20 Best Tours and Trips in San Gimignano in 2026/2027 - Compare Prices

Cycle the Via Francigena - Parma to Siena

(1 review )

No booking fees

Best price guaranteed

Excellent trip - the bike was great - all hotels also very good with good breakfasts. Was very impressed with the logistics - no dramas!

Bicycle toursSightseeing Tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Siena, Parma, Aulla, Massa, Lucc

Siena, Parma, Aulla, Massa, Lucca, San Miniato Alto, San Gimignano

Duration9 days

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Rome, Florence & Tuscany Family Adventure

(3 reviews )

Trip customizable

Best price guaranteed

Hi Stefania! Sorry to take so long to write back. It has been crazy trying to get back into the swing of things at work after that trip. Italy was amazing!! We absolutely loved it! As for feedback on the trip, we really don't have anything that was negative. We loved everything that was planned! We especially loved how you planned the sites that we went and how the pattern flowed (not sure if you did it on purpose but we think so). Also, thank you for being very accessible to us during the whole planning of the trip. You helped put us at ease and it was very reassuring that we chose the right company. That is all that I can given you that might be considered constructive. The rest I could say would just be compliments on everything else. If I can think of anything else that I think is useful I will definitely email you. Hope all is well, Jane P.S. - Does your company only provide trips for Italy or other countries as well, just wondering for the future :)

Food tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Rome, Florence, Tuscany, San Gim

Rome, Florence, Tuscany, San Gimignano, Chianti, The Vatican

Duration8 days

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Via Francigena: Walk from Lucca to Siena

(1 review )

Trip customizable

Best price guaranteed

Discover the Tuscan countryside and culture on this 8-day self-guided walking tour. Through the extensive footpath network of the area, roughly following the traces of the Via Francigena, one of Europe’s most important ‘highways’ in medieval times, you walk from village to village and experience a full immersion in the world-famous Tuscan landscape. The tour is perfect as an introduction to the region and a great choice for people who love museums, galleries and Gothic and Romanesque architecture. You have plenty of time to visit attractions on most of the days. You will also have time to visit all the beautiful medieval villages and historic towns along the Via Francigena: starting from beautiful Lucca, you’ll pass through Fucecchio, San Miniato, Gambassi Terme, the stunning San Gimignano with its medieval skyscrapers and Monteriggioni, admired by Dante in his Divine Comedy. An optional detour can bring you to beautiful Colle Val d’Elsa and the tour ends in Siena, arguably the most perfectly preserved medieval town in Tuscany. This tour threads together some of the most attractive towns and villages in Tuscany in an eloquent procession. However, the emphasis of the tour is to enjoy the countryside, the rolling vineyards, the poppies in spring and the wild cyclamen in autumn. The area north of Siena is an amazing landscape of rolling hills, alternating vineyards and forests, while cypresses line the way leading to the distant farmhouses. Walking here is an unforgettable experience and many of the views have barely changed for hundreds of years. Accommodation and some meals are included. You spend a night in one of the best agriturismos in Tuscany, and the final night in the heart of Siena, in one of the most characteristic little hotels. This is a moderately easy tour which is suitable for those who have some experience of walking and a good general physical condition.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel, Hostel

Age Range

18-99 yrs

Operated in

English

Destinations

Siena, Tuscany, Lucca, Altopasci

Siena, Tuscany, Lucca, Altopascio, San Miniato Alto, Gambassi Terme, San Gimignano, Monteriggioni

Duration8 days

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Super Sales

Premium Sicily and Tuscany

No booking fees

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Experience the timeless allure of Italy on the "Premium Sicily and Tuscany" tour, a 17-day sightseeing adventure that journeys from the vibrant streets of Palermo to the enchanting canals of Venice. Designed for travelers with a taste for culture and comfort, this trip uncovers the best of Italy and Sicily’s natural beauty, warm hospitality, and celebrated cuisine. Travel through iconic cities such as Rome and Venice, explore the ancient ruins of Agrigento, and savor exclusive moments like a private visit to a nobleman’s home in Rome. The itinerary features unforgettable highlights, including a scenic drive up the slopes of Mount Etna—Europe’s most active volcano—and hands-on culinary experiences that go far beyond the typical guidebook fare. Throughout your small group journey, enjoy top-tier accommodations, delicious local dishes, and the expertise of knowledgeable guides. The unique selling point of this tour is its curated access to authentic local experiences and off-the-beaten-path encounters, offering a deeper connection to Italy’s living heritage. Prepare to immerse yourself in art, history, and regional flavors on an Italian tour package that promises sophistication, comfort, and lifelong memories.

Sightseeing ToursWalking tours

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

15-99 yrs

Operated in

english

Destinations

Palermo, Rome, Chianti, San Gimi

Palermo, Rome, Chianti, San Gimignano, Florence, Venice, Marsala, Agrigento, Siracusa, Catania

Duration17 days

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Premium Italy in Depth

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Italy’s rich tapestry unfolds on the "Premium Italy in Depth" walking tour, an expertly crafted 15-day journey designed to balance leisure with discovery. From the historic streets of Bari to the shimmering waterways of Venice, experienced travelers will delight in the country’s cultural and culinary treasures. Highlights include an exclusive audience with a Roman nobleman, overnight stays among the rolling vineyards of Tuscany, and a guided exploration of Pompeii’s ancient ruins. Along the way, savor traditional Italian cuisine, unwind on pristine coastal beaches, and discover charming villages alongside vibrant urban centers. Led by an attentive local guide, this small group tour ensures both comfort and connection, offering unique opportunities to interact with locals and venture off the tourist trail. What sets this trip apart is its seamless blend of must-see landmarks with insider experiences—ideal for those seeking both iconic sites and hidden gems on a truly immersive Italian adventure.

Walking tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Venice, Polignano A Mare, Bari

Venice, Polignano A Mare, Bari, San Gimignano, Florence, Nardò, Matera, Naples, Rome

Duration15 days

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Super Sales

Italy Real Food Adventure

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Savor the flavors of Italy on the Italy Real Food Adventure, an eight-day journey for food lovers seeking to uncover the country’s culinary heart. Travel from Venice to Rome, sampling street eats, local wines, and homemade favorites in Tuscany, Bologna, and beyond. Each region reveals its own specialties, from cicchetti in Venice to rustic Tuscan fare and the vibrant food scene in Rome. This easy-paced tour is led by locals who guide you through markets, vineyards, and kitchens, ensuring you experience both classic dishes and hidden gems. Whether you’re a seasoned gourmand or simply curious, the trip’s USP is its regional diversity—showing you that Italian cuisine is much more than just pizza and pasta. Perfect for anyone with a passion for food and culture, this tour package promises a journey through Italy’s most delicious traditions.

Food tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Bologna, San Gimignano

Duration8 days

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Super Sales

Premium Rome to Dubrovnik

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From the rolling hills of Tuscany to the sun-drenched shores of the Adriatic, the "Premium Rome to Dubrovnik" trip is a 23-day odyssey through Italy, Slovenia, and Croatia. Explore world-renowned cities like Rome, Venice, and Dubrovnik, marvel at natural wonders like Lake Bled and Plitvice Lakes, and soak in the ambience of ancient towns and coastal gems. This easy-paced, expertly guided itinerary is perfect for those who want to savor Europe’s art, architecture, and cuisine in style. The real highlight? The sheer variety—each day unfolds a new layer of culture, scenery, or culinary delight, ensuring a truly memorable European tour package.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Dubrovnik, Rome, Bled, Rovinj, P

Dubrovnik, Rome, Bled, Rovinj, Plitvice Lakes National Park, Zadar, Split, Korčula, San Gimignano, Florence, Venice

Duration23 days

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Super Sales

Premium Rome to Split

No booking fees

Best price guaranteed

Picture yourself wandering through the cobbled streets of Rome, gazing at the shimmering lakes of Slovenia, and soaking up the sun along Croatia’s Adriatic coast. The "Premium Rome to Split" tour is a 16-day journey that captures the essence of Italy, Slovenia, and Croatia’s most enchanting destinations. From the rustic vineyards of Tuscany to Venice’s iconic Piazza San Marco, and from the medieval marvel of Bled to the cascading waterfalls of Plitvice Lakes National Park, each day brings a new discovery. The itinerary is thoughtfully crafted for a gentle pace, making it especially welcoming to mature explorers and those who appreciate leisurely sightseeing. What sets this trip apart is the seamless blend of local cuisine, cultural immersion, and natural wonders—all guided by seasoned leaders who share insider stories and exclusive access, ensuring an unforgettable European adventure.

Culture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Split, Rome, Bled, Rovinj, Plitv

Split, Rome, Bled, Rovinj, Plitvice Lakes National Park, Zadar, Chianti, San Gimignano, Florence, Venice

Duration16 days

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Super Sales

Premium Sicily and Italy in Depth

No booking fees

Best price guaranteed

Embark on the ultimate Italian journey with the "Premium Sicily and Italy in Depth" tour, a 24-day guided adventure for experienced travelers and seniors. Starting in Palermo and concluding in Venice, you’ll traverse the length of Italy, from the volcanic slopes of Mount Etna to the canals of Venice. Savor local wines at a family-run vineyard, learn to roll pasta like a pro, and explore the marvels of Pompeii and the Tuscan countryside. With three unforgettable Feature Stays and a knowledgeable local leader, this tour package offers a comprehensive immersion into Italy’s culture, cuisine, and history—the perfect Italian odyssey.

AdventureSightseeing Tours

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

15-99 yrs

Operated in

english

Destinations

Venice, Palermo, Bari, Nardò, Ma

Venice, Palermo, Bari, Nardò, Matera, Naples, Rome, San Gimignano, Florence, Marsala, Agrigento, Siracusa, Catania

Duration24 days

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Super Sales

Local Living Italy - Tuscany San Gimignano

No booking fees

Best price guaranteed

If Tuscany has ever called your name, this is your chance to answer. For seven days, you’ll settle into a charming farmhouse in San Gimignano — your home for the week and your base for exploring the heart of central Italy. Wake up to vineyard views, stroll medieval streets, and soak up sunsets over rolling hills, all at a pace that feels truly local. With free days to embrace the countryside or head out on day trips to Florence, Siena, and Volterra, this isn’t just a visit — it’s living Tuscany, one unforgettable day at a time.

Local culture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Florence, San Gimignano

Duration7 days

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All San Gimignano Tours and Trips

Create a customized tour to San Gimignano and Italy

Page 2 of 23 Trips in San Gimignano with 374 Reviews

Cycle the Via Francigena - Parma to Siena

Rome, Florence & Tuscany Family Adventure

Via Francigena: Walk from Lucca to Siena

Premium Sicily and Tuscany

Premium Italy in Depth

Italy Real Food Adventure

Page 2 of 23 Trips in San Gimignano with 374 Reviews

Premium Rome to Dubrovnik

Premium Rome to Split

Premium Sicily and Italy in Depth

Local Living Italy - Tuscany San Gimignano

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Polar

Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

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All San Gimignano Tours and Trips

Create a customized tour to San Gimignano and Italy

Page 2 of 23 Trips in San Gimignano with 374 Reviews

Page 2 of 23 Trips in San Gimignano with 374 Reviews