Three great Italian cities, one coherent journey – and no driving. This 14-night holiday links Venice, Florence and Rome by high-speed train, with well-located hotels, private walking tours and time to wander at your own pace. It is for travellers who want to see Italy’s most iconic places properly – not as a coach dash, but as a sequence of lived-in, walkable city stays.

This itinerary is designed for travellers who want to fit “the Italy they’ve always imagined” into one well-organised trip. It suits first- or second-time visitors who prefer high-speed trains and central hotels to group tours, and who like the idea of seeing Venice, Florence and Rome with enough nights in each place to breathe, sit in cafés and add the odd day trip without feeling frantic.

On your first full morning, a local guide meets you at the hotel for a 3-hour orientation walk. You will see St Mark’s Square and the Doge’s Palace area, cross the Rialto and duck into quieter campi and canals that most visitors miss. After that, the city is yours to explore using our self-guided notes for Dorsoduro, Cannaregio and the Grand Canal at dusk.

We help you focus on a few highlights rather than trying to tick off everything.

With five nights, Venice becomes an effortless hub for day trips:

Padova & Vicenza in one day – around 20 minutes from Venice to Padova, another 20 minutes on to Vicenza and about 50 minutes back. Morning among Giotto’s frescoes and university cloisters; afternoon with Palladian façades and aperitivi.

Verona – Roman Arena, riverside walks and handsome squares, perfect for a full day.

Treviso – smaller, quieter and laced with canals and arcades.

We will match the destination (or combination) to your interests and how energetic you want your days to be.

Early in your stay a 3-hour private walking tour gives you bearings and stories: the Duomo and Baptistery, Piazza della Signoria, the riverfront and perhaps a first foray into the artisan quarter of the Oltrarno. After that, you can follow our notes for slow laps of the city and evenings in favourite wine bars.

Prefer public transport? Florence is perfectly placed for independent day trips:

Siena – a classic Tuscan hill town with a spectacular shell-shaped piazza, striped cathedral and views over rolling countryside – all reachable by bus, so there’s no need for a car.

Lucca – walk or cycle the tree-lined Renaissance walls.

Pisa – the Leaning Tower and Campo dei Miracoli, easily combined with quieter corners.

We provide simple route notes and train/bus suggestions so you can travel with confidence.

On one of your first mornings, a 3-hour private walking tour will focus either on Ancient Rome (Colosseum, Roman Forum, Palatine area) or on the historic centre (Pantheon, Piazza Navona, Trevi Fountain, Spanish Steps) – or a blend of both. Another day can be built around our self-guided walks through Monti, Trastevere or the Aventine, with viewpoints and café stops along the way.

For those who want to push a little further:

Naples – about an hour by high-speed train for seafront walks, street food and a very different energy.

Sorrento – a longer but rewarding day for clifftop views over the Bay of Naples.

We will only suggest these if they match your interests and energy; the holiday works perfectly well without them.

You spend five nights in Venice, four in Florence and five in Rome, moving between them on 1st-class high-speed trains that link city centre to city centre in a couple of hours. There are no airport transfers, no car hire desks and no need to navigate ZTL zones or Italian motorways.

In each city, a 3-hour private walking tour at the beginning of your stay gives you context and confidence; after that, you are free to follow your curiosity with our self-guided notes and suggestions. The extra time in each place means you can say yes to a day trip or private excursion without the whole holiday feeling like a race.

On paper it might sound busy, but in practice the rhythm is surprisingly leisurely: morning sightseeing, long lunches, an hour’s rest back at the hotel, then an evening stroll and dinner somewhere we would happily choose for ourselves.

Once we have understood your interests and how full you like your days, we can add a second layer of experiences on top of the core city stays:

From Venice – a gentle kayak along the quieter canals, an evening cicchetti walk, lagoon island visits or a curated Padova–Vicenza loop by rail.

From Florence – timed entry for Uffizi or Accademia, wine-bar tastings, or a full-day private driver through Chianti and Siena for vines, hill towns and a leisurely lunch.

From Rome – guided visits to Ancient Rome or the Vatican Museums, rooftop aperitivi, a full-day private driver to Tivoli (Villa d’Este & Hadrian’s Villa), or a powerful WWII day out at the Monte Cassino battlefields with expert guide Anna Priora.

When we speak, we will pick out the few that make most sense for you and leave the rest of the time free for your own discoveries.