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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 45 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....

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Travel specialist Melanie Rapuano
active 7 mins ago

Melanie Rapuano

My name is Melanie and I'm a Travel Specialist based here in Italy! I'm half Italian and half British and I come from a city just off the Amalfi Coast! I've always loved creating travel plans for...

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Travel specialist Rita Pagano
active 1 min ago

Rita Pagano

"Travel as much as you can, as far as you can, for as long as you can. Life is not meant to be lived in one place." This is my motto. I’m from Italy, specifically Naples (yes, the birthplace of...

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Travel specialist Anita Matijasevic
active 3 mins ago

Anita Matijasevic

I am passionate about travels, positive and enthusiastic people and exploring new places off the beaten path. Always ready for new life adventures and exciting experiences that make my heart beat...

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Trip Reviews for Italy

The latest reviews by travelers who booked their trip on kimkim

Wonderful trip to Italy
Italy | May 10 - May 17, 2026

S
Scott H.
Ashburn, VA | Reviewed on May 18, 2026
We very much enjoyed our trip to Cinque Terre and Rome. Leslie took the time we had available and our particular desires and made a truly memorable experience. The choice of Sestri Levante in particular was great as a base for going to Cinque Terre. The Colosseum and Roman forum tour with Gigi was phenomenal as was the Appian Way ebike tour with Alessandro from Bikeology. Kimkim provided stellar customer service and handled the details making this an easy trip. It was especially helpful to... Read more

We very much enjoyed our trip to Cinque Terre and Rome. Leslie took the time we had available and our particular desires and made a truly memorable experience. The choice of Sestri Levante in particular was great as a base for going to Cinque Terre. The Colosseum and Roman forum tour with Gigi was phenomenal as was the Appian Way ebike tour with Alessandro from Bikeology. Kimkim provided stellar customer service and handled the details making this an easy trip. It was especially helpful to have they there to help when a 3hr customs line caused us to miss our train and they seamlessly obtained new tickets. They also were able to get a refund from a tour that was moved to a location and time that didn’t suit due to weather. Truly great customer service and I would highly recommend them to anyone visiting Italy.

Local specialist: Leslie Tranchina

Flawless Experience
Italy | Apr 29 - May 9, 2026

Heather
Heather V.
Seattle, WA | Reviewed on May 17, 2026
The WhatsApp support group during the trip was amazing! Prompt, helpful, and proactive to make sure we were setup with everything we needed on our trip. Read more

The WhatsApp support group during the trip was amazing! Prompt, helpful, and proactive to make sure we were setup with everything we needed on our trip.

Hotel Reviews
Hotel Modigliani
Roma

Charming spot, super nice and helpful staff, safe location.

Authenticity & Character
Upgraded but still had older charm elements
Location
A bit of a walk to main attractions, but nice neighborhood and fun to walk around to things nearby.
Staff
Very willing to help with luggage, bar, breakfast, etc.
Cleanliness & Comfort
Palazzo Tritone
Sorrento

Fabulous location for exploring Sorrento! Clean and spacious

Authenticity & Character
Unique setup, with some modern touches
Location
Short walk to dining and shopping and main Sorrento attractions
Staff
Cleanliness & Comfort
Villa Accini

Great location, kind staff, great outdoor relaxation space.

Authenticity & Character
Some components were a little dated, but it gave it charm.
Location
Close to town.
Staff
Super kind and helpful
Cleanliness & Comfort
Spacious room and clean!
Alfieri9 Boutique Hotel
Florence

Adorable setup, extremely clean, wonderful staff. Was a little bit of a walk to main attractions, but not bad. Would recommend and stay again.

Authenticity & Character
Unique, cozy, great decor
Location
Little closer to main attractions.
Staff
Friendly and helpful
Cleanliness & Comfort
No issues in room or lobby.
Activity Reviews
Private Pompeii Tour
Private Pompeii Tour
Pompeii

More to see than expected and pleasantly surprised at the different bits of history to take in.

Quality of Experience
The 2 hours was plenty to take in the history and have time in the day for other things.
Guides, Drivers and Staff
Guide shared lots of facts we wouldn't have known otherwise. We were able to see highlights and most important things in a timely manner. Very nice and thoughtful with answers and conversations.
Transport
Hiking the Path of Gods
Hiking the Path of Gods
Sorrento

The most incredible views! Great to experience the landscape and learn about the communities in the area.

Quality of Experience
The views and the guide sharing info along the way made it more memorable.
Guides, Drivers and Staff
Wonderful - outgoing, kind, and knowledgeable!
Transport
the drive to the starting point is a bit curvy and slow, so plan time accordingly.
Private Colosseum Tour with Underground Access
Private Colosseum Tour with Underground Access
Rome

The guide was so sweet and knowledgeable. Was able to share info that made what you were looking at and walking through so much more meaningful.

Quality of Experience
Learning while seeing ruins was a great experience.
Guides, Drivers and Staff
Sweet and smart guide. She enriched the experience and made it worthwhile.
Transport
Meeting point was easy to navigate.
Vatican Guided Tour
Vatican Guided Tour
Rome

We were happily surprised how great the tour went. The right amount of time and highlighting of key points of interest. Especially cool to learn things you wouldnt know if you didnt go with a guide.

Quality of Experience
So much history and info shared that only a guide would know.
Guides, Drivers and Staff
David was incredible - helpful with questions, balance of time to absorb and experience, but got through a lot of things to see!
Transport
Meeting spot was easy and the line didnt take long to get through.
Chianti Wine & Olive Oil Tour from Florence
Chianti Wine & Olive Oil Tour from Florence
Florence

The guide was funny, insightful, and made the experience really great.

Quality of Experience
The wineries and staff at the wineries.
Food
Lunch at the winery was authentic and paired well with the wine.
Guides, Drivers and Staff
shared lots of great history and info to make the drive and in-between time go by quickly
Transport
Bus was great
Local specialist: Irene Lappa

Loved Tuscany, Amalfi coast, Pompeii and Moun...
Italy | May 4 - May 15, 2026

J
Joel A.
Parole, MD | Reviewed on May 16, 2026
Loved Tuscany, Amalfi coast, Pompeii and Mount Etna! Read more

Loved Tuscany, Amalfi coast, Pompeii and Mount Etna!

Hotel Reviews
Hotel Tirrenia
Sorrento

Lovely hotel with great views

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Agriturismo La Pievina
Montepulciano

Great host great location!

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Activity Reviews
Sailing the Amalfi Coast: From Sorrento to Amalfi & Positano
Sailing the Amalfi Coast: From Sorrento to Amalfi & Positano
Italy

One of the highlights of the trip!

Quality of Experience
Guides, Drivers and Staff
Transport
Cooking Class in a Real Tuscan Farmhouse
Cooking Class in a Real Tuscan Farmhouse
Italy

Great experience

Quality of Experience
Food
Guides, Drivers and Staff
Local specialist: Anita Matijasevic
Anita
Anita Matijasevic
Local specialist in Madrid & Florence | Replied on May 18, 2026

Hi Joel, thank you for your review! I’m glad the cooking class and the sailing along the Amalfi Coast were such highlights of your trip. I also appreciate your kind words about Agriturismo La Pievina and Hotel Tirrenia, and I’ll make sure to pass your feedback along to the hosts and staff.
It was a pleasure helping you plan this journey, and I’d be happy to help you again whenever you start thinking about your next trip. Wishing you all the best, Anita

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