Magic of Miles in Italy: Florence, Portofino, Pisa, and Milan

Please note that I receive compensation for many links on this blog. American Express and other banks are advertising partners of this site. Read my Advertiser Disclosure policy to learn more.

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.

DSC00474 (1)


DSC00583 (1)

Arena Verona

DSC00534 (1)

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!

Editorial Note: The opinions expressed here are mine and not provided, reviewed or endorsed by any bank, card issuer, or other company including (but not limited to) American Express unless otherwise stated. Comments made in response to posts are not provided or commissioned, and they have not been reviewed or endorsed by any bank. It is not the responsibility of any advertiser to make sure that questions are answered.
Unauthorized use and/or duplication of the material on this site without express and written permission from this blog’s author and/or owner is strictly prohibited.

  1. Christina

    Melinda – I am so excited to follow your blog! What. Wonderful start.

    • Melinda

      Thank you, I’m excited too!

  2. Jane

    I’m anxious to read about your hotel experiences and perhaps recommendations for Verona, Lake Garda and Venice. We will be there next year and are now beginning to determine where we want to be. We are also looking at AirBnB and Home Away.

    • Melinda

      Jane – I’ll make sure to hit some of those destinations in the next round. Thanks for reading!

  3. Randy Petersen

    Whoa. Are you sure you are not a pro photographer as well? Stunning photos. Good luck and count me in as a regular reader.

  4. Gail Smith

    I am looking forward to your blog, Melinda. We stayed at the Hotel American Dinesen in Venice, in an apartment attached to the hotel, and were very pleased with the accommodations.

  5. Rob

    I just took a very similar trip! Park Hyatt Milan, Westin Excelsior Florence, Lucca, Riomaggiore, Verona, Sirmione, Venice, Lucca, Pisa, via train and rented car. Plus Bellagio, Rome, Tuscany… The country is so beautiful and relaxed, except for the drivers who are uniformly maniacal.

  6. Paul

    Seems your blog name is woefully misleading? Only a few points being used but tons of cash being spent. You should be able to get there and stay in better hotels for the fraction of the cost of what you spent. But you’re the “expert”. Sigh. At least you aren’t pimping cards every second sentence so thank you for that.

    • Melinda

      Hi Paul. Thanks for the feedback. Each trip I take is different. For this one to Italy, I used a combination of points and good offers. For the review already published for Pisa, I used a members only private sale Leading Hotels of the World 50% off promotional rate so actually paid only a fraction of what that property typically costs. Plus I got double stay credits, which count towards a free night typically after 5 which means for this offer you only have to stay 2.5 stays to get a free one. I like the Leaders Club program because I can spend at cheaper properties and then redeem at more expensive ones. I am sorry I didn’t include that much detail in the post; in the future I’ll try to add more specifics. Thanks for reading!

  7. romantic hotel

    just returned from a 4 night stay on a bed breakfast and evening meal basis. The hotel was recently renovated and in excellent condition. Good value for money paid,

    • Melinda

      Great to hear, Romantic Hotel. Thanks for reporting back too!