Rome vespa tour Italy

A two week Italy itinerary: highlights

When Italy Beyond the Obvious new client Betsy first contacted us about their trip to Italy, she wrote:

My father would like to take us on a big adventure and we decided Italy is the place to go! Our family has never been to Europe before, although my dad is well-traveled.

There’s a lot of planning that goes into an Italy itinerary like theirs, but after several months of putting together activities and hotels that everyone, including their three boys, would enjoy, we came up with a fabulous two week Italy itinerary!

Their two week Italy itinerary started with a few days in Venice.

In Venice, a local guide introduced them to Venice’s vast history and main sights with a private walking tour, and they had time on their own to explore (and get lost in!) Venice’s small streets and canals. They also had some downtime to recover from the travel and adjust to the six hour time difference.

Venice, also known as VeneziaWe booked the family on a rowing lesson which everyone enjoyed! Betsy said:

Our guides were great and in addition to sharing lots of information about the canals and boats, they gave us a sense of what it was like to grow up in Venice. Very cool!

Rowing lessons, Venice Italy

Learning to row in Venice

Next stop on their two week Italy itinerary: Florence!

It was so helpful to have all of our train tickets for each leg of the trip! We’ve never traveled by train before and the kids really liked it. We were so thankful that we decided not to rent cars at all. Traveling by train was easy and relaxing.

Florence Italy

Florence, also known as Firenze

They started their visit with a segway tour of Florence.

We loved the Segway tour! Our guide was wonderful. It was so incredibly hot and humid in the city – over 100 degrees. If we had been on a walking tour, the boys never would have made it. We got to see a ton in a relatively short amount of time.

Segway tour Florence Italy

Seeing the sights of Florence on a segway!

Their visit Florence also included a visit to the famous Uffizi Gallery, of course.

The Uffizi tour was great. The guide was very interesting to listen to. She was very dramatic in her delivery and clearly passionate about art history. She led us efficiently through the gallery focusing on only about 20 paintings that really captured the Renaissance. I have to say, I was most intruiged by her fearlessness in creating space! She wasn’t worried about getting in anyone’s way and spoke to us as though only the seven of us were in the entire gallery.

Uffizi Gallery, Florence Italy

Uffizi Gallery, Florence

They also spent time relaxing by the hotel pool and chatting with the locals.

The bartender at the hotel bar was one of our favorite people we met on our trip! He was about 65 years old, on his third wife, has a five-year-old. He was like a character from the Godfather.

Since they decided not to have a rental car, we booked them with a private guide for a day trip exploring the Tuscan countryside.

Our guide was funny and nice and engaging with the boys. We stopped at a vineyard and toured the cellar and had a wine tasting – first time for the boys! They enjoyed it as much as we did. Then we went to a farm and had the best meal of the entire trip.

Sant'Agnese farm, Tuscany, Italy

Farm in Tuscany, the best meal of the trip!

Before leaving Florence, they did a pizza and gelato making class, always a hit but kids especially love this class!

Pizza gelato Florence Italy

Making pizza in Florence

Then they did a day trip to “Motor Valley” where they visited the Lamborghini and Pagani factory floors, drove Ferraris, and visited all three museums.

Everyone enjoyed our tours at Pagani, Ferrari, and Lamborghini. This was a highlight of the trip for my dad!

Lamborghini, Motor Valley, Modena, Italy

This Lamborghini ain’t light!

Next stop on their two week Italy itinerary: the Amalfi Coast!

From their base in the town of Amalfi, they explored the iconic towns of the Amalfi Coast, and spent a day renting a private boat.

The boat rental was great. Domenico suggested a place to eat lunch in Nerano and told us if we pulled up in the boat someone would meet us in a smaller boat and lead us to a buoy to moor and give us a ride to the restaurant. We thought “really? They will just see us and come get us?” That’s exactly what happened. We had a great lunch of seafood and pasta.

Positano, Amalfi Coast, Italy

View of Positano from the sea

They even braved the Path of the Gods hiking trail in 100 degree heat!

The views were amazing and we were so glad we did it, but this hike nearly killed us!

Path of the Gods, Sentiero degli dei, Amalfi Coast, Italy

Hiking on the Path of the Gods, high above the Amalfi Coast.

On their last day in the Amalfi Coast, they stopped to visit Pompeii with a private guide.

The trip to Pompeii was the most efficient sightseeing ever! Our driver delivered us right to our guide, who brought us to the luggage storage area and got our luggage set. Pompeii was so hot and sunny and crowded, but he brought us around and avoided crowds, always stopping in a shady spot. I can’t imagine trying to do all that without a guide or in a large group. It was perfect having him there to give us a great synopsis of the history of the place. He led us around for approximately 2 hours, got our luggage, led us to the train station, bought our tickets for us, and put us on the train. Perfect!

Pompeii, archeaology, Italy

Listening to the guide in Pompeii

Last stop on their two week Italy itinerary: Rome!

They kicked off three days in Rome with a night tour of the Colosseum:

We were so glad to be doing this at night without the crowds and without the heat! It was really cool seeing it with all the lights. Our guide was great.

Colosseum, Rome, Italy

Photo by thinkrorbot via Flickr, public domain

They also visited the St. Peter’s Basilica and the Vatican museums (of course), a tour that included a VIP early visit to the Sistine Chapel before everyone else was allowed in. But they all loved the vespa tour the most.

This was absolutely a highlight of the trip for all of us! Even my dad, who was wary of the safety of this tour before we got started, absolutely loved it! We got a wonderful overview of Rome and its history. Valerio was great, as were all of the other drivers. I think I might need to buy a Vespa because that was so much fun.

Rome vespa tour Italy

Visiting Rome by vespa!

When they returned from their trip they wrote to us:

We had a wonderful trip! We did so many amazing things and experienced many wonderful places yet never felt like we were running ragged. Everything moved along seamlessly. It truly was the trip of a lifetime.

All photos belong to the Italy Beyond the Obvious client, and were used with permission.

Client Testimonials

"We had a wonderful trip! We did so many amazing things and experienced many wonderful places yet never felt like..."

"We thank you so much for all you gave us, guided us to, arranged for, and detailed for us. Not..."

"We are in love with Venice and the Dolomites. The ski adventure was amazing and beyond anything we could have..."

"Absolutely everything that you planned went off without a hitch. Every tour, every restaurant, every train and activity came through..."

"Thank you again from all three of us for your help in planning such a delightful trip. I know that..."

"Madeline carefully planned a fabulous, personalized 19 day itinerary (Lake Garda, Dolomites, N/S Tuscany, Rome) that enabled us to be..."

Read More Client Testimonials

Italy Advice & Tips In Your Inbox

Italy Advice & Tips In Your Inbox

Italy Advice & Tips In Your Inbox

Join our mailing list to get the free Driving In Italy eBook

Your name(Required)

Going Somewhere Other Than Italy?

The Travel Expert Network

Check out the Travel Expert Network where you’ll find Certified Travel Experts™ like us ready to plan custom bucket trips for you all over the world!

Visit the Travel Expert Network →

Office Locations

San Francisco
+1 773 621-3024
Contact San Francisco

Milan
+39 320 028 6827
Contact Milan

Rome
+39 331 222 2349
Contact Rome

Free Driving In Italy eBook
Start Dreaming About Your Next Italy Trip

Start Dreaming About Your Next Italy Trip

Subscribe to our newsletter.

Your name(Required)