Two Incredible Weeks In Italy: The Complete Itinerary

There is so much to do and see in Italy that planning a trip can be quite a daunting task. After living in Italy for almost a year, I am constantly adding adventures to my Italy Bucket List and never seem to run out of places to go. To help make planning easier, I have carefully selected all of my favorites to create the perfect two week itinerary.

The Route

The best part about this itinerary is that it is designed to make your trip easy to do by train, no rental car or additional flights needed! You’ll hit Milan, Venice, Florence, Cinque Terre, Rome, the Amalfi Coast and Naples, all in the span of 14 days.

Italy’s capital of fashion and design, Milan is widely believed to be Italy’s most modern city. However, Milan is not without it’s historical charms! A visit to Italy’s fashion and commercial hub will expose you to amazing architecture, high end shopping and dining, and the contemporary side of Italian life.

What to do:

Milan Cathedral, Duomo di Milano

This Gothic Cathedral, nearly 6 centuries in the making, is one of Milan’s most iconic sites. Both the interior and exterior are stunning. The best part is you can climb to the top for fantastic views of the city.

Santa Maria delle Grazie

You might have heard of a little fresco done by Leonardo da Vinci called “The Last Supper”. If you want to see this masterpiece, The Church of Santa Maria delle Grazie is the place to do it. Make sure to reserve a ticket in advance to avoid missing this iconic work.

Galleria Vittorio Emanuele II

You can’t visit one of the world’s fashion capitals without making a stop at its oldest shopping mall! The Galleria Vittorio Emanuele II was built in the 1800s and features gorgeous glass ceilings, incredible architecture, and luxury shops and dining.

Day Trip to Lake Como

Escape from the city and take in the beautiful scenery that surrounds Lake Como. Enjoy a day exploring the deep-blue waters, white capped-mountains, and forested foothills of one of Italy’s most scenic lakes. It’s no wonder this natural beauty has gained fame as a popular luxury tourist destination.

Discover how to spend 1 day in Milan here!

Train from Milan-Venice: 2.5 hours, 30-45 Euro

In the words of Fran Lebowitz “If you read a lot, nothing is as great as you’ve imagined. Venice is — Venice is better.” (Check out this post to see why!) This “floating city” of canals, bridges, and gondolas is unlike any in the world, and is a colorful and unique destination to add to your Italy itinerary. If you can, consider visiting during Carnevale!

What To Do:

Piazza di San Marco

The piazza di San Marco is Venice’s main square and is also the site of the incredible Basilica di San Marco. Here you can grab a coffee at the iconic Caffè Florian (the world’s oldest coffee shop opened in 1720), admire the basilica, or chase after the famous pigeons of Venice.

Basilica di San Marco

A visit to the basilica is not to be missed. Step inside the church for the chance to view exquisite byzantine mosaics and a ceiling covered in gold. If you have time during your visit, I also recommend touring the connected Doge’s Palace for a glimpse into Venice’s rich history.

Take a Gondola Ride

Discover the sights of venice as they were meant to be seen-from the water! Though gondola rides can be pricey, you won’t regret the experience of meandering through Venice’s canals in one of these charming and traditional boats.

Bridge of Sighs

Just before the piazza di San Marco stands the Bridge of Sighs, a bridge which connects the Doge’s Palace to its prison. This bridge was made famous by Lord Byron, who invented the name as he believed prisoners crossing the bridge would stop and sigh as they took a last look at Venice before their imprisonment.

Peggy Guggenheim Collection

One of my favorite museums in the world, the Peggy Guggenheim collection is an incredible modern art museum located in a palace on the Grand Canal. Spend a few hours viewing the works of Picasso, Dalí, Pollock, Calder and other visionary artists just a few steps away from the waterfront.

Realto Bridge

The Realto Bridge is the oldest (and most famous) bridge that crosses the Grand Canal. I recommend stopping in this area to grab a few pictures of this renowned landmark and also enjoy a seafood lunch or spritz at a local restaurant on this main watery thoroughfare.

Burano & Murano

If you deviate from the itinerary and decide to stay in Venice for more than a day, Burano and Murano are two excellent islands to visit. Murano is home to the famed “Murano glass” and Burano is known for its extremely colorful buildings.

Train from Venice-Florence: 2 hours, 28-40 Euro

Florence, or Firenze, is regarded as the birthplace of the Renaissance (and happens to be where I currently reside). Today this Tuscan city remains a window into history, with much of the city’s architecture from this time still intact. Spend a few days in Florence taking in the incredible Renaissance architecture, masterpiece-filled museums, and take a day trip or two to discover other breathtaking Tuscan towns just a bus or train ride away. If you can only manage to spend 1 day in Florence, be sure to optimize your time by using this 1 day Florence itinerary.

What To Do:

Florence Cathedral, Duomo di Firenze

Since its construction was completed in the 15th century, the Duomo di Firenze has become a symbol of the city. Its massive dome created by Brunelleschi, towering campanile by Giotto, terracotta tiled roof, and marble covered intricate facade make it hard to miss. Read my tips for visiting here.

Galleria degli Uffizi

The Uffizi Gallery is one of Florence’s most well-known museums, and is a must see. Leave a decent chunk of time open for visiting this incredible gallery, as space which in and of itself is a work of art. See paintings, sculptures, and other works by masters such as Michelangelo and Brunelleschi.

Galleria dell’ Accademia di Firenze

The Accademia is an art museum in Florence which has gained fame as it houses Michaelangelo’s iconic David. While you will also find other sculptures by Michelangelo and a collection of Renaissance paintings, most visitors flock to the museum specifically to see this masterpiece. If you are limited on time, I recommend choosing the Uffizi over the Accademia.

Piazzale Michelangelo

The best things in life are free-like the view of Florence from the Piazzale Michaelangelo. Grab a bottle of vino and catch a breathtaking sunset over the city from this vantage point. You may have to embark on a small hike to get there, but the view is more than worth it!

Ponte Vecchio

The Ponte Vecchio, or “Old Bridge” is a medieval bridge spanning Florence’s Arno river. It is known for its small shops that appear to be hanging off the bridge, as once was common in medieval times. Today the bridge is also known for its history of jewelry making, and those looking to take home some bling can marvel at the gold items adorning the storefronts today.

Take a day trip

One of the best parts about visiting Florence is its proximity to other incredible tourist destinations. Florence is between 1 and 3 hours by bus or train of many enchanting cities such as:

Pisa, Siena, and San Gimignano

Verona

Vespa Tour of Chianti

Or a 1/2 day trip

Fiesole

Appennine Colossus

I spent the past year living in Florence, so be sure to check out all of my best tips to discover the best dining recommendations, hidden gems, and things to here! 

Train From Florence-Pisa-La Spezia: 2 hours, 16-25 Euro

The “five lands”, or Cinque Terre, refers to 5 unforgettable towns situated on the Ligurian coast of Italy. The colorful buildings the towns are known seem to stack, one on top of the other, overlooking the Mediterranean. Depending on how much time you’d like to reserve for hiking (the towns can only be reached by train, foot, or boat) you can simply do Cinque Terre as a day trip from Florence, or stay in one of the towns overnight to enjoy this bucket-list destination for longer. For a detailed Cinque Terre itinerary, try reading The Ultimate Guide To Visiting Cinque Terre (Plus Sample Itinerary!). 

What To Do:

Hike

Lovers of the outdoors can rejoice as there are several hiking paths to guide visitors from town to town. My personal favorite hike is between the 4th town, Vernazza, and the 5th town, Monterosso. This particular hike takes about 1.5 hours, and leaves you with plenty of time to enjoy Monterosso’s beach.

Train

Not into hiking? You’re in luck. You can easily see all 5 towns in a day on the trains. Trains leave roughly every 30 minutes from La Spezia and travel through all 5 towns, making it easy to hop on and off, or even switch from hiking to the train. A great time saver for those only taking a day trip.

Explore The Towns

Each town in Cinque Terre has its own unique charms. Spend a few hours exploring each one, window shopping, and trying local cuisine (I recommend seafood, pesto, and the local Cinque Terre white wine). My personal favorite towns to spend more time in are the beautiful Vernazza, and the incredible beaches of Monterosso.

1. Riomaggiore
2. Manarola
3. Corniglia
4. Vernazza
5. Monterosso

Train from La Spezia-Pisa-Rome: 3.5 hours, 40-60 Euro

Ah, Roma, Italy’s capitol city, a city dripping in history, ancient wonder, papal majesty, and antique architecture. Though it is possible to “conquer Rome in a day” (check out my tips for getting the most out of one day in Rome here) two days will allow for a more relaxed schedule and give weary travelers a break.

What To Do:

Vatican Museum & St. Peter’s Basilica

Step outside of Italy and into the world’s smallest country, the Vatican City. Be sure to book your tickets in advance to avoid missing out on this wonder. The Vatican Museums and St. Peter’s Basilica are absolutely stunning, and not to be missed. Highlights include Michelangelo’s Sistine Chapel, the Pieta, Vatican Museum Collection, and the interior of St. Peter’s Basilica. A guided tour is a great way to learn about the history behind the majestic Papal city.

Colosseum and Roman Forum

A combo ticket to the Colosseum and Roman Forum is the perfect way to explore Rome’s ancient wonders. Step in the footsteps of Rome’s gladiators and marvel at the construction involved in creating such a large amphitheater. Afterwards, head over to the Roman Forum for some incredible views overlooking Roma and get a feeling for what this ancient town was once like.

Trevi Fountain

Speaking of fountains, a visit to Rome wouldn’t be complete without a trip to the newly restored Trevi Fountain. Legend has it that if you toss a coin in, your wish to someday return to Rome will be granted!

Piazza Navona

Head to Piazza Navona and enjoy a delicious lunch or dinner overlooking the piazza. This is my favorite piazza as it is home to Bernini’s “Fountain of Four Rivers” as well as an ancient Egyptian obelisk. Just a short walk from the Pantheon, I prefer visiting at night when the fountain is dramatically lit.

Pantheon

A visit to the “temple of all gods” is awe-inspiring, and, best of all-free! Step inside of the concrete rotunda and take in the beautiful marble, geometric design, and the massive dome which comprise this ancient wonder. The Pantheon is ancient Rome’s most well-preserved landmark.

Villa Borghese

The Villa Borghese is probably my favorite museum in all of Italy. With stunning frescoes, intricate and gorgeous Bernini statues, an impressive collection of artwork, and pretty gardens, if you have time, I highly recommend a visit. Just be sure to book your tickets in advance, as spots fill up quickly!

Train From Rome-Naples-Sorrento: 3 hours, 28-46 Euro

The Amalfi Coast, or Costiera Amalfitana, is home to some of the most beautiful beaches and stunning views in all of Italy. For those who love the beach, the Amalfi Coast is a perfect addition to an Italy itinerary. The glamourous island of Capri, costal town of Sorrento, black sand beaches of Positano, and ancient ruins of Pompeii are all located in this area, reachable by car, bus, or train.

What To Do:

Stay in Sorrento

I recommend staying in the beautiful coastal town of Sorrento and taking day trips to Capri, Positano, and Pompeii & Mt. Vesuvius. There is delicious food, lots of shopping, and a lovely atmosphere to be found in Sorrento, not to mention the ferry to Capri and trains and busses to Positano and Pompeii are also found here. However, if you have more room in your budget, a night in Capri or Positano would be fantastic as well.

Capri

The glamorous island of Capri is the perfect way to kick off a few days in the Amalfi Coast. The island is known for its beauty, luxury shopping, and brilliant blue water, and is a favorite among celebrities and tourists alike. Take a boat tour around the island, head inside the Blue Grotto, and visit the Garden of Augustus for the best view in town. To plan an epic day, check out the post: Capri For A Day: Top 10 Things To Do.

Positano

The black sand beach in Positano is one of my favorite beaches in all of Italy. The colorful seaside buildings, phenomenal selection of shops, beachside restaurants, and signature orange-and-yellow beach chairs are simply unforgettable. Rent a paddleboard or boat and cruise around, catch the sun on the beach, swim in the beautiful water, or stay on land and enjoy shopping and first class delicious seafood. For more suggestions on things to do in Positano, click here.

Pompeii & Mt. Vesuvius

History lovers, you’re in luck. Head towards Naples and spend the day at the ancient ruins of Pompeii, and climb to the top of Mount Vesuvius. Thanks to the eruption of Mt. Vesuvius in 79 AD, visitors to the site today are able to wander around some of the most well preserved ruins in Italy. Original wallpainting, mosaics, and pottery survive. You can spend anywhere from 2 hours to a full day at this site-after all it was once an entire city! Afterwards, climb Mt. Vesuvius for an incredible view of Naples. Be sure to use this helpful guide to visiting Pompeii to plan your visit!

Naples

End your trip in Amalfi in Naples, the city known for its pizza! Spend a day enjoying the city’s museums, incredible churches, seaside castles, and even take a tour of the city’s 3rd century catacombs. Naples is the perfect place to end your trip, as you can take a train to Rome, Florence, or other major cities as you prepare to fly home at the end of the day.

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There you have it! A tour guide’s tips for the perfect 2 weeks in Italy!

Download the FREE printable 2 Week Italy Itinerary, subscribe!

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Keep the planning going with these helpful posts, or search through all of my Italy travel tips here!

• 50 Travel Tips For Visiting Italy
• 30 Incredible Destinations In Italy Travel Bloggers Love
• Bucket List Italy: 20 Unforgettable Adventures To Add To Your List
• 7 Fantastic Day Trips To Take From Florence
• Racing Through Roma: How to Conquer Rome in a Day
• The Ultimate Guide To Visiting Cinque Terre (Plus Sample Itinerary!)