By: Alicia Peacock Writer & Journalist | Specialist Arts & European travel

Tuscany is a well-loved destination for an unparalleled group holiday experience, offering the perfect blend of captivating landscapes, rich cultural heritage, and delicious cuisine. 

Whether you are fascinated by the art and culture of Florence, want to deep-dive into the stunning Chianti Classico countryside or would rather catch up by the private pool at your villa rental in Tuscany with a crisp glass of Vernaccia di San Gimignano, Tuscany caters to a wide array of interests. Here are five reasons why Tuscany is the perfect destination for luxury group vacations. 

Five reasons why Tuscany is the perfect destination for luxury group vacations

Breathtaking Views and Tranquil Surroundings

Tuscany is renowned for its breathtaking scenery – rolling hills, vineyards, olive groves, and quaint medieval towns. It is a paradise for outdoor lovers who love leisurely hikes and bike rides. And, you won’t be short of immersive tours of wine cellars and vineyards. No matter what your group’s interests are, Tuscany offers the perfect blend of relaxation and adventure.

Breathtaking Views and Tranquil Surroundings - Villas in Tuscany


Our top three recommendations:

Cultural and Historical Riches

Tuscany is renowned for its wealth of cultural treasures and lavish ancient history. Cities like Florence, Siena, and Pisa are home to iconic landmarks, museums, and art galleries showcasing Renaissance masterpieces. Group members with an interest in history, art, and architecture will find plenty to explore. And with famous landmarks within easy reach, wherever you stay, it's easy to find a balance that works for everyone. 


Must-see destinations for art and history lovers:

  • Have our expert concierge team book your tickets to the Uffizi in Florence. Or, better yet, take an exclusive tour with a Tuscan artist when you book an art retreat at your villa! 
  • The Palio in Siena is one of the most significant historical events in the Tuscan calendar. Experience the thrilling race with Sienese locals and get straight to the heart of the region’s local traditions.
  • If you are planning a trip to see the Leaning Tower of Pisa, don’t forget to stop in lovely Lucca. The home of Puccini is a treasure trove of historic churches, beautiful piazzas and fascinating museums. It is also a fantastic destination for cycling enthusiasts

World-class Wine and Gastronomic Excellence

Tuscany is a paradise for food and wine enthusiasts. The region is famous for its world-class wines, including Chianti, Brunello di Montalcino, and Vernaccia. A luxury group holiday wouldn’t be complete without the endless choice of wine tours, tastings, and visits to local vineyards. Plus, Tuscany's cuisine is celebrated for its seasonal, high-quality ingredients. There couldn’t be a better opportunity for group members to enjoy quality time together over delicious local dishes.

World-class Wine and Gastronomic Excellence


Three wine and food experiences we couldn’t do without:

  • The ease, intimacy and authenticity of private three-course dinners served by an in-villa chef! Our concierge can arrange in-villa catering and our fully-staffed villas with chefs are perfect for large group vacations.
  • In-villa wine tastings with a local winemaker! This is a unique way to experience the greatest wines in Tuscany. The best part is you don’t have to leave your villa! 
  • A hands-on cooking class with a local chef — master the art of fresh pasta making or plan a pizza party for your group.

Charming Tuscan Villages and Hill-Towns

The Tuscan hills are dotted with some of the country’s prettiest villages and towns, each with its own unique character and charm. Exploring places like San Gimignano, Lucca, and Montepulciano allows groups to experience the authentic Tuscan lifestyle. Wander through narrow cobblestone streets and savour the relaxed pace of life. These smaller towns offer a more intimate setting for group interactions and shared experiences.

Charming Tuscan Villages and Hill-Towns - Montepulciano


You cannot miss:

  • San Gimignano — visit the famous towers and stay for some of Tuscany’s best gelato.
  • Montepulciano — fine wine, pretty streets, Renaissance palaces and a rare steak. What more could you want? 
  • Pienza — Val d’Orcia views to make your heart sing, pecorino for days and a relaxed, rustic Tuscan vibe.

Luxury Villas Tailored to Large Groups

Renting a luxury villa in Tuscany is perfect for bringing larger groups of friends and family together. They provide you with the privacy and space to unwind and reconnect. Our villas at Tuscany Now & More offer plenty of outdoor space for alfresco living, private swimming pools, dining areas with stunning views and everything you may need to enhance your group travel experience. 

Our Villa Specialists are here to help you find the perfect villa for you and your party. Contact us to kickstart your travel plans, whether that be a reunion, a birthday party, or a destination wedding.

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Book your luxury villa holiday

All experiences are exclusively available to you when you book a luxury villa in Italy with Tuscany Now & More. Too add on any enriching extras, contact our local Villa Specialists to share your villa shortlist and secure your stay.

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