How to Plan for a Trip to Italy
Where do I start to plan a trip to Italy? Help!! Should I hire a travel consultant? Should I join a tour group?
We say, “No!” Save your money!! You can do this! Here are 5 Easy Steps to Plan a Trip to Italy in 2024/2025:
Step 1. Decide: When do you want to go? What kind of traveler are you?
When is your vacation? When can you go? Would certain months be more advantageous to YOU?
If you have no constraints, the “shoulder months” typically have the mildest weather, and less tourists. These months include May, September, and even October. Set your dates.
How long can you stay? For most people, these are expensive airline tickets, so stay long enough to see all the sights you want to see and to make your stay worthwhile. We usually stay at least 2 to 2 and 1/2 weeks.
Do you like a laidback day? Or are you a “go-go-go” kind of person? Or a combination of both? If you are happy to be busy everyday, great. Otherwise, be sure to schedule in time for wandering and relaxing.
Step 2. Develop an Itinerary.
Is this your first time in Italy? If so, you might want to include Rome to see what I call the Big Three: the Vatican and St. Peter’s, the Colosseum, and the Trevi Fountain. How many days for this? Three days or more if you like.
Other choices are endless: What cities do you want to see? What sights are non-negotiable for you? Do you want to see Michelangelo’s David in Florence, the Leaning Tower in Pisa, Venice’s gondola’s and canals, the hilltop villages of Tuscany,
the Amalfi Coast, the home of St. Francis of Assisi? Schedule at least two or three days at each stop, so you can get a good idea of the city, its sights, its people, and its culture.
HINT: Train connections are quite easy in Italy between big cities (Venice/Florence, Rome to Florence or Venice or Milan, Milan to Rome or Florence or Venice.) Renting a car is needed to travel to Tuscany and will make life easier in Assisi.
Here are our sample itineraries
Fly into Rome. Three days in Rome, pick up car and drive to Assisi for a two day stay, three days in Tuscany, two days in Florence. Check in car upon arrival in Florence. Train to Venice for three days. Fly home.
Step 3. Book transportation.
Now is the time to book those flights and rental cars, and schedule trains as well.
Flights. We suggest that you stick to one carrier for the purpose of accumulating points for future travel. Check to see which cities your carrier flies into. We fly United and its partners exclusively, and like to fly into either Rome or Venice.
Rental Cars. Though in the US we may sometimes use Priceline or Expedia to get a better deal and many people may tell you to go with European companies, when traveling internationally we stick to Budget, a trusted U.S. company, and have had the best luck in every location.
We like the freedom to choose our own hours and destinations that a rental car provides. If going to Tuscany, a car is a must-have.
Trains. Though you may have good luck buying tickets from a kiosk, I like to have my tickets in hand and paid for before I even leave the U.S. The company we use is Italiarail, available at www.italiarail.com. Seats are usually available about six months in advance.
All communication is in English, and you can choose the class of car you want (If you have more luggage, you might consider reserved seats in first class). See the differences in prices and choose accordingly, then you can choose your seats and pay. Be sure to purchase refundable tickets in case you have a change of plans. Hint: Also print your tickets as wi-fi may be questionable on the train.
Step 4. Book hotels.
Reviews and recommendations are key here. Where do you find these reviews? I have faithfully used Trip Advisor (only booking hotels that have a “Traveler’s Choice Award”, which means it meets a high standard of reviews). I also use youTube videos, and guide books such as Frommer’s or Rick Steves.
Hint: I always check the best reviews and also the worst. Why was it the worst? Was it because of a cranky desk clerk, or was it because of bedbugs? Quite a difference there!
Then I look at the locale and price.
If you have anyone traveling with you that has mobility issues, you may want to book a more centrally located hotel, for ease of visiting sites and maneuvering transportation.
I love Booking.Com. Their prices are always competitive and it is so easy to adjust your dates/times or even cancel. When planning an international trip, I suggest always booking the refundable option to account for glitches along the way.
For our 2024 trip, we are booking:
In Rome: Doubletree by Hilton Rome Monti. Why? We want to explore the Monti neighborhood, and this hotel gets great reviews and as a bonus, it comes with Hilton points.
In Florence: Hotel Pendini. Why? We want to be centrally located, we need elevators, and this hotel is Frommer and Trip Advisor recommended. Pendini turned out to be a fabulous hotel.
In Tuscany: La Casa di Adelina in Monticchiello. Why? The host, Francesco, makes gourmet breakfasts every day served on colorful Italian pottery dishes. This will be our third time booking with him. Nestled in the incomparable Val D’Orcia, this home base is easy access to the heart of Tuscany.
If you add Assisi on the way to Tuscany: Hotel Ideale. Why? Great reviews, great breakfast, free parking, and easy access to all of town. We have stayed with Laura and her family three times.
In Venice: Hotel Firenze. Why? Great reviews and steps from St. Mark’s Square.
Step 5. Book Experiences.
For the main attractions you want to visit, booking tickets in advance is an absolute must. For example, the line around the Vatican Walls to get into the Vatican (Probably standing in the hot sun) takes hours. The same for St. Mark’s Cathedral in Venice, or the Accademia Museum to see Michelangelo’s David in Florence. Why spend your precious time in line, when it is so easy to book ahead?
If you would rather book a group tour, I love the ones that Viator offers. Again, they are easy to communicate with and are flexible.
Here are a few we are booking with them, and those we have booked in the past:
VATICAN/ST. PETER’S: Complete Early Morning Vatican Tour/ Small Group
VIP Vatican Breakfast with Guided Tour & Sistine Chapel
COLOSSEUM: Colosseum Arena Floor, Roman Forum, and Palatine Hill Guided Tour
Colosseum and Roman Forum by Night.
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