The vibrant, rocky cliffs around the Cala del Gesso, overlooking the colourful waters below, in monte argentario, Tuscany, Italy.
The Vitaleta Chapel, sat among the vibrant fields of Tunscany surrounded by the lush mountains near San Quirico d'Orcia, Siena, Italy.
A large body of water at the nature reserve of Diaccia Botrona, with a colony of flamingos walking the calm waters of Castiglione della Pescaia, Tuscany, Italy.
A vibrant view of downtown Siena, with the distant Siena Cathedral overlooking the lush greenery surrounding the city on a sunny day in Tuscany, Italy.
The sun breaking through patches of clouds onto the vibrant vineyards of Radda in Chianti, overlooked by the distant estate in Siena, Tuscany, Italy.

The Luxury Tuscan Collection – Chianti to Maremma

8 nights from $6,610pp

Enquire about this trip

Discover central Tuscany, between the peninsula’s lofty Apennine ridge and the Tyrrhenian Sea – an almost endless succession of gentle hills, each unique and distinctive. Gourmets and wine buffs descend on Tuscany to enjoy the simple yet wonderful cuisine and wine…

If you are looking for a mixture of relaxation and activity… biking/hiking/cooking and drinking wine, this luxury Italy wine tasting tour has it all!

Highlights of our Luxury Tuscany Tour

  • Four night’s accommodation in the heart of the Chianti Classico producing region. Enjoy elegant accommodation in a five-star estate with panoramic views from its exceptional location in the Chianti Hills.
  • Half-day guided mountain bike ride or afternoon hiking trek
  • Full-day (private) wine guide to accompany you for a private tour around Chianti with visits to a number of local and prestigious wine estates with tours and numerous tastings
  • Indulge your love of Italian food in Tuscany, and enjoy a full-day tour that combines a cooking class and wine tasting.
  • Full-day Tuscan cycle ride experience with lunch and tastings. Support vehicle and guide to manage the day and ride.
  • Four night’s accommodation in an elegant, historic and unique small hotel situated on Tuscany’s Argentario peninsula.
  • Day trip to discover Giannutri, a small island in the Tuscan Archipelago National Park
  • An enjoyable full-day cycle ride through the Maremma countryside. Support vehicle and guide to manage the day.
A road winding through the stunning, lush fields of the Tuscan countryside, decorated with beautiful, pointy cypress trees, heading into the distant sunset over Italy.

Day 1: Arrival in Tuscany

On arrival at the airport, relax with private luxury transfers from Pisa into Tuscany. The next four nights you will be staying in a luxury five-star hotel in the heart of the Chianti Classico producing region. The hotel offers an indoor heated pool, sauna, Turkish bath, jacuzzi and the stunning outdoor pool with a panoramic hilltop view overlooking the Chianti scenery.

Fresh tagliatelle pasta being cut from a pasta machine, held by flour covered hands during a cooking class in italy.

Day 2: Full-Day Tour Combining a Cooking Class and Wine Tasting

Your local English-speaking wine guide will meet you at your accommodation after breakfast for a full-day private wine tasting experience. Indulge your love of Italian food in Tuscany, and enjoy a full-day tour that combines a cooking class and wine tasting. Following the cooking class enjoy lunch at the estate, tasting yet more wines and local olive oils. Visit the village of Castelnuovo Berardenga. Often treated as a kind of appendage of Siena, the town and its surroundings are full of charm, character, and history.

In the early afternoon visit a small, unique wine and olive oil producer. Visit the olive groves, sample the wine and oil accompanied with a bruschetta and beans tapas. In the afternoon visit another superb producer on the southern border of Chianti Classico, followed by late afternoon transfers back to your accommodation.

Beautifully aligned vineyards in the Tuscan countryside at sunset, with cloudy skies beyond the hills in Italy.

Day 3: Cycle Through Tuscany, Taking in the Wine and Scenery

Your local English-speaking cycle guide will meet you at your accommodation after breakfast for a full-day biking experience – private rides are tailored to clients’ specific preferences and biking abilities (please note you will have a support vehicle and guide to manage the day and ride). You’ll cycle at your own pace on peaceful country lanes, through an endless panorama of vineyards, olive groves and centuries-old stone farmhouses. Along the vineyard cycle route enjoy a morning tour and tasting, and you’ll also enjoy a truly delectable Tuscan lunch featuring local products and wine pairings in a stunning Tuscan wine estate. Relax with private transfers back to your accommodation.

A vibrant view of downtown Siena, with the distant Siena Cathedral overlooking the lush greenery surrounding the city on a sunny day in Tuscany, Italy.

Day 4: Relax in Your Chianti Hotel Before Exploring Siena

The morning to relax and enjoy the panoramic outdoor pool with incredible Chianti vineyard views. Take the hotel transfer into Siena for the day! A day to explore Siena, built on three hills and surrounded by well preserved walls, Siena is filled with fine examples of Gothic architecture and has one of the world’s most unique piazzas, Piazza dal Campo, dominated by the greatest Gothic building in Tuscany, the Palazzo Pubblico.

For those who want to be pampered by different wellness treatments, the hotel offers a range of spa treatments (please ask for details).

The vibrant, rocky cliffs around the Cala del Gesso, overlooking the colourful waters below, in monte argentario, Tuscany, Italy.

Day 5: Arrive in Maremma Before exploring Monte Argentario

In the morning, relax with private luxury transfers to the Maremma. Enjoy four-night’s accommodation in an elegant, historic and unique small hotel situated on Tuscany’s Argentario peninsula. This is a luxury hotel well known for its beautiful aspect and its Michelin-starred restaurant.

A former island off the coast of Tuscany, now connected to the mainland via three narrow sandbars, Monte Argentario is quite a special rugged spot for those looking to mingle sea and mountain fun, all in one place. A special place where the Italian elite seeking out a hidden getaway enjoy the groves of Argentario’s coastline.

The two restaurants (one of which is Michelin starred) offer unique atmospheres, they share mouth-wateringly good traditional Italian dishes with a modern twist, taste bud tingling vintages and stylish surroundings.

A little bay with clear blue waters, flanked by rocky shores with various small boats scattered throughout in Giannutri, Tuscany.

Day 6: Take a Ferry to the Island of Giannutri

Discover Giannutri, a small island in the Tuscan Archipelago National Park. Shaped like a half moon, the island of Giannutri will bedazzle you with its unique underwater world and the ruins of imposing Roman villas. The rough rocky coast of the most southern Tuscan island sinks only twice, to form accessible bays. Hop onto a ferry from Porto Santo Stefano to visit Giannutri, a simply stunning place to explore and relax with a local lunch on the island.

The hillside buildings in Porto Ercole, overlooking the busy waters before it, with brick walls running along the top of the hill in Tuscany, Italy.

Day 7: Explore the Sights around Porto Ercole

Today is yours to explore. Head to 16th-century Forte Stella at Porto Ercole, built in the shape of a star and a remnant from the island’s former Spanish invaders. Take a walk along the high-end boutiques of Porto Ercole towards the ‘borgo antico’, or old part of the village. Continue towards the ‘la rocca’ fortress for amazing views with lunch in the old town. Or simply relax and enjoy the panoramic seaview from the pool.

A large body of water at the nature reserve of Diaccia Botrona, with a colony of flamingos walking the calm waters of Castiglione della Pescaia, Tuscany, Italy.

Day 8: Cycle Through the Maremma countryside

Your local English-speaking cycle guide will meet you at your accommodation after breakfast for a full-day biking experience – private bike routes have optional extensions, so you can choose the perfect amount of biking to suit your ability. The ride takes you through medieval towns, beautiful vistas and ends at the Tyrrhenian sea with a swim along the way. Enjoy an enjoyable ride through the Maremma countryside. Enjoy an amazing local lunch to end the trip – A wide range of local flavours ensure a stunning Tuscan lunch paired with wines in a memorable setting. Late afternoon (chauffeured) transfers back to your accommodation.

A cosy terrace at Hotel La Fontanelle, furnished with contemporary, cushioned seats beneath the large parasols, with the stunning views of the lush countryside of Tuscany, Italy.

Day 9: Final Day in Tuscany

After a final breakfast in the hotel, relax with private transfers to the airport for your flight home.

Where You Could Stay in Tuscany

A road winding through the stunning, lush fields of the Tuscan countryside, decorated with beautiful, pointy cypress trees, heading into the sunset.
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Tuscany Travel Articles

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