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5 days in Italy

When my parents decided to come to Germany for our son’s graduation this month, I encouraged them to turn it into a two week visit so we could enjoy his celebration and also tack on a few days in “Bella Italia.” My folks have visited me quite a few times over the years in Germany, however, we’ve never made it to Italy. Now having been there myself several times in the last few years, I knew I had to introduce them to the culture, the food and my friends. 

If you are stationed here near Stuttgart, Italy can be a quick trip. Traveling through the Swiss Alps will get you to the Riviera in only seven hours, Tuscany a mere nine hours, and then there’s Venice at only six. Well, the way I drive it is. Here is a look at our amazing five day journey and itinerary. If you have family visiting this summer and need to squeeze in an Italian experience, I hope this helps you put something together. Let me know if you need additional help by commenting below!

TWW - Swiss Alps
Swiss Alps

Day 1 – Piemonte

Having discovered the Piemonte region with my friend Ellen a few years ago and making new friends, I knew I would have to make a stop in Canelli with my parents to see the beauty of this land and it’s people. Canelli, Piemonte is a frequent stop on my tours through Italy, our TWW trip to the Riviera will include a wine tasting with my friend Claudia Cordara of Cordara Wines

When we were planning the trip, I emailed Claudia to ask her where we should spend the night and she recommended Affitacamere Il Castelleto with Enrico and Gaia. A new B&B just around the corner from her winery and what a lovely stay we had, we wished it was for longer. 

What an authentic experience for my family. Enrico and Gaia made us a beautiful meal for dinner in the lovely dining room and then we took a stroll through the countryside because of our “very full bellies!” 

If you haven’t met my folks yet, they are very active and love to walk, run, practice yoga, spin, bike and do “muscle pump.” Sitting idle was not an option unless it was to enjoy a aperitif on the veranda on this trip. 

The next morning we woke up early to walk the hills again, this time in another direction and we discovered the little village of Calamandrana. Here they celebrate the ancient farmer who discovered “truffles.” While we were there the church bells rang out gloriously to wake up the residents to begin their day of work. Upon our return Gaia and Enrico pampered us with cappuccino, tea and fresh juices as well as a very hearty breakfast.

After saying our “Ciao’s” with hugs and promises for our next visit we headed down the hill to see Claudia for a special wine tasting. Then it was off to the Riviera.

Day 2 – Riviera

Only a few hours drive from Canelli is the Italian Riviera. There are many, many places to stay on the Riviera. For some reason, my heart loves the little ancient town of Diano Marina. It is far from perfect, well-manicured or austere. It’s real. It’s a beach town and has been for generations and generations. It shows wear and tear but also survival and beauty. It’s people genuinely greet me upon my return and I can see from their faces they are glad it’s a sunny day.

TWW - Diano Marina

Tourism has been hit hard this season all over Europe because of the weather and all the rain. I hear this in every store, B&B, hotel that I stop in, from Germany to Italy.

We stayed in a typical summer resort, the Hotel Gabriella. I’ve stayed here before for spring break last year, so I knew our accommodations would include a view of the Riviera, wonderful beaches (rocky) and exceptional breakfasts, (full with scrambled eggs and bacon.)

After we changed into our bathing suits we headed out for a walk along the beach and found ourselves at a seaside cafe where we enjoyed charcuterie (salami plate), cheese, complimentary chips and, of course, a few drinks, including a Bellini, (a peach drink with champagne.) The board walk was alive with a flea market, something my little one, Jessica was very excited about.

We had dinner that night at one of my favorite restaurants, Fra Diavolo. Be sure to make reservations if you have a large group. While in the Ligurian region, I must have pizza. So close to Genoa, Genovese Pesto is everywhere. If you like pesto, you’ll love it here.

Day 3 – San Gimignano and Cortona

Our next stop was Cortona but not before we stopped in the tower town of San Gimignano. Last year I stayed four days in this little town with my older daughter Katy and we fell in love. My heart is filled as I see the streets lined with tourists, yay! San Gimignano is only three and a half hours from Diano Marina and our GPS took us all along the coast which was excellent because we could enjoy and admire more of the Riviera.

TWW - San Gimignano towers

Once you make the climb to the San Gimignano, it’s just beautiful. There is parking outside the walled city that makes it easily accessible by foot. I typically try to park in the P1 or P2 parking lots. The cost will range between €1.50 & €2/hour for parking.

After a short stroll through the main alley of this walled city we decided to stop for lunch. There are many places for you to choose from, whether it’s the main square or one of the side alleys. We chose DulcisinFundo ristorante in San Gimignano. Here we enjoyed pasta, gnocchi (potato pasta) and Tiramisu.

Next was, Il Negozio delle Curiosità, an exceptional hand-made Italian pottery store and buying a few more souvenirs from Gianni Martini. Gianni was wonderful and told me all about the pottery of the region. My interest is peaked and already I begin formulating another trip to see my new friend. 

TWW - Mom and Dad San Gimignano
Mom and Dad – San Gimignano Valley

So back in the car we go, heading towards Cortona. At this point, you can stop in Florence or Siena. Both beautiful towns and worthy of a stop, we just didn’t have enough time. Maybe on another trip.

TWW - Cortona square

Day 4 – Cortona

In Cortona, you must park outside the city, no problem, it’s FREE! Typically, only residents are allowed to park inside this steep, cobblestoned covered alley and walkway town. Be prepared for a little trek. I made reservations with Paolo at Cortona Astrico, I knew I would like her instantly through our email correspondence. We also signed up for cooking classes in her kitchen. I was so excited since both of my parents are amazing Chef’s and have been in the kitchen most of their lives and still are to this day. We had a small hiccup with our room reservations though, mostly because of my lack of Italian. Something I hope to remedy this year.

TWW - Cortona valley

Paolo was sweet enough to walk us across the alley to a friend’s hotel, the Hotel San Michele. This 15th century renovated palace was stunning. Here is where we met Matteo, who was gracious enough to tell us what to see while we were in Cortona. A recent graduate of the hospitality college near Cortona, his warmth, humor and welcome were exactly what you think of in “Bella Italia.”

TWW - Paolo e Paolo we begin!

On our fourth day, we did join Paolo back at Cortona Astrico for our authentic Tuscan Cooking class. This is when we also met the other “Paolo.” The Paolo’s were an amazing team in the kitchen, completely professional and simply perfect. We learned how to make fresh pasta, (gravy/ragu/sauce), chocolate almond anise biscotti, bruschetta and so much more. I’ll let the pictures speak for this though.

My parents are movie buffs, so am I, my girls too. Therefore, our visit to Cortona would not be complete without looking for Bramasole. The beautiful villa that Frances Mayes restored in her book and whom Diane Lane so eloquently played in the 2003 movie “Under the Tuscan Sun.” This famous book and movie have forever made this ancient city famous. Forever grateful to Matteo for giving us walking directions and learning that an “Italian mile,” is slightly different than an American mile. However, needing to walk off the amazing lunch we prepared with Paolo it was time for a little hike through the hills of Cortona. 

I always have a story on my trips. This trip is no different, on our return walk to Cortona a farmer in a truck stopped to show us his DVD (in Italian) of the movie and say in very loud voice how much he loved Frances Mayes. Much to his wife’s chagrin. This little story provided us moments of laughter throughout the rest of the trip.

After a very “full” day, I went to rest. Meanwhile, everyone else headed out for some pizza and gelato on the square. Happily, my daughter and her grandfather shared how they watched the Euro soccer game on the big screens in the piazza when the Italian’s scored. She also told me, “Mom, they are super affectionate when they score!”  I know this is a memory she will never forget either.

TWW - Lake Garda Desanzano Marina

Day 5 – Lake Garda

Today was a sad day when we knew we would have to say “Ciao”to Italy and head back to Germany. But not before we stopped in Lake Garda, a popular lake spot for Germans, Swiss and the French for vacation travel. This gorgeous mountain lake town of Desanzano Lake Garda is a perfect place to grab a bite to eat not too far off the return home. 

However, it became cloudy and misty, so after a nice lunch and more gelato on the Marina and a stroll through town we got back on the road. Luckily, the views are breathtaking and this time our GPS took us through the Austrian Alps.

An absolutely amazing trip in five short days, but oh so much to see, taste and do. Once again, I met amazing people along the way, learned more about their culture and customs and this time I was able to share it with my family. Every time I visit Italy, I learn something new. I look forward to my next trip in September where we learn more about the region of Tuscany and Umbria.

Notes for traveling in Italy

Tolls, tolls, tollsyou WILL have tolls throughout Italy if you are driving

  • our tolls totaled – €83.40


  • Switzerland (€46)
  •  Austria (10-day pass) €10.10
  •  You can pick these up at any ADAC office
  •  MUST have them to travel from Germany through these countries
    • **very expensive fine**


  • ESSO cards are ONLY used in Germany not Italy
  • Rations for a rental car over 7 days are for 200l
  • total gas cost – €264.42

Credit/Debit cards

  • notify your bank that you will be traveling to other countries, prior to your departure
  • if you stop at an ATM, don’t take out large sums, I don’t take out any more than €200 at any given time (for safety and for spending) helps me both ways.

PLEASE don’t tip!

  • I can’t emphasize this enough. If you feel you must then just round to the nearest Euro. It is actually discouraged in Italy because your service fee (tip) is included in your price. The locals get unhappy with us when we do it because expectation builds. Fight that American urge to tip more than that, and enjoy the rest on your trip for wine or souvenirs.


  • In Italy sometimes pan-handlers and begging happens. However, due to an increase in these events some towns/cities actually fine the “giver,” not the asker.  Please be aware of your surroundings. 

Go with the flow…

  • when you are traveling, no matter how organized you are, things happen. Try to go with the flow if you can. By embracing Paolo’s suggestion for a new hotel we were able to stay in a beautiful palace overlooking the Cortonese valley as well as build new connections.

Until next time… happy travels!



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