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Travelzoo Experience: Italy by Rail, 4 Cities in 10 Days

One of the most coveted perks at Travelzoo is the Travelzoo Experience, in which Deal Experts and other employees take advantage of the same travel, entertainment and local deals we publish to our subscribers and report back on their experience.

Disclaimer before you continue reading about my trip to Italy: This itinerary for a European vacation is not intended for those traveling with small children, anyone who needs six+ hours of sleep per night, or those opposed to consuming high volumes of espresso.


We started our adventure visiting family in Milan. In December, Fly.com published a Newsflash compiling airfare deals from NYC to popular destinations throughout Europe. To our luck, Milan was on the list of destinations, and we saved $400 per ticket on a trip we thought would take us years to save up for. The second largest city in Italy, Milan is best known as a fashion capital. Prada, Versace and Armani are among the houses headquartered in the city and can be found in the country’s oldest shopping mall, the Quadrilatero d'Oro (Golden Quadrilateral).


As we were about to leave the train, a fellow traveler explained the best way to see Venice, “don’t ask for directions and just keep walking.” The most famous portion is made up of 118 islands in the shape of a fish connected by countless bridges. What people might not realize before coming is that Venice is designed for walking and exploring -- don’t be afraid to follow a path that appears to be a dead end, this is how we found our favorite slice of pizza in all of Italy. Coming from Manhattan, we were surprised to find that almost all bars and restaurants close around 10 and everything is completely dead by midnight. We pilfered some wine from our host and shared the bottle in a completely empty St. Mark’s Square, crammed with tourists by daylight.


I’m definitely not a “foodie,” but even I was excited to eat in Florence. Much like New York, Italians prefer to eat late and most restaurants require a reservation, so pop in early to get your name on the list for an evening of people watching almost as good as the food. We crossed the Ponte Vecchio bridge just before Medici’s jewelry shops closed up for the night and somehow found Piazza della Passera (too small for a map), the locale of Trattoria i 4 Leoni. Modern art and rustic wood furnishings share the intimate space and the menu’s Tuscan cuisine is anything but traditional Italian -- try the Fagottini dip ere e asparagi, or pear ravioli.


We stayed in ancient Rome, which was ideal for seeing the Coliseum, Roman Forum and a central location to easily hit Vatican City, the Spanish Steps and other notable sights in a short amount of time.

We were welcomed to the Italian capital by freezing rain. While others might use this as an excuse to spend the evening in their hotel room with a bottle of Italian wine, we took to the abandoned streets and came away with incredible, unobstructed photos of Rome’s most recognizable landmarks.

A pope-less Rome meant the Sistine Chapel was closed for the Cardinals’ conclave. Because we aren’t Catholic, we wandered to Vatican City in hopes of running into the American media and ended up opting for our own photo shoot instead of joining the two-hour, 36 Euro (US$46) museum queue.

Back to Milan in a Flash:

Always a Deal Expert, whether home or abroad, I found a two-for-one ticket on the ItaliaRail high speed rail, Frecciarossa. Traveling at up to 360 km/h (220 mph), this got us back to Milan in only three hours -- plenty of time to celebrate Fest de la Donna, the annual celebration of women, with our friends and family before flying back to NYC in early the morning.

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Tips by

Deal Expert, New York
Wednesday, March 20, 2013
See more Tips from
Elisabeth Barker