Tailor-made Italy holidays, at your pace

ExpertoItaly · Your Italian holiday specialist

Tailor-made Italy holidays, at your pace

Italy’s art cities, lakes, countryside and coast — brought together in a holiday that feels right for you.

ExpertoItaly plans the route, chooses the places to stay and arranges the journeys between them, with time for the things you enjoy.

Sunlit stone buildings across the hillside in Ragusa, Sicily

Thoughtful routesThe right stops, in a sensible order.

Places with characterAccommodation chosen for your holiday.

Personal planningOne conversation, a holiday built around you.

Where would you like to go?

Find your corner of Italy

Start with somewhere you have always wanted to see, or explore a region that is new to you. We can help you decide what to combine and where to linger.

Venice’s Grand Canal

Venice & Italy’s art cities

Art, neighbourhoods and city stays with room to explore.

Explore the region →

How do you like to travel?

A holiday that fits the way you travel

You might want several contrasting stops, a journey without a car, or one comfortable base. These are starting points: we shape the details with you.

Ideas to build on

A few ways your holiday could unfold

These sample itineraries show how different places can work together. We can adapt the length, accommodation and pace to suit your dates and interests.

Naples & Ischia

City life, then island time

Naples & Ischia

Explore Naples before slowing down among Ischia’s gardens, coastal villages and thermal pools.

View sample itinerary →

Venice, Florence & Rome

Three cities, connected by rail

Venice, Florence & Rome

A starting point for art, architecture and local life, with the balance of guided visits and free time tailored to you.

View sample itinerary →

Palermo, the first stop on a Western Sicily holiday

Palermo, Menfi & San Vito Lo Capo

Western Sicily

Combine Palermo’s markets and historic streets with wine country and a stay by the sea.

View sample itinerary →

More multi-centre holiday ideas →

Worth staying a little longer

The place to stay is part of the holiday

A hotel can change how you experience a destination. Here are three pairings we like — an island retreat, a quieter lake and a country estate close to Urbino.

San Montano Resort & Spa — Lacco Ameno · Ischia

Lacco Ameno · Ischia

San Montano Resort & Spa

Mediterranean gardens, thermal pools, sea-view terraces and spa time make the resort a substantial part of the holiday.

Discover the hotel →

Casa Fantini — Pella · Lake Orta

Pella · Lake Orta

Casa Fantini

An eleven-room Piero Lissoni hotel with a garden pool and lake and island views.

Discover the hotel →

Aerial view of Tenuta Santi Giacomo e Filippo with vineyards, farmhouses, and swimming pool in the Marche countryside near Urbino.

Near Urbino · Le Marche

Tenuta Santi Giacomo e Filippo

A rural estate for cultural outings, local food, wine and spa time, with grounds worth enjoying between excursions.

Discover the hotel →

Explore our hotels and accommodation collections →

Planning with ExpertoItaly

Good holidays begin with a conversation

Tell us what you enjoy, where you have been and what you would like this holiday to feel like. We will help turn those ideas into a practical, personal itinerary.

That means looking beyond the list of sights: the location of your hotel, the time spent travelling, and the days you leave open matter too.

About ExpertoItaly →

  1. Share your ideas

    Start with your dates, interests, travelling companions and an idea of budget.

  2. Shape the holiday together

    We suggest a route and accommodation, then refine the balance with you.

  3. Let the details come together

    We arrange your accommodation and agreed travel within Italy, so you know how each stage fits.

Your next Italian holiday

Where shall we begin?

A favourite region, a special occasion or a few places you would love to connect — tell ExpertoItaly what you have in mind.

Start planning your holiday