Tips for Organizing Your Travel ✈️to Italy (or Anywhere)

Plus what author Virginia Pye is reading! 📚

A beautiful day on the Palatine hill in Rome. c. Crystal King 2018

That feeling of anticipation that comes when travel is in the future is a slow-blooming excitement. I don’t know about you, but I DO count the days down. For me, it’s a digital widget in Notion that lets me track each passing day, drawing me closer to that next trip. You can create your own countdown here.

I love the planning process, although since I go to Italy once a year, there is a little less chaos in the mix. I know how the systems work, the things that could trip us up. In my mind, organizing a trip to Italy is a blend of meticulous preparation and the willingness to embrace a little spontaneity. You’ll want to map out must-see sights, confirm train times, and book that perfect restaurant—but also leave some breathing room for unexpected moments and curveballs (for example, I really believe everyone should let themselves get lost in Venezia). But alongside the usual itineraries and hotel hunts, here are a few extra details—like dealing with transportation strikes and nabbing the best dinner reservations—that can make all the difference.

I am not a one-city-and-done type of traveler. In my mind, getting to know a city and its people for 4+ days makes for a much richer experience. That takes a bit of planning, however. Before you set everything in stone, do some googling and determine if there are any holidays or special events to be aware of (for example, traveling around Easter or an event like the Venice Marathon or Carnivale can significantly boost your costs, and also the number of other tourists you’ll need to contend with). You’ll also want to take stock of the weather in the month you are going. November is the rainy season in Rome, for example. Also, the weather in Sicily will be drastically different than that of, say, Verona, in the same time frame, so make sure you have a sense of that before you begin packing.

I start by plotting everything out on a spreadsheet just to get a sense of how to manage time. Many museums in Italy are closed on Monday, and often restaurants are closed on Tuesday. In Rome, when everything is closed on Monday though, the Colosseum and Roman Forum are usually open. The spreadsheet lets me spitball the possibilities.

Then I move all the things set in stone into Wanderlog.

Wanderlog is a fantastic tool to plan your trip, save all your tickets, and to share everything with other travelers. I’m planning an upcoming trip in a few months with friends and it’s great to be able to see all our flight information, tour details, train tickets, and restaurant reservations in one place. If you need help planning, you can even tap into their AI assistant for recommendations.

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Transportation Tips—Including Strikes

Italy’s train network is one of the best ways to get around, connecting major cities quickly via high-speed lines like Trenitalia or Italo. Booking tickets in advance through their websites often secures a discounted fare. However, Italy sometimes experiences transportation strikes (scioperi), which can disrupt train or public transit schedules. Strikes are always announced in advance, so it’s wise to:

1. Check Official Updates: Sites like Trenitalia, Italiarail, or local news outlets often post strike schedules.

2. Build a Buffer Day: If your itinerary is tight, a strike could throw off connections. An extra day between major moves keeps stress levels in check.

3. Have a Backup Plan: If trains are canceled, consider buses, hiring a driver, or renting a car for that leg of the journey.

Within cities like Rome, Milan, or Naples, you can often pick up a travel card for unlimited bus, tram, and subway rides if you rely heavily on public transit. Keep your ears open for local or regional strikes, and you’ll be ready to pivot if needed. More on managing strikes here.

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Locking Down Restaurant Bookings
In Italy, food is more than a meal—it’s an experience. For popular restaurants—especially those with Michelin stars or stellar reputations—you’ll want to book ahead, sometimes weeks in advance. Here’s how:

1. Call Directly: Many trattorias still prefer reservations over the phone. If you don’t speak Italian, a quick “Posso prenotare un tavolo per due, per favore?” (May I book a table for two, please?) goes a long way. But don’t worry too much…most people picking up the phone, especially in larger cities will generally speak some English.

2. Use Booking Apps: Platforms like TheFork, Quandoo, or a restaurant’s own website (if they have online booking) can streamline the process.

3. Timing Matters: Italians typically eat dinner later, 8:30 to 9:00 pm or later. Plan accordingly if you’re hoping to dine early. You’ll also need to get used to the 24 hour clock for all your reservations.

4. Be Prepared for Downtime: Some restaurants close in the mid-afternoon for a riposo (break). If you’re hoping for a late lunch, double-check opening hours to avoid showing up when the doors are locked.

If you prefer a spontaneous approach, you can still discover hidden gems by wandering local neighborhoods. Just remember that walk-ins might mean a wait on busy weekends or during peak tourist seasons.

One more tip: Avoid restaurants in touristy areas with a big English menu on a sign outside.

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Strategic Planning Meets Flexibility
One unavoidable truth in Italy: schedules can shift. A beloved museum might close for a special event, a restaurant could take a random Monday off, or a sudden train strike might force you to change your plans. Rather than viewing these twists as trip-ruiners, see them as opportunities. Pack a list of “backup” sights, keep offline maps handy, and stay open to the idea that your favorite memory might come from a serendipitous detour. One great app is Atlas Obscura, which will show you all the weird, strange places around you. It’s seriously a lot of fun and will take you to all sorts of wild, off-the-beaten path areas of a city.

A few final pointers:

• Carry Some Cash: Even in major cities, small shops and cafés might not accept cards. This is especially true in Italy, where a lot of businesses don’t want to deal with credit card fees (or perhaps paying taxes).

• Taxes and Charges

  • City Tax: At hotels or B&Bs, a city tax (tassa di soggiorno) is often paid in cash upon checkout.

  • Coperto: Don’t get upset when you see a coperto, or cover charge on your restaurant bill.

  • Tipping: Don’t worry about tipping, unless you are in a very fancy place, then maybe leave a few euros, as an extra thank you. If you are in a restaurant and the waiters are suggesting/pressuring you to leave a tip, you are choosing the wrong restaurants.

And one last tip. Remember to leave space for the unplanned—because sometimes, the best adventures are the ones you never see coming. Buon viaggio!

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What We’re Reading

Virginia Pye is the author of four award-winning books of fiction, including two post-colonial historical novels set in China, River of Dust and Dreams of the Red Phoenix, and the short story collection, Shelf Life of Happiness. Her most recent novel, The Literary Undoing of Victoria Swann, is a love story to writers and readers, set in Gilded Age Boston. Her essays have appeared in The New York Times, Literary Hub, Publisher’s Weekly, Writer’s Digest and elsewhere. She is Fiction Editor at the literary journal Pangyrus and serves on the boards of the Women’s National Book Association, Boston Chapter. Visit her at: https://www.virginiapye.com.

What I Just Finished Reading:

Milkman, by Anna Burns. An Irish novel told in the entertaining voice of young woman who's one vice is reading books while walking. This habit makes the people of her small town curious about her. They imagine she's involved with a dangerous radical leader of the Troubles. The novel artfully shows the inescapable violence of those times in a unique way.

What I’m Currently Reading:

Jennifer Finney Boylan's latest novel, Cleavage: Men, Women and the Space Between Us. An entertaining, honest account of her life since her transition twenty years ago. I'm friends with Jenny and this book makes clear, once again, her brilliance and her big-hearted perspective.

What I’m Looking Forward To Reading:

I’m excited to read Isola, a new novel by Allegra Goodman. Her last novel, SAM, was a touching story about a contemporary American girl, but this one couldn’t be more different. It’s an historical saga about a young noblewoman in 16th-century France.

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What’s Bringing Me Joy This Week

• OMG this donkey made me laugh like a freak.

pubity

A post shared by @pubity

• Gina at Buon-A-Pettiti shows you how it’s done. My husband loves her channel because she sounds just like his Nonna, who was also from Puglia.

• I’ve been playing a little Avowed when I have a few spare moments (which are scarce these days!). Super fun.

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Thanks for Joining Me

If you love food and love Italy, and haven’t read THE CHEF’S SECRET or FEAST OF SORROW, click the links to learn where to buy your copy! And now you can order my latest, IN THE GARDEN OF MONSTERS!

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