Mike and Stephie
May 03, 2021

Ever thought off staying in a hilltop Tuscan castle and exploring the villages and sampling the amazing local cuisine and wines. Sounds like you – then you’re invited to join our small group tour to visit amazing Tuscany and other highlights in Italy escorted by our own Tuscan driver, AND when we say small, we mean it! On this special tour for 8 lucky people we get right off the beaten track and enjoy amazing Italian food and wine.

Just one of the highlights is a 4 night stay in a Tuscan castle villa with day trips to surrounding villages and visits to San Gimignano, Siena and Florence.

Then experience the famous Cinque Terre “five lands”. The five coastal villages are a UNESCO World Heritage site. The most popular trail, Sentiero Azzurro, runs nearest the water. It's about 6 kilometers long and takes about five hours. You will also visit the “5 Terre” by ferry boat or by train – we give you a full day rail pass so you can explore at your own pace. The first village is Riomaggiore and after a short visit, we continue to Manarola, where the houses are pastel, the water is turquoise, and the rock on which the town sits is black. Don't miss the “Lovers’ Path” that links Manarola and Riomaggiore. Next stop is in Vernazza, with the only natural port. Famous for its elaborate architecture. See the Castle of the Doria, the watchtower, and the Romanesque sanctuary of Our Lady of Reggio.

Last stop is in Monterosso, the largest village and surrounded by hills covered in vineyards and olive groves. We then continue to Pisa and onwards to the beautiful Italian Lakes.

Our groups are a mix of solo travellers and couples. Just because you choose to travel by yourself - you WILL definitely NOT be travelling alone as we have social opportunities, dine and explore together.


May & September. $8,295 pp t/share. Single supp plus $1,995.

Some highlights ...

  • 4 night stay in a classic Italian castle
  • Tuscan wine tasting
  • Wonderful Tuscan dinners
  • Montipulciano
  • Montalcino – the home of brunello
  • Greve
  • Florence
  • San Gimignano
  • Siena
  • Cinque Terre
  • Italian Lakes
  • Stresa
  • Medieval villages
  • Maximum of 8 in our groups

Whats Included

  • Minibuses
  • 4 star boutique hotel accommodation
  • Breakfasts
  • Special welcome and farewell dinners
  • Our driver/guide
  • Transfers
  • Sightseeing
  • Entrance fees


Arrive Rome and transfer directly north. On arrival at the accommodation we enjoy a welcome drink. Tonight we have a welcome dinner included and the chance to meet the rest of our small group. Accommodation 4 nights at our Castello in the heart of Chianti and wine-production for 600 years. The estate retains its original form of a tranquil country estate, surrounded by woods, vineyards and olive groves. The owners continue to devote themselves to winemaking, with an uncompromising approach to excellence, an eye towards innovation and an abiding respect for the land. The past and present unite in the amazing Tuscan landscape and the wine estate provides the ideal setting for visitors to enjoy Tuscany the way it was meant to be experienced – surrounded by soft, green rolling hills and lush vineyards, sipping elegant wines and indulging in fresh regional cuisine. D

Accommodation: Castello di Fonterutoli, Castello Meleto or similar. Castellina In Chianti

Following our breakfast we depart for the wonderful medieval town of Montipulciano. Light lunch today with tasting of Vino Nobile di Montepulciano. This afternoon visit two hilltop towns including Montalcino, famous not only historically, but also for their local food and excellent wine including the Brunello. We have wine tasting at Alessandros enoteca. Tonight’s dinner is at a local Chianti area restaurant. B,D

After a leisurely breakfast and time to relax enjoy a tasting of locally produced wines. This Afternoon for the visit to two of the hilltop towns (Vertine, Volpaia, Gaiole in Chianti or Radda in Chianti. Return to Chianti. Dinner included tonight. B,D

After breakfast we depart for Greve in Chianti to explore the Medieval Square, visit the Wine Museum and to taste the “La Bottega del Chianti Classico”. Lunch today is in a typical regional restaurant in Greve in Chianti. Continue to Florence with free time to explore or shop in the old town area. Return to Chianti area for included dinner. B,D

After breakfast we depart for San Gimignano, famous for its medieval towers and featured in the movie “Tea with Mussolini. Optional tonight subject to weather, watch the sunset from the old castle ruins. Accommodation for the next 2 nights is in the beautiful hilltop Tuscan village of San Gimignano. B

Accommodation: Leon Bianco or similar San Gimignano

Free morning to explore the medieval city of San Gimignano at leisure. This afternoon visit beautiful hilltop city of Siena, the home of the Palio festival and magnificent Duomo. Hear the story of the Sienese Contrade and their famous horse race. Tonight we dine in the central swquare area of San Gimignano – watch out for the street performers and cultural groups. B

After breakfast depart San Gimignano for the Cinque Terra area, passing the magnificent ancient marble mines at Carrara. Our accommodation for the next 2 nights is in the port city of La Spezia – the ideal place to start our exploration of the Cinque Terra villages. B

Accommodation: NH La Spezia or similar La Spezia

World Heritage Walkway and day rail passes are provided for today so that we can spend the whole day exploring the Cinque Terra – one of the most famous and picturesque walks in the world. Dinner tonight at a coastal restaurant, before returning to our hotel. B,D

Depart after breakfast for The Italian Lakes. Accommodation 3 nights in Stresa on the shores of beautiful Lake Maggiori, with views across the lake to the Borromean islands and Switzerland. After check in there’s free time to relax and enjoy this beautiful location. Time for a drink tonight together before dinner to chat over our shared experiences. There are a number of good and reasonable restaurants in the town square or near the lake to choose from tonight. B

Accommodation: Hotel Astoria or similar. Stresa

Today we visit two of the beautiful islands in Lake Maggiori - Isola Bella and Isola Madre.Free afternoon until our included farewell dinner tonight. B,D

We depart Stresa this morning for Milan International Airport, Malpensa arriving mid morning for onward flights. B Included: Meals as per the final itinerary. B = Continental breakfast, L = Lunch, D = Dinner. Group arrival and departure transfers.

From Malpensa Airport we drive to Turin viaordevolo to look at Passion Play theatre. Accommodation 2 nights Turin. B

Accommodation: Best Western Piemontese or similar.Turin

10am - viewing of the Shroud of Turin – four spaces booked (3 pax plus Alessandro), followed by local sightseeing highlights, long lunch and time to relax, stroll or retail therapy. B

Depart Turin for Milan Malpensa Airport. Arrival late afternoon. Alternative drop off in Milan city at Central Rail Station. B

Optional Turin extension is subject to minimum numbers.

Included: Meals as per the final itinerary. B = Continental breakfast, L = Lunch, D = Dinner.

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