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Medieval Towers & Wine Tasting

Maremma, Val D’Orcia, San Gimingnano, Florence, Forte dei Marmi

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Designed by Molly

This example itinerary from


11 days


  • Explore the famous rolling hills and historical cities of Tuscany
  • Join your private guide for a unique insight into Florence, Italy’s most beautiful city
  • Visit the birthplace of Renaissance art and spectacular medieval towns
  • Sail out to sea to visit Tuscan islands for the day
  • Hunt for truffles with trained dogs, taste some of the world’s best wines, and learn the art of Italian cooking

What’s Included

  • 10 nights Bed & Breakfast
  • 11 days car rental
  • Private guided city tours
  • Wine tasting
  • Daily local experiences
  • Private boat excursion
  • International Economy class flights
  • All domestic transfers

Example Itinerary

Day 1-3


  • Drive along the clifftop Via Panoramica for incredible coastal views
  • Take an elevator down the cliff to the hotel’s private esplanade

Made famous by wealthy Italians and a ‘Romeo and Juliet’-esque love story, this is our favorite corner of the Tuscan coastline.

Begin your journey by stopping at Porto Ercole, along the Argentario Coast, and spend two nights at Il Pelicano, an exquisite boutique hotel in a beautiful cove. With sea views to die for and bougainvillea-drenched terraces, unpack your swimmers and start your Tuscan adventure in paradise. When you’re not reading a book by the pool, hop aboard a boat and enjoy a breezy day on the water. Dip into the glittering seas, discover hidden coves and snorkel in crystal clear water. Leap onshore at Giglio island and visit little shops, restaurants and bars.

Day 3-5


  • Truffle-hunt for black truffles with trained dogs in a location famed for this exclusive product
  • Join chef Giancarla and learn how to create Tuscan delicacies

Without a shadow of a doubt the most beautiful part of the Tuscan countryside, Val d’Orcia is worth the extra journey.

Next, head inland to Val d’Orcia region and spend two nights at Monteverdi, a spectacular hotel on a medieval hilltop. Steeped in history, your base is set among rolling fields, cobbled streets, vineyards, a church and walled cities. Take part in cooking classes with chef Giancarla at the culinary academy and prepare Tuscan dishes such as boar ragu and pici pasta. With this small town producing a vast majority of the world’s precious truffles, don’t miss an afternoon of truffle hunting in the valley’s outstanding countryside.

Day 5-7


  • Marvel at medieval Italian architecture in this UNESCO hilltop town famous for its 14 towers
  • See the Tuscan hill towns from the sky in a hot air balloon

This is everything you would want out of a Tuscan escape, with rolling hills, a choice of vineyards and hilltop towns for gelato or lunch.

From here, switch off in the medieval town of San Gimignano by spending two nights at Belmond Castello Di Casole, a medieval castle encompassed by farmland, vineyards and rolling green countryside. Immerse yourself in food and rural traditions, joining cheese-masters on a tour of this country estate, or explore the tree-lined pathways by bicycle. If you fancy venturing out from the tranquil poolside surroundings, join your local guide for a walking tour around one of our favourite medieval cities, Siena.

Day 7-9


  • Let a private guide show you all that Tuscany’s capital has to offer
  • Look out onto the River Arno from your bedroom balcony

A city with a wealth of galleries, a rather famous bridge, and a church for every week of the year.

Perfect for art and history lovers, a trip to Florence is next. Spend two nights at Hotel Lungarno, which is built on the River Arno and boasts the best location in the city, with Ponte Vecchio a stone’s throw away from your bedroom window. A city tour led by a local expert is unmissable; get a taste for this historically rich city with highlights such as the Accademia Gallery. For an unrivalled evening experience, upgrade to enjoy supper in a jewellers shop on Florence’s signature archway, Ponte Vecchio.

Day 9-11


  • Visit the famed marble caves of Michelangelo
  • Enjoy local delicacies with a reservation at the famed Michelin-starred restaurant

A coastal destination with culture to rival the seaside experiences – an ideal place to end your trip.

For the final stop, travel to Forte dei Marmi, one of Tuscany’s chicest coastal resorts, and stay at the elegant Hotel Byron for two nights. Seek tranquility from villas hidden behind high walls and set within verdant gardens. Visit the poolside Michelin-starred restaurant La Magnolia, run by Cristoforo Trapani, to experience wholesome, local Tuscan flavours. For explorers, a boat trip around Cinque Terre is the perfect way to soak up the beautiful and steep coastal villages. A short distance from the sea, visit Carrara and the Apuan Alps, famous for its white marble and quarries.

The Fishers

Our family are hooked on Italy and Molly‘s passion and knowledge means she keeps finding us something new. The latest trip was in the Dolomites – Rosa Alpina is the dream. Officially our favourite hotel ever. We’re going to Puglia next but we have to wait until next year for that!

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These accommodations are the best of the best, showcasing top hospitality, exceptional design and world-class food, in the most exclusive locations around the world.


A very high standard of five-star properties, with top-notch service and a wide range of amenities and experiences ensuring an unforgettable stay.


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