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Trip Planning for Italy: Why Not to Let AI Plan Your Italy Vacation

Updated: Mar 13

trip planner italy

I keep hearing about people trying to use Chat GPT and other AI tools as a trip planner for Italy with little effort. I decided to try it and discovered advice that made me laugh, groan, and scream at my screen a few times. The scary thing is first-time visitors couldn’t possibly know just how bad the advice is! Read on to see what our robot overlords are telling you to do paired with reality checks from twenty-plus years of experience planning trips to Italy.

How To Start Planning Your Italy Itinerary

AI says: Before you delve into the details, start with a broad vision for your trip. Italy is diverse in its landscapes and experiences, so consider what you want to see and do. Do you dream of wine tasting in Tuscany, exploring the ancient streets of Rome, or cruising the Amalfi Coast? Begin by listing down your must-visit destinations and potential activities. This initial step forms the backbone of your travel plans to Italy.

Tool Tip: Skyscanner – Use this to find the best flight options and monitoring prices for your chosen dates.

Reality check: Most people won't know that Italy only has two international airports -- Milan and Rome. Skyscanner will search for the cheapest route, often sending you through smaller regional airports like Pisa, with unusual connections, lots of opportunities to lose your luggage, and a lack of taxis upon arrival. You may save a few bucks on the flight itself, but a taxi from Pisa airport to Florence will cost far more than a fast train from Rome to Florence.

Instead, simplify your route by making any necessary connections in your home country to get a direct international flight to Rome or Milan. In high season, you will find direct flights from Philadelphia and Newark to Naples and a few direct flights to Venice, but overall, finding the best price for a flight should not always be a top priority because you will likely spend much more on correcting the pitfalls of an unusual route.

Italy vacation itinery

How to Craft Your Italy Itinerary

AI Advice: A well-thought-out itinerary is key to a successful trip. Italy's extensive and efficient transportation network makes traveling between cities quite straightforward. However, to make the most of your time:

  • Prioritize your destinations: Focus on a region or select cities to avoid spending too much time in transit.

  • Allocate time wisely: Larger cities like Rome and Milan require more time to explore, while smaller towns like Siena or Cinque Terre can be enjoyed in a day or two.

  • Consider travel time: Always factor in the time it takes to travel from one place to another.

Tool Tip: TripIt – This app consolidates all your travel plans in one place, making it easy to visualize your itinerary and stay organized.

Reality Check: Oh my, my blood pressure is starting to rise. First, Cinque Terre is not a small town but a series of five villages inside a national park. They are also one of the most crowded destinations in all of Italy. The Cinque Terre are the poster child and the cautionary tale of over-tourism and how the cruise industry is crushing parts of Italy.

Siena is a smaller town than Florence, yes, but it is also very crowded, especially with day trippers, and intolerably so during the high season. One good piece of advice here is TripIt, as I like to have all my need-to-know information in one place.

Also, how awful the above AI-generated artwork is!

How to Book Accommodation and Logistics

AI Advice: When it comes to accommodations, Italy offers a range of options, from luxury hotels to charming B&Bs. Booking in advance is advisable, especially during peak season. Also, consider:

  • Location: Staying centrally can save time and money on transportation.

  • Amenities: Decide what's important – free breakfast, Wi-Fi, proximity to major attractions, etc.

Tool Tip: Airbnb or – Both offer a variety of lodging options with detailed descriptions, photos, and reviews from travelers.

Reality Check: One of the most frequently asked questions I receive during Trip Consultations is whether to choose an Airbnb or a hotel. The most important thing to remember about Airbnb or VRBO is that these are platforms, not brands. That means each one of the listings is like its own small business, and you need to be very careful about reading reviews.

You also can’t assume that a home in Italy has the same features as an American home. You won't find it in an apartment or home rental if you’re used to cold air conditioning or a dryer. If you rent a villa in the countryside from Airbnb, remember you’ll need to go grocery shopping. And if the price seems too good to be true, look to see that the price includes linens and towels. Many European travelers who drive to Italy bring those things with them to cut down on costs.

Apartment rentals often make a lot of sense for families or people navigating dietary restrictions who would prefer not to eat out for every meal. But the services and guarantees that come with a hotel, plus the advantage of a front desk or concierge who speaks English, are invaluable.

italian cuisine and robot

How to Experience the Best of Italian Cuisine

AI Advice: No trip to Italy is complete without indulging in its culinary delights. Italian cuisine varies greatly from region to region. Embrace this diversity by trying local specialties and wines wherever you go. Remember, in Italy, dining is an experience, not just a meal.

Tool Tip: TheFork or Yelp – Discover the best local restaurants, read reviews, and make reservations.

Reality Check: This may be the worst piece of advice so far. If you’re reading reviews of Italian restaurants on Yelp or TripAdvisor in English, you may be taking the advice of someone who has only ever had Italian food at the Olive Garden.

Italians use Instagram to find good local restaurants. Better yet, use Google Translate to read the best-of-restaurant reviews by Made in Italy. When it comes to food, trust Italians, not robots.

How To Choose Must-See Attractions and Hidden Gems

AI Advice: Your itinerary should include a mix of popular sights and off-the-beaten-path experiences. While the Colosseum and the Vatican are unmissable, Italy is also full of hidden gems waiting to be discovered. Research lesser-known attractions and allocate time for spontaneous exploration.

Tool Tip: GetYourGuide – Find and book unique experiences and guided tours, often with skip-the-line privileges.

Reality check: The above-mentioned corporate behemoth is an aggregator that takes an enormous commission from the provider. Many smaller companies will work with them to get off the ground, but once they do, they often sever their ties as soon as possible because price aggregators have no respect for the real work of sharing history and culture. If you only care about price and want an aggressively mediocre tour of the Colosseum with a fair chance of being canceled, go ahead and book with them. Or, if you prefer experiences given by passionate professionals who are paid a living wage for their expertise and time, book directly with a tour company like Context Travel. Also, if you're working with a travel agent or advisor who books tours for you on GetYourGuide, fire them immediately.

polite robot

Cultural Etiquette and Italy Travel Tips

AI Advice: Italians are known for warmth and hospitality, but respecting local customs will enhance your experience. Simple gestures like greeting with 'buongiorno' (good morning) and 'grazie' (thank you) go a long way. Also, be mindful of dress codes, especially when visiting religious sites.

Tool Tip: Rome2Rio – This provides comprehensive options for travel between locations, including estimated costs and journey times.

Reality check: Let me tell you about the time I received an email from a stranger who heard me on a podcast, desperate for someone to help her figure out what to do in the small town where she was stranded. How had that happened? She used Rome2Rio. Instead, use Google Maps to estimate distances and for driving directions, and use Omio to get train and bus schedules that actually exist on planet Earth.

Budgeting and Money-Saving Tips

AI Advice: Italy can be enjoyed on various budgets. Here are a few tips to keep your finances in check:

  • Travel during the shoulder season for better rates.

  • Enjoy delicious yet affordable meals at trattorias and pizzerias.

  • Consider city tourist cards for free public transport and access to attractions.

Tool Tip: Trail Wallet – This travel budget app helps you track your expenses and stay within your budget.

Reality Check: This is pretty vague advice, but the takeaway is that you should have a budget for your trip. Don’t carve it up into hotels, food, trains, etc. Instead, know the overall amount you feel comfortable spending, then prioritize the experiences you most want. If your dream is to see the Sistine Chapel, I highly encourage you to spend $450 on a tour where you can enter at 6 am in a group of just 20 people. Trim your budget elsewhere. By prioritizing your experiences and knowing your overall budget, the rest of your planning will more easily fall into place.

Packing Essentials for Italy

AI Advice: Packing for Italy varies depending on the season. Essentials include comfortable walking shoes, a universal power adapter, and appropriate clothing for the weather. Remember, Italians are stylish, so a smart-casual wardrobe will help you blend in.

Tool Tip: PackPoint – A packing list app that customizes what you need based on your travel destination and duration.

Reality Check: Here’s the only packing advice you need: bring less than you think you need, and prioritize neutral colors so you can easily mix, match, and make several outfits from everything in your suitcase. The only single-purpose outfit should be something for a fancy night out -- and only if you have one planned. Also, don’t pack any “costumes” like a lemon-printed dress. It’s a fun idea when dreaming about your trip, but you’ll feel silly wearing it when you’re there.

Most phones and computers will automatically convert the electrical current, so you only need an adapter for the outlet. And don’t bring a hairdryer -- the energy converters can’t handle it. All hotels and many apartments will have a hairdryer available.

bored italian tour guide and robot AI

How To Book Day Trips in Italy

AI Advice: Consider day trips to enrich your Italian experience. Cities like Florence and Rome are excellent bases for exploring nearby towns and countryside. Research and plan these excursions to maximize your time.

Tool Tip: GetYourGuide – Offers a wide range of day trips and guided tours from major Italian cities.

Reality Check: Once again, if you want a tour given by someone who is being extorted by a tech behemoth for an enormous commission and would like to contribute to the death of small business, knock yourself out.

Overcoming the Language Barrier

AI Advice: While English is widely spoken in tourist areas, learning a few Italian phrases can be helpful, especially in rural areas. Language apps and pocket dictionaries are great tools for communication.

Tool Tipl: Google Translate – Useful for quick translations and understanding basic Italian phrases.

Reality Check: Finally, Robot Overlords, some good advice! Also, learn a few key phrases before you go, as it will eliminate a lot of stress when you get lost or need to use the bathroom.


How to Hire a Human Who Speaks Italian to Arrange Unique Experiences in Italy

An Italian family hosting guests for lunch and a winetasting.
Post-lunch at Il Cancilere, a family of natural winemakers in Southern Italy and an experience you can't find online or with AI.

Planning the perfect Italian getaway can be a complex task that the robots cannot do. Our expert trip consultation and planning services eliminate the hassle of organizing your dream vacation. With personalized itineraries, insider tips, and continuous support, we ensure your Italian adventure is seamless, memorable, and tailored just for you.

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