ITINERARY FOR THE WEEKEND OF MAY 3 - MAY 4, 2025

Siena’s May Weekend: Medieval Charm and Tuscan Sunshine Await

Experience the magic of Siena this May weekend, where medieval charm meets the warmth of the Tuscan sun. From a breathtaking hot air balloon ride to a captivating day trip through Tuscany’s historic gems, this is a journey you won’t want to miss.

Morning Majesty: A Balloon Ride Over Tuscany

As the sun begins its gentle ascent over the Tuscan hills, the air is crisp and filled with the promise of adventure. On the morning of May 3rd, the skies above San Casciano in Val di Pesa beckon with the allure of a balloon ride like no other. This is not just a flight; it is an ethereal journey through the heart of Tuscany, where the landscape unfolds like a Renaissance painting.

The experience begins with a warm welcome from the expert crew, who ensure every detail is attended to, from the safety briefing to the celebratory Champagne toast upon landing. As the balloon ascends, the world below transforms into a tapestry of undulating hills, dotted with charming villages and ancient castles. The vineyards and olive groves stretch as far as the eye can see, their colors vibrant under the morning sun.

“Wonderful and charming experience - Guido and Renato were responsive and kept communication open from the time we booked the hot air balloon to the evening before, to keep us updated on the weather forecast and provide exact coordinates. On the day itself, all of the crew members were friendly and helpful. I did the hot air balloon with my sister and 2 other friends, and since it was their first time, they were initially a little afraid but the safety briefing provided by the pilot Gigi made them feel at ease and they enjoyed the whole experience a lot. Views were extremely breathtaking, and we were thankful to be able to take many wonderful pictures against the sunshine and blue sky. The mini breakfast that was provided after consisted of Tuscan bread, cheese, prosciutto ham and cheese with champagne (there’s OJ for those who do not take alcohol) was definitely a nice touch to the end of the experience. All in all, a very smooth and pleasant experience. Will definitely recommend to anyone thinking of taking a hot air balloon ride in Tuscany!” — Reviewed at 2025-01-12

This serene flight, available from 6:00 AM to 9:30 AM, is a perfect start to a day of exploration, offering a perspective of Tuscany that is both intimate and grand.

Siena’s Timeless Allure

As the afternoon sun casts its golden glow over Siena, the city reveals its medieval charm in all its splendor. The historic Piazza del Campo, with its unique shell shape, is the heart of Siena, a place where history and culture converge. Here, the echoes of the Palio, Siena’s famous horse race, linger in the air, a testament to the city’s vibrant traditions.

Strolling through the narrow streets, one can almost hear the whispers of the past. The Gothic architecture, with its intricate details and soaring spires, tells stories of a time when Siena was a powerful city-state. The Duomo di Siena, with its stunning façade and breathtaking interior, is a masterpiece of art and architecture, a must-see for any visitor.

For those seeking a deeper understanding of Siena’s rich history, a guided tour offers insights into the city’s past, from its founding to its role in the Renaissance. The tour, available from April to October, is a journey through time, revealing the secrets of this enchanting city.

A Day Trip to Remember: Siena and San Gimignano

On May 4th, as the clouds gather in a gentle embrace over Tuscany, embark on a day trip that promises to be as enriching as it is delightful. This journey from Florence to Siena and San Gimignano is a celebration of Tuscany’s medieval gems, a day filled with history, culture, and culinary delights.

The day begins with a scenic drive through the Chianti region, where the rolling hills and vineyards create a landscape of unparalleled beauty. In Siena, a guided walking tour unveils the city’s architectural treasures, from the majestic Duomo to the bustling Piazza del Campo. Afterward, enjoy free time to explore at your own pace, perhaps indulging in a leisurely lunch at a local trattoria.

The journey continues to San Gimignano, a town frozen in time, where the iconic towers rise like sentinels against the sky. Here, the narrow streets invite exploration, each corner revealing a new facet of this UNESCO World Heritage site. The day concludes with a visit to an organic winery, where a three-course lunch paired with exquisite Chianti wines offers a taste of Tuscany’s culinary heritage.

“Professional, knowledgeable staff. - We had an amazing tour with City Wonders Tours. Our tour guide, Elisabetta Benedetti, shared interesting details en route and at each location. She provided a WhatsApp number to make sure we could contact her if we had any questions or issues during our free time. Elisabetta was very professional, knowledgeable, and personable. The lunch with wine tasting was incredible and our driver, Baar, was reliable, professional, and safe. With Elisabetta and Baar, we were in excellent hands. I highly recommend City Wonders Tours.” — Reviewed at 2025-04-19

This day trip, available from 8:00 AM to 5:00 PM, is a journey through Tuscany’s past and present, a day of discovery and delight that will linger in your memory long after the sun sets over the Tuscan hills.

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