Leisurely afternoons sipping prosecco on the shores of Lake Como. The medievel wonder of the walled cities of Lucca and Siena. The magical art of Florence. The canals of Venice. The summer playgrounds of Capri, the Amalfi Coast and the Cinqueterre. Italy abounds with year round pleasures and incredible scenery and history. The best bet for awards is to search flights to Milan Malpensa airport (MXP). Seats can sometimes be found to Rome (FCO), and Nice (NCE) is only a couple hours drive from Portofino and the rest of Northern Italy. While summer gets very busy, try looking for late spring or autumn flights, when the crowds are gone and the weather still pleasant.
Most major Italian cities have international airports, such as Venice (VCE), Florence (FLR), Naples (NAP). However,
the best largest international airport is Milan Malpensa (MXP), so it's the best bet to start searching for award
flights. American, United and
Delta all fly direct from the US to MXP. Additionally, thir major alliance partners
such as Lufthansa (Star Alliance), BA (OneWorld)
and Air France and KLM (SkyTeam)
have good connections into Milan from their hubs, so can be good candidates for awards as well. Of course with OneWorld
(ie AA, IB and BA) be very careful that your routing doesn't pass through the UK on a BA flight as that will incur huge cash surcharges
tacked on to the fare.
Milan is in the northern part of Italy, so if your ultimate destination is somewhere in southern Italy (for example the Amalfi Coast, Capri, Sicily, Sardinia), it's worth looking into flights into Rome Fiumicino Airport (FCO) or even Naples (NAP). Flights are more difficult but not impossible to find. One sweet spot would be United's new service from their hub in Newak (EWR) direct to NAP, the first US airline to fly direct to this beautiful southern Italian town.
You might be surprised, but really the art of optimizing miles and points involves knowing
when NOT to use them, and instead use cash. (Domestic US flights are often an example). While
AwardSecrets are huge fans of award travel, we would not recommend using miles
or points domestically in Italy.
Italy, like most European countries, has fantastic public transportation options, and for longer distances (e.g. Milan to Venice, Venice to Florence, Florence to Rome), we prefer taking the train. Trenitalia is the primary train operator in Italy, and their website is very useful for viewing train schedules. Tickets can be booked online or in convenient kiosks at most train stations, and the trains are generally comfortable, convenient and relatively inexpensive. Do watch out for the occasional strikes. You can look in train stations or ask at the station if there are any strikes - "Ci sono scioperi?"
Most major tourist sites of interest in Italy have small and large hotels that are part of the major points chains.
During summer months many of these hotels can charge rates well in excess of USD $400 per night, so some high-value
award redemptions can found. Some of these properties can be extraordinarily beautiful, in fine old buildings with
significant historical and cultural interest. Some examples using dates in early summer:
Hotel Cala di Volpe in Sardinia, a beatiful summer playground, can be booked for 85,000 Marriott Bonvoy points per night, or EUR €604 per night.
A great option using Hyatt's partnership with Small and Leading Hotels is to book the beautiful Centurion Palace, directly on the Grand Canal in Venice, for 40,000 Hyatt points or EUR €506.
And in Rome, an interesting aspirational award would be staying at the Cavalieri Waldorf Astoria for 254,000 Hilton HHonors points or EUR €706. Many of the rooms have absolutely awesome views over St. Peter's and the Vatican to the rooftops of Rome and beyond.
We have 3 tips for enjoying time in Italy.
Tip #1: The food in Italy is world famous, but many restaurants close to key tourist sites are not that great. When in doubt, ask a local or at your hotel for good recommendations (and even bookings). Additionally, the best experience can often be had by not actually looking at a menu, but instead asking your waiter what's fresh and good today. Most restaurants take great pride in their food in Italy, and won't steer you wrong. Note that many countries' perceptions of "Italian food" are not actually italian food, which varies greatly by region. Try the "Cacio e Pepi" in Rome, or a Boar Ragu in Umbria. Near the coast, today's fresh seafood is usually outstanding.
Tip #2: Many famous locations can be incredibly packed with tourists at key times of the year. St. Mark's square in Venice for example is often a let down for visitors, and Tuscany can get very crowded from May to October. Instead, get off the beaten path. Umbria is a fantastic less touristed alternative to Tuscany, and in Naples you can experience all the charms of large Italian cities, yet be the only traveler in sight.
Tip #3: The far north and far south of Italy are beautiful and relatively less touristed. The Dolomites for example have some of the best skiing in the world, paired with extraordinary mountain vistas and alpine thermal baths. The Aeolian Islands off the coast of Sicily are incredible summer vacation locations, without the crowds of the Amalfi coast. And instead of piling into the tourist boat with 500 others to Capri for the day, take the empty boat to Ischia or Procida, and swim in the same waters and eat better food for a fraction of what you'd pay with the instagramming hordes in Capri.