Tailor-Made Trips to Italy

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Italy Travel Insights

Tour Rome's iconic Colosseum
Map of 5 Days in Italy - 5 Unique Itinerary Ideas
5 Days in Italy - 5 Unique Itinerary Ideas

If you have five days in Italy, it's best to focus on one city or region—otherwise, you'll likely feel like you're spreading yourself too thin. On these five unique itineraries, you'll discover northern Italy's food scene, explore a corner of Sicily, road-trip between coastal villages on the Amalfi Coast, cycle through Tuscany's wine roads, or get to know the Eternal City.

The laid-back beaches on the Amalfi Coast make a wonderful getaway
Map of 1 Week in Italy - 5 Unique Itinerary Ideas
1 Week in Italy - 5 Unique Itinerary Ideas

With one week to explore Italy, you can focus on the country's must-see highlights while hopping between Rome, Florence, and Venice. Or, swap in the Amalfi Coast and a day trip to Capri if you're eager for a slice of idyllic coastline. If you're a traveler who enjoys the freedom of a rental car, you'll find Tuscany the ideal road-tripping destination, while Sicily and hiking in the Italian Dolomites are a great fit if you're seeking a more specialized trip.

Sunset over Venice
Map of 10 Days in Italy & Greece - 5 Unique Itinerary Ideas
10 Days in Italy & Greece - 5 Unique Itinerary Ideas

Ten days may seem like a short time to see both Italy and Greece, but you'll still get to experience all the main destinations, with enough time for a beach day or two. Focus your trip on a particular theme—like history, wine, or family—to fully immerse yourself in your favorite day-to-day adventures. Regardless of which itinerary you choose, it's easy to modify any of these trips to give you a bit more time in your favorite places.

St. Peter's Basilica at dawn in Vatican City, Rome, Italy
Map of 2 Weeks in Italy & Greece - 5 Unique Itineraries
2 Weeks in Italy & Greece - 5 Unique Itineraries

Two weeks in Italy and Greece is enough time to get a feel for the Mediterranean culture and experience the best of what interests you, especially if you choose a focus to guide your trip: highlights, family-friendly, beaches, history, or food and wine. Although you can opt to spend more time focused on your favorite activities, each itinerary includes a well-rounded set of experiences: historic sites, bustling city markets, quiet neighborhood cafes, and sunny beaches, perfect for soaking in the sunshine.

Discover Italy's Veneto region and make a stop to check out the wooden bridge of Bassano del Grappa
How Many Days to Spend in Italy

Italy has 20 regions, each with its own identity. Landscapes, cuisine, and dialect differ greatly from one to the next, and each merits its own visit. If your time is limited, you'll be able to see Italy's highlights in a matter of days—but spending two weeks or more means you'll get to explore multiple regions and fall in love with authentic Italy.

Old Town and port of Mandello del Lario in late summer
Best Time of Year to Visit Italy

The best time of year to visit Italy is the late spring, early summer, and September, when the weather is warm, the crowds are manageable (particularly along the coasts), and most destinations and attractions are accessible. Summer is very warm, especially in the south, along with plenty of visitors in pursuit of "la dolce vita." Fall brings moderate temperatures throughout the country and beautiful foliage in Tuscany—this is also a quiet time of year in Rome and Florence, making it ideal for sightseeing.

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Meet our Local Travel Specialists

Experienced travel agents with a passion for Italy
Travel specialist Leslie Tranchina
active 6 mins ago

Leslie Tranchina

Born and raised in the heart of Italy, in Bologna—a city perfectly nestled between the Dolomites and Rome—I have always been passionate about nature, hiking, culture, and savoring incredible food....

read more...
Travel specialist Manuela Cardillo
active 15 mins ago

Manuela Cardillo

Born in the heart of Naples, but now calling the northern beauty of Brescia home, I am a travel enthusiast on a mission to share the wonders of Italy with other explorers. From Madrid and...

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Travel specialist Eirini Daouka
active 3 hours ago

Eirini Daouka

I was born in Thessaloniki, Greece's second largest and —to my belief— most vibrant city, and a gastronomic paradise. I always loved being a traveler of my own birthplace, collecting all the city...

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Travel specialist Eleonora Arrigoni
active 5 hours ago

Eleonora Arrigoni

Born and raised in Milan, I graduated in Tourism Sciences and Local Community. Passionate about the travel industry from a young age, I explored the world of luxury hospitality between Dubai and...

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Trip Reviews for Italy

The latest reviews by travelers who booked their trip on kimkim

30th Anniversary Southern Italy Trip
Italy | Sep 10 - Sep 22, 2025

Glenn
Glenn Z.
Atlanta, GA | Reviewed on Sep 24, 2025
My wife, Lindsay, and I had a fantastic 30th anniversary trip -- BIG THANKS to KimKim as well as our travel planner Melanie Rapuano! We also had nice help from Giovanna, with Italy Charme (partnered with KimKim). This was a special vacation not just because of our anniversary, but also because I wanted to go to the town where my Italian side of my family is from. The challenge? It's a VERY small town in a relatively remote area of the Basilicata region. Melanie and the KimKim team made... Read more

My wife, Lindsay, and I had a fantastic 30th anniversary trip -- BIG THANKS to KimKim as well as our travel planner Melanie Rapuano! We also had nice help from Giovanna, with Italy Charme (partnered with KimKim). This was a special vacation not just because of our anniversary, but also because I wanted to go to the town where my Italian side of my family is from. The challenge? It's a VERY small town in a relatively remote area of the Basilicata region.

Melanie and the KimKim team made everything easy. Yes, I could have booked most of the trip on my own. But it would have been SO much more time consuming...which company should I rent a car from? Which hotels are the best for our needs? Where should we go first, second, etc...? All of these kinds of questions are where Melanie was a tremendous help. She was ALWAYS available...before and during the trip. She listened to what we wanted, asked a number of questions at the beginning of the process, and then NAILED IT with every aspect of the trip -- from the hotels she chose for us, to the fast answers to every question, every detail was taken care of.

Here's where we went:
* Flew into Naples from Atlanta (USA)
* Spent two nights in Salerno, with a day-trip to Positano / Amalfi coast.
* Picked up a rental car and drove to the Basilicata region...stayed two nights at Aura Glamping (HIGHLY recommend!) and visited my family's hometown of Accettura, as well as two incredibly beautiful nearby towns (Pietrapertosa and Castlemezzano)...did the zipline between both towns, billed as one of the longest and highest in Europe.
* Drove to Matera and stayed one night (incredible town!)
* Drove to Tropea, in Calabria, and stayed 5 nights. Melanie helped arrange for a private snorkling trip as well as a cooking class in the countryside -- both were PERFECT and very memorable.
* Drove back up to Naples and spent two nights there, including a walking food tour of the town, before flying back home.

I would highly recommend KimKim. And if you're traveling to Italy, request to work with Melanie -- she's the BEST!

Glenn

Hotel Reviews
Napoli Tree - Lungomare
Naples

Fantastic B&B very close to the waterfront.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Rocca della Sena
Tropea

We will be back. That should say enough! It's a great hotel, with friendly staff and a to-die-for view, perched right above the beach.

Authenticity & Character
Location
Excellent location with easy access to the beach and many lidos (we enjoyed Lido Charley for food, and Lido Costa Degli Dei for it's great position on a sandy part of the beach).
Staff
Big thanks to Georgia at the front desk (such a nice person!) and to Francesco, behind the bar (appreciate the grappa and also the fact that he knew how to make a great Old Fashioned!).
Cleanliness & Comfort
Very clean and super comfortable!
Aura Glamping Experience
Accettura

This is owned by my 3rd cousin, Giuliano. So, yes, I'm a little biased. But I would say this even if he wasn't my cousin -- Aura Glamping is AMAZING! If you want a relaxed place to stay, off the beaten track, and have plans to be in the Basilicata region...you need to consider Aura Glamping!

Authenticity & Character
Location
The views of Accettura and the surrounding countryside are amazing!
Staff
Giuliano is a gracious host, and he brings a morning breakfast in a beautiful picnic basket...complete with everything you could want!
Cleanliness & Comfort
The "yurt" was spotlessly clean, and has a very nice bathroom with toilet, sink, shower, bidet -- a true luxury in a camp setting (the reason for calling this "Glamping!"
Hotel Montestella
Salerno

A very nice hotel, close to the waterfront and ferries that take you to the Amalfi coast. Great shopping and restaurants within walking distance from the hotel. They have an awesome breakfast as well! The only reason I didn't give it 5 stars is that we arrived a little early and our room wasn't ready. We waited for nearly two hours in the lobby...the person at the front desk never told us when our room was ready (despite walking by us several times, and seeing my wife asleep in the lobby). Checkin was supposed to be 2:00. We still hadn't been told the room was ready, and had to go to the front desk and ask if it was ready yet. The response? "Your papers?" AGAIN -- this was annoying but we were early, so I kind of understand. Otherwise, the hotel was fantastic!

Authenticity & Character
Location
Staff
Cleanliness & Comfort
The lobby, breakfast area, and rooms were spotless. The only downside was that the paint was peeling from above our terrace and dropping in large pieces onto the table outside of our room.
Activity Reviews
Naples walking food and historical tour
Naples walking food and historical tour
Italy

Very nice walking tour of Naples. I wish there was more food involved, but we learned a lot!

Quality of Experience
Guides, Drivers and Staff
Transport
Private Cooking Class in the Tropea Countryside
Private Cooking Class in the Tropea Countryside
Tropea

Excellent class -- highly recommend!

Quality of Experience
Food
Guides, Drivers and Staff
Transport
Costa degli Dei - Tropea Capo Vaticano in a Dinghy!
Costa degli Dei - Tropea Capo Vaticano in a Dinghy!
Tropea

Melanie made this extra special by booking a private snorkling tour, rather than this larger group that we had initially planned to be with. So, I can't really provide a review of this trip "by dinghy." Instead, we were on a bow-rider outboard engine boat, skippered by a guy named Lorenzo. He was an incredible host and knew all the best spots to snorkel. Lorenzo also has a vast knowledge of the local history -- we not only had a great time snorkling, but also learned a ton!

Quality of Experience
Guides, Drivers and Staff
Transport
Local specialist: Melanie Rapuano

Our experience with KimKim, Elisa and Lorenzo...
Italy | Sep 12 - Sep 20, 2025

Shawn
Shawn H.
Ashburn, VA | Reviewed on Sep 24, 2025

Our experience with KimKim, Elisa and Lorenzo was fantastic. The hotels in Rome and Florence were in the perfect location and so unique and wonderful. Our drivers were all wonderful and communicative. The tour guides took us on the most unique adventures and took the time to show us special, authentic local eateries, artisans and cultural areas. The hotels, tours and transportation were all flawless. Everything was timed perfectly I can't say enough about the wonderful experience we had on our trip. I highly recommend and will absolutely use them again!

Local specialist: Elisa Sciabica
Elisa
Elisa Sciabica
Local specialist in Milan | Replied on Sep 24, 2025

Shawn, thank you so much for your incredible feedback! 😊 I’m absolutely thrilled to hear that you and Amy had such a wonderful time in Italy and that everything went perfectly. It means the world to us to know that the hotels, drivers, and tours truly made your trip special, and that we could give you a taste of authentic local experiences.
If you ever plan another trip, we’d love to help you explore even more of what Italy has to offer.
Thanks again for your kind words and your trust in us. Can’t wait to work with you again! 😊

Travel needs= Kim Kim
Italy | Sep 9 - Sep 19, 2025

Mary Rita
Mary Rita G.
Niles, IL | Reviewed on Sep 24, 2025
We have used Kim Kim for our trips to Spain, Scotland and Italy. Love the personalized service and small group tours. They are always helpful when we have questions and like how you send messages dsily on our trip. Read more

We have used Kim Kim for our trips to Spain, Scotland and Italy. Love the personalized service and small group tours. They are always helpful when we have questions and like how you send messages dsily on our trip.

Hotel Reviews
La Maison du Sage
Florence

Wow!!! Such a great B&B/hotel. Loved the atmosphere and the rooms. Felt like i was at home. All the staff was great. The breakfast and service was wonderful.

Authenticity & Character
Such a unique B&B with a front desk.
Location
Across the street from Basilica of Santa Croce and short walk to everything
Staff
Amazing staff. Daniel is the bomb. Got us reservations where we wanted you go and suggested great restaurants.
Cleanliness & Comfort
Great/clean/love the patio
Hotel Ca' d'Oro
Venice

This was a nice hotel. Pleasant and helpful. Not a fdn of their breakfast. The view out our window was beautiful.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Activity Reviews
Masterpieces of the Renaissance: Uffizi Gallery Tour
Masterpieces of the Renaissance: Uffizi Gallery Tour
Florence

Great to have an expert walk you around to see the important art work. Our your guide was wonderful. She pointed out things you might walk by.

Quality of Experience
Guides, Drivers and Staff
Transport
Best of Florence Walking Tour with David & the Duomo
Best of Florence Walking Tour with David & the Duomo
Florence
Quality of Experience
Guides, Drivers and Staff
Transport
Murano Excursion with boat
Murano Excursion with boat
Venice

Great idea. Not a fan of this tour. Too expensive and rushed us off the island to Burano. Wanted to walk around. They only catered to people spending thousands of dollars. Did not like the jewelry. Wish we could of gone yo another site.

Quality of Experience
Guides, Drivers and Staff
Transport
Visit to a Peggy Guggenheim Museum and Palace
Visit to a Peggy Guggenheim Museum and Palace
Venice
Quality of Experience
Guides, Drivers and Staff
Transport
Welcome Walking Tour to Venice: The comprehensive view of the Floating City
Welcome Walking Tour to Venice: The comprehensive view of the Floating City
Venice

Great walk around Venice with a very knowledgeable local.

Quality of Experience
Guides, Drivers and Staff
Transport
Ok
Local specialist: Jessica Proietti

Why travelers love kimkim

Custom trips for independent travelers who are too busy to plan
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Authentic travel experiences

Kimkim’s local specialists ensure that you will have the best experience based on up-to-date local insights. On top of that, the vast majority of your money will go straight to support and grow local economies.

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Local support during your trip

You can always reach your local specialist with a quick message or call in case you hit a snag during your trip, or simply want some great local recommendations.