Italy luxury vacations 2024 & 2025

Italy’s key attractions are food, wine, ancient and Renaissance history, and art, but what many visitors love best is the country’s pursuit of la dolce vita. To taste the sweet life yourself, you can venture into the country’s many renowned wine regions, like Barolo, where we can arrange a vineyard visit and wine tasting. Or you can head into the Tuscan hills to hunt for elusive truffles. Meet a nonna in her kitchen for a cooking class featuring her family’s heirloom recipes or sample Sicilian dishes on a guided food tour through Palermo.

Beyond Italy’s robust culinary traditions, you can also experience the country’s rich history and culture. In Rome, you can take a guided tour of the Vatican, see the Colosseum, and explore the city’s backstreets via Vespa, seeing places that only locals go. While in Venice, you might learn to make a Carnavale mask from a master artisan in his workshop.

For your first visit, you might want to visit the three best-known cities — Rome, Venice, and Florence. Known collectively as the Art Cities, these three ancient metropolises are treasure troves packed with museums, galleries, art, architecture, and archaeology, not to mention Michelin-starred restaurants, sunny cafes, and relaxed trattorias.

For some relaxation, oenophiles and gourmets may want to add a few days to lounge amid the sun-gilded hills of Tuscany, indulging in the food and wine that made the region renowned. If you’re looking for glamour, you can instead end your trip by heading north to the Italian Lakes region, which has attracted everyone from Roman emperors to Hollywood royalty. Or, head west to the Amalfi Coast for sun, sea, and sophisticated luxury.

Our specialists will build your trip to suit your personal tastes, but you can get inspired by browsing our example itineraries.

From converted family farms to city palaces, where you stay in Italy depends on where you’re visiting and your personal style. Cities offer a wide range of options, from opulent Renaissance palazzi that are the byword for European luxury to modern boutique hotels with just a few guests.

In the countryside, you might choose to stay on a working family farm that accepts guests — known as an agriturismo. These are often tucked into some of the most beautiful regions and can vary from rustic simplicity to lavish stays with pools, spas, Michelin-starred eateries, and other luxuries. In regions like the Amalfi Coast and the Lakes region, you can opt to stay in classic grand dame hotels, often built in the late 1800s or early 20th century. Our specialists have hand-picked some of the best places to stay in Italy on our accommodation page.

A direct flight from Toronto to Rome takes about 8.5 hours, depending on airline.

The best way of getting around Italy is via train. There’s a good network of high-speed trains between cities, making it easy and quick to move around. Within the cities, you can walk or take taxis.

Driving yourself is also an option — we can provide detailed driving directions. You’ll need your valid Canada driver's license as well as an official translation in Italian or an International Driving Permit.

The time zone in Italy is UTC +1.

Visitors from the Canada do not require a visa for travel to Italy. Canada passport holders are required to have at least three months validity remaining on their passports as well as two blank pages for the entry stamp.  If you’re not a Canada passport holder, you can check the visa requirements here.

Your doctor can provide you with vaccine advice for Italy, but you should also ensure you’re up to date with the recommended vaccinations for your home country. You can also check the suggested vaccinations on the Government of Canada - travel vaccinations website.

Your packing list for Italy should include modest clothing for religious sights, stylish outfits for dinner, comfortable shoes, a sun hat, and a small day bag that’s worn across your body. Additionally, we suggest you pack light if you’re catching a train — trains have limited space for luggage and few porters, so you’ll be managing your bags yourself.

Most churches and cathedrals, including the Vatican, won’t admit visitors with exposed knees, shoulders, cleavage, or midriffs, so plan to wear long pants or skirts, and modest tops when visiting those sights.

Fine-dining in Italy is an experience and very casual clothing is frowned upon, so pack some stylish, smart-casual outfits for eating in the evenings. Pizzeria’s are more relaxed, where casual clothing is normal.

For exploring, we strongly suggest wearing comfortable walking shoes and a sun hat, especially in the summer.

Food is serious business in Italy and following these rules will make your dining experience more pleasurable: consider making reservations, dress smartly, and expect a coperto (table charge) on the bill.

Your hotel concierge can make reservations for you — we suggest planning at least two or three days in advance if you want to eat at a certain restaurant at a certain time. Most Italians eat at 8 or later.

Almost every meal comes with a coperto — this small charge covers the table, which is yours for the night, as well as things like bread, oil, and vinegar. You’ll also (probably) pay separately for the water.

One last suggestion: Avoid eateries near any major sights, like the Vatican or Doge’s Palace. You’ll find much better food if you walk just fifteen minutes away.

In Italy, you’ll need a standard European-style, two-prong, type-C plug adapter. If you plan to bring electronic items that have a heavy draw, like a hairdryer, electric razor, or CPAP machine, you’ll also need a convertor.

Your hotel should be able to provide laundry services, but you can also pack laundry soap for washing small items in the bathroom sink.

Many museums and sights are closed on Mondays and sometimes Tuesday. Your specialist will arrange your trip with this in mind, but it’s something to consider when you’re planning how to spend your free time.

Many museums and other sights don’t allow backpacks or large bags — either you’ll have to stand in line to check the bag or you’ll be refused admission. Instead, we suggest bringing a satchel or cross-body bag that’s no bigger than a sheet of paper.

If you’re planning to use your phone in Italy, call your provider to determine what your overseas options are. You’ll have access to Wi-Fi in all your hotels as well as many sights and cafes, so some visitors prefer to put their phones on airplane mode and only use Wi-Fi.