Florence & Tuscany Explorer - 5 Days

Once you have arrived in Florence, you will make your way to your accommodation for check-in from 2 PM. After settling in, we will head out with our guide to explore the historic centre of the city and discover some of Florence’s most iconic landmarks. During our walk, we will admire the impressive Duomo, the lively Piazza della Signoria, and the famous Ponte Vecchio spanning the Arno River.

In the evening, you will have free time to experience Florence at your own pace. You may choose to enjoy dinner in a traditional trattoria, relax with a glass of Tuscan wine in a local café, or continue wandering through the city’s charming streets. For those wanting a more local experience, you can also join an optional Florentine aperitivo with spritz and regional specialities.

Meeting point: We meet at the reception of your hotel in Florence, Italy (Check-in available from 2:00 pm. Meet your guide in the afternoon to join the walking tour, 14:00 - 17:00)

Please note: This tour is designed for younger travellers looking for a backpacker-style experience and to meet like-minded people. The average age on this tour is around 21 - 35, and we are unfortunately unable to take any travellers over the age of 39. We have lots of group tours across our destinations that are suitable for travellers of all ages, browse our website or get in touch to find the perfect trip!

Today, you will have a full day to experience Florence at your own pace. From Renaissance landmarks and world-famous galleries to lively piazzas and hidden side streets, the city offers countless opportunities to explore its rich history, art, and atmosphere.

You may choose to visit some of Florence’s iconic sights, relax in a local café, browse artisan boutiques, or simply wander through the historic centre and soak up the city’s unique character. If you are interested in joining any optional activities during the day, your guide will be happy to assist with recommendations.

Florence - Chianti - San Gimignano. After breakfast, we will leave Florence behind and journey through the rolling countryside of Tuscany, passing vineyard-covered hills, cypress-lined roads, and traditional hilltop villages along the way. Our first stop will be a boutique winery in the Chianti region, where we will learn about the area’s long-standing winemaking traditions while enjoying a guided tasting of local wines paired with regional specialities.

We will then continue deeper into Chianti to visit a family-run estate, where we will sample more of the region’s renowned wines and hear stories about the heritage and traditions that have shaped Tuscan wine culture for generations.

Later in the afternoon, we will arrive in the UNESCO-listed town of San Gimignano, famous for its medieval towers and beautifully preserved historic centre. Here, we will have time to wander through the cobbled streets, browse artisan shops, and admire panoramic views across the Tuscan countryside.

Tonight, we will stay within the historic centre itself, giving us the opportunity to experience the quieter side of San Gimignano after the crowds have departed. You will have the evening free to enjoy the town’s relaxed atmosphere, take in the sunset over the hills, or enjoy dinner in one of the local restaurants.

San Gimignano - Siena - Cortona - Montepulciano - San Gimignano. This morning, we will set out on a full-day journey through some of Tuscany’s most celebrated towns, travelling through scenic countryside landscapes along the way. Our first stop will be Siena, a beautifully preserved medieval city known for its historic streets, impressive Gothic architecture, and the famous Piazza del Campo. We will have time to explore the city centre, admire the cathedral, and soak up the atmosphere of one of Tuscany’s cultural highlights.

From Siena, we will continue to the hilltop town of Cortona, made famous by the novel and film Under the Tuscan Sun. Here, we will take in panoramic views across the surrounding valleys, wander through the charming streets, and discover local artisan shops. During our visit, we will also stop at a countryside farm to enjoy a tasting of regional food specialities prepared with fresh local ingredients.

Later in the afternoon, we will visit Montepulciano, a historic hilltop town renowned for its elegant Renaissance buildings and celebrated Vino Nobile wines. You will have time to explore the medieval streets, enjoy views across the Val d’Orcia, and experience the town’s rich wine culture and history.

In the evening, we will return to San Gimignano, where the rest of the night will be free to relax and enjoy the atmosphere of this historic Tuscan town.

San Gimignano - Florence. Today, we will take part in a hands-on Tuscan cooking class led by a local chef, where we will learn how to prepare traditional regional dishes using authentic ingredients and recipes. After the class, we will sit down together to enjoy the meal we have prepared, accompanied by a glass of local wine.

Later in the afternoon, we will return to Florence, arriving back in the city by approximately 5 PM. You will then make your way to the airport for your onward flight. Safe travels!

End point: Florence, Italy between 17:00 - 17:30