Italy Holidays: An Overview

More UNESCO World Heritage sites than any other country on the planet, food that is tantalisingly close to perfection and landscape that has something for pretty much everyone. Sold.

Dave, Claudia and Flora are here to help give you the inside track.

Why we think you’ll love it

  • Pizza, pasta, coffee and ice cream. Often imitated, never bettered and rarely sold at such thoroughly reasonable prices. The south of Italy, particularly Puglia and the Campania region (including the Amalfi coast) is perhaps best for the food
  • Rome, the "Eternal City". History at every turn, with more jaw-droppingly grandiose architecture than anywhere else
  • The Dolomites - Europe's undiscovered skiing gem. If mind-melting scenery and low-key Michelin-starred eateries on a budget are your thing, you'll love this superb skiing area
  • Learn more and find out when to go in our in-depth guide
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Original Highlight

Italian coast - luxury holiday destination

Marvelling at incredibly well-preserved Baroque architecture, swish boutiques and drinking some of Europe’s best wines in the sun…even in November. South-eastern Sicily has it all.

Dave, Original Traveller

A note on price

A no-expense-spared, tailor made Italian holiday exploring the country's artistic and cultural centres over a week – think Venice, Verona, Florence, Siena and Rome - staying in some of the world’s finest hotels can cost around £8,000 per person. However, a weekend city break can be done for £400 per person including flights. Learn more about our pricing

Top picks for Italy

The Venice Canal

Venice

Italy

Simply one of the world's most beautiful and romantic cities and a must-visit destination.

Where to go

Venice
Swimming Pool at Masseria Torre Maizza, luxury hotel in italy

Masseria Torre Maizza

Puglia

The more elegant and sophisticated sister property of Masseria Torre Coccaro, is about five minutes’ walk across an olive grove and located on a nine hole golf course.

Where to stay

Masseria Torre Maizza
Via Ferrata

Via Ferrata

The Dolomites

Not recommended for anyone with vertigo, the Via Ferrata in the Dolomites, consisting of iron wrung ladders, footpaths and rope bridges, are an exhilarating series of routes that allow non-mountaineers to experience the higher peaks and most dramatic scenery of this most beautiful of mountain ranges.

What to do

Via Ferrata
Kite Surfing on the Italian Lakes

Kite Surfing on the Italian Lakes

Italian Lakes

Kite-surfing? In the Italian Lakes? Surely not? Actually, it’s one of the best spots in Europe to try this, the fastest growing watersport in the world.

What to do

Kite Surfing on the Italian Lakes
Capofaro hotel. luxury hotel in Italy

Capofaro

Sicily & the Aeolian Islands

Set amidst a working vineyard producing Malvasia wine, Capofaro is arguably the best boutique hotel on Salina Island.

Where to stay

Capofaro
View of Florence, Italy

Tuscany & Umbria

Italy

Historic towns and cities, peaceful county retreats and outstanding regional cuisine.

Where to go

Tuscany & Umbria
Umbreallas on the Costa Smeralda Beach

Sardinia

Italy

Sardinia's north-eastern coast is impossibly glamorous and home to seriously luxurious hotels, whilst the rest of the Island is relatively untouched.

Where to go

Sardinia
Traditional Trulli house, Puglia, Italy

Puglia

Italy

Puglia, on the heel of Italy's boot, is a destination apart, both culturally and geographically.

Where to go

Puglia
Amalfi Coast View, Italy

The Amalfi Coast & Cilento

Italy

Enjoy fine food, cliffs, coves, and hilltop towns such as Positano or Amalfi or in unspoilt Puglia.

Where to go

The Amalfi Coast & Cilento
Canne Bianche

Canne Bianche

Puglia

Canne Bianche Hotel & Spa is a whitewashed, beachfront chic boutique hotel in Fasano, nestled between Brindisi and Bari on the Puglian coast.

Where to stay

Canne Bianche
The Maddalena Islands

The Maddalena Islands

Sardinia

Rent an inflatable rib and head over to the beautiful Maddalena Islands Marine Park where the uninhabited islands have pink sand beaches and the water is as clear as any in the world.

What to do

The Maddalena Islands
Verdura Golf & Spa Resort, luxury hotel in Italy

Verdura Resort

Sicily & the Aeolian Islands

Located on the South coast of Sicily, this luxury Rocco Forte property caters for all, with extensive grounds, a sea front location, and fantastic facilities including a world class championship golf course.

Where to stay

Verdura Resort
View of the Italian Lakes

Italian Lakes

Italy

Stunning scenery, elegant hotels, boat trips and excellent Italian cuisine.

Where to go

Italian Lakes
Marcus Aurelius Column, Rome

Rome

Italy

The world’s greatest open-air museum is also one of the most alluring and vibrant of modern cities.

Where to go

Rome
Masseria San Domenico hotel, luxury hotel in Italy

Masseria San Domenico

Puglia

Located on the Adriatic coast of Puglia, the Masseria San Domenico is one of the finest hotels in south east Italy.

Where to stay

Masseria San Domenico
Borgo Egnazia, luxury hotel in Italy

Borgo Egnazia

Puglia

From the owners of the Masserias San Domenico and Cimono respectively comes Borgo Egnazia, the single smartest luxury hotel on the Puglian coast, with private villas for families and a boutique hotel for couples.

Where to stay

Borgo Egnazia
Aerial view of Hotel Raya, luxury hotel in Italy

Hotel Raya

Sicily & the Aeolian Islands

Hotel Raya is one of the most beautiful hotels in the Mediterranean, an immaculate, whitewashed property of elegant simplicity on the tiny Aeolian island of Panarea.

Where to stay

Hotel Raya
Ski The Secret Dolomites

Ski The Secret Dolomites

The Dolomites

To many people the Dolomites are something of a secret anyway, but word is getting out about this staggeringly beautiful region, and its skiing (and eating) potential.

What to do

Ski The Secret Dolomites
Blue Grotto

Blue Grotto

Capri & Ischia

A natural phenomenon and major attraction on the island of Capri, the Blue Grotto definitely lives up to its billing.

What to do

Blue Grotto
Grand Hotel Timeo, luxury hotel in Italy

Grand Hotel Timeo

Sicily & the Aeolian Islands

If there was a 'hotel with the best location in the world' award, the Grand Hotel Timeo would be a serious contender... Set high in the rocky hills on the east coast of Sicily, Grand Hotel Timeo has long been known as one of Italy’s most glamorous retreats, and has now had a serious - and arguably much needed - overhaul by the Belmond group.

Where to stay

Grand Hotel Timeo
Masseria Torre Coccaro hotel, luxury hotel in Puglia, Italy

Masseria Torre Coccaro

Puglia

Masseria Torre Coccaro is a 16th-century watchtower just outside the ancient fishing village of Savelletri di Fasano near Brindisi.

Where to stay

Masseria Torre Coccaro
One of Florence's Many Bridges

Florence

Italy

With its magnificent Duomo, Uffizi gallery and the Ponte Vecchio, Florence is quite simply one of the world’s finest open air museums.

Where to go

Florence
View of the sea from Hotel Raya, Sicily

Sicily & the Aeolian Islands

Italy

An extraordinary diversity of sights in one small area, from the classical ruins and beaches of Sicily to the volcanic outcrops of the Aeolian Islands.

Where to go

Sicily & the Aeolian Islands
Boat Trips

Boat Trips

Capri & Ischia

While nothing beats a traditional passagiatta or wandering around the streets at sunset marvelling at the sites of Capri or Anacapri, a boat trip gives a sense of the dramatic nature of the island and allows visits to parts of the island not accessible by land.

What to do

Boat Trips

Where can I start? It was our best trip yet. Everything went smoothly. It was a wonderful package at a very good price, well organised by Original Travel and we felt totally spoilt.

Paul & Jenny

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