OOPS!

Back track a moment. April 17th, the last day we had to cancel the agriturismo without cost came and went without me doing anything more with regards to booking the trip. We were still talking about the trip all the time, but I was still waiting to hear Lou's final decision on Sicily. And I wasn't ready to start paying deposits for the hotels we planned to stay at or the tours we planned to take. I spent the first week of July booking the hotels while Lou played on Google maps. Our trip was taking shape.

Or was it?

Which oops should I tell you about first? Should I tell you about how I booked most of our hotels for the wrong dates, remembering incorrectly the dates that I'd booked the agriturismo in October? Should I tell you about the oops with Lou's family, that they didn't really care if we stopped by to visit them when we were "in the neighborhood"? Or should I tell you the oops about the travel insurance? Or how about the oops with the points for our flights? Seriously, wasn't I a travel agent as recently as 15 years ago? Except for the family stuff (which I'm not even going to go into), how could I have made mistakes such as this?

First, the flights. We decided on the dates we wanted to travel and started looking at flights. We planned to use miles to pay for our tickets. It appeared that I only had enough points for myself but that Lou might possibly have had enough points for both of us. (The past few months my son, Steve, has been trying to teach me the ins and outs of using airline miles to purchase tickets. Since so many of them involve applying for new loyalty credit cards, we decided to make due with the miles we already had.) My miles were on United. Lou's were American Express Rewards points. When we went on our honeymoon, the American Express points were great. We transferred them to the mileage plan of our choice and got our tickets that way. In the interim years, American Express has limited their partnerships and made it more difficult to use points. Why should we pay over $1100 to use points to fly roundtrip from Orlando to Milan? Makes no sense, right?

We finally figured out that we could transfer his points to Delta's program and as much as I don't love Delta, we could fly on Delta using Lou's points. Only we miscalculated the points. Even after the transfer, he still didn't have enough points for both of us to fly. I suggested that he fly on Delta, I fly on United (or their Star Alliance partner, Lufthansa) and we meet. Nope, he wasn't going for that.

At this point, I remembered that Steve had mentioned something about airlines now letting you use miles to pay for one way tickets. I quickly logged into my United frequent flier account and saw that we could fly one way on Lufthansa and that I had enough points to do so. Lou checked on Delta and verified that we could also book one way on Delta, so we decided he'd book our flights home. I booked our outbound flight that night. We were going to Italy!

I then (ignorantly thought) that I had two weeks to book our travel insurance. Yes, I was a travel agent for many years. But... in my career as a travel agent, I had other people booking my clients' travel insurance. In the large agency I worked out, there were people who specialized in booking travel insurance. Once I was working on my own, I had my Canadian friend Marilyn helping me find the best deal for my clients for travel insurance. In my mind, I had two weeks after making my first payment to secure travel insurance in order to have preexisting conditions covered.

The day after I booked our flights, in early July, I went to the website that my friend Carolyn had given me, to look at choices for travel insurance. (It was, coincidentally, the same website that the agriturismo in Siena had sent to me over 6 months earlier, with the urging that I should book travel insurance soon.)

Here I am, looking at the choices, what it takes to get preexisting conditions covered and YIKES! I was supposed to have purchased a policy within 2 weeks of first giving my credit card to anyone. Like the argriturismo that I guaranteed with a credit card back in December! What do I do now? Well, in typical fashion, I spent several sleepless nights worrying about this, I finally confessed the dilemma to Lou and then I bucked up and called the phone number on the website to ask how I could recover from such a serious error. She quickly eliminated most of the plans I'd look at, she explained that anything we saw a doctor for in the past 60 days would be considered preexisting (awesome that we'd been in New York for most of the past month and weren't able to see any doctors). I quickly purchased what seemed to be the best plan - and imagine this, I slept like a baby that night.

The hotels being booked on the wrong nights was the least of our problems. Now that we had our outbound flights booked, I went to organize all my printed confirmations in date order. That's how I realized that ALL the hotels I'd booked in the past few weeks were booked for the wrong dates. The agriturismo dates were etched in stone by then. In very methodical fashion, I went about canceling and rebooking most of the same hotels. Some weren't available. (One said it wasn't available but when I clicked on "book," Expedia came back with a confirmation number.)

We fly into Milan, arriving early afternoon, giving us enough time to drive from Milan to somewhere around Lake Como, check in, walk around - and go to bed! I found it very overwhelming to pick a place to stay in the Lake Como area. Most of the hotels I booked as a travel agent, were way out of our price range. Which town was best, given our budgetary constraints? This part of our trip was on Lou's wishlist and I wanted to get it right. I finally booked a hotel in Tremezzina. I'm hoping that it's as convenient to seeing the sites as I think it should be. We'll stay there 3 nights.

Next, we're driving to one of the spots on my wish list, San Pellegrino Terme. We'll only spend two nights there, which will allow us to visit the spa on our one full day in town. (Booking the spa was another complete OOPS! The website for the spa is awful. Each time I'd try to add a service, the date would revert back to the current date in Italy. When I realized what I had done in booking the spa, because it was already that date in Italy, it was too late to cancel online. Thankfully, an understanding person in Italy corrected this oops for me.)

After seeing Letters to Juliet on the flight home from Milan in 2010, I've wanted to see Juliet's balcony. We'll swing by Verona for a quick lunch on our way out of San Pellegrino Terme towards the Venice area.

Then came the big Venice decision. To stay on the island or not. This was also high on Lou's wish list and like Lake Como, I want it to be just right. In the end, finances dictated. We'll spend one night off the island in Mestre (at what appears to be a lovely hotel), we'll spend one night on the island (and oh, what choices I had to make while booking that hotel. For a brief moment, we were booked into a religious, Jewish, kosher hotel... with not the best reviews) and then we'll go back to the first hotel in the Venice area for a night of sleep before heading to Siena the following day.

A week on a farm in Siena... that's been booked for almost 9 months.

Then on to Sorrento where we'll be staying at the hotel that Lou's nephew and his wife fell in love with on their trip to Italy in 2011 or 2012.

Since we're driving from Sorrento to Sicily, we picked a point along the way to spend the night. We'll be in Amantea. From my research, it seems as though not a whole lot of Americans - or foreigners - stay in Amantea. Should be an experience. And by then Lou's Italian should be in better shape to help us be able to communicate with people who rarely come in contact with Americans.

Our last three nights will be spent in Milazzo. We'll fly from Catania (the nearest airport) to Milan on EasyJet (that was another experience in booking), spend the night at a hotel near the airport and fly home via JFK the next day.

I hope I've got it covered. And did you notice that we still don't have a car booked? Or return flights?