Anyone who has seen Roman Holiday, Summertime, Room With A View or Under The Tuscan Sun has dreamed about a trip to Italy!
I went on my first trip to Italy 40+ years ago and I will never forget all of my “firsts”: seeing iconic buildings like the Colosseum, walking onto the Piazza San Marco in Venice at sunset, standing in front of the David in Florence.
And, of course, my first gelato!
I wish I had a dollar for every person who has asked me to help them plan their first trip to Italy. The answer is simple: don’t try to see it all!
What's Your Passion?
I always start with a needs assessment to understand what kind of traveler you are:
- Do you prefer cities or small towns?
- What kind of pace are you looking for? Total relaxation? Sightseeing? Or a bit of both?
- Do you like museums? Art? History?
- Is food important to you? Wine?
- Are you a beach person? A golfer? A hiker?
- Are you comfortable traveling by train?
- Have you ever driven in a foreign country?
- Do you like small inns and B&Bs or do you prefer a larger American-style hotel?
- How many days do you want to spend in Italy?
Note: And never tell me one week! No trip to Italy should be less than two weeks! You lose two days just traveling!
But most importantly, when you think about Italy, what have you always dreamed about seeing?
Next Stop?
Based on the answers to these questions, I formulate an itinerary.
For people who want to see “the majors” I typically design an itinerary of Rome-Florence-Venice, with a one-day trip from each major city (two-day trips if they are staying longer).
Rome with Day Trip to

Orvieto
Orvieto, perched atop a hill in Italy's Umbria region, is famed for its stunning Duomo, a Gothic architectural marvel with a mosaic-adorned façade.

Pompeii
Pompeii, the ancient Roman city frozen in time by the eruption of Mount Vesuvius in 79 AD, offers tourists a fascinating glimpse into ancient life through its well-preserved ruins and hauntingly vivid frescoes.
Florence with Day Trip to

Siena
Siena, a jewel of medieval architecture in Tuscany, is celebrated for its fan-shaped central square, Piazza del Campo, renowned for hosting the thrilling Palio horse race, and its magnificent Duomo, a masterpiece of Italian Gothic architecture.
Venice with Day Trip to

Padua
Padua, a charming city in the Veneto region of Italy, is famed for the Scrovegni Chapel adorned with Giotto's breathtaking frescoes, its historic university where Galileo once taught, and the lush Prato della Valle, one of Europe's largest squares.
There are many more day trip options; too many to list here!
Beach, Foodies and Townies
If they are beach people, I typically recommend starting in Rome and then visiting the Amalfi Coast and/or Ischia.
For foodies, after a few days in Rome head up north to Emilia Romagna to visit Bologna, Parma, and Modena.
And for people that love small towns, either Tuscany (Montepulciano, Lucca, Arezzo, etc.) or the Veneto in the north (Padova, Verona, Vicenza, etc.).
The Road Less Traveled!
For more seasoned travelers who’ve seen the majors, I always recommend Umbria, Puglia, and, of course, my beautiful Sicily (that will be a separate post!).

Italy has 20 regions. I’m still working my way through the country and I’ve been there numerous times!
Italy is a feast for the senses: seeing the beauty of the art and architecture, the aroma of the food and freshly baked bread, the taste of the delicious wine, pasta, gelato, and well everything!
Take your time. Savor every moment. Sit in a café in the piazza and people watch while sipping an aperitivo.
We have an expression: la dolce far niente. The sweetness of doing nothing!
There is no place better on earth to experience la dolce vita (which also happens to be another wonderful Italian movie!)
Ci vediamo!
Our site contains links to products and services, which may provide us with a commission. Prices provided are up-to-date when posted. As an Amazon Associates, we earn from qualifying purchases.
Share this post:
Author
-
Fran is a proud Italian-American and dual-citizen, splitting her time between NYC and Italy. Her passions are family, friends, food and faith + theatre and travel. (And finding the perfect Manhattan). Fran’s treasured memories are centered around breaking bread with her loved ones and feeding an appreciative audience (literally and figuratively). Fran started her career on the stage but traded it in early on for a successful 40 year run in corporate America. She always says the best part of that experience is the life-long friendships made over the years.
View all posts
Love Ms Frannoli! I’d travel anywhere on the planet w/you!
Ditto! You must come back to Sicilia now that I know where I know where all the good cannoli are!