Positano landscape views--tips & tricks for traveling to Italy as first timers. 3 days in Positano.

7 Tips & Tricks for Traveling to Italy as First Timers

Traveling to Italy as first timers can be both exhilarating and frightening. When I first began planning our trip, I honestly had no idea where to begin. We wrestled with the idea of booking with a travel agent, but I ultimately decided to take on the task. Now that we’ve returned from our trip, I wanted to share some tips & tricks, all in one place, that I learned while planning and throughout our travels.

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7 Tips & Tricks for Traveling to Italy

1. Book Accommodations 8-12 Months in Advance

I can’t stress this enough, BOOK EARLY! I was able to book our accommodations 9 months before our trip. When I looked up the same room closer to our trip, the prices had doubled or more. Booking early also assures you have a room at your desired hotels.

When we booked, we weren’t asked to pay anything up front, either. While they did require our credit card to reserve our rooms, we would only be charged if we cancelled within a certain time frame or of course, upon our arrival. This gave us some peace of mind considering we were booking something so early, though, you should always purchase travel insurance.

2. Travel During Shoulder Seasons

Italy’s peak season tends to be mid June-August. By going in April, May, or even September, you can usually expect slightly lower prices and fewer crowds.

In addition, the weather should still be great during the shoulder seasons. Oddly enough though, we experienced more rain and cooler temps during our visit the first week of May. The locals assured us though that the weather we were experiencing was not typical.


3. Notify Hotels of Any Special Occasions

When I was first planning our trip, a friend gave me this tip. When making your reservations, if you’re celebrating a special occasion, let them know!

We happened to be traveling to Italy to celebrate our 10 year anniversary. I made notes of this to two of our hotels and one of our dinner reservations. When we arrived in Sicily, the hotel staff at Atlantis Bay had a tray of sweets in our room, along with a bottle of local liquor. At our dinner reservation we were welcomed with Prosecco. And finally, our hotel in Positano also gifted us a bottle of Prosecco and allowed us to enjoy it on the terrace as they served us numerous appetizers.

4. Book Taxis in Advance

I know everyone wants to save money when they travel, but take it from me and spend the money to book your taxis in advance. Especially as a first-timer, I feel like pre-booking your taxis just adds a little more safety.

I was able to communicate with our drivers via WhatsApp and if we were meeting at an airport/train station, they had a sign with our name. They were also always early and never left us waiting.

John and Brittney Naylor taking a selfie in front of one of the seven wonders of the world, the colosseum in Rome, Italy. 36 hours in Rome, tips & tricks for traveling to Italy as first timers

5. Make Meal Reservations in Advance

Most of our trip in Italy was well curated and planned. I had every meal reservation and activity planned. But, I failed to make any reservations in Rome. Since I waited until we were in Rome to make any reservations, all of our top picks were booked.

I suggest creating a list of restaurants you want to dine at in each city you visit. From there, check out their Instagram or website. This will usually prompt you as to how early you can make a reservation, when reservations for your travel dates become open, or if they’re already booked. We booked most of our reservations 2-3 months before our travel dates. Since we were also traveling during shoulder season, we didn’t have any issues booking what we wanted. However, if you’re traveling during peak season, you may want to make reservations earlier.

6. Don’t Forget to Ask for the Bill at Restaurants

We learned this our first night, but if you don’t ask for your bill, you’ll likely be waiting until you do. You may also notice that the wait staff doesn’t check in as frequently as you would expect in the United States. Which isn’t necessarily a bad thing, just know if you need something make sure to let them know when they stop by, otherwise they may not come around for another 15-20 minutes.

7. All Dining Will Include a Coverage Charge

Somehow during all my planning, I never came across anything that talked about a coverage charge (coperto). After having our first several meals in Italy, we quickly realized each meal included a coverage charge. Typically the cost was between €2 to €4 per person. This charge covers things like bread, oil, and utensils.

In addition, it’s not customary to tip in Italy. If you feel you received exceptional service, then you’re more than welcome to leave a tip. Usually, we would just round up to the nearest euro rather than wait for change.


Planning a trip or even traveling through Italy can be a daunting task. But with these tips & tricks at hand, I hope you’re better prepared to embark on your own Italian adventure. Enjoy every second, savor every bite of pasta, and soak up Italy’s charm. Safe travels! 

As always, don’t forget to follow us on Instagram for the most up-to-date travel adventures.

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7 Tips & Tricks for Traveling to Italy as First Timers from A Mom Well Traveled Blog

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