Italy rewards choosing one region well: lemon terraces at Amalfi, Tuscan hill towns, lake villas and the lagoon light of Venice.
The mistake most people make with Italy is trying to see all of it. Rome, Florence, Venice and the Amalfi Coast in ten days means five hotel changes and a lot of time on platforms. Two regions, well chosen, make a far better holiday than four rushed ones.
We plan around the kind of days you want. The Amalfi Coast is for long lunches and time on the water. Tuscany and Umbria are for farmhouse stays, wine and walking between hill towns. Lake Como mixes grand villas with gardens, and Puglia in the heel is slower, whiter and more rural.
The honest caveat is August. Much of Italy goes on holiday around Ferragosto on 15 August, the coast is full, the cities are hot and some family restaurants close. Late May, June and September are better in almost every way.
The experiences we plan most often, with the months they are at their best.
The coast road is slow in summer, so see the coast from a boat. A private day takes in the Li Galli islands, the narrow inlet at Furore and a swim stop below Praiano, with lunch at a beach restaurant reachable only by sea. Go on a weekday in late May, June or September, when the water is warm and the ferries are less full.
South of Siena, the Val d'Orcia is the Tuscany of cypress avenues and rolling wheat fields. Base yourself in a farmhouse near Pienza, buy pecorino in the village, and spend a day tasting Brunello in Montalcino and Vino Nobile in Montepulciano with a driver. September and October bring the grape harvest and a softer, lower light.
Venice changes completely once the day visitors leave. Stay at least two nights so you can walk across Piazza San Marco at seven in the morning and spend evenings in the bacari of Cannaregio eating cicchetti. November to March is cold and misty but the city is at its calmest.
Lake Como is best seen by boat, hopping between Bellagio, Tremezzo and Varenna. Villa del Balbianello sits on its own wooded point, and the gardens at Villa Carlotta are known for their azaleas and rhododendrons in April and May. Many lakeside hotels close from November to March.
Rome is easiest early and late. We book the Vatican Museums at opening time with a private guide, leave the middle of the day for a long lunch of cacio e pepe or carciofi alla giudia in the old Jewish quarter, and walk the Forum in the evening. Spring and October are warm without the summer heat.
Puglia is flatter, quieter and more rural than the Amalfi Coast. Stay in a restored masseria, a fortified farmhouse among olive groves, and spend days in the Valle d'Itria between the trulli of Alberobello and the white town of Ostuni. Eat orecchiette with turnip tops, burrata from Andria and raw sea urchins in Polignano a Mare.
Choose by the rhythm you want. On the Amalfi Coast, Positano is the steepest and the busiest; Ravello is quieter and higher up. In Tuscany, a farmhouse estate with a pool gives you space; a palazzo in Florence gives you the city on foot.
A 22-room villa hotel on a 300-acre organic farm in southern Tuscany, where the sheep, kitchen gardens and vineyards feed two restaurants.
A thousand-year-old castle hotel on a 3,700-acre private estate in the Umbrian hills, with horses, a candlelit bathhouse and two restaurants.
A classic Rome hotel between Piazza del Popolo and the Spanish Steps, built around a terraced Secret Garden at the foot of the Pincio.
A family-run hotel built down the cliff east of Positano, where every room has a sea-view terrace and a lift runs through the rock to a private cove.
An 18th-century villa above Lake Como with 24 rooms spread across the Villa, the Palazz and a house on the water, and terraced gardens down to the shore.
A seafront resort on 230 hectares of Sicily's south-west coast, with 45 holes of golf, a large thalassotherapy spa and sea-view rooms.
Sample routes to start from. Every one can be changed.
Three nights in Rome between Piazza del Popolo and the Spanish Steps, with a private guide for the Vatican and the Forum, then the fast train south and five nights on the cliff outside Positano with a lift down to the sea.
Four nights on an organic farm estate in southern Tuscany, with a spa that uses its own herbs, then three inside the walls of an Umbrian castle with a candlelit bathhouse in the old wine cellars. Siena and Montalcino in between.
Italy has two seasons that matter: the shoulders. Late April to June brings flowers, long evenings and a sea that warms through the month. September and October bring the harvest, warm water in the south and cooler air for walking.
Summer is high season on the coast and hard work in the cities, with August the busiest and hottest month. Winter suits Rome, Venice and Florence, with shorter queues and cold, clear days, while the Amalfi Coast and Lake Como largely close from November to March.
A first trip that stays in three places rather than five: the capital, a Tuscan farmhouse and the coast, joined by fast train and private driver. 7 nights.
Arrive at Fiumicino and transfer to a hotel near Piazza Navona. An early private tour of the Vatican Museums, then an evening walk through the Forum.
Drive north to a farmhouse near Pienza. Days for Montalcino wine tasting, the thermal pools of Bagno Vignoni and long lunches.
Fast train from Florence to Naples and a private transfer to Positano. A full day on a private boat to the Li Galli islands and Amalfi.
A last morning swim and coffee on the terrace, then a private transfer to Naples airport for the flight home.
Practical notes checked against their sources. For entry and safety, the FCDO advice for Italy (opens in a new tab) is always the authority.
Rome Fiumicino is about two and a half hours direct from Heathrow, and other Italian cities have direct London flights too. Flying into one city and home from another saves backtracking.
UK passport holders can visit Italy without a visa for short stays, and new Schengen border checks are being introduced. Rules change, so read the FCDO entry requirements for Italy (opens in a new tab) before you book and again before you travel.
Read the FCDO entry requirements for Italy (opens in a new tab)
Check the TravelHealthPro page for Italy (opens in a new tab) and the FCDO health page well before travel. Summer heat in the cities is the most common problem, so plan sightseeing for mornings and evenings and carry water.
Italy uses the euro. Cards are widely accepted, but carry some cash for small cafés, markets and village restaurants. Always ask for and keep your receipt.
Surcharge-free roaming in the EU is no longer guaranteed for UK customers, so check your provider's charges before you go. Hotels and most restaurants have Wi-Fi, and a local or e-SIM is simple for longer trips.
Tipping is not compulsory in Italy. Leaving around 10 per cent when you are happy with the service is customary; in a café, a coin or two is plenty.
Two or three at most in a week to ten days. Rome plus Tuscany plus the Amalfi Coast works because fast trains and drivers link them easily. Adding Venice and the lakes turns a holiday into a tour, so we save them for a second trip.
It is beautiful but very busy, the coast road is congested and hotels are at their fullest. If August is your only option, stay somewhere with its own beach club or sea access and book a private boat so you spend the days on the water rather than in traffic.
It helps if you are staying on a rural estate, but many travellers prefer a driver for wine days so nobody has to stay sober. Leave the car outside walled town centres, which restrict traffic, and walk in; parking at the edge of Siena or Montepulciano is simple.
May, June and September. The gardens are at their best in spring, the lake is warm enough to swim by late June, and September is quieter once schools return. Many hotels and some ferry routes shut or reduce service between November and March.
Tell us a little and a specialist will reply with ideas, dates that work and a price. Best months: May, June, September and October.
Greece is really a choice of islands: the Santorini caldera, quieter Paros and Milos, the gorges and palaces of Crete.
France is close enough for a long weekend and big enough to keep coming back: Paris, Provence, the Riviera and the wine regions.
Croatia is the Adriatic by boat: Roman Split, the walls of Dubrovnik and islands such as Hvar, Vis and Korčula in between.
