Italy is one of my favorite countries to visit. This summer I’ll be doing a series of hotel reviews and primers for many areas around Italy, including – Portofino, Lake Maggiore, Florence, Venice, Verona, Rome, Lake Garda, Pisa, and Milan.

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Arena Verona

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Lake Garda

Which one will be your favorite?

I’m starting off with a trip report to the area that includes Florence, Portofino, Pisa, and Milan.

Trip Report Index:

1. Introduction
2. Transit Notes
3. Hotel Review: Bagni di Pisa Palace & Spa
4. Visiting Pisa
5. Visiting Lucca
6. Hotel Review: Westin Excelsior, Florence
7. Room Service Review: Westin Excelsior, Florence
8. Day in Florence
9. Hotel Review: Hotel Laurin, Santa Margherita Ligure, Italy
10. Day in Santa Margherita/Portofino area
11. Hotel Review: Park Hyatt Milan
12. Day in Milan
13. Room Service Review: Park Hyatt Milan
14. Retrospect

I wanted to go for a quick trip in the early summer just before the school year let out, when the weather was warm but the crowds were still on the smaller side.

I hadn’t been to the Tuscany region before, but could picture myself leisurely strolling through cobblestoned streets


and sampling the delicious local cuisine. Fresh ingredients are key in Italy, which results in mouthwatering meal after meal.


I thought about the famously tilted tower in Pisa, marble Cathedral of Santa Maria di Fiori, terraced gardens previously tended by the Medici family, the Galleria dell’Accademia and Michaelangelo’s David.

I excitedly started by booking flights one way from Chicago to Pisa via London on British Airways in First Class for 62,500 American Airlines miles along with $480 (fuel surcharges) per person. It was a little steep in fees, but I wanted the BA first class experience across the pond.

For Pisa I booked a paid hotel stay, as Leading Hotels of the World was having a sale. I reserved a Hertz one-way rental car, which I planned to take from Pisa through the rolling countryside, then stop for a few nights in Florence to explore.

In Florence, one hotel stay would be using points, one would be paid, and then I’d take the train to Milan to soak up the vibrant atmosphere for a couple days before heading home. I booked the return flight as a revenue ticket on American, and I was done.

Sounds perfect, what could go wrong?

Come join me on my tour of Italy!