3 Week Italy Itinerary

Looking for the perfect 3 week Italy itinerary?  We split our trip into 1 week each in Sicily, Amalfi Coast, and Florence/Tuscany to really relax, settle in, and fully enjoy everything these places had to offer. I had the trip of a lifetime on my honeymoon and would love to share this incredible 3 week Italy itinerary with you!

This post contains affiliate links, which means I may earn a small commission at no extra cost to you if you make a purchase through one of these links.

Week 1: Sicily

Days 1-2: Palermo

• Start your 3 week Italy Itinerary in Palermo. I highly recommend staying two nights in this vibrant city. It comes alive at night with al fresco restaurants and bars and has so much history.
• Check out the Palermo Cathedral and pay the fee to climb to the rooftop for a beautiful view of the city. Tip: Women must have their shoulder’s covered
• Walk through the Quattro Canti, a beautiful square that connects the four ancient districts. 
• Have lunch in the historic center with live music all around and explore the vibrant street markets. 

How to get to Sicily

• Fly into Palermo airport then rent a car to drive around the island
• You can also reach Sicily by ferry from ports in Italy, Malta and Tunisia

Where to Stay in Sicily

• In Palermo we stayed at a lovely hotel right in the city center called Boutique B & B Vintage. 
• In Linguaglossa we stayed at a hotel called Shalai, it was great with a Michelin star restaurant, but definitely upgrade to the bigger rooms because the basic rooms are tiny!

Where to eat in Palermo

• I Cucci for a drink and lunch in the historic center
• Pasticceria Costa for an espresso and cannoli!
• Ai Lattarini for drinks at night for a fun, local atmosphere
• Osteria Ballaro for a more upscale lunch or dinner with a great wine list

Days 3-8: Taormina and Mt. Etna

• Rent a car in Palermo and drive 3 hours to Linguaglossa at the base of the active Mt. Etna Volcano. I recommend 5 days here to experience wine tasting, volcano hiking, and a day trip to Taormina. You could also stay in Taormina and day trip to the volcano, but you’ll see the prices in Taormina are much higher!
• You can stop along the way at Cefalù, a beautiful beach town, for lunch!

Things to do near Mt. Etna

• Go wine tasting on the volcano. I recommend I Custodi, Donnafugata, Benanti, and Planeta. Make a reservation in advance! (Planeta was the winery that they went to in White Lotus season 2)
• Hike the Volcano! This can range from an easier 3 hour hike around the craters, which is what I did, but you can also spend a full day with a more intensive hike all the way to the top. 

Where to eat in Linguaglossa

• You must make a trip to Cave Ox, nestled in the mountains, for either lunch or dinner. They have an incredible wine list and food to die for. 
• The town of Linguaglossa is limited in restaurants, but we stumbled upon Trattoria Linguagrossa and the food and wine were to die for! One of our favorite meals of the trip. 
• For very fine dining you can make a reservation at the Shalai hotel Michelin Star restaurant. This has a very high price tag, but is a full blown tasting menu experience. 

Things to do in Taormina (fun fact, this is where they filmed season 2 of the White Lotus!)

• Day trip to Taormina and see the Teatro Antico di Taormina, the remains of an ancient Greco-Roman theatre. If you time it right, you can even see a show there!
• Go shopping along the cobblestone streets and stop for a gelato or aperol (or limoncello spritz!)
• Walk down to the beach and visit Isola Bella, a small island that you cross a causeway to get to. Dip into the refreshing water and relax!

Week 2: Amalfi Coast

Days 9-12: Amalfi & Positano

• Fly into Naples airport and book a transport or drive to your hotel. 
• We stayed at La Conca Azzurra Hotel which was one of the most incredible hotels I’ve ever stayed in about 10 minutes from the Amalfi town. Unbeatable view of the sea and private sun chairs with access to the sea. The only downside is that it isn’t walking distance into town so you will need to rely on your own car, busses or taxis to get around, but I think it’s worth it for the privacy and beauty you get!
• Spend 3 days relaxing by the sea and exploring local towns like Amalfi and Positano
• Hike the “Path of the Gods” hike from Bomerano to Positano for the most breathtaking views!
• Explore the Grotto dello Smeraldo in the Conca dei Marini

How to get around the Amalfi Coast

• The most affordable way to get around is by bus. Public busses run constantly from town to town and are very convenient when not busy, but be aware that in the peak of tourist season the busses can get so packed that they won’t stop for you and you can end up waiting over an hour for a bus.
• Taxis are readily available, but they price gouge like crazy. Think 50 euro for 10 minutes! So these are a very convenient, but very expensive way to get around.
• Renting a car or scooter will allow you the most flexibility and will be more affordable than taxis, but beware that the roads are extremely narrow and curvy right above huge cliffs so you have to be an extremely confident driver to brave the roads. 

Days 13-15: Sorrento

• Hop on a bus and ride about an hour to Sorrento, and check into your hotel
• We stayed at Hotel Grand Vesuvius which had a beautiful pool and very convenient shuttle into the main town. 
• Explore and go shopping in the town of Sorrento, enjoy all the delicious restaurants and bars
• Take a ferry to Capri and then book a boat to take you on an island tour and to the famous Blue Grotto.

Week 3: Florence & Tuscany

Days 16-18: Florence

• For the last leg of your 3 week Italy Itinerary, travel from Sorrento to Florence. We took the train that was about 4 and a half hours, but you can also drive, take a bus, or fly from Naples airport. 
• Check into your hotel. We stayed at Hotel Relais Il Castello and it was a great hotel with a convenient location close to the city center, but in a fun local neighborhood.

What to do in Florence

• Eat a Florentine Steak. We went to Fuoco Matto and it was to die for!
• Visit Michaelangelo’s David Statue, the Duomo, and the Uffizi Gallery
• Shop along the Ponte Vecchio
• Visit Il Santino wine bar for incredible wine, meat and cheese!

Days 19-21: Tuscany

• rent a car in Florence and drive into Tuscany
• Spend 3 days wine tasting, relaxing and exploring Siena, San Gimignano and Lamole

Where to stay in Tuscany

• I highly recommend staying at an agritourismo which is like a Farmhouse right in the heart of a Tuscan winery. We stayed at the one at Castello di Verrazzano and it was incredible and so peaceful!
• There’s also a lot of beautiful luxury hotels like Borgo Scopeto Wine & country Relais if you’d like a pool, breakfast buffet and spa. 

Best wineries to visit in Tuscany

• Tip: I highly recommend making reservations for tastings and tours
• Right outside of Florence is Antinori nel Chianti Classico, a famous winery with gorgeous architecture which is a great stop as you drive into Tuscany
• Castello di Verrazzano is a winery located in a castle that has been around for 1000 years. They offer a tour, tasting and lunch. Lunch is 5 courses and absolutely incredible, an experience like no other!

Best towns to visit in Tuscany

• Siena – a Medieval city known for the Piazza del Campo that has a historic horse race held there twice a year
• Lamole – the heart of the Chianti Classico region and has a restaurant with a beautiful terrace overlooking vineyards
• San Gimignano – known for its medieval towers and is a UNESCO World Heritage site for its historic buildings and architecture. It’s also the birthplace for the unique Vernaccia di San Gimignano wine that you have to try when you are there. 
• Pisa – famous for the Leaning Tower of Pisa

Check out my Tuscany itinerary for a more detailed guide!

3 Day Tuscany Itinerary

After this incredible 3 week Italy itinerary you can drive back to the Florence airport and fly out! Arrivederci Italy!