San Gimignano May 2027 Tours and Trip packages

Rome and Tuscan Highlights - May 2027

4.7

(51 reviews )

No booking fees

Best price guaranteed

I chose this trip because of the 6 nights in Tuscany - Montecatini Terme. Cinque Terre, Lucca, Siena and San Gimignano were highlights of this tour. The food for the special dinners was amazing. Rosella and Massimo kept things on track. Organizing and coordinating tickets, transportation (2 ferries, train and bus) and firsthand knowledge of the areas visited was well exhibited by Rosella. The specialty tour guides were knowledgeable and added extra flair to the excursions. Enjoyed the trip immensely.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Montecatini, Florence, Vin

Rome, Montecatini, Florence, Vinci, San Gimignano

Duration9 days

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Ultimate Italy - May 2027

(34 reviews )

No booking fees

Best price guaranteed

It was a great experience with many highlights throughout our tour. We particularly enjoyed the many immersive stops (i.e. wine tasting, weaving, truffle hunting, pasta making, etc.) in addition to our guided tours. Our tour guide, was very well versed, knowledgeable, and helpful and provided good insights and tips throughout our trip. I can't imagine someone else doing a better job than she did! The local experts were also on top of their games.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Lodge, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Capri, Perugia, Sa

Rome, Venice, Capri, Perugia, San Gimignano, Florence, Rapallo

Duration12 days

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Tuscany Walking and Wine - May 2027

4.7

(9 reviews )

No booking fees

Best price guaranteed

Excellent trip and very good guide in AJ. Only negative was hotel in Florence. Good location (change from original hotel) but was tired and cleanliness could have been better. Very cramped solo room 🙁 Highlights were Pienza and Castellina in Chianti. Great hotels, beautiful walks and really good food and wine. 😀

Walking tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Florence, Pisa, San Gimignano, T

Florence, Pisa, San Gimignano, Tuscany, Pienza, Montalcino

Duration8 days

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Mediterranean Coastal Journey Spain, France & Italy - May 2027

4.5

(25 reviews )

No booking fees

Best price guaranteed

I loved seeing everything and hearing all the history. The tour guides were wonderful and knowledgeable. The food and hotels were great. Our tour guide Carlos played music for us on the bus according to which country we were in. He also was able to find a famous guitar players music and played it for a man who was on our trip. It was wonderful music and the musician was great. I would and do recommend it to all my friends.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

1-99 yrs

Operated in

english

Destinations

Barcelona, Tuscany, Nice, Genoa

Barcelona, Tuscany, Nice, Genoa, San Gimignano, Costa Brava, Figueres, Marseille

Duration16 days

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Rome, Florence & Tuscany Family Adventure - May 2027

(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 - May 2027

(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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Premium Italy in Depth - May 2027

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Best price guaranteed

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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Premium Sicily and Tuscany - May 2027

No booking fees

Best price guaranteed

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 Rome to Split - May 2027

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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Tours and Trip Packages to San Gimignano in May 2027

Get a customized trip to San Gimignano in May 2027

12 Trips in San Gimignano during May 2027 with 153 Reviews

12 Trips in San Gimignano during May 2027 with 153 Reviews

Rome and Tuscan Highlights - May 2027

Italian Elegance - May 2027

Ultimate Italy - May 2027

Tuscany Walking and Wine - May 2027

Mediterranean Coastal Journey Spain, France & Italy - May 2027

Rome, Florence & Tuscany Family Adventure - May 2027

Via Francigena: Walk from Lucca to Siena - May 2027

Premium Italy in Depth - May 2027

Premium Sicily and Tuscany - May 2027

Premium Rome to Split - May 2027

Europe

Asia

South America

Africa

North America

Oceania

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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Tours and Trip Packages to San Gimignano in May 2027

Get a customized trip to San Gimignano in May 2027

12 Trips in San Gimignano during May 2027 with 153 Reviews

12 Trips in San Gimignano during May 2027 with 153 Reviews