Hotiday in Italy
Italy Vacation Ideas 202710–11 Oct 2026 · 2 Guests
10 Oct - 11 Oct
2 Guests
Find your perfect Italy vacation for 2027
Italy is one of the most visited countries in the world – and for good reason. Ancient ruins, Renaissance art, volcanic islands, medieval hilltowns, crystal-clear sea and a food culture that changes completely from one region to the next. The challenge isn't whether to go. It's knowing where to start.
This guide covers the best Italy vacation ideas for 2027: the destinations that deliver, the hidden alternatives to the obvious stops, and where to stay with Hotiday – handpicked properties in the right place, at the best direct price.
Whether you're planning your first trip to Italy or your tenth, there's always somewhere new to discover.
Most popular destinations for 2027
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Best Italy vacation ideas by type
Beach vacation. Italy's best coastlines are in the south and on the islands. Sardinia tops the list – the water around Baja Sardinia and the Costa Smeralda is Caribbean-clear, and Hotiday Room Collection – Baja Sardinia is one of our most-requested summer properties. In Puglia, Hotiday Gallipoli Lungomare and Hotiday Otranto Baia Resort sit steps from some of the finest sand beaches on the Italian mainland. In Tuscany, Hotiday Marina di Bibbona combines pinewood, quiet sea and easy access to the hilltowns of the interior.
City break. Naples is the most electric city in Italy – a UNESCO World Heritage Centre where street food, baroque architecture and ancient ruins exist on the same block. Hotiday Spaccanapoli Borbone and Hotiday Napoli Lungomare cover the two best areas of the city. In Sicily, Hotiday Palermo Massimo puts you next to the island's best street market and opera house. For a smaller city with enormous character, Hotiday Ortigia Opera in Syracuse sits on one of the most beautiful baroque islands in the Mediterranean.
Amalfi Coast and Sorrento. The most iconic stretch of Italian coastline works best with the right base. Hotiday Room Collection – Sorrento gives you easy access to Pompeii, Capri and the Amalfi drive. For the full cliffside experience, Hotiday Positano Sea View and Hotiday Positano Suites and View are two of the most sought-after properties on the coast.
Lakes and mountains. The Italian Lakes are a completely different Italy: Alpine scenery, Belle Époque villas and boat trips between lakeside towns. Hotiday Malcesine Garda sits in one of the most photogenic villages on Lake Garda. Hotiday Room Collection – Stresa on Lake Maggiore is the gateway to the Borromean Islands – some of the most extraordinary gardens in Europe.
Hotiday in Italy
How to plan your 2027 Italy vacation
The biggest mistake most first-time visitors make is building an itinerary around a list of cities rather than around a feeling. Italy is not a checklist. It's a country where the best moments tend to happen between the sights – in a trattoria with no English menu, on a ferry crossing a lake at dusk, in a piazza at 10pm when half the town is still outside. The more you leave room for that, the better the trip.
Start by picking a region, not a highlights reel. Italy's geography means that genuine variety – coast, hills, cities, food culture – is available within almost any single region. Tuscany alone offers medieval hilltowns, Renaissance art, beach resorts and some of the world's best wine, all within a two-hour drive. Puglia covers baroque architecture, prehistoric trulli, white sandy beaches and a food tradition unlike anything else in Italy. Sicily is practically a country in its own right. You don't need to cross the whole peninsula to have a complete trip.
Think seriously about timing. May and June are the best all-around months for Italy: the light is extraordinary, temperatures are warm without being overwhelming, and the most popular sites are far easier to navigate than in high summer. September is the other sweet spot – the sea is still warm, the crowds thin out after the first week, and the food calendar peaks with grape harvests, truffle season and sagre in almost every region. July and August work best in the north – the Lakes, the Dolomites, the cooler Tuscan coast – and less well in the cities, which become genuinely exhausting in the heat.
Plan your transport before you plan your hotels. Italy's train network is excellent between major cities – Rome to Naples takes just over an hour on the high-speed line, Florence to Venice is under two hours. But the south and the islands require a different approach: a car is almost essential in Puglia, Calabria and rural Sicily, and on Sardinia it's the only way to reach the best beaches. Knowing how you're moving determines where it makes sense to stay.
Book direct, and book early. For summer travel to the Amalfi Coast, Sardinia and Taormina, the best properties fill up three to six months in advance. Every Hotiday property is available at the best price when you book through our site. Members receive an additional 5% off instantly at checkout.