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.

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San Gimignano Essentials

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.

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!

San Gimignano Itineraries

Tuscan hill towns, robust red wines, and local cuisine are the stars of the show on this romantic week in Italy

A Romantic Tuscan Road Trip: Food, Wine & Thermal Baths - 7 Days

Reconnect with your significant other on this seven-day road trip across Tuscany. This is the perfect Italian itinerary for lovers of food and wine, and the trip is jam-packed with wine tastings, cooking classes, and traditional Tuscan dining. Hand-in-hand you'll explore the sights and culture of San Gimignano, Siena, and Montalcino before wrapping up with two nights at a 5-star spa resort in Tuscany's off-the-beaten-path Maremma region—where thermal springs dating back to the Romans await.

Savor a Tuscan sunset on the terraces of Montalcino

A Romantic Tuscan Road Trip: Food, Wine & Thermal Baths - 10 Days

Fall in love with the beauty of Tuscany on this romantic 10-day Italian vacation. Begin in Pisa and snap a picture with the famous Leaning Tower before grabbing the keys to a rental car and venturing into the Tuscan countryside. You'll fly above hill towns in a hot-air balloon at dawn, go wine tasting at an esteemed school, join a traditional cooking class to learn about Tuscan cuisine, and join a truffle hunt to find the prized ingredients. After a busy week, you'll slow down at a luxury thermal springs resort.

Follow in the footsteps of history on the Francigena Way in Tuscany

Walk Italy's Via Francigena: San Miniato, San Gimignano & Siena - 5 Days

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.

Cycle through the scenic Tuscan countryside

Tuscany By Bike: San Gimignano, Siena & Murlo - 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? 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.

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.

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.

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.

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.

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.

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.

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 - 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.

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.

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.

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.

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 - 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

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.

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 - 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.

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.

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.

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.

Board a gondola for a romantic cruise of Venice's canals

Romantic Italy: Rome, Florence & 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 of 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'll truly understand why Italy is called the "bel paese"!

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.

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.

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.

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.

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.

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.

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.

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.

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

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 · Milan · Naples · Palermo · Lakes District · Lake Como · Lake Garda · Taormina · Verona · Syracuse · Siena · Cinque Terre · Sorrento · Italian Riviera · Emilia Romagna · Capri · Bologna · Agrigento · Chianti · Piedmont · Turin · Catania · Umbria · Puglia · Alberobello · Lecce · Bari · Dolomites · Aeolian Islands · Ragusa · Montepulciano · Sardinia · The Langhe

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