I like to use these companies when I book travel to and within Italy.
Book Flights to Italy
Expedia. Good ol’ Expedia has been around for a while, which is why I keep coming back to them — especially when I need to book a flight or package deal (flight/hotel/car). Members get reward points that they can use toward future purchases. Also under the Expedia Group umbrella are the booking websites Orbitz and Travelocity.
Kayak. Kayak is your one-stop site for searching a wide variety of travel sites. Find deals for flights, hotels, cars, cruises, and travel packages.
Momondo. A newer travel search site with an eye-pleasing interface, Momondo lets you search 900 travel websites at a time to find the perfect deal on flights, hotels, and more. You can also use filters to find flights that don’t charge a change fee.
Scott’s Cheap Flights. This membership site sends you cheap flight alerts for your preferred destinations. Some flights are up to 90% off! SCF is the best place to find out about “mistake fares,” which could mean, for example, that you score a $100 ticket for $10.
Best Sites for Booking Hotels in Italy
Booking.com. This is pretty much my go-to site for hotel bookings because it’s so easy to use and many places offer free cancellation up to 24 hours in advance. Go here first to get a glimpse of the city or area where you want to stay.
Hotels.com. Another good choice for browsing hotel choices for Italy or elsewhere. Thanks, Captain Obvious!
VRBO. VRBO has less inventory than their name-brand competitor, but they make up for it in the quality of listings. VRBO stands for “Vacation Rentals by Owner” and the company has been around since 1995.
Individual Hotels and Hotel Brands. If you have your heart set on a certain hotel, then just go old school and contact them directly. They will often offer you deals that are equivalent or less than what is quoted on hotel reservation sites. This is particularly important for small, family-run hotels so that they don’t incur all the extra costs associated with listing their properties on hotel reservation sites. Furthermore, if you have a hotel brand that you love and trust—like Marriott, listed above—book with them directly to make sure that you are getting loyalty points for your stay. Some hotel brands that have hotels in Italy include IHG Hotels and Hilton Hotels.
Top Villas. If you want to go big for your trip to Italy—and who doesn’t?!—you may want to search for a villa on Top Villas. The hideaways featured on Top Villas are often luxurious in addition to having ample room for a group. Great idea for a special birthday or anniversary trip or for a family get-together.
Transportation Booking Sites in Italy
Trains & Buses
Trenitalia. Italy’s state-run rail company offers train service to locations big and small. Its fleet of Freccia high-speed trains provides quick service between Italy’s biggest cities.
Eurail. The easiest way to book train tickets for Italy for non-Europeans. Get an Italy pass and ride as many trains as you want within a certain time frame. Works with Trenitalia trains and some ferry lines, too.
Interrail. The same as Eurail, but for European travelers. Get a pass for Italy and ride the rails.
Italo Treno. This competitor of Italy’s national rail service (Trenitalia) has high speed connections to main cities in Italy, often at a discount.
Save a Train. Book discount train tickets for Italy and Europe on the fly.
Omio. Omio lets you search and compare flights and train travel. But it also has bus and ferry bookings, which can be very helpful if you’re traveling to a small village or to an island.
Auto Europe. Auto Europe specializes in…renting out automobiles in Europe. They work with Europcar and other companies to get customers the best rates.
Best Sites for Booking Italy Tours
Viator. Great way to find all kinds of tours and tickets, from guided museum visits to unique day trips outside the city.
GetYourGuide. Provides an easy-to-navigate website to help match you with the perfect guide for your travel interests.
Tiqets. Book tickets to your favorite museums and attractions, including skip-the-line tickets and combined attraction tickets.
Multi-Day and Package Tours
Both Context Travel and Viator, listed above, have a few options for multi-day tours. Also consider:
Best for Booking Italy Travel Insurance
Here’s a whole post about booking travel insurance for a trip to Italy.