Just Back: A Travel Advisor’s Trip to Italy – Rome, Florence & Venice
Why Italy, you ask? Why not Italy?! Italy is a classic for good reason. It’s a destination so many of my clients want to explore for the first time or return to again and again. And there’s no better way to help plan the perfect itinerary than to experience it firsthand. So, I packed my bags and headed off on a whirlwind, week-long trip to Rome, Florence, and Venice.
I partnered with Travelive and WTB Hotels to craft a seamless itinerary filled with beautiful hotels, curated experiences, and a few delightful surprises. Here’s a day-by-day look at what I experienced.

My Italy Travel Itinerary: Rome, Florence, and Venice
Day 1: Rome Tour by Golf Cart
On the first day, we all arrived early in the morning. To help us beat jet lag, we did a Rome Tour by Golf Cart. I always recommend doing some sort of city tour on the day of arrival. It helps you get your bearings and figure out where you want to spend more time. While on this tour, we got to see some famous spots like the Trevi Fountain, the Spanish Steps, the Pantheon, Piazza Navona, and the Colosseum.

Day 2: The Best of Rome in One Day
Typically, we would break this tour up into two or three days. But since we had very limited time in Rome, we packed it all into one day. The day consisted of:
- The Vatican Museums and St. Peter’s Basilica
2025 is the year of Jubilee in the Catholic Church. Once every 25 years, the Pope opens the Holy Door of St. Peter’s Basilica in the Vatican. Many groups and individuals make the pilgrimage to experience this holy time. Whether or not you’re Catholic, visiting the Vatican is a magical experience. Doing so during the Jubilee and being able to walk through the Holy Door was very special.


- Street Food Tour
I love the Street Food Tour we did. We tried restaurants and foods I would have never thought to try. I was worried it was going to be a ton of food and it would end up being wasted, but we tried small dishes at three different restaurants, which was perfect. One of my favorites was the fried artichoke at Sheva in the Jewish Ghetto.


- Colosseum Express Tour
Since I’m not a huge history buff, the one-hour express tour of the Colosseum was just the right length. The Colosseum is, of course, a huge tourist attraction, but the history behind it and the fact that it’s still standing today is quite mind-boggling.

Day 3: From Rome to Florence via Orvieto
Today, on our private transfer from Rome to Florence, we spent about 4 hours exploring the picturesque hilltop town of Orvieto, located in Umbria. Umbria is a wonderful alternative to Tuscany, an easy day trip from Rome. We walked the whole town, did some shopping, and had a wonderful lunch at Ristorante Maurizio. I highly recommend Orvieto for a day trip or to spend a few nights at Palazzo Petrvs for a slower, more relaxed pace.


Day 4: Exploring Tuscany – San Gimignano and Siena Tour with Wine Tasting
Today was one of my favorite days. I loved getting out into the Tuscan countryside.
San Gimignano is a historic Tuscan town encircled by a 13th-century wall. I’m glad we visited this town first and earlier in the morning. It’s a smaller town and can get packed with tourists quickly. Make sure to take time to just explore the streets, shops, and restaurants here!
In between San Gimignano and Siena, we had a wine tasting and lunch at a nearby winery called Podere la Marronaia.
Our final stop was Siena, a much larger medieval city. It’s well known for its historic city center and Palio horse races. I highly recommend taking a tour to learn about the history and hidden gems.

Day 5: Walking Tour of Florence with the Academy Museum and Transfer to Venice
Today we did a walking tour of Florence and stopped at the Academy Museum to see the famous David by Michelangelo.
After a morning of walking, pizza and gelato were a must! Make sure to grab the salted caramel gelato at La Sorbettiera when you’re in Florence!


For our transfer from Florence to Venice, we took the train to be able to experience this type of transfer. We went with business class for extra comfort and convenience for the 2-hour train ride from Florence to Venice.
Once we arrived in Venice, we caught our water taxi to the hotel. Many transfers in Venice end up being water boats due to all the canals! It is a really fun way to show up at your hotel in style.


Day 6: A Day in Venice – City Tour, Food & Wine Tour, and a Gondola Ride
Today was a full day of experiencing Venice. Typically, I wouldn’t recommend doing all of this in one day, but with our short time frame, we packed it all in. We started with a Venice City Tour. It’s easy to get lost in Venice, so it was nice to have a guide show us around and share a little history. Then we enjoyed another food and wine tour. You just cannot get sick of all the delicious food and wine in Italy! It’s definitely my favorite country for food. And finally, we ended with a classic gondola ride. Very touristy, of course, but a peaceful and enjoyable way to see Venice from the waterways. I’d definitely recommend experiencing a gondola ride in Venice at least once!


Where to Stay in Italy – Rome, Florence, and Venice
One of our partners for this trip was WTB Hotels. While our specialty is in luxury travel, many of our clients prefer to spend their money on experiences rather than splurging on higher-end hotels in every destination on their Italian adventure. WTB Hotels are perfect for this situation. They are 4-star plus quality hotels located in prestigious locations in Rome, Florence, and Venice.
While on this trip, we got the opportunity to stay at Hotel L’Orologio Roma, Hotel L’Orologio Firenze, Hotel Santa Maria Novella, and Hotel L’Orologio Venezia. The location and quality of service reaches that of 5-star hotels. When you stay at these unique properties, make sure to ask about the history and stories behind the designs. It’s a special treat, especially for those interested in horology.



My Top 3 Recommendations from My Trip to Italy
- Set expectations early.
Italy is busy all the time, no matter when you visit. It is especially busy from April through October. Italy is the number one travel destination for US travelers, so it’s hard to avoid the crowds. As long as you have set your expectations, it’s not an issue. - Dine at Trattorias
By far, my favorite part about visiting Italy is the food. In each city, we had the opportunity to dine at a local Trattoria. Trattorias are less formal restaurants. They have a very homey and welcoming feel. They are family-run and serve regional dishes. We dined at Ristorante Lagana in Rome, 13 Gobbi in Florence, and Casa Cappella in Venice. - Add More Time
If you want to do a similar itinerary to what I did (Rome, Florence, and Venice), add a day to each city. My preference would be to add an additional 2 days to Florence since there are so many day trip options from Florence, like Cinque Terre and Tuscany.

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