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 picturesque Tuscany 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 Eirini Daouka
active 42 mins 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 Martina Venturi
active 5 hours ago

Martina Venturi

After obtaining a Bachelor Degree in Art History at Milan University, I worked as event planner and tour guide, fostering my obsession for organizing experiences. I then traveled the world,...

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Travel specialist Rita Pagano
active 2 mins 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 Chris Gravas
active 3 mins ago

Chris Gravas

My name is Chris and I have a passion for authentic experiences, cultural awakenings, and nature explorations. As a partner of a local boutique travel agency, I take every chance to explore Greece...

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Trip Reviews for Italy

The latest reviews by travelers who booked their trip on kimkim

Flexible, dedicated professionals who curate wonderful experiences
Italy | May 22 - Jun 3, 2025

Gretchen
Gretchen C.
North Lauderdale, FL | Reviewed on Jun 04, 2025
Arianna spent almost nine months working with me on a specialized tour of Northern Italy, that offered us flexibility to visit family as well as unusual, less toursity areas of the country. Over that time, significant changes occurred requiring alterations to our trip plan (e.g., number of people traveling, exact dates, locations to visit, accommodations needed, availability of direct flights, etc.) Arianna professionally and graciously lept into action to cooperatively problem-solve. When I... Read more

Arianna spent almost nine months working with me on a specialized tour of Northern Italy, that offered us flexibility to visit family as well as unusual, less toursity areas of the country. Over that time, significant changes occurred requiring alterations to our trip plan (e.g., number of people traveling, exact dates, locations to visit, accommodations needed, availability of direct flights, etc.) Arianna professionally and graciously lept into action to cooperatively problem-solve. When I needed suggestions, she delivered helpful information, but there was never any pressure or inflexibility. Every traveler need is thoughtfully addressed, with patience and aptitude, and the things you don't even know you want are delivered.

The accommodations she secured for us in Sirmione and Cortina d’Ampezzo were spectacular. We expressed our overall travel preferences and budget and Arianna found lodging that far exceeded our expectations in some locations, while meeting expectations in the others.

Tours and experiences Arianna booked offered us unique, high-quality, individualized access to information and places we would never have found on our own. We wished we booked more!

Hotel Reviews
Lancaster Hotel
Milan

The hotel is an older accommodation in a decent location. Its staff are shining stars, however, and had the attitude and approach of a high-end place. It was relatively quiet and comfortable, with a typical breakfast.

Authenticity & Character
It is clearly an older facility, with some character and charm in its bones. Tiny elevator, old fashioned decor.
Location
If you like walking, which we do, this,was a great distance from the main attractions. There isn't much in the immediate vicinity, but it keeps it quieter outside.
Staff
Every person was kind and professional. The breakfast and front desk team were top notch, but special shout out to the guy who made us cappuccino at 4:50AM the day we departed.
Cleanliness & Comfort
While it definitely felt clean in our room and breakfast room, the common areas were quite run down in places. The walls in our room had paint peeling, scuffs, scratches, and the baseboards were badly damaged. The antiques in the room match the general decor and were a nice touch, but need better care. We could hear a lot of interior noise (neighbors above and along our hallway), although outside was quiet.
HOTEL de LEN
Cortina d'Ampezzo BL

If I had to live in a hotel, this would be the one. Everything about its unique character and exceptional delighted my soul, but the location and staff make it even more special than the architect and interior designer could have envisioned. Every glorious concept is so thoughtfully executed. The rooftop spa is something magical. Truly. I cannot wait to get back to it.

Authenticity & Character
This hotel should be winning design awards, and does, because it's stunning. I fear that after the winter olympics in 2026 bring more focus on this place, this hotel may become so well-known that it is impossible to maintain its current perfect character. The natural wood offers a rustic marriage to a modern, sometimes industrial, interior design. The communal spaces are welcoming, sleek, open, yet private. The transparency of the spa offered an authenticity and character that took my breath away several times.
Location
Staff
Unbelievably kind and considerate staff. They were "waiting for us" when we arrived, later than expected, after long drive. They offered us refreshments during a quiet and personalized check-in process on another floor, which was such a nice touch. People knew us by name and checked on us regularly during our stay. The spa staff, especially Francesca, were extraordinary.
Cleanliness & Comfort
The rooms are appointed in simple, tasteful decor. Bathroom with double sink was a nice touch. Everything was spotless. From a comfort standpoint, we found the inability to control room temperature or towel heating rack, lack of a refrigerator, and absence of extra bedding (lighter blanket to adjust to the fluctuations in temperature), downsides. Towels and bathrobes were high quality. Balcony was large, but with so much construction happening in the town, it was hard to enjoy being outside or having the windows open.
Hotel Ocelle Thermae & Spa
Sirmione

A resort and spa with a very luxe look and feel. Staff were impeccably dressed to indicate their role and function, underground parking was available, including electric charging, the entire facility was gated and closely controlled. The breakfast filled two rooms and included every option imaginable, including accommodating various dietary restrictions. The location was stellar--only a five-minute walk to Scaliger castle. But the spa facilities themselves were amazing. We sadly had little time to enjoy many aspects, as we were doing tours and visiting with family, but we wished we could have booked a few more days to enjoy the thermal baths and spa services. Notes: it is adults only, and the thermal spa comfortably accommodates a small number of guests at a time.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Gombit Hotel
Bergamo

The hotel was a marvel of renovation and in a great, central location in the upper città. Bed was comfortable, service was excellent, breakfast was good. The only notes I would offer for fellow travelers to this location are that it is adjacent to a tourist destination (park and fountain) over which our room faced, so it was quite loud. The nightly cost to park a car is quite high.

Authenticity & Character
A renovated historic building in an ancient corridor within the limited traffic zone, requiring a specialized permit.
Location
The proximity to the funicolare and many historic sites was perfect. Dozens of wonderful markets, stores, bars, and restaurants exist within a 10-minute walk. We were easily able to walk to the lower city and back from the hotel.
Staff
I wish I could remember them all by name, but the staff with whom we interacted were consistently warm, pleasant, and helpful.
Cleanliness & Comfort
The room was spotless and the towels were good quality. Everything felt new.
Activity Reviews
Milan Last Supper Tour with City Highlights
Milan Last Supper Tour with City Highlights
Milan

Wonderful, moving experience to the the Last Supper and fully-appreciate how remarkable it is that the piece has survived, and restoration of this meticulous sort, has been achieved. The other highlights of the tour were also fantastic--ancient historical buildings, artworks, culture, politics--across thousands of years. Deborah was patient and excellent.

Quality of Experience
Guides, Drivers and Staff
Cooking Class in the Dolomites
Cooking Class in the Dolomites
Italy

The chef we worked with was passionate about his craft and taught us special techniques for making homemade pasta, unique to the region. It felt odd cooking in the dining room so near the entrance, using a portable stovetop, and not in a kitchen, but it was still a great experience. A bit rushed.

Quality of Experience
Sirmione Walking and Boat Tour & Scaliger Castle
Sirmione Walking and Boat Tour & Scaliger Castle
Italy

Wonderful, knowledgeable tour guide who showed us the highlights of Sirmione by walking and private boat ride. Highly recommend.

Quality of Experience
Guides, Drivers and Staff
Transport
Boat tour was great! Wish it was longer...
Local specialist: Arianna Zampieri
Photo taken by Gretchen C
Photo taken by Gretchen C
Photo taken by Gretchen C
Photo taken by Gretchen C
Photo taken by Gretchen C
Photo taken by Gretchen C
Photo taken by Gretchen C
Photo taken by Gretchen C
Photo taken by Gretchen C
Photo taken by Gretchen C
Photo taken by Gretchen C
Photo taken by Gretchen C
Photo taken by Gretchen C
Photo taken by Gretchen C
Photo taken by Gretchen C
Photo taken by Gretchen C
Photo taken by Gretchen C
Photo taken by Gretchen C
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Salvo and Petre (Our driver for all things Si...
Italy | May 16 - May 28, 2025

S
stefanie p.
Kansas City, MO | Reviewed on May 29, 2025
Salvo and Petre (Our driver for all things Sicily) were incredible. Read more

Salvo and Petre (Our driver for all things Sicily) were incredible.

Hotel Reviews
Hilton Rome Airport Hotel
Fiumicino

A nice Segway to getting back to American life.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Hotel Livingston
Syracuse

Everything about this hotel was amazing from location to staff!

Authenticity & Character
the view of the sea from our room made the stay so enjoyable.
Location
we liked it because it was just far enough away from the hustle.
Staff
every single person was attentive and wanted to make sure everything was perfecto!
Cleanliness & Comfort
La Residenza Fiorentina
Firenze
Authenticity & Character
Location
Staff
Reception staff not seen unless checking in or out. When had a question about the room temperature was dismissed as that’s just the way it has to be
Cleanliness & Comfort
Hotel La Griffe
Rome

Loved the bartender!! He was fun! The shower was extremely small but used to American bathroons

Authenticity & Character
Location
great to be a part of the action in central Rome but was a bit noisy at night
Staff
Cleanliness & Comfort
Activity Reviews
Private driver at disposal
Private driver at disposal
Italy
Quality of Experience
Guides, Drivers and Staff
Transport
Beach day in Noto area
Beach day in Noto area
Syracuse
Quality of Experience
Guides, Drivers and Staff
Our driver was so amazing
Transport
Our driver for 3 days was absolutely amazing. He went above and beyond.
Ortigia Walking Tour: The Heart of Syracuse
Ortigia Walking Tour: The Heart of Syracuse
Italy

This honestly was a GREAT EXPERIENCE with Salvo! He knows the history of not just this area but all of Syracuse.

Quality of Experience
Guides, Drivers and Staff
Winery tour in Chianti Area
Winery tour in Chianti Area
Italy

The winery itself is beautiful, it’s big production!

Quality of Experience
Guides, Drivers and Staff
Transport
very quiet
Central Food Market & Tuscan Cooking Class
Central Food Market & Tuscan Cooking Class
Florence

The whole experience from the market to the class was 5 star all the way

Quality of Experience
Food
Guides, Drivers and Staff
Our chef was fun!! The wine flowed as we were waiting for the pasta to cook!
Vatican Tour with Vatican Museums, Sistine Chapel & St. Peter's Basilica
Vatican Tour with Vatican Museums, Sistine Chapel & St. Peter's Basilica
Rome

I mean it’s the Vatican!

Quality of Experience
Guides, Drivers and Staff
Colosseum & Ancient Rome Tour with Roman Forum
Colosseum & Ancient Rome Tour with Roman Forum
Rome
Quality of Experience
Guides, Drivers and Staff
Frascati Tour: Enjoy Wine Tasting & Visit "Castelli Romani" area
Frascati Tour: Enjoy Wine Tasting & Visit "Castelli Romani" area
Italy

Such great knowledge of the area. The wine is spectacular ordered a lot and they graciously are shipping direct to us

Quality of Experience
Guides, Drivers and Staff
Guide and staff were very knowledgeable about the area
Transport
Local specialist: Jessica Proietti
Photo taken by stefanie p
Photo taken by stefanie p
Photo taken by stefanie p
Photo taken by stefanie p
Photo taken by stefanie p
Photo taken by stefanie p
Photo taken by stefanie p
Photo taken by stefanie p
Photo taken by stefanie p
Jessica
Jessica Proietti
Local specialist in Italy | Replied on Jun 01, 2025

Ciao Stefanie,

Thank you so much for your kind words!
We’re thrilled to hear that our drivers Salvo and Pietro, made your Sicilian experience so memorable. They both take great pride in offering warm hospitality and seamless service — we’ll be sure to share your lovely feedback with them!

We hope to welcome you back soon for another unforgettable Italian adventure.

Warm regards,
Jessica & the Storywalking Team

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10000/10
Italy | May 19 - May 27, 2025

Mackenzie
Mackenzie T.
Ashburn, VA | Reviewed on May 29, 2025
I cannot say enough good things about this trip. Kimkim's questionnaire process made the planning aspect easy to begin and Arianna handled everything else with excellence. The information given to us beforehand as far as cultural tips, food recommendations, etc. was all so helpful. Once we finally arrived to Italy and began our trip, everything worked out perfectly and my first time traveling abroad could not have been made any easier on myself. All of our reservations went off without a... Read more

I cannot say enough good things about this trip. Kimkim's questionnaire process made the planning aspect easy to begin and Arianna handled everything else with excellence. The information given to us beforehand as far as cultural tips, food recommendations, etc. was all so helpful. Once we finally arrived to Italy and began our trip, everything worked out perfectly and my first time traveling abroad could not have been made any easier on myself. All of our reservations went off without a hitch, all drivers were on time, all instructions easy to follow, etc. We were even able to check in early to each accommodation -- a bonus! And each accommodation exceeded our expectations. It is hard to pick out one experience as our favorite... We loved every single one of our tour guides and each big group excursion we did turned out fabulous. Our Italian Travel Ambassador was easily accessible during business hours and quick to respond to any questions or concerns we had. I loved how she checked in at the end of everyday as well as provide details of the following day's itinerary and important information so that we did not have to frequently check our actual itinerary. I will not travel without Kimkim again!

Hotel Review
Locanda Leon Bianco on the Grand Canal
Venice

Our room was AMAZING! Private pier, kitchenette, excellent bathroom, etc. Easy to check in/out. Staff very friendly.

Authenticity & Character
Unique decor with mix of antique and modern furniture.
Location
Right on grand canal with lovely water sounds, boat watching, and great lighting. Felt safe even having a private pier leading into our room on the canal.
Staff
Super friendly and accommodating
Cleanliness & Comfort
Local specialist: Arianna Zampieri
Arianna
Arianna Zampieri
Local specialist in Italy | Replied on May 30, 2025

Ciao Mackenzie,
Thank you very much for your kind words!
I am very happy that you enjoyed a wonderful seamless graduation trip that exceeded your expectations. I want to thank you also for your more detailed feedback regarding the guides, drivers, and hotels, and I can’t wait to help you plan your next adventure.
Warmest regards to everybody!
Arianna & the Storywalking Team

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