Tuscany – Italian Riviera – Lake Como

Here are all the places you dream about.

Italy is a feast for the eyes and a seduction of the soul from charming hilltop medieval villages to the crystal blue seas of the Cinque Terre to the surreal beauty of Lake Como.

Adored for its perfect countryside and beautiful villages and cities, Tuscany conjures up the image of fertile rolling hills, winding white roads bordered by cypress trees and honey coloured stone farmhouses with terracotta roofs.

Everything you imagine, it’s true.

Itinerary

Rome x 2 days

Rome is fascinating, impressive, chaotic and irresistible. There is never enough time to discover the secrets of the ‘Eternal City’, full of layers and hidden secrets. To wander and explore beyond the surface, delve deeper and discover the ancient neighbourhoods of Trastevere, Monti and the Jewish Ghetto is to feel the heart and soul of a city that is 2,779 years old. Choose your unforgettable day, whether it be losing yourself in the Colosseum and Roman Forum with an expert local guide; visiting the Sistine Chapel before it opens to the public, or on the back of a vespa on a guided tour to places within the historic centre you would not normally see.

Montepulciano x 3 days

Travel via private transfer to ancient Orvieto and Civita di Bagnoregio, a tiny town stuck in the middle ages perched on a pinnacle high above a vast canyon, only accessible by a footbridge. Arrival late afternoon in the walled hilltop medieval town of Montepulciano, famous for sweeping views over Tuscany and Vino Nobile di Montepulciano. Over the next two days we will visit gorgeous neighbouring hilltop towns including Montefollonico for lunch in a secret garden and Pienza to sample the pecorino cheese it is renowned for. For the more adventurous, hire an e-bike to ride the rolling green hills or walk the winding white road bordered by cypress trees and vineyards from one tiny village to the next.

Siena x 3 days

Less than an hour’s drive from Montepulciano is rustic, romantic Cortona sitting majestically atop a 1,700 foot hill surrounded by Etruscan walls around 3,000 years old. A few hours here will have you dreaming about finding your own Tuscan villa before we head to our 16th century villa on 18 acres, just outside the walls of Siena. The next day after breakfast on the terrace, we meet Roberta who will show us why many consider Siena to be the most perfectly preserved medieval town in Europe with an easy to enjoy soul. Day three is an indulgent Tuscan day with a private transfer to three quintessential Tuscan villages quite close to Siena.

Monterosso al Mare x 3 days

There will always be irresistible places in Italy that will be on every traveller’s bucket list, and the Cinque Terre is no exception. Unless you stay three nights, it is impossible to appreciate the landscape, the different personalities of each of the five villages and the delicious food and wine. A day of full immersion begins with a ferry to Riomaggiore to see the villages from the sea before walking the coastal track. On our last day we have a private transfer to the nearby seaside resort town of Santa Margherita and glamorous Portofino. A short ferry ride takes us to a secluded cove for lunch on a pebbly beach in tiny San Fruttuoso, accessible only by boat or foot.

Bellagio x 3 days

A private transfer after breakfast will have us in picture perfect Bellagio for lunch. It is impossible not to fall under the spell of this dreamy hamlet sitting on a promontory that divides the two branches of Lake Como. Ferries crisscross the lake all day and evening from Bellagio, allowing you to visit several of the villages, all of which offer unique experiences. There are stunning walks, beautiful lakeside gardens to linger in, a morning kayak when the lake is glassy, shops to tempt as you are in the home of silk and a wonderful choice of restaurants for a long, lazy lunch.

Milan

Private transfer after breakfast to Milano Centrale, the main train station in Milan. For those leaving there are frequent trains to Malpensa Airport and all other destinations in Italy. For those continuing on the next Ciao Italy tour, we take the train to Rome.

Tour Inclusions

Your Italian adventure includes:

Deb is your Tour Leader from the start of the journey to the end

Accommodation x 14 nights in a twin share/double room in boutique hotels or villas centrally located

Hotel city taxes

Breakfast every day

Transfers in private, luxury airconditioned minibus:

  • Rome to Montepulciano via Civita di Bagnoregio and Orvieto
  • Montepulciano to Siena via Cortona
  • Siena to San Gimignano, Volterra and Monteriggioni – full day
  • Siena to Monterosso al Mare via Lucca
  • Monterosso al Mare to Santa Margherita return
  • Monterosso al Mare to Bellagio
  • Bellagio to Milan

Entrance fee for Civita di Bagnoregio

Guided historic walk of Siena with local guide, Roberta Piccinetti

All walks on ancient trails guided by Tour Leader

Cinque Terre day passes and train tickets

Ferry ticket Monterosso al Mare to Riomaggiore

Ferry ticket Portofino to San Fruttuoso return

Ferry ticket Portofino to Santa Margherita

Gratuities for drivers and guides

Dates & Rates

17th April to 1st May, 2026

16th to 30th September 2026

Package: 15 days / 14 nights

$7,200 per person for twin/double accommodation. Single supplement $1,650.

Email deb@ciaoitaly.com.au for full itinerary.

“Deb took us to many amazing little out of the way places as well as many of the ‘must sees’. She knew all the great little cafes, bars, restaurants and sights that were off the normal tourist grid. This made the experience an authentic and truly memorable one. Unlike many tours there was plenty of flexibility in the itinerary to do your own thing and explore on your own terms. I thoroughly recommend anyone who wants the real Italian experience to travel with Deb.”

Roger Marek