Italy 2-Week Trips & Itineraries

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The traditional two-week vacation is just enough time to plan the ideal Italian getaway. You could embark on a food and wine tour that involves pizza making on the Amalfi Coast, wine tasting in Tuscany, and sampling the famous hams of Parma. You could also explore famous cities like Venice, Florence, and Rome, laze on the sun-kissed beaches of the lesser-visited Puglia region, or go on a family adventure that mixes kid-friendly museums with fun walking tours and even gladiator training.

Italy Travel Insights

Cefalú at sunset
Map of Spectacular Self-Drive Tour Around Sicily - 14 Days
Spectacular Self-Drive Tour Around Sicily - 14 Days

Experience Sicily in all its glory by driving around the island in 2 weeks. Highlights of this tour include Palermo, a cultural melting pot with stunning monuments and vibrant local markets and Taormina, the elegant village famous for its Greek theater and the postcard views. You'll also visit Syracuse and Agrigento, with their archaeological masterpieces, and hike Mt. Etna—Europe's most active volcano.

Florence, Italy
Map of Highlights of Italy: Venice, Florence, Rome, Naples - 14 Days
Highlights of Italy: Venice, Florence, Rome, Naples - 14 Days

Discover the sights and delights of Italy on this two-week highlights tour. Explore the floating city of Venice, the Renaissance jewel of Florence, and the Eternal City of Rome. Ride a Vespa through the picturesque Tuscan countryside and discover the beautiful Amalfi Coast. Soak up the culture, food, and wine while you fall in love with Italy.

Aperitivo hour in Rome's Campo di Fiore
Map of Food & Wine in Italy: Venice, Bologna, Florence, Rome & Amalfi Coast- 14 Days
Food & Wine in Italy: Venice, Bologna, Florence, Rome & Amalfi Coast- 14 Days

Indulge in a 14-day culinary odyssey across Italy's foodie hotspots. Begin in Venice with local cicchetti, and venture to Bologna for 11th-century architecture and the best parmigiano and prosciutto. Admire Florence's Renaissance masterpieces and savor Tuscan Chianti with traditional farm-to-table fare. Conclude your trip in Rome and the Amalfi Coast, where you'll master the art of Neapolitan pizza and savor the Eternal City's famous street food and pasta dishes.

Typical house facade
Map of Explore Tuscany: Florence, Siena, Pisa, & Lucca - 14 Days
Explore Tuscany: Florence, Siena, Pisa, & Lucca - 14 Days

Discover why Pisa's famous tower leans so much (and why it's not the only one!), plus much more on this exploration of Tuscany. Start in Florence to see Da Vinci's 'The Annunciation' and other famous Renaissance works in the Uffizi Gallery. Look for treasures in the San Lorenzo market, browse shops on the medieval Ponte Vecchio, and explore history in the medieval cities of Siena and Lucca. End your trip with sweeping ocean views on the Cinque Terre hiking trail.

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.

Take a gondola ride to check out the historic buildings flanking the canals in Venice, Dorsoduro district
Map of 2 Weeks in Italy - 4 Unique Itinerary Ideas
2 Weeks in Italy - 4 Unique Itinerary Ideas

With two weeks in Italy, you can see many of the country's top sights in one trip—Rome, Florence, Venice, the Amalfi Coast—or spend your time exploring a particular region in depth, like Tuscany or Sicily. On these four unique itineraries, you'll take a pizza-making class in Naples, road-trip around Sicily, explore the wine-growing region of Chianti, or get a taste of several Italian cities, moving quickly between destinations on the country's network of high-speed trains.

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Meet our Local Travel Specialists

Experienced travel agents with a passion for Italy
Travel specialist Leslie Tranchina
active 5 hours 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 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 Melanie Rapuano
active 1 min 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 Anita Matijasevic
active 50 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

Fabulous trip!
Italy | May 5 - May 14, 2026

Joe
Joe M.
United Kingdom | Reviewed on May 21, 2026
The trip was amazing! Except for a few hiccups along the way, things ran pretty smoothly. Our favorite part was the food tour in Palermo with our tour guide Angelo. He was great! The next favorite was the boat ride along the Amalfi Coast. Third favorite was the gelato making experience. The weather was great and the local people so friendly and helpful! Read more

The trip was amazing! Except for a few hiccups along the way, things ran pretty smoothly. Our favorite part was the food tour in Palermo with our tour guide Angelo. He was great! The next favorite was the boat ride along the Amalfi Coast. Third favorite was the gelato making experience. The weather was great and the local people so friendly and helpful!

Hotel Review
Hotel Plaza Sorrento
Sorrento

Beautiful accommodations, view and staff! Great location as well!

Authenticity & Character
Felt like Italy!
Location
Centrally located with a great view.
Staff
Carlo was exceptional.
Cleanliness & Comfort
Bed was very comfy and room very clean!
Activity Review
Palermo by Night: A Local Street Food Experience
Palermo by Night: A Local Street Food Experience
Italy

Angelo our guide was born and raised in the area of Palermo where the food tour was conducted. He did an incredible job describing not only the history of the area, but also of the different food and wine we sampled.

Quality of Experience
Food was outstanding!
Food
All of it!
Guides, Drivers and Staff
Angelo our guide was the best!
Local specialist: Giorgia Torre
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Rome & Apulia 50th Anniversary
Italy | Apr 25 - May 17, 2026

A
Adrienne R.
Newark, NJ | Reviewed on May 21, 2026
I would not hesitate to use Kimkim again for travel planning. From beginning to end of planning, Leslie from Storywalking was a great help and advisor and tailored everything to our needs, from train tickets to cooking classes. Once in Italy, Francesca was our devoted and helpful contact. All our tours and guides were excellent. Our 50th anniversary trip to Italy (with our whole family in Apulia) was a great success and will be a cherished memory. Read more

I would not hesitate to use Kimkim again for travel planning. From beginning to end of planning, Leslie from Storywalking was a great help and advisor and tailored everything to our needs, from train tickets to cooking classes. Once in Italy, Francesca was our devoted and helpful contact. All our tours and guides were excellent. Our 50th anniversary trip to Italy (with our whole family in Apulia) was a great success and will be a cherished memory.

Hotel Review
The Great View
Rome

It certainly was “A Great View!” A clean comfortable apartment in a fantastic location. Sitting on the terrace or looking out the windows we had views of all of Rome including the Colosseum and the Forum. Wonderful!

Authenticity & Character
Everything
Location
Nearer to public transportation
Cleanliness & Comfort
Local specialist: Leslie Tranchina
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Danielle was a great guide for our tour of Tu...
Italy | May 12 - May 18, 2026

Gregory
Gregory H.
Chicago, IL | Reviewed on May 21, 2026
Danielle was a great guide for our tour of Tuscan hill towns and a delightful lunch at a local farm. Danielle was outgoing, humorous and very knowledgeable. Read more

Danielle was a great guide for our tour of Tuscan hill towns and a delightful lunch at a local farm. Danielle was outgoing, humorous and very knowledgeable.

Hotel Review
Relais degli Angeli
Siena

Beautiful hotel in a former home. Great location in Siena.

Authenticity & Character
Beautiful
Location
Easy walk to significant sights.
Staff
Cleanliness & Comfort
Local specialist: Leslie Tranchina
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