How to plan a trip to Italy on your own

What are the best mountains in Italy?

If you’re headed to Italy for a hiking trip, you are in the right place.

• The Dolomites (South Tyrol): Known for their distinctive limestone peaks, the Dolomites are popular for skiing in winter and hiking in summer. The region also has a unique culture and great food.
• Monte Bianco/Mont Blanc (Valle d'Aosta): The highest peak in Western Europe, offering dramatic views and challenging climbing routes.
• Gran Paradiso (Piedmont): Italy’s first national park, home to wildlife like ibex and chamois, and offers excellent hiking trails and alpine lakes.
• Monte Rosa (Piedmont/Valle d'Aosta): The second-highest peak in the Alps, perfect for hiking and climbing with views into Switzerland.

What are the best hidden gems in Italy?

Italy’s smaller towns often feel more authentic than the bigger cities. Take Civita di Bagnoregio in Lazio, for example — it sits on a volcanic plateau, only reachable by footbridge, and gives you a real sense of medieval Italy.

In Umbria, Spello is a quieter alternative to Assisi, with its Roman gates and Renaissance frescoes. Then there’s Matera in Basilicata, famous for its cave dwellings, which has earned UNESCO World Heritage status. Bergamo, in Lombardy, is also worth checking out—it's got two distinct areas: Città Alta, the medieval old town, and Città Bassa, the more modern lower town, connected by a funicular.

Step 3: Start your booking with the basic components

When to start: at least 5 months before

Booking your main travel components early helps you spread out the cost of your trip and ensures you get the best options before they’re sold out. Popular flights and hotels tend to have flexible cancellation policies, so it’s often better to book sooner rather than later—just double-check the terms first.

At this stage, you'll want to book:

• Plane tickets / transportation
• Accommodation

How to save on plane tickets

I’d say the sweet spot for booking flights to Italy is about 4 to 6 months ahead of time. Flights on Tuesdays, Wednesdays, and Saturdays are typically cheaper. If you’re planning to visit a few cities, consider flying into one (like Rome) and out of another (say, Venice). This way, you can avoid backtracking. Major airports in Italy include Rome Fiumicino (FCO), Milan Malpensa (MXP), and Venice Marco Polo (VCE).

Use flight trackers like Google Flights or Skyscanner — they’re great for setting up alerts that can help you snag a deal. Setting those alerts really can save you money.

How to get to Italy from the US

Direct flights to Italy depart from major hubs like New York, Chicago, Miami, Los Angeles, and Atlanta. The flight will take anywhere from 8 to 13 hours, depending on where you’re flying from.

If you don’t mind a longer trip, think about adding a stopover in a city like London, Paris, or Amsterdam. Sometimes it can lower your fare, and it gives you a chance to explore another place while you're at it. 

Where should I stay?

In the bigger cities like Rome, Florence, and Venice, you'll find all kinds of accommodations, from budget to luxury. But location really matters—staying within walking distance of major attractions saves you time and money on transport. Here are some areas I recommend:

• Where to stay in Rome: Centro Storico, Trastevere, Monti 
• Where to stay in Florence: Santa Croce, Santo Spirito
• Where to stay in Venice: San Marco (a bit pricey but super convenient), Dorsoduro, Cannaregio
• Where to stay in Milan: Piazza del Duomo, Navigli, or Brera

If you're looking for something unique, Agriturismo (farm stays) could be perfect. These are working farms that offer accommodations, often in scenic areas like Tuscany, Umbria, or Sicily. Many of them serve fresh meals made with local ingredients, and they might offer activities like cooking classes or wine tastings. This is a great way to travel sustainably.

Step 4: Start planning your activities

When to do this: at least 4 months before

Popular attractions in Italy can get booked up quickly, especially during the busy seasons. You don’t have to plan every activity or day in advance, but making sure you prebook some things (like tours) will help so you don’t miss out on the big ones.

Decisions to make:

• What attractions need advance booking?
• What are the best vineyard tours?
• What day trips are worth taking?

What attractions need advance booking?

If any of these locations made your list, know that early booking is essential for these popular sites:

• Vatican Museums and Sistine Chapel (Rome): Try to get tickets for first thing in the morning or late in the afternoon to avoid the crowds. The Museums are free on the last Sunday of each month, but be prepared — it gets really crowded. Booking a tour can help you skip the line.
• Uffizi Gallery and David at Accademia (Florence): If you want a quieter visit, go for the first entry slot (8:15 AM). Also, keep in mind the Uffizi is closed on Mondays.
• Colosseum and Roman Forum (Rome): Your combined ticket is good for 24 hours, but if you want to see more, consider booking a guided tour that takes you into the underground areas.
• Last Supper (Milan): Tickets go on sale 2-3 months ahead of time, and they sell out fast—only 30 people are allowed in every 15 minutes, so grab yours early.

What are the best vineyard tours?

Italy's wine regions are full of character, each offering something special. If wine tasting is high on your list, be sure to see our guide to planning the perfect wine tour.

If you’re in Tuscany, don’t miss a visit to Castello di Brolio, one of the oldest estates in Chianti, known for its stunning views and top-tier wines. Another great stop is Antinori nel Chianti Classico, a modern winery with deep roots in Tuscany’s wine history.

In Piedmont, the Barolo and Barbaresco regions are world-renowned, and you can visit the family-run Marchesi di Barolo for a taste of some of the area’s best wines.

For something unique, head to Sicily and explore the volcanic vineyards of Planeta on Mount Etna, where the soil gives the wines a distinct flavor.

What day trips are worth taking?

Having a base in the city and exploring from there is nice because you don’t have to bring all of your luggage with you. Here are some of my favorites:

• From Florence: San Gimignano, with its medieval towers, and Siena, with its historic charm, are both great day trips through the Tuscan countryside.
• From Rome: You can’t miss Pompeii’s ancient ruins or the preserved streets of Herculaneum, both offering a fascinating look at Roman life. If you’re craving coastal views, the Amalfi Coast is just a short trip away.
• From Venice: Head to Murano to check out its famous glassmaking or Burano to admire the colorful houses and lace-making tradition.
• From Milan: Villa del Balbianello on Lake Como is a beautiful spot with stunning gardens and some Hollywood film history. Take an early train to make the most of your day.

Step 5: Let’s talk food in Italy

When to do this: 3-2 months before until up to your trip

If you’re anything like me, very top of my list is seeing what food I can try. You could build an entire trip around taking a food tour of Italy. 
Italian cuisine is all about regional pride, and you’ll notice that each area sticks to its culinary traditions. Traditional meals are often structured in courses: antipasto (appetizers), primo (pasta or rice), secondo (meat or fish), contorno (vegetables), and dolce (dessert).

Decisions to make:

• How do I book the best restaurants?
• What is the best food in Naples?
• What is the best food in Bologna?
• What is the best food in Piedmont

How do I book the best restaurants?

For popular restaurants, especially Michelin-starred ones, booking 2-3 months ahead is crucial. I recommend using TheFork app (the Italian version) for hassle-free reservations, or you can always email the restaurant directly. Keep in mind that Italians usually eat lunch between 1:00-3:00 PM and dinner from 8:00-10:30 PM, with many places not opening for dinner until 7:30 PM.

What is the best food in Naples?

Naples is where pizza was born, and the art of pizza-making (pizzaiuolo) is so significant it’s UNESCO-listed. True Neapolitan pizza must follow strict rules: hand-kneaded dough, cooked in a wood-fired oven at 485°C for no more than 90 seconds. And it’s not just pizza here. Naples is also known for spaghetti alle vongole (spaghetti with clams), ragù napoletano (a rich, slow-cooked meat sauce), and mozzarella di bufala.

Where to eat in Naples?

• L'Antica Pizzeria da Michele: Dating back to 1870, this pizzeria serves just two types of pizza — marinara and margherita—and they do them to perfection. The margherita here is the definition of simplicity done right.
• Tandem Ragu: A tiny spot dedicated to Naples’ iconic ragù sauce. Their pasta al ragù, cooked for at least 8 hours, is a must-try.

What is the best food in Bologna?

Bologna is so famous for its food, it earned the nickname “La Grassa” (The Fat One). The city is known for its fresh egg pasta, a tradition dating back to the Middle Ages. Tortellini, which are believed to be inspired by Venus’s navel, is one of Bologna’s signature dishes. And the true Bolognese ragù simmers for at least 4 hours, using beef, pancetta, and very little tomato — definitely not like the spaghetti bolognese you know from the international menu.

Where to eat in Bologna

• All'Osteria Bottega: Anthony Bourdain’s Bologna pick. Hidden away from the tourist crowds, this place serves extraordinary platters of culatello and mortadella, plus seasonal mushroom dishes during porcini season that are unforgettable.
• Trattoria Anna Maria: Watch the sfogline (pasta ladies) hand-roll pasta through the window, then enjoy their legendary tortellini in brodo. Anna Maria has been hand-making pasta since 1985.

What is the best food in Piedmont 

Piedmontese cuisine feels aristocratic yet deeply connected to the land. The House of Savoy and the region’s agricultural heritage shaped it, and it’s known for being some of the best food in the world. Piedmont’s signature dishes include vitello tonnato (tender veal in a creamy tuna sauce) and carne cruda (raw beef dressed with olive oil and truffles). And the region’s Barolo wine, made from Nebbiolo grapes, features in many dishes, like brasato al Barolo (wine-braised beef).

Where to eat in Piedmont

• Da Renzo (Cervere): This traditional Piedmontese restaurant, run by the Beglia family since 1954, serves classics like cardoon gratin with fonduta sauce and tajarin with butter and white truffles—simple elegance.
• Centro Storico (Serralunga d'Alba): A wine bar and restaurant with over 60,000 bottles in the cellar. They serve perfect vitello tonnato and raw Fassona beef, paired with rare Barolo vintages, in a relaxed atmosphere that feels like home.

Truly, I could go on forever about the food in Italy, but if you’re wanting to read more, don’t miss our guides to the best foods in Florence, or our Foodies Trip Plan.

Step 6: The nitty gritty details

When to do this: 3 months before at least

It’s best to start handling these tasks about three months before your trip. That gives you enough time to sort out your passport, any necessary visas, and other important bookings and documents.

Decisions to make:

• Travel insurance
• How do you stay connected?
• Other details to check

Travel insurance

Travel insurance is definitely something you’ll want for Italy. Healthcare can be expensive, and trips don’t always go as planned. Look for a policy that covers medical emergencies, trip cancellations, and lost luggage. Some credit cards include basic travel insurance

How do you stay connected?

WiFi is available in most public places in Italy, but it’s not always reliable. To stay connected, I recommend getting a local SIM card or eSIM. SIMCorner, a trusted Rough Guides partner, offers good options without the risk of high or hidden costs. They work with top telecom providers and offer contract-free plans, so you can pause your plan when you’re not using it—super flexible and simple.

Other details to check

Check that your passport is valid for at least three months beyond your planned departure date. If you need a Schengen visa, make sure you get that in time, and be sure to make copies of your important documents. Italy uses type C and F plugs (230V), so grab the right adapter if needed. You might also want to look into museum passes like the Roma Pass or Firenze Card — they can save you money and skip-the-line access if you’re planning to visit a lot of sights.

Step 7: Get ready for take off

When to do this: one week before

With everything in place, really what’s left is packing. You want to gather all booking confirmations and make both digital and physical copies. 
I find making a Google doc with my day-to-day itinerary with confirmation numbers and addresses can be super handy, and easy to share with a group.

Decisions to make:

• Do I need to bring cash?
• What should I pack for Italy?

Do I need to bring cash?

While cards are widely accepted, cash can still come in handy. Small restaurants, taxis, and local markets often prefer cash, so it’s a good idea to carry around €100-200 in smaller bills. For cash withdrawals, use ATMs attached to major banks instead of airport exchange counters. 

Make sure to notify your bank ahead of time, and if possible, use a bank like Charles Schwab, which reimburses international ATM fees. Some smaller towns might have fewer ATMs, so it’s worth planning ahead.

What should I pack for Italy?

If you want to blend in, Italians tend to dress smart. One thing you definitely should think about is bringing a day bag or cross body bag that has some kind of anti-theft element. Pick pocketing is very common, especially in places like Rome. They can be very clever! Be sure to keep your phone and wallet somewhere safe.

If you’re going to any major churches like the Vatican, you’ll want to bring something that covers your shoulders.

Always leave some space in your luggage, Italy is known for great souvenirs.

Planning a trip to Italy with seniors

Italy’s historic cities can be tricky for seniors, especially with uneven paths at places like Pompeii and Ostia Antica or the cobblestone streets in cities like Rome and Florence. But many places are becoming more accessible — like the Roman Forum, which now has a barrier-free route, and the Vatican Museums, which offer wheelchair services. 

When it comes to where to stay, it’s a good idea to book somewhere central, like the Pantheon area in Rome or San Marco in Venice. It might cost a bit more, but it saves you from long walks or complicated transport. Also, many historic buildings are now hotels, but make sure to ask for a room with elevator access, as some only have stairs. All in all, planning a trip to Italy with seniors can be a fantastic experience for all.

Planning a Italy family vacation with kids

Italy is a great spot for families, especially with so many hands-on activities. You can try gladiator school in Rome or mask-making workshops in Venice — both are great fun for kids. To break up museum visits, consider interactive things like climbing the Duomo in Florence or checking out the catacombs in Naples. 

Skip-the-line tickets will help avoid the long waits, and you might want to book a private guide who’s good at keeping kids engaged. For more active kids, parks like Villa Borghese in Rome offer bike rentals and boat rides.

How can I save money planning my trip to Italy?

Traveling during the shoulder season (April-May or September-October) is a smart way to avoid crowds and get better prices in Italy. You might also want to base yourself in less touristy cities, like Bologna or Verona, and take day trips to the main attractions. When booking accommodations, check out quieter residential areas rather than staying in the heart of the tourist zones.

To save on museums, look out for free days (usually the first Sunday of the month) or consider a city pass. For meals, try the local routine: have a light breakfast at a bar (standing), go for a big lunch with the “menu del giorno” (which tends to be cheaper than dinner), and stop by an aperitivo bar where drinks often come with a small buffet. Also, using a credit card with no foreign transaction fees and good travel rewards can save you a bit too.

Planning a trip to Italy with experts

If you’re head is spinning from information, you’re not alone. Figuring out these details takes hours of research and planning. With our tailor made trips, you can go on a trip custom designed for you by a local travel expert who knowns the ins and outs of the area. You’ll also have support 24/7 during your trip.

Take your time and remember to enjoy

It’s easy to feel the pressure to rush through all the must-see attractions, but some of the best parts of Italy come from those quiet moments when you slow down. Now that you’re all set, let go of the need to check off every box and focus on enjoying the experience — truly the best thing to do in Italy. If you’re looking for inspiration, see our trip ideas gallery.