Tuscany – Italian Riviera – Lake Como

Day 1  |  Rome

Meet at the Spanish Steps for a Twilight City Stroll around the centro historico and be enthralled at what you will discover.  Accommodation is in a 16th century building high above the Spanish Steps that began as a convent.


Day 2   |  Rome

Visit the Sistine Chapel, Vatican Museums and St. Peter’s Basilica well before the crowds arrive with one of the best guides in Rome or roam the Colosseum with a passionate guide that will bring history alive.  Or wander the hip Monti neighbourhood, once the city’s seedy underbelly, but now buzzing with cool bars and places to eat as well as tiny shops with incredibly talented artisans at work.


Day 3   |  Montepulciano

Travel to ancient Orvieto and Civita di Bagnoregio, a tiny town stuck in the middle ages and perched on a pinnacle high above a vast canyon, only accessible by a suspended footbridge.  Arrival late afternoon in the walled hilltop town of Montepulciano, famous for sweeping views over Tuscany, great local produce and Vino Nobile de Montepulciano (red wine).


Day 4  |  Montepulciano

Walk a winding white road bordered by cypress trees across rolling green hills to the walled medieval village of Montefollonico, or learn how to make ‘pici’ pasta in a local cooking class.


Day 5  |  Montepulciano

Cruise the country roads on a Vespa or wander nearby Pienza, a mix of old stonework, potted plants, sweeping views . . . and famous for Pecorino cheese.


Day 6  |  Siena

A visit to rustic, romantic Cortona for a traditional Italian lunch and time to relive ‘Under the Tuscan Sun’ before arriving at our 18th century Tuscan villa set on 18 acres just outside the walls of Siena.


Day 7  |  Siena

Following breakfast on the terrace, we meet with Roberta, a talented local guide, who will walk us through a maze of alleys and tell us stories not found in guide books.  Afternoon free to wander.

Day 8  |  Siena

So much to enjoy and experience in Tuscany’s quintessential “hilltop” town or visit nearby San Gimignano or Florence for a memorable day of discovery.


Day 9  |  Monterosso al Mare

Lunch in delightful Lucca with time to explore the traffic free streets within the surrounding four kilometre wall, by bike or foot. Arrival late afternoon via a spectacular drive from the mountains down to the seaside village of Monterosso al Mare in the Cinque Terre.


Day 10  |  Monterosso al Mare

Ferry to Riomaggiore for the chance to see all five villages from the sea before walking the coastal track (Sentiero Azzurro) of the Cinque Terre, taking time to linger in each village, savour the local produce and chat to locals.


Day 11  |  Monterosso al Mare

A private transfer only an hour away to the seaside resort town of Santa Margherita and famous, ritzy Portofino.  Spend a lazy day in Portofino or take a stunning walk along the breathtaking coastline to tiny San Fruttuoso for lunch.  Boat it back to Santa Margherita followed by a private transfer to Monterosso al Mare.


Day 12  |  Bellagio

Arrival in picture perfect Bellagio on Lake Como for lunch on the water and a leisurely, scenic walk along the narrow, cobblestoned streets and lakeside esplanade.


Day 13  |  Bellagio

An optional two hour guided kayak tour past hidden nature spots and beautiful lakeside gardens, followed by an afternoon ferry to Cadenabbia for a magical walk halfway up a mountain, passing only donkeys and goats, for the best views of Lake Como.


Day 14  |  Bellagio
Be tempted by the gorgeous shops in Bellagio, boat hop between the lakeside villages or take a fast boat to Como.


Day 15  |  Malpensa Airport and Milan
Transfer to Malpensa Airport and Milan

  • Tour leader on hand for duration of tour from the start of the tour in Rome to the last day
  • Accommodation x 14 nights in a twin share/double room in boutique hotels or villas centrally located
  • Breakfast every day
  • Transfers in private, luxury, air conditioned mini coach:
    – Rome to Montepulciano via Orvieto and Civita di Bagnoregio
    – Montepulciano to Siena via Cortona
    – Siena to Monterosso al Mare via Lucca
    – Monterosso al Mare to Santa Margherita return
    – Monterosso al Mare to Bellagio, Lake Como
    – Bellagio to Malpensa Airport and Milan

  • Guided Twilight City Stroll around Rome’s historic centre with ‘Walks of Italy’ guide
  • Guided Historic Walking Tour of Siena with Roberta Piccinetti, local guide Siena
  • All walks on ancient trails guided by Tour Leader
  • Cinque Terre day passes and train tickets
  • Gratuities for drivers and guides
  • Hotel city taxes

Tour dates

  • 19th May – 2nd June 2019
  • 25th June – 9th July 2019
  • 16th – 30th September 2019




  • Tour Cost:  $5400 per person twin share/double accommodation
  • Single room supplement:  $1050
Tuscany tour map
  1. A booking is confirmed by payment of a deposit of $500 per person.


  1. Payments can be made by transferring funds into the bank account of Ciao Italy and completing the Booking Form which will be emailed on request. Transfer fees are the client’s responsibility.


  1. The final payment of the balance is due eight weeks prior to departure.


  1. Cancellations – If you decide to cancel your booking, the following charges will apply:
  • 60 days or more before the start of the tour: $500 (your deposit)
  • 59-30 days before the start of the tour: 50% of tour costs
  • 29 days before the start of the tour: 100% of tour costs


Cancellation of a tour must be received in writing – please click here to email Deb.

  1. It is compulsory for clients to have full travel and medical insurance and provide a copy of the policy prior to departure.


  1. The tour price includes all items listed in the package. It does not include flights, accommodation additional costs (e.g. telephone, minibar etc) and any other items not specifically mentioned in the package details.


  1. Occasionally, circumstances beyond our control may necessitate changes to itineraries. Ciao Italy reserves the right to make changes if required, but will endeavour to operate the tour as close to the original itinerary as possible.

Contact Deb today and start planning your Italian adventure!

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