explore Tuscany: Florence, Siena, & Montepulciano - 10 Days
Explore Tuscany: Florence, Siena, & Montepulciano - 10 Days

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.

Orvieto, in the Umbria Region
Map of Rome, Orvieto, Florence, & Verona - 15 Days
Rome, Orvieto, Florence, & Verona - 15 Days

This route takes you through the highlights of Italy while exploring more of each region. Start in Rome, visiting the Vatican and Colosseum before making your way up to the lesser-known Umbria region for a stopover in Orvieto. Enjoy your time away from the big city and delight in the local life. Continue up to the birthplace of the Renaissance, Florence. This city's incredible plazas and cathedrals never disappoint. Finish off your trip in the Veneto region, staying in lovely and romantic Verona and visiting its neighboring city, Venice.

Leaning Tower of Pisa
Map of Tuscany Self-Drive Tour - 7 Days
Tuscany Self-Drive Tour - 7 Days

Explore Tuscany's incredible art and history on this itinerary. Start your trip in Florence, where world-famous works by Michelangelo, da Vinci, and others dominate the art scene. On a self-drive tour, explore the Tuscan countryside to see 13th-century churches in Siena and try the renowned Chianti wine. Visit the leaning tower of Pisa and relax on the beaches of Cinque Terre before ending your trip back in Florence.

Orvieto, in the Umbria Region
Map of Rome, Orvieto, Florence, & Verona - 14 Days
Rome, Orvieto, Florence, & Verona - 14 Days

This route takes you through the highlights of Italy while exploring more of each region. Start in Rome, visiting the Vatican and Colosseum before making your way up to the lesser-known Umbria region for a stopover in Orvieto. Enjoy your time away from the big city and delight in the local life. Continue up to the birthplace of the Renaissance, Florence. This city's incredible plazas and cathedrals never disappoint. Finish off your trip in the Veneto region, staying in the lovely and romantic Verona and visiting its neighboring city, Venice.

Views from Perugia
Map of Rome, Perugia, & Florence - 10 Days
Rome, Perugia, & Florence - 10 Days

From the Sistine Chapel in Rome to Michelangelo's 'David' in Florence, this trip is perfect for travelers who want to see Italy's top sights at a relaxed pace, while getting a glimpse at a more off-the-beaten-path region as well. Start in Rome for trendy wine bars, nighttime foodie crawls, and a visit tour of Vatican City, end in Florence to explore the medieval cathedral and plazas. Nestled between the two big cities is the lesser-visited and equally stunning region of Umbria, where you'll stop to admire the landscapes to round out your trip. 

Main square of Cortona
Map of Tuscany Road Trip: Florence, Siena, & Montepulciano - 8 Days
Tuscany Road Trip: Florence, Siena, & Montepulciano - 8 Days

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.

Skyline of Florence
Map of Discover Venice, Tuscany, & Rome - 12 Days
Discover Venice, Tuscany, & Rome - 12 Days

From the canals of Venice to Rome's buzzing nightlife, this incredible trip through the highlights of Italy is perfect for travelers who want to see it all, making your way across the country with a mix of trains and rental car. Start in Venice to see the famed Grand Canal, then head to Florence for its famed cathedrals and da Vinci's art. From here, start the self-drive portion of your trip exploring the stunning region of Tuscany to its fullest before ending in Rome, where ancient history, eclectic neighborhoods, and a vibrant food scene await.

Streets of Tuscany
Map of Discover Venice, Tuscany, & Rome - 15 Days
Discover Venice, Tuscany, & Rome - 15 Days

From the canals of Venice to Rome's buzzing nightlife, this incredible trip through the highlights of Italy is perfect for travelers who want to see it all, making your way across the country with a mix of trains and rental car. Start in Venice to see the famed Grand Canal, then head to Florence for its famed cathedrals and da Vinci's art. From here, start the self-drive portion of your trip exploring the stunning region of Tuscany to its fullest before ending in Rome, where ancient history, eclectic neighborhoods, and a vibrant food scene await.

Arno River in Florence
Map of Rome, Orvieto, Florence, & Verona - 13 Days
Rome, Orvieto, Florence, & Verona - 13 Days

This route takes you through the highlights of Italy while exploring more of each region. Start in Rome, visiting the Vatican and Colosseum before making your way up to the lesser-known Umbria region for a stopover in Orvieto. Enjoy your time away from the big city and delight in the local life. Continue up to the birthplace of the Renaissance, Florence. This city's incredible plazas and cathedrals never disappoint. Finish off your trip in the Veneto region, staying in the lovely and romantic Verona and visiting its neighboring city, Venice.

Medieval buildings in Siena
Map of Tuscany Self-Drive Tour - 9 Days
Tuscany Self-Drive Tour - 9 Days

Explore Tuscany's incredible art and history with this itinerary. Start your trip in Florence, where world-famous works by Michelangelo, da Vinci, and others dominate the art scene. On a self-drive tour, explore the Tuscan countryside to see 13th-century churches in Siena and try the renowned Chianti wine. Visit the leaning tower of Pisa and relax in the charming villages of the Cinque Terre before ending your trip back in Florence.

Orvieto, in the Umbria Region
Map of Rome, Orvieto, & Florence - 10 Days
Rome, Orvieto, & Florence - 10 Days

This route takes you through the highlights of Italy while exploring more of each region. Start in Rome, visiting the Vatican and Colosseum before making your way up to the lesser-known Umbria region for a stopover in Orvieto. Enjoy your time away from the big city and delight in the local life. Continue up to the birthplace of the Renaissance, Florence. This city's incredible plazas and cathedrals never disappoint.

Siena's main square
Map of Discover Venice, Tuscany, & Rome - 16 Days
Discover Venice, Tuscany, & Rome - 16 Days

From the canals of Venice to Rome's buzzing nightlife, this incredible trip through the highlights of Italy is perfect for travelers who want to see it all, making your way across the country with a mix of trains and rental car. Start in Venice to see the famed Grand Canal, then head to Florence for its famed cathedrals and da Vinci's art. From here, start the self-drive portion of your trip exploring the stunning region of Tuscany to its fullest before ending in Rome, where ancient history, eclectic neighborhoods, and a vibrant food scene await.

Skyline of Florence
Map of Discover Venice, Tuscany, & Rome - 13 Days
Discover Venice, Tuscany, & Rome - 13 Days

From the canals of Venice to Rome's buzzing nightlife, this incredible trip through the highlights of Italy is perfect for travelers who want to see it all, making your way across the country with a mix of trains and rental car. Start in Venice to see the famed Grand Canal, then head to Florence for its famed cathedrals and da Vinci's art. From here, start the self-drive portion of your trip exploring the stunning region of Tuscany to its fullest before ending in Rome, where ancient history, eclectic neighborhoods, and a vibrant food scene await.

A coffee in Rome
Map of Discover Venice, Tuscany, & Rome - 11 Days
Discover Venice, Tuscany, & Rome - 11 Days

From the canals of Venice to Rome's buzzing nightlife, this incredible trip through the highlights of Italy is perfect for travelers who want to see it all, making your way across the country with a mix of trains and rental car. Start in Venice to see the famed Grand Canal, then head to Florence for its famed cathedrals and da Vinci's art. From here, start the self-drive portion of your trip exploring the stunning region of Tuscany to its fullest before ending in Rome, where ancient history, eclectic neighborhoods, and a vibrant food scene await.

Skyline of Rome
Map of Rome, Orvieto, & Florence - 9 Days
Rome, Orvieto, & Florence - 9 Days

This route takes you through the highlights of Italy while exploring more of each region. Start in Rome, visiting the Vatican and Colosseum before making your way up to the lesser-known Umbria region for a stopover in Orvieto. Enjoy your time away from the big city and delight in the local life. Continue up to the birthplace of the Renaissance, Florence. This city's incredible plazas and cathedrals never disappoint.