Traveling to Italy


As our posts here have caught up to our current circumstances and are no longer looking back at previous experiences, things will likely slow down a bit.  So many people have expressed sincere desire to visit Italy after reading our stories and most have asked if we have any travel secrets.  Given the openness of the Internet I don’t think there is any such thing as a travel secret but I do think it requires some effort and research to find the best deal.  Disclaimer: I am not a travel agent and do not pretend to hold any professional knowledge.  Here are some resources I have found helpful:

Flights: Aleth and I fly out of San Francisco so apologies if this is biased toward our departure city.  We have attacked this 13-hour flight with various itineraries, airlines and destinations.  First, there isn’t a direct flight from SFO to any airport in Italy so we either fly to John F. Kennedy airport in New York City or Heathrow in London as our first leg.  The JFK stopover is ideal because we get to fly Virgin America, our favorite domestic airline, and at 40% of the total flying time it breaks up the time somewhat evenly.  The second leg of the JFK stopover for us has been Emirates A380 into Milan, which is 2.5 hour drive north of our house.  The other route we have taken is the 10+ hour flight from SFO to Heathrow on British Airways.  The obvious advantage here is the short 2-hour flight from Heathrow to Pisa, which is less than an hour from our house.  If your schedule is flexible I strongly suggest you check out a new app called Hitlist.

Hitlist App

Hitlist is simple to use and delivers incredibly low airfares available between your home airport and desired destinations.  For example, Hitlist sent me a notification last night that British Airways is offering a roundtrip fare between San Francisco and Rome for $544.  Think of Hitlist as your personal watchdog who is always searching for great airline deals on the places you want to visit.  I also use the SkyScanner website/app often as they seem to index more international carriers and sometimes try unique stopovers that I probably wouldn’t consider. One of my favorite things about Europe is that nearly every place is a 1-2 hour flight away.  We have flown Vueling and Ryanair for these shorter flights.  I can say the rumblings about Ryanair as a nickel and dime airline are very true as they charged us $99 each to print out our boarding passes because we didn’t have a printer at our house when we checked in the night before.  I was furious as our original one-way flights from Pisa to Ibiza were only $49 so a $99 fee to print boarding passes was beyond insanity and they can say goodbye to our future business.  OMG, I nearly forgot the nonstop flea market atmosphere on Ryanair as they sold food, drinks, perfumes and lottery tickets during our flight.  The complete opposite can be said of our experiences on Vueling, a Spanish airline that nearly matches the coverage and prices of Ryanair but does so in a professional manner.  Other recommended regional carriers would include: Aegean, Air Nostrum and Air Malta.

Hotels: I am not overly picky when it comes to hotels.  I’m going to list the websites/app that I find helpful with reasoning when appropriate.

HotelTonight (app): Significant savings if you are willing to wait until the last minute to book your room.  Worldwide coverage.  One of my favorite apps.  Get status and unless more savings.

Airbnb (web/app): We recently used Airbnb for a single night stay in Milan and we found a very cool, funky apartment for $70/night.  Not much experience here (yet).

VRBO (web/app): My search experience with VRBO demonstrates they are very strong in Europe while Airbnb seems to win in the US.  You can find great deals in Italy on VRBO.

ClickStay (web): ClickStay is a villa only search engine.  They list over 1,000 villas in Italy alone and cover many other countries around the world.  Perfect for the person who wants to search the creme de la creme.

Hipmunk (web/app): I discovered Hipmunk many moons ago thanks to their “agony” flight search results but have since enjoyed using their hotel search as they pull listings in from a wider assortment than most other search engines.

Car Rental:  I previously wrote a lot about renting a car and driving in Italy.  So have a read here to revisit that information if you missed it.  Overall, plan ahead when it comes to renting a car. almost always has the lowest prices as they include many of the local rental companies that are ignored by the larger auto search engines.  In full disclosure, I usually rent from Hertz as they often upgrade my rental class (last time, Jaguar sedan) without additional fees and they usually don’t nitpick small scratches that may have happened during extensive driving over 2-3 weeks. Avis jacked me for $1,000 for a fairly decent scratch on the front left bumper that happened during our rental time, but must have been when it was parked because I didn’t hit anything.  Goodbye Avis, hello Hertz!

While this isn’t meant to be a definitive travel planning guide, I hope it provides some assistance when planning your trip to Italy.  If you have found other helpful resources, please add it in the comments below.  Thanks in advance!





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