The Luxury Tuscan Collection - Chianti to Maremma

9 days

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 trip has it all!

Trip Highlights

  • Four night’s accommodation in the heart of the Chianti Classico producing region. Enjoy elegant accommodation in a 5-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, 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

  • Full day cycle ride. An enjoyable ride through the Maremma countryside. Support vehicle and guide to manage the day

from $6,213 per person

This is a guide price based on 2 people travelling together and sharing a room.


Enquire online now

Trip details

Day 1

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 5 star hotel in the heart of the Chianti Classico producing region. The hotel offers a indoor heated pool, sauna, turkish bath, jacuzzi and the stunning outdoor pool with a panoramic hilltop view overlooking the Chianti scenery.

Day 2

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 a cooking class and wine tasting. Following the cooking class enjoy  lunch at the estate tasting yet more wines and tasting local olive oils. Visit the village of Castenuovo Beradenga, 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.

Day 3

Your local English speaking cycle guide will meet you at your accommodation after breakfast for a full day biking experience – Our 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.

Day 4

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)

Day 5

In the morning, relax with private luxury transfers to the Maremma. Four night’s accommodation in an elegant, historic and unique small hotel situated on Tuscany’s Argentario peninsula. 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 star) offer unique atmospheres, they share mouth-wateringly good traditional Italian dishes with a modern twist, taste bud tingling vintages and stylish surroundings.

Day 6

Discover Giannutri, a small island in the Tuscan Archipelago National Park. Shaped like a half moon 1 , 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, an incredible island unspoiled and breath taking. Visit Giannutri the southernmost island in the Tuscan Archipelago, a simply stunning place to explore and relax with a local lunch on the island.

Day 7

A day 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.

Day 8

Your local English speaking cycle guide will meet you at your accommodation after breakfast for a full day biking experience – Our 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 Tyrrehnian 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.

Day 9

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

Recent Google Reviews

SmoothRed planned a truly fabulous trip from Paris through Brittany to Normandy and back to Paris. Every part of the trip was wonderful and seamlessly executed. It was a trip of a lifetime! Without any hesitation or qualifications, we heartily recommend SmoothRed. They customized an extraordinary family trip.

Dorothy Weinstein

Very well organised trip to Tuscany, getting in 2 wine regions. Lovely hotel with amazing view. The best part was our guide Paula who ensured our wine tasting tours were with smaller wineries which have authenticity and care for the environment. Highly recommend SmoothRed!

Warren De Villiers

To Adam & the SmoothRed Team. Our recent trip to Bordeaux and the Medoc/St Emillion has been a wonderful trip & experience. One I would have no hesitation in saying is top class. I would certainly use SmoothRed & their travel associates in future wine tasting trips. The entire group…

Paul Green

SmoothRed did an outstanding job providing chauffeured driven wine tour through Bourgogne and the Rhone valley (France). The multiple vendors they used were all Courteous, Prompt, and very fluent in English. This 7 day trip went without problems. I would highly recommend SmoothRed.

Dan Lepley

We came to Bordeaux for part of our honeymoon and took the First Growth Bordeaux tour. SmoothRed worked with us to curate a trip based on our desires. The 8 Chateaux we visited, the 3 delicious lunches, and the hotel were wonderful, but what set the trip apart was our…

Tibita Kaneene

“Thanks for taking the time and trouble to call. You really have set the standard by which we compare all other companies!! Thank you so much for organising a fantastic itinerary with such an interesting and varied range of stop-overs. We are already starting to think about next year’s trip to France so would welcome any suggestions.”

Hilary Alder

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