Why I Split My Italy Trip Into Two Styles

Italy has always been one of those destinations that feels both exciting and… a little overwhelming to plan. Between trains, hotels, regions, and experiences, I wanted the freedom to explore, but I also didn’t want to miss anything important.

So I decided to do something I now recommend to many of my friends and clients:

 Week 1: Independent travel: TUSCANY
 Week 2: Small group tour experience: APULIA

This combination ended up being the perfect balance.

If you’re trying to decide how to plan your own Italy trip, here’s exactly what it was like, and what I’d do again (and differently).

Week 1: Independent Italy Travel in Tuscany

For the first half of the trip, I followed a custom itinerary in the Tuscany region with pre-booked hotels, but everything else felt flexible and self-paced.

How I Got to Florence

Luckily I had upgraded my seat on the flight from the USA and was able to change my flight and arrive in Florence, and in turn, save money as the new flight ended up being less expensive.

I was relieved to arrive at the hotel in Florence earlier than expected and soon no longer identified as a solo traveler as my son Matt joined me for lunch and the next couple of days.

Where I Stayed and Explored 

I spent the afternoon wandering around the streets where the Medici family ruled for hundreds of years.  After reading several books and watching the Medici series on Netflix, actually seeing the streets, buildings and bridges holding so much history was inspiring.

We checked out of the hotel the next morning and rented a car near the train station for the next 3 nights.  I drove us out of Florence and into the beautiful Tuscany countryside. On our way to Siena, we stopped for lunch in San Gimignano, a medieval city that boasts tall towers among it’s skyline.  

On our way to Siena it started to rain, and we made the wrong turn into the ZTL zone – most cities in Italy seem to have an area that you may not drive into.  It’s great for pedestrians, but not so welcoming to drivers.  It is anticipated that I will get a fine in the mail for that mistake.

In Siena, we stayed at the Hotel Athena on the outskirts of the city center.  This made walking into the beautiful city easy, even in the light rain.  

My son Buddy and his wife Charlotte met us in Siena and we found a terrific local dining establishment called Osteria Permalico that all the local men seemed to be enjoying.  The food was amazing and this is a great find in Siena!

After touring in the morning by listening to Rick Steves audio tours (walking tour and tour of the Duomo) we left Siena for an agriturismo called LaChiusa Tuscany in Montefollonico. I wanted that country feel outside of the city centers and this place delivered.  

We enjoyed a lovely farm to table dinner served in their own dining room, walked through paths in the olive groves and explored the small medieval, walled city with a population of 150. Then enjoyed the afternoon sunshine with a friendly cat on site.

Having a car made driving to the different places in Tuscany easy. We had a Pecorino cheese and wine tour and tasting at Podere Il Casale, a local farm with sheep, a donkey and several cats.  

We took a hike in Pienza and walked the trail to Maximus’ house from the Gladiator movies.  Then later for dinner, we went into Montepulciano, another medieval city on a hill with incredible views of surrounding vineyards and rolling hills.

We enjoyed breakfast outside and another walk before driving back to Florence and our first hotel.

 For dinner we took a Viator sunset dinner tour that featured the famous wine windows, Florentine steaks and of course gelato on the Ponte Vecchio.  Our guide led us up and down streets we would never find on our own and we had the best meal and a lot of fun ringing the bell and getting wine through the window.

What I Loved Most

• • Waking up without a strict schedule

• • Wandering through towns like Florence and Montepulciano at my own pace

• • Discovering unexpected restaurants and views

• • Being with my family 

The Challenges (That No One Talks About Enough)

• • Coordinating logistics (especially transportation
  • Driving in foreign cities, not as easy as it may seem.

• • Making sure reservations lined up perfectly

• • Decision fatigue—constantly choosing what to do next

Week 2: Group Tour Experience (The Ease Factor)

The second week shifted completely. I joined a small group tour of 18 women, most who were widows, and everything was handled for us.

What Was Included

• • Transportation between cities

• • Hotel accommodations with breakfast included

• • Several meals and curated experiences

• Daily tours with a knowledgeable and friendly guide.

Staying 4 nights in Ostuni made day trips convenient and gave me a chance to unpack and even clean a few items.  All the bathrooms have a heated drying rack which is great.

Our driver took us to Lecce, known as the Florence of the South.  Our guide gave us a tour and we enjoyed wine and olive oil tasting, lunch on our own and some shopping. After a busy week or so traveling, I took advantage of the spa in the hotel.  I opted for the “melted chocolate” massage which was as weird as it sounds!

One of the sights you see a lot when you mention Puglia region, also called Apulia, is Alberolbello. It’s known for its trulli, whitewashed stone huts with conical roofs. We enjoyed our guided tour and time to shop.

Next we were treated to a wine tasting with food at Cantina Masseria Torricella, then a walk around the town of Locorotondo which was small but quite the labyrinth of small pedestrian lanes but easily found a gelato shop.

On the way to Bari we stopped in the coastal town of Monopoli where I loved being so close to the sea. Then another delicious group lunch with wine tasting (some women ordered wine to be shipped back to the states) then a few hours in Polignano. The last city was my favorite with access to the rocky beach and I finally got to touch the Adriatic sea and even purchased a hand-painted oyster shell from a nice artisan.

Bari is known as the Milan of the south and is a busy port city that hosts ferry service to Croatia and Greece. Our guide once again gave us a tour which ended with a food tasting of southern Italy specialties.  The highlight for the group was seeing the Italian ladies on the street making orecchiette pasta which we learned how to make on our first day in Italy. They make it look so easy!

The best part about traveling with this group was that many of us are widows on different stages of our journey and sharing stories and creating more fun once-in-a-lifetime experiences truly brought joy and created new, lasting friendships.

What I Loved

• • Zero stress, everything was organized

• • Access to experiences I wouldn’t have booked myself

• • Meeting like-minded travelers

• • Learning the deeper history and stories behind each place

The Trade-Off

• • Less flexibility

• • Set schedule (you move with the group)

• • Less spontaneous exploring

But for many travelers, especially first-time visitors, this structure is incredibly valuable.

Independent vs. Group Travel: Which Is Better?

The truth? It depends on you.

Independent Travel Is Perfect If You:

• • Love flexibility and slower mornings

• • Want a more personal, immersive experience

• • Feel comfortable navigating logistics (or have someone plan it for you)

Group Travel Is Ideal If You:

• • Want everything handled for you

• • Prefer structure and efficiency

• • Value expert guides and curated experiences

The Real Sweet Spot: A Hybrid Trip

After experiencing both, I can confidently say:

The combination of independent + group travel is the best of both worlds

You get:

• • Freedom and ease

• • Personal discovery and expert insight

• • Flexibility and structure

What I’d Do Again (and What I’d Change)

I Would Absolutely:

Combine both travel styles again
Spend more time in fewer places during my independent portion
Keep at least one week structured with a group experience

I Might Change:

• • Slightly reduce the number of hotel changes

• • Build in more “do nothing” time, especially by the sea. 

Final Thoughts: How to Plan Your Italy Trip the Smart Way

If you’re feeling torn between planning everything yourself or joining a tour, you don’t actually have to choose.

A thoughtfully designed itinerary can give you both.

And that’s exactly what I help my clients do, create personalized trips that balance independence with the right level of support.

Want Help Planning Your Italy Trip?

Whether you want:

• • A fully customized itinerary

• • The perfect small group tour

• • Or a hybrid trip like mine

I can help you design something that fits your travel style perfectly.

Reach out here to start planning your Italy experience.

kristin.markey@cruiseplanners.com