Karina Style Travels 08/02/25

Our Two Week Italy Itinerary

When I think of the ideal Euro summer vacation, my mind immediately lands on Italy. There are so many dreamy aspects about an Italian getaway, and one major bonus to this destination is that there’s a large variety of scenery, activities, and culture you can experience.

Brian and I recently jetted off on a trip to Italy to celebrate our anniversary, and I’m so excited to be sharing all the details here with you. Whether you’re planning a honeymoon, celebrating a milestone, or simply checking this country off your bucket list, you’re in for such a treat.

Our vacation was 14 days long, the same length of the South of France trip we took last summer. Now that we’ve done several two-week trips to Europe, I can honestly say it feels like the perfect amount of time to be away from home. You can check most of your “musts” off of your bucket list without feeling like you’re itching to get back to your normal routine.

Regardless of your personal plans, I hope this Italy travel guide inspires you in some way. I’m sharing our complete Italy itinerary, which highlights some of the activities we did, restaurants we enjoyed, and places we stayed.

I have to shout out my incredible travel planner, Katie of @GerlingGetaways, who truly took the burden of planning all of this off of our plates. She was a total rockstar at putting our itinerary together. All of the details of our trip were organized in an app and we could easily click on each day to see what we had in store. Plus, all of our tickets were located in the same place, which made traveling to multiple places much more organized and stress-free. I’d highly recommend working with her if you want to seamlessly put together a Euro itinerary!

2-Week Italy Itinerary

Day 1: Arrival in Rome

After a long flight, we were certainly ready to get checked in and kick our trip off! We decided to stay at Hotel Palazzo Galla, which was such a convenient, central location—it was just a five minute walk to the Trevi Fountain and super close to the Roman Forum, and the Pantheon.

Upon checking in, we couldn’t help ourselves and had to take a nap. I’d suggest arriving at noon or later when you fly in — otherwise, you have too full of a day ahead and it’s easy to fade quickly.

We did a bit of shopping and exploring on our first day, but overall, it was focused on getting settled and then heading out for a dinner reservation at Settimo.

We instantly felt like this rooftop dining experience was one of the area’s best kept secrets! We enjoyed a sunset dinner, delicious food and wine, along with stunning views of Rome (and the Vatican!) The restaurant had such a lovely atmosphere that felt tucked away from more touristy areas and it was quick to become a highlight of our time in Rome!

Also, as we were toasting to our trip at Settimo, our wedding song happened to start playing. Given that this trip was centered around the celebration of our anniversary, this made it all the more special (it really is all about the little things.)

Day 2: Colosseum and Ancient Rome Tour

Once we caught up on some shut-eye, we jumped right into the action with a half-day tour of the Colosseum and Ancient Rome. We got to see the entrance where the gladiators walked into the arena and we explored Nero’s Palace. We also explored the Roman Forum and Palatine Hill. The tour was a small group, so it felt way more relaxed and personal than I imagine most of these are.

I will say that it entailed a lot of walking (and climbing up and down stairs) but this tour is a must for history buffs or first-time Rome visitors!

Many of you loved when we shared our tour guide details when we were in Monaco last summer, so I wanted to shout out Valentina from Liv Tours—she made our time in Rome so educational (and fun!) She was actually the main tour guide at The Vatican for over a decade and did the tours of many high profile celebrities, presidents, and VIPs. She’s a seventh generation Roman and served as a well of knowledge.

After our 3.5-hour tour, we grabbed gelato at FLOR Gelato Italiano (our first of many scoops.) Even after such a robust tour, it was hard not to appreciate every little detail in this magical city. The ruins area is by far my favorite—so much history, so much charm.

For dinner we walked to La Fraschetta di Castel Sant’Angelo, which I have nothing but positive things to say about. I wanted to enjoy an authentic Roman meal and that’s exactly what was delivered. I ordered the spaghetti carbonara (and a glass of red wine) and enjoyed every last bite. The ambiance was casual and local, which both Brian and I prefer over touristy.

Day 3: Vatican Tour

Before we left Rome, we took an early (7:30 am) private tour of the Vatican and the Sistine Chapel. We couldn’t leave without checking this off of our bucket list, and much like you hear, it didn’t disappoint. While it was certainly quieter than it would have been if we took a later tour, we were both surprised at how crowded it was by 8 am.

As far as the tour went, I love Renaissance art more than any other time period, and this was arguably the richest art site I’ve ever visited. I couldn’t possibly sum up everything we learned and saw during this tour (and during our overall time in Rome), but just trust me when I say it’s all worth it.

After our tour, we both indulged in some much-needed espresso and hopped on the train to Tuscany!

Day 3 (Continued): Arrival in Tuscany

Travel days are never the most exciting, but because we kicked the day off with a tour of the Vatican, then unwinded on the train, the venture to Tuscany felt more enjoyable. We grabbed our rental car upon arrival and then made our way to our hotel.

We checked in at Locanda le Piazze, a dreamy property set between the rolling hills of Florence and Siena. The boutique hotel showcased the perfect blend of Italian charm and modern luxury, flaunting views of olive groves and beautifully lined vineyards.

Our dinner reservation was booked at Tavola di Guido, a farm-to-table restaurant that was located on the hotel’s property. The convenience of being able to unpack and stay close by was just what we needed after a busy day! Between the meal, the wine pairings, and the ambiance, I can’t recommend this spot enough. We ordered the five-course tasting menu and it was simply divine.

Day 4: “Day Off” to Explore

We asked our travel planner, Katie of @GerlingGetaways, to leave a day open for us to explore in each destination we visited. I swear by this method of planning a trip because you never know what you’ll want to see/do more of until you get there. There’s nothing worse than feeling like you missed out and this provides an opportunity to fill in the gaps with what you really want to do.

With our free time, we decided to use Ebikes to check out the surrounding area. We ended up riding around 15 miles and had so much fun taking Tuscany in at our own pace. There were so many adorable villages that we passed through and it made for such great sightseeing. We snagged a coffee and some water before heading back up the hills to our hotel.

Afterwards, we squeezed in some R&R by lounging and enjoying lunch at the pool.

Next up was a visit to the hotel’s spa and then dinner at Sotto le Volte, another special experience that neither of us will forget.

Day 6: Cooking Class

I also love to squeeze in a cooking class while traveling, and Tuscany offered the most stunning setting to do just that. We took our class at Chianti Farmhouse, which featured Tuscan-style dishes and a background in the deep culture and roots in the area. The local chef highlighted so many special details about Tuscany along with secrets to their way of cooking and a recap of the go-to ingredients of their tradition.

We made pasta and enjoyed a glass of organic wine from the nearby vineyards during the process. Overall, the vibes were high and it was nice to be in the kitchen during such a long time away from home!

After the cooking class, we made a pitstop in Castellina In Chianti to go up the infamous tower. The views were certainly worth the trek (and it’s a great spot for photo opps.)

For our last dinner in Tuscany, we went to Passo Dopo Passo Osteria—and we were treated to an amazing sunset and delectable dishes. This restaurant was only a 10 minute walk from our hotel, which was an added bonus!

Day 7: Arrival in Florence

Our arrival in Florence was a bit stressful as we had to return our rental car. You can actually drive through the city center but you have to have a permit from your hotel so that you don’t get fined. We weren’t aware of this so it was hectic, but we made it!

We booked a room at Hotel Calzaiuoli, which was another property that boasted a central location! After checking in, we did a bit of shopping and stopped for one of the famous focaccia sandwiches for lunch (along with a $5 Euro spritz!) Then we got ready for some laid-back rooftop hangs at Loggia Roof Bar. I actually came across this spot on TikTok and think it’s a must-visit for a drink in the summer!

Day 8: Sightseeing at Our Own Pace

We had a slow morning, which was such a little luxury after lots of moving about. The day was pretty leisurely and I loved that we stumbled upon a great place to enjoy some gelato (Venchi 1878.) For lunch, we went to Piazzale Michelangelo, a spot I would encourage you to add to your “must-eat at” list. It offered a great view of Florence and felt a bit tucked away/less crowded than other options we passed.

Shopping and strolling took up most of our afternoon, and before we knew it, it was time to get ready for our dinner reservations at La Giostra Firenze.

Day 9: Walking Tour in Florence

Can you tell we like to take tours? I know that this isn’t everyone’s cup of tea, but I feel like it really showcases each destination you visit. We started in Piazza di San Marco and experienced many of the Tuscan capital’s top attractions like Michelangelo’s “David” in the Academia Gallery.

The tour typically entails a visit to the Duomo, the city’s iconic, gothic-style cathedral, but we did the Opera instead. If I could describe the tour in one word, it would be breathtaking. Also, just as a tip, half-day tours are wonderful because you don’t get too tired or lose interest—the full day tours can be much more draining.

We worked up an appetite so we headed to Gucci Osteria for lunch (where I had the prettiest and tastiest salad), did some shopping, and grabbed more gelato. We had an early departure to our next stop the following morning so we decided to have a relaxing evening.

Day 10: Head to Positano

Rather than just going directly to Positano, we stopped in Naples for a winery lunch and tasting at Cantina del Vesuvio. It made for a long day but allowed us to see another destination that is so highly coveted. The vineyard was everything I hoped it would be and more and we loved every last sip of vino.

We also stopped in Pompeii, another place that’s packed with rich history and incredible ruins. There were lots of Greek temples here and I learned that this part of Italy once belonged to Greece!

Our final stop of the day took us to Positano, a place that I can confirm lives up to the hype. As soon as you arrive, you almost feel as if you’re in a movie. It truly looks like a postcard and I can’t wait to go back one day.

I had heard rave reviews about the boutique Eden Roc Hotel and I’m so grateful that we decided to stay here! The center of the town and the beach area are just steps from the hotel, so you’re quite literally in the heart of Positano. Since we had such a long day, we stayed on the property for a casual (yet fun) pizza dinner.

Day 11: Anniversary Day

The special day that we traveled so far to celebrate was finally here—and both Brian and I felt so grateful that we could mark this milestone in Italy. When we were considering options of what to do on our actual anniversary, we thought, “what could be more fun than an elevated beach day?” Katie helped us pull off our vision to a tee.

We went to Arienzo Beach Club, which was located right on the water’s edge, offering sweeping views of the turquoise blue Mediterranean. You have to take a short boat ride from the Positano beach to get to a private beach, which made the overall experience all the more special.

Being greeted with a bottle of Champagne was a special touch that fit the occasion. We were also served a two course Mediterranean lunch while we soaked up the sun. Our day was everything we wanted it to be and I’d suggest booking a beach club day if you visit! I know this one gets booked quite quickly (and families are welcome) so be sure to plan far in advance.

For our anniversary dinner, we went to Adamo ed Eva Ristorante and got so lucky with our table. We had a view of the ocean and all the little houses and buildings along the cliffside—so, so special.

Day 12: Explore and Beach Club Day

Since there’s no such thing as too much beach time, we figured we would visit another beach club while in Positano. We took our time exploring the town in the morning and then ventured off on a quick boat ride to explore a different sandy shore.

On our way back from the beach, we stumbled upon the cutest little restaurant and decided that would be where we’d have dinner on our last night in this special place. I just love the unexpected visits and stops while traveling—they typically make for the best experiences and memories!

Day 13: Arrival in Sorrento

We ended our trip in Sorrento, another place I would revisit in a heartbeat. We checked in at Hotel Belair and freshened up before going to visit La Masseria Farm. We took part in an olive oil, wine, and limoncello tasting—and we loved learning about the family-owned background of the property. The farm specializes in limoncello making but they also are a self-sustaining farm that produces everything they eat and sell.

At the end of the day, we had a meal cooked for us by the mom, and served by the kids. Everyone was so inviting and it was such a personable Italian countryside experience. This would be a wonderful activity for a family or large group!

When we got back to our hotel, we decided to open the bottle of wine we bought during our cooking class in Tuscany. We sat out on our balcony and watched the coast and kayakers, then the most incredible thing happened. Fireworks started shooting off directly in front of our hotel, providing us with such a pleasant surprise that felt completely dreamy.

Day 14: Boat Day in Capri

As the last hoorah for our trip, we ventured out for a private boat day in Capri. Everything about this was to die for—the glimmering waters, the perfect weather, the gorgeous caves. We swam, we lounged, and we sipped Prosecco. I felt like we really got to unplug and relax before traveling back to the states—a must before a long-haul flight.

For dinner, we decided that we would stay at our hotel and order room service. This speaks volumes as to how much we adored our hotel! The views, the food, the service—everything was top-notch.

Day 15: Last Day!

Ahhh, time to head home. A bittersweet feeling when you feel endless gratitude for the experiences in front of you, yet you crave the normalcy of your day-to-day routine.

Because we had a lot of travel ahead of us, we took it easy on our final day in Italy. We rested by the hotel pool and had a sunset dinner at Bagni Delfino. It was the icing on the cake before we set off!