11-day Italy Travel Itinerary


Venice, Italy - Gondolas on the canal

It seems appropriate that my first blog post is about my favorite country in the world, ITALY So… I put together an 11-day ITALY Travel Itinerary just for you!

One of the most common questions I get is, “what is your favorite place you’ve ever visited?” … Now let’s be honest, picking your favorite country is like picking your favorite child… I have SO many things I love about SO many counties, cities, national parks, historical sites, etc. but all-in-all, if I had to pick, Italy would be my favorite! avel Guide

Maybe I’m partial to Italy because I lived there and was immersed in the culture or maybe it’s just because it’s the most EXTRAORDINARY country! The history & cobblestone streets, the food & wine, the late night dinners & becoming friends with each restaurateur, the melodic language & how each sentence could become a beautiful song, the animation of the Italian people when they speak to one another, and let’s not forget about daily gelato!

I lived in Siena, Italy in 2006 for a summer abroad in college and it was beyond my wildest dreams! I’ve been back several times and my most recent trip in October 2021 might have been my most memorable of them all (despite the fact I was hoping my boyfriend would propose in my favorite place but no such luck… Don’t worry he’s now my husband and we are happily married! I’ll save our engagement story for another blog post)!

Allora, (Italian filler word and so much more beautiful than “umm”!)…  A proper Italian vacation deserves AT LEAST 2 weeks but our busy work schedules didn’t allow that so we packed some of the best places to see into our 11-day Italy Vacation.

Here are some of the best places to stay in Italy: The Best Place to stay at in Italy

11-Day Italy Itinerary:

Flight to Rome

Rather than staying in Rome immediately grab a train to Venice. You’re already at the airport & grabbing the train from here is super easy. This also allows you to start your Italy Tour from the top and work to the bottom before finishing your trip in Rome and fly out of the same city.

Train – Rome to Venice

2 Days in Venice

Hotel: Hilton Molino Stucky Venice – located on Giudecca Island with great views of the Venice. Private hotel shuttle boat to and from Piazza San Marco.

Some Venice highlights: breakfast in Piazza San Marco, a gondola ride (very touristy but I love seeing the city this way), walking the streets all day and night and stumbling upon various shops, taking our photo in front of the Bridge of Sighs, and having drinks at Settimo Cielo rooftop bar which is the highest rooftop terrace in the city.

Train – Venice to Florence

2 Days in Florence

Oh how I LOVE this city! It will always have my heart.

Hotel: Grand Hotel Baglioni – the rooms weren’t anything spectacular however the location was unreal – You are steps from the train stop and their dining room has giant windows with views of Duomo di Firenze. You MUST plan to have an early breakfast and watch sunrise over the Duomo… It was quite possibly one of the best sunrises I’ve seen in my life!

Italy duomo

  • The Duomo – If it works with your schedule, see it at night for the first time. There’s nothing like coming around the corner to its magnificent beauty all lit up! You will still LOVE it in the daylight so don’t stress if you see you before nightfall – you’ll probably love it enough to see it multiple times. Dining around The Duomo is also great, albeit it will be more expensive but the view is worth it!
  • The Ponte Vecchio – Italy’s oldest bride and one of the most iconic things to see. Do a little shopping and I highly recommend supporting, local G. Biscioni… His family has owned this store for hundreds of years!
  • Michelangelo’s statue of David – located in Accademia Gallery
  • You must plan to see sunset from Piazzale Michelangelo (Michelangelo Square). We rented bikes to get there – I promise, there’s no better place to see the whole city and watch the sun set.
  • One of our favorite meals in Florence was at IL LATINI – it’s nothing fancy but OMG the food was divine!

Pick up Rental Car

2 Days in Tuscany

Day 1:

Drive from Florence to Siena, half day in Siena with lunch on Piazza del Campo. My college city and it was SO fabulous to be back, would have stayed but just not enough time and we also wanted to see Montalcino & Monticchiello.

Drive from Siena to Argiano Winery in Montalcino. This winery dates back to 1580 & the wine was beyond delicious.

Drive to Monticchiello, the most incredible medieval village in Tuscany. This tiny village with a population of approximately 600 wowed us! You absolutely have to stay the night in the Airbnb Ancient Tower in the center of the Monticchiello Village. Enjoy dinner and breakfast at Ristorante Daria – two of our most memorable meals of our entire vacation and Daria is there to greet you, she’s beyond adorable!

Day 2:

Explore Monticchiello then drive to Amalfi Coast

2 Days Amalfi Coast

Day 1

Explore the coast – Summer traffic along the Amalfi Coast is insane – fall is SO much better, just know many hotels close for the season near the end of October.

We drove from Positano up the coast to Ravello & Amalfi making stops along the way. Our first stop was Fiordo di Furore – the most amazing inlet with a small beach and area to swim in the sea. You will walk down hundreds of stairs to get to the beach. Make sure to bring your bathing suit and towel! Next stop, lunch in Ravello – pizza, capers salad, and lemon gelato of course! We timed it perfectly so we were driving back to Positano at sunset – there are viewing areas you can park in which make for the most gorgeous photo ops!

Day 2

Breakfast on our rooftop pool and drive to Rome.

Return the rental car as you do not want to deal with driving in Rome, although it’s a large city it’s very walkable + bike and scooter friendly.

Just FYI the hardest part of our rental car experience was returning it in Rome… Rome freeways are busy and if you miss your exit (like we did) you can’t turn around for sometime so make sure you are paying attention!

3 Days in Rome 

Hotel: Lifestyle Suites Rome – located in Piazza Navona and an incredible adults-only hotel. The hotel connected us with a chauffeur who met us at the rental car drop-off and drove us back to the hotel.

3 days in Rome isn’t enough but it was all we had time for but we saw almost everything we wanted to – some of my favorites include Trevi Fountain, the Pantheon, and the Spanish Steps which we easily walked to from our hotel. When visiting Trevi Fountain make a wish and throw a coin over your LEFT shoulder!

For the Colosseum, I recommend doing an underground tour… this gives you the perspective not only from below where the gladiators entered but also from above where the crowd watched. We booked through Viator, a company we like booking tours through although I will admit, the Roman Forum part of this tour was far too long and I got bored.

We LOVED our Rome by Night E-Bike Tour, do this on your first night in Rome then over the following days you can decide what places you want to go back to. Our local guide was amazing, he guided us through all the back streets to avoid traffic & travel like a local. You stop at each historical site to learn the history & take photos. We had a family with kids on our tour, my husband and me, and one other guy who my hubby became friends with.

If you haven’t been to Italy… Run, don’t walk to the airport.


Ciao, Bella
xoxo ~ Jenny, Classy Sassy Travel


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