The 10 Commandments for Planning an Italy Trip

Updated 2019.

Buon Anno my fellow Italophiles!

Now, January is a big month in terms of Italy travel. Why? It is when people are planning and booking their trips for the coming year. I’d love to share 10 insights I’ve gained in how to plan ahead for the best trip to Italy imaginable. I call them the “10 Commandments of Italy Trip Planning.” Some are based on common sense, some are based on hard lessons but if you keep them in mind when planning, I know you will have a more enjoyable, more authentic trip.

1. Practice acceptance. “God grant me the serenity to accept that I cannot see even half of what I would like to in any one trip to Italy.” Yup, this is such a tough one, I think we all need a version of the Serenity Prayer. Pick those two or three cities or small areas you MUST see and let the rest go. You simply have to…Italy is so packed with treasure there’s a strong temptation to do too much.

2. Buy your plane tickets now. Flight capacity — especially on non-stop flights from the U.S. — to Italy is limited. If you’re going in summer or aren’t very flexible on dates absolutely don’t wait. Can I guarantee the price won’t fluctuate and maybe go down $100 or $200? No, but that’s rare for high season and that extra money is worth the piece of mind versus paying $500 more because you waited. If you can get anything less than $1,300 roundtrip in summer, that’s a deal. (Tip: Most recently, I’ve gotten the best fares at

3. Remember September is high season. In the 11 years I’ve run DOI, one trend is for sure, September is now one of THE most popular months to go to Italy. Folks feel like they should avoid August and the height of summer and September sounds — and is — lovely. Just remember everyone else is thinking this too, so book your flights and accommodations well in advance.

4. Make it a two-night minimum. I hate hate hate to see proposed itineraries where travelers are changing hotels five times in 10 days. Does that sound like a relaxing Italian sojourn? NO! For this reason, I insist folks stay on one place for at least two nights, preferably three (heck, I’m a fan of renting a villa for a week and doing day trips). You can explore more than one place — say you stay in Bologna two nights but take the train to Ravenna for the day.

5. Do not underestimate travel (and recovery) time. When I look at proposed itineraries, I cringe at how much people expect to pack into just a few days in any one city and they completely forget travel time. So you’re spending day one and day two in Venice and day three you’re going to Rome, don’t expect to see THAT much in Rome that first day. Remember, you have to figure in travel time from hotel to train station, waiting time, actual train journey, travel from train to new hotel, a tiny bit of a rest. Well, you’re not ready to see Rome till 3 or 4 p.m.

6. Pre-book but don’t get crazy about it. If you’re on a tight schedule and it is high season, then go ahead and buy your train tickets, certain museum tickets and even restaurants ahead. The extra money (and time savings) can be worth the peace of mind. Unless you’re going to a Michelin-star place, calling a week or two ahead should be fine to secure a spot at a restaurant you can’t miss. Some sources for site tickets include and

7. Plan around special festivals and events. No one does local festivals and musical concerts like the Italians do. So do some research to include some in your itinerary. If you’re going in the summer, you’re in luck, there are more festivals and events than you can imagine.

8. Get a tour guide. No, you don’t need one everywhere and if you are limited in your funds to hire a guide, skip one for museums (you can get an audio guide) and hire one for the ancient ruins especially. A great guide can truly make you feel like you’ve stepped back in time and give you the context you can never get from a guidebook or app. Plus you don’t have to get a private guide, you can join a small group walking tour. How to find one? We have a list of more than 70 of Italy’s best tour guides — all over the country.

9. Get to know the locals. The magic of a trip to Italy isn’t just the beauty of the country but the amazing Italians, themselves. The pages of Dream of Italy are filled with experiences to bring you into the local fold. One of our favorites is Home Food, where you can have dinner with English-speaking locals. Learn a little bit of Italian and use it — Italians truly appreciate any effort.

10. Embrace the fact that you will get lost. Whether you’re in the city or countryside, you’re going to get lost — no matter how good your GPS (and we highly recommend one) is. But the great thing is that getting lost is amazing! It might be the only way you will come across that hidden vineyard where you stop for some wine or the most beautiful secret courtyard. I remember being so lost driving out of Naples that I ended up in a very, very seedy area. It was nerve-wracking but my reward was seeing a rainbow that I still remember six years later.

Photo by Gary Ashley,