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Classic Italy

21 Days | Journey through the classic and the lesser-known italy on this 21-day itinerary.

CAD $8,243
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The enduring phrase ‘la dolce vita’ – or the good life – truly captures the essence of Italy. Spend 21 days discovering the heart of all things Italian on a culturally rich adventure between Rome and Venice from the well-known Florence and Pisa to the less travelled Umbria. Peer into Pisa and marvel at its Leaning Tower, take to the trails of the Cinque Terre for some stunning coastal views, walk the Portofino Peninsula to be one with its glamourous residents and hike the picturesque Umbria countryside with a wine tasting await. You’ll soon understand why Italy remains in the hearts of all who visit.

Trip overview

Map of Classic Italy including Italy
Rome, Italy
Rome, Italy
Physical rating
Indicates how physically exerting a trip is, and how fit you will need to be to enjoy it. More info on physical ratings
Min 15
Group size
Min 1 - Max 12
Trip code
This trip generates 21.86 kg of CO2-e per person per day.
We offset these emissions on your behalf. But we know that is not enough, so we also have a carbon reduction target.

Why you'll love this trip
  • Spend a free day exploring the beautiful villages, estates and gardens dotted around Lake Como, criss-crossing the lake by ferry, and consider exploring the grounds of Bellagio's grand Villa Melzi.
  • Test yourself on the hilly trails of the Cinque Terre, stopping by the picturesque pastel colour villages of Manarola, Riomaggiore and Vernazza. If you get tired, just jump on the train for the rest of your day!
  • Spend a free day exploring the beautiful villages, estates and gardens dotted around Lake Como, criss-crossing the lake by ferry, and consider exploring the grounds of Bellagio's grand Villa Melzi.
  • Italy’s iconic Rome, Florence and Venice are a haven of renaissance architecture and historic sights. With plenty of time to discover at your own pace, you have the power to decide what you’d like to see.
  • Explore the quintessential medieval town of Gubbio, one of the oldest towns in the region, it’ll be like stepping back in time as you wander the cobblestone streets and marvel at gothic palaces.
  • Unwind in the Italian countryside during a farm stay, where you’ll hike through vineyards and enjoy rolling vistas before enjoying a wine tasting followed by dinner prepared with ingredients fresh from the farm.

Is this trip right for you?
  • The primary means of transportation on this trip is by train. Train travel is a fast way to traverse long distances, allowing you to avoid traffic jams and arrive right into the city centre. Trains are comfortable and all have toilets, however can often be quite busy.
  • Please note that you'll have to carry your own luggage on and off the trains, and up and down stairs at train stations and at hotels, so make sure it doesn’t exceed our weight and size recommendations. You can find this information in the 'Packing' section of the Essential Trip Information. You may want to consider taking a backpack rather than a wheelie bag, however this is up to your personal preference and what you feel more comfortable with.
  • Summer temperatures can be extreme in many of the regions visited (over 40°C), which can be uncomfortable. It’s important to use sun protection, wear layers to combat the heat and drink plenty of water. Many hotel rooms in Europe are not equipped with air-conditioning. Please carefully consider the time of the year you wish to travel and your suitability to that season.
  • Hotel rooms in Europe can seem rather small by American or Australian standards and often don't have double beds, but rather two single beds that can be pushed together.
  • On this trip you must pack as lightly as possible because you will be expected to carry your own bag and although you won't be required to walk long distances with your luggage (max 30 minutes), we strongly recommend keeping the weight between 15kg / 33lb. Most travellers carry their luggage in a backpack, although an overnight bag with a shoulder strap would suffice if you travel lightly. Smaller bags or backpacks with wheels are convenient although we recommend your bag has carry straps to accommodate the cobbled streets, uneven surfaces, stairs and steps you are likely to encounter while carrying your luggage. You'll also need a day pack/bag to carry water and a camera etc for day trips.


Map of Classic Italy including Italy



16 breakfasts, 1 lunch, 1 dinner


Train, Public bus, Metro, Cable car, Boat, Private Vehicle


Hotel (19 nights), Farm Stay (1 night)

  • Lucca - Bicycle Tour
  • Pisa - Half Day Trip to Pisa
  • Cinque Terre - Day Trip, including Cinque Terre Pass
  • Portofino Peninsula - Walk and Boat Ride
  • Asti - Village Winery Visit & Wine Tasting
  • Milan - Duomo Rooftop Visit
  • Milan - Half Day Trip
  • Lake Como - Ferry Pass
  • Venice - Traghetto Ride
  • Venice - Orient Experience Snack Stop
  • Verona - Orientation walk & Juliet's Balcony
  • Gubbio - Cable car to Basilica of Sant'Ubaldo
  • Assisi - Basilica di San Francesco guided tour
  • Umbria countryside - Bevagna’ Sculpture Park hike
  • Umbria countryside - wine tasting & lunch
  • Umbria Farmstay - Farm to table dinner
  • Rome - Leader-led orientation walk
Add on activities
  • Rome - Christian Catacombs - EUR10
  • Rome - Castel Sant'Angelo - EUR14
  • Rome - Galleria Borghese - EUR16
  • Rome - Keats-Shelley Memorial House - EUR6
  • Vatican City - St Peter's Dome Climb & Elevator - EUR10
  • Vatican City - Vatican Museum - EUR22
  • Florence - Foodies Walk Urban Adventure - EUR79
  • Florence - Baptistry, Museo Opera del Duomo, Giotto Bell Tower and Brunelleschi Dome - EUR30
  • Florence - Accademia - EUR17
  • Florence - Uffizi Gallery - EUR24
  • Florence - Bargello Museum - EUR14
  • Pisa - Leaning Tower of Pisa - EUR20
  • Pisa - 5 Monuments Combo Ticket - EUR10
  • Lucca - Cathedral of San Martino & Ilaria del Carretto Tomb - EUR3
  • Lucca - Guinigi Tower Climb - EUR6
  • Lucca - National Gallery Villa Guinigi - EUR5
  • Lucca - Day Trip to Barga (by public bus) - EUR9
  • Lucca - Palazzo Pfanner House & Gardens - EUR6
  • Lucca - Cathedral Museum - EUR4
  • Lucca - Puccini concert - EUR20
  • Asti - Bike Hire - EUR3
  • Asti - Archaeological Museum - EUR5
  • Milan - Castello Sforzesco - Free
  • Milan - La Scala Museum - EUR9
  • Milan - Leonardo da Vinci's 'The Last Supper' - from - EUR29
  • Lake Como - Villa Balbianello - EUR22
  • Lake Como - Villa Carlotta in Tremezzo - EUR12
  • Lake Como - Villa Melzi Gardens in Bellagio - EUR10
  • Lake Como - Vezio Castle in Varenna - EUR5
  • Venice - St Mark's Basilica Treasury - EUR5
  • Ca’ D’Oro - Galería Franchetti - EUR15
  • Venice - Accademia Gallery - EUR16
  • Peggy Guggenheim Collection - EUR17
  • Venice - St Mark's Campanile - EUR12
  • Venice - Doge's Palace & Bridge of Sighs - EUR30
  • Venice - Gondola Ride - EUR80
  • Gubbio - Ducal Palace - EUR5
  • Gubbio - Diocesian Mueum - EUR7
  • Gubbio - Civic Museum - EUR6
  • Gubbio - Museum of Majolica - EUR6
  • Assisi - Eremodelle Carceri and Mount Subasio - Free
  • Assisi - Museo e Foro Romano - EUR4
  • Assisi - Museum of San Rufino Cathedral - EUR4
  • Assisi - Basilica of St Clare - Free
  • Spello - Half Day Trip to Spello - Free
  • Spello - Enoteca Wine Tasting & Lunch - EUR30
  • Rome - Pantheon One Hour Guided Tour Urban Adventure - EUR35

Dates and availability

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Important notes

1. A single supplement is bookable on this trip, excluding day 6&7. Availability is limited due to small properties we use. Please speak to your agent for further information.

Essential Trip Information

Want an in-depth insight into this trip? Essential Trip Information provides a detailed itinerary, visa info, how to get to your hotel, what's included - pretty much everything you need to know about this adventure and more.

Read Essential Trip Information


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Classic Italy
CAD $8,243