Italy Trip Planning

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Our 15th wedding anniversary is in September of this year, and we decided to take a trip to Italy to celebrate!  With no family living nearby, we had to schedule our vacation around the school break schedule so that we could take the boys to my parents. We decided to go over their spring break, roughly 5 months before our anniversary.  Hopefully an early celebration isn’t bad luck!

When we came up with the idea of dedicating this decade to family travel, we hoped to be able to take an international trip every year.  The first year was a little bit of a cheat, as the boys went to the Bahamas on a Disney Cruise.  Not exactly a case of immersing yourself in another country and its culture but they did set foot on foreign soil for the first time.  Now the second year was apparently going to be a trip without them.  Sorry boys!  But they did get to go to Epcot this year, and we visited lots of countries in the World Showcase.  That counts, right?

It had been a long time since I had planned a trip without kids and honestly I felt a little lost.  The focus is different.  Family friendly hotels?  Doesn’t matter.  A good selection of kid’s activities?  Not necessary.  Winery tours?  Yes please!  Ok, maybe this wouldn’t be all that hard.

We decided to split the trip between Florence and Cinque Terre.  That was our starting point.  We were using airline miles and started researching flights.  But getting from Charlotte to Florence proved to be difficult.  Every possibility had multiple layovers. And every ticket seemed to use British Airways for at least the overseas flight.  That may not sound like a big deal but it was.  British Airways charges outlandish fees to book American Airlines awards tickets on their flights.  Outlandish.  Seriously, we were looking at tickets with three legs that would have cost us 60,000 miles and over $850 in fees each.  EACH!  How is that a reward?  Use all your miles and still have to pay almost two thousand dollars in fees?  (British Airways calls the fees “fuel surcharges”.)  It’s absolutely ridiculous.  We could have paid out of pocket about the same amount and saved all our miles.

So flying into Florence on miles seemed to be completely out.  We started looking into other options and found direct flights from Charlotte to Rome on American.  Guess what?  Those tickets cost the same 60,000 miles but only about $20 in fees.  Sold.

Well, actually it wasn’t quite that easy.  I had to fly the boys up to NJ and drop them off with my parents.  That meant my flight had to originate in Newark and fly back through Charlotte where I would meet up with Blair.  So slightly more complicated to book but still possible with no extra fees.  We booked these well in advance.  With our dates and our tickets finalized almost 9 months before, we put the rest of the planning on hold until closer to travel time.

As it got closer, the first step was to plan how many nights in each place.  While we hadn’t originally planned to visit Rome, I knew we wouldn’t want to take an overnight flight, land in Rome in the morning, and then immediately get on a train to Florence (especially since I had an extra flight up and back to NJ squeezed in there).  So we decided to spend the first day and night in Rome and then catch a train to Florence the next morning.  The rest of the itinerary fell into place pretty easily – we knew we wanted two full days to hike in Cinque Terre, which meant spending 3 nights there.  So we backed in to 2 nights in Florence.

Hotels were a bit harder to nail down.  Both Rome and Florence are huge cities with endless hotel possibilities.  We knew very little about what areas we wanted to stay in.  It felt very overwhelming.  I must have read a thousand hotel reviews but without  being familiar with the cities, it seemed impossible to choose.  Ultimately we narrowed it down to about a dozen in each city based on Trip Advisor reviews.  Then we researched each one individually and figured out which seemed to be the best location and hotel.  We settled on The Fifteen Keys Hotel in Rome and Hotel Porta Rossa in Florence.  In Cinque Terre we looked at hotels across all five of the small towns and landed on Hotel Villa Steno in Monterosso.

The rest of the planning was the fun stuff.  What sights did we want to see?  What tours did we want to do?  This part was much less stressful and got us really excited about the trip.  And actually, we ended up making very few specific plans.  We had highlights in each city that we wanted to see but kept it open as to when we would see them.  The only official tours we booked were a wine tour in Tuscany and a boat ride in Cinque Terre.  The rest would be decided on the go.

So the important details were booked and the trip outline was in place.  Now we just had to wait until the trip finally arrived.  And deal with two boys who wanted to know why they couldn’t come.  RB seemed to have the most logical reason as to why we would possibly leave them behind: “Is it because there are so many naked statues in Italy?”