Tips, Tricks and Lessons From My Recent Trip to Italy

So I just returned from a nearly two-month trip to Italy that can only be described as completely epic. I brought my dog along which was pretty amazing in and of itself, saw so many old friends, filmed some episodes of season 3 of my PBS series Dream of Italy and honestly truly found myself again after a number of brutal years.

I can’t wait to tell you all the details of where I went and what I did and some of the crazy serendipity that happened along the way as well as more about my personal transformation, but I thought that I would start with the practical – tips, tricks and lessons from my most recent trip to Italy. (FYI – A few of the links below give me a small commission when you buy using them. Most of the links are not affiliate related.)

I am usually not someone who plans my travel far ahead but for two of the bigger things – I did – and for this I am grateful. After all, this was a big travel summer and nothing was in higher demand in the peak summer months than rental cars, especially automatic. Since I knew I would be going for an extended time, I actually opted for a lease through Auto Europe (open to non-EU residents for lease of minimum 21 days up to 90 days). I got a new Renault car  at a rate much cheaper than a regular rental. Also, if you lease during one of Auto Europe’s promotions, you get free cancellation and date changes as I did. You can save 5% at Auto Europe with my code: IATA 72002261 I always, always put any kind of rental car on my American Express card because they have amazing rental car coverage. If you’re planning to travel to Italy during high season 2023 – please please book your car rental NOW! My lease cost $3,000 for 2.5 months. When I priced a rental, it was $10,000 because automatics were in such short supply!

I also booked my plane ticket way ahead. I opted to fly La Compagnie – a new business class-only airline with just 76 seats flying Newark to Milan. I bought my ticket during a promotion and paid $2500 roundtrip. (La Compagnie has a similar promotion right now if you fly during the winter.)  I lucked out on both ways when there was no one seated next to me, so I had SO much room. There were only about 50 people on each flight so everything was easier from fewer people at immigration and luggage pick up to a just more comfortable ride.

La Compagnie is also a great option for people flying with their pets as I was. I was lucky my dog Phineas aka Finney could ride with me in the cabin. La Compagnie differs from other airlines in that the airline will take dogs up to 33 pounds, in a carrier, in cabin. You must reserve for your pet and there is a small additional charge. I know many of you have questions on getting your dog over to Italy without putting your dog in cargo and size matters. I also follow a Facebook group that organizes charter flights for travelers with pets but it isn’t cheap, think $8,000 one way and more for people who are making a move.

Paperwork is KEY when taking your dog to Italy. Your pet must visit a  USDA-accredited veterinarian for a health certificate within 10 days of arrival in Italy. The health certificate then need to be endorsed by the USDA. (It is uploaded electronically and then mailed to you by express mail.) My vet recommended that I use Pet Relocator to handle the USDA requirement and everything went smoothly, even when I had to reschedule my trip because of illness and my paperwork expired. I went back to my vet and paid the fee to Pet Relocator again but they got me everything on time.

Now on my way back from Italy, I was advised that I needed another health certificate issued by a specific type of Italian vet within 10 days of travel. My friends at Tuscan Hound helped me get this vet appointment in Florence. Other friends who travel with their dogs have never been asked for this certificate and I wasn’t asked for it on my return trip. I’m still looking into what the official regulations are but didn’t want to chance it. (I will be writing a full article on traveling with my dog in Italy so stay tuned…)

I was ordering from Amazon like crazy in the days before my trip and I will tell you the single best thing I bought which may help humans as well as dogs out there… My dog is diabetic and I needed a way to keep his insulin cool at all times. This made me really nervous until I bought this USTA-approved cooler vial that works with a freezer pack as well as a USB port.  That USB charger was key. i could keep it plugged in in the car and trust me, I drove more than 3,000 miles so we were in the car often!

The two other things I bought from Amazon that rocked my trip were Apple AirTags to put in my luggage that went on the plane, my luggage that was shipped (more on that in a moment) and even my dog! Yes, Finney wore an AirTag on his collar during our whole trip in case for some reason he got lost. Remember that this was the summer of lost luggage so I couldn’t be too careful. My love for AirTags even made it into The Washington Post – along with Finney! And the next item will seem like a little thing but I am allergic to fragrance and heavy dry cleaning products and needed some fragrance-free detergent for my trip. I bought these detergent strips which were easy to travel with (no spill) and worked like a charm if I was hand washing, using a machine or asking the hotel to do laundry for me! I will never travel without them.

On that weird allergy front, I’m also allergic to off-gassing plastic which was a problem because I needed new luggage and everything at T.J. Maxx smelled like plastic. I ended up buying two hard-back (my preference for luggage) suitcases from Trips 2.0 at Macy’s and I LOVE THEM! Since I was able to sniff them in person, I knew they were already off-gassed and they held up in a lot of intense travel.

Oh my gosh and I also used the best carry-on I have ever owned. It is Props, a roller bag that has built in legs so no need for a luggage stand and it can double as a desk or side table. I was so happy to meet inventor Maggie Gerth this summer and give her new suitcase a real-life travel test. Maggie just emailed me that the price on the suitcase has been lowered to $399 plus you can save 10% more with code: dreamofitaly This is a bag you will have for life and perfect for business travelers!

If you follow me on Instagram, you already know I had a lot of luggage. After all, I was going for two months, filming a TV show during two different seasons of the year and was bringing some things for my dog. I decided to ship most of my suitcases with Luggage Forward and man was it worth it. They deliver door-to-door and on the way, it took about a week, for the return shipping it was only four days. I will continue to do this anytime I have more than one bag. Save 5% with my code: dreamofitaly The one caveat is that because of customs restrictions and shipping via cargo so you can’t pack any food products, medicine or electronics. (I had wanted to put my dog’s special dry food in there but couldn’t.)

On the ground in Italy, I always have cash on me. Italy is still a cash economy even though credit cards are more widely accepted than ever. For instance, I went to a chiropractor (all that driving and the luggage I did need to handle) and he only took cash!  If you’re in a store and buying a significant amount, always ask for a discount (sconto) if you’re paying cash. I asked for one in a store where I was using a credit card – I was buying many things and they gave me 10% off. Italians bargain. I also make sure to have multiple credit and debit cards that I’ve called ahead to make sure they work in Italy so that in case one doesn’t work, another will. And in this day and age, there is NO excuse for not using a credit card that doesn’t charge a foreign transaction fee.

Some of the things that I did right:

  • Bringing my dog! I’ve been to Italy I don’t know more than 50 times but this is the first time I brought my dog. Italy is actually much more dog-friendly than the U.S. (I struggle with how true this is when I see so many strays especially in southern Italy though.) You can bring your dog into restaurants, shops, the supermarket, even the Autogrills which was a God send. It was so hot, how could I leave the dog in the car while driving alone? EVERYONE talks to you when you have a dog too!
  • Being kind and gracious to customer service people. This is how I always am but it definitely has its perks. For example, I needed to change my departure date and return date on my plane tickets. Both times, the customer service rep waived the change fees I think simply because I was calm and nice and they understood my predicament.
  • Need to say it one more time – shipping my luggage! My bad back is still thanking me.
  • Making sure my MedJet membership was up-to-date. If you are hospitalized anywhere in the world, more than 150 miles from home, MedJet will fly you back to the hospital of your choice at no cost. This is NOT something included in most travel insurance policies!
  • Trying to always say yes to an aperitivo invitation! This is the before-dinner drink with snacks and an Italian mainstay. On days when I had a big lunch and was ready to go to bed early, I would have this and skip dinner. People often bring friends to aperitivo so you meet new people and it is just so civilized!

Some of the things that I did wrong:

  • Using to expedite my new passport. It was the simple worst consumer experience of my life and I have NOT gotten a refund. They had NINE weeks to get me my passport and kept making excuses and charging me more. I should have – because I had time – gone the old-fashioned route – directly through the U.S. Department of State.
  • Everyone loves to share a Google pin drop for how to find their agriturismo or villa. I only had Apple maps. So when I clicked on the location, it pulled up Google in a browser. What did I not know? It was in WALK MODE! Mamma Mia. Only after hours (it should have taken an hour to get to my destination) of driving on country dirt roads, cursing my brains out and absolutely refusing to go down one super narrow road, I realized my mistake! I could and should write a whole article on map apps, distance and all those roundabouts in Italy.
  • When one gas station wouldn’t take my credit card, I tried to put a 100-euro bill (yes, because gas is so high in Italy, I figured it would be about that to fill up) not looking at the machine that the largest note it would take was 50 euros. There was no staff at that gas station and well I didn’t get my money back NOR get gas. The machine just kept it. Ouch!

— Kathy McCabe