2 Weeks in Italy: The Perfect Guide From Napoli to Sicily
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I have spent many months in Italy over the past 2 years, and I have the cutest little road trip guide for you – perfect for two weeks in Italy – especially southern Italy from Napoli all the way down to Sicily.
Between the Sicilian pasta, Neapolitan pizza, gelato, and good old Italian wine, I gained about 5 pounds – and regret absolutely nothing!
Now to the itinerary, complete with hidden gems and the best places to eat, what to do, and where to stay for an adventure that can only be described as La Dolce Vita.
2 Weeks in Italy “At-A-Glance”
Here is the whole trip at a high level, including where I recommend you lodge for a few nights and the logistics of public transportation if you choose not to rent a car for any part of the trip.
A few notes about logistics:
- Uber is not something you can count on in Italy.
- I’ve linked where to get your ferry tickets in the detailed itinerary below, but no travel day took more than 2-3 hours.
- Having a car will make it easier, especially for the second half of the trip when you have to get to Maratea and Sicily. In fact, there are a few Hidden Gem Italian Towns in South Italy that are worth exploring if you end up renting a car.
Here’s what I use to check car rental options and prices:
▶️ DISCOVER CARS: Check Prices for Italy! ◀️
Before you hit the road, make sure you review Renting a Car in Italy: Common Mistakes & Tips, where I go into a few unique road rules, documentation requirements, and experience driving through the land of La Dolce Vita.
2 Weeks in Italy Itinerary
Let’s dive into the 2 week itinerary for Italy, including tips on where to stay and how to spend your time.
Day 1: Arrive in Napoli
Welcome to Napoli! When I first set out on this 14-day trip in Italy, I almost skipped Naples because of how many people warned me about the dangers – “hide everything”, “gangs of gypsy thieves!”. This is a bunch of bullsh*t.
You should absolutely practice caution any time you travel, but I found the city to be bustling, alive, friendly, chaotic, and all the good things I imagined a slice of local Italian life to be.
Where to Stay
📍 Le Sciantose Relais (Spanish Quarter)
You’ll be making Naples home base for three nights. I booked myself a lovely spot in the Spanish Quarter (Quartiero Spagnolo), which is within walking distance of the main attractions and the historic center.
What to Eat
Do not leave the city without eating a Neapolitan Pizza or the Traditional Ragu. Neapolitan cuisine, in general, is renowned for its use of fresh ingredients and simple yet flavorful recipes. Here are my top recommendations for each!
- L’Antica Pizzerie da Michele – Neapolitan pizza, great any time of the day and wonderful jetlag recovery food.
- Tandem Ragu – Traditional ragu over handmade pasta in a low-key nook of town. Make sure to get a reservation for dinner.
Day 2: Explore Napoli
The city of Naples is often overlooked by travelers to Italy, who go for better-known destinations like Rome and Florence.
But those who take the time to explore Napoli for at least a full day will be rewarded with a wealth of history, culture, well-renowned museums, art galleries, churches, parks, and overall natural beauty. That said, the city is huge, busy, and you’ll want a guide.
➡️ For a historical guided tour that makes Napoli come alive, book Naples Private Walking & Food Tour.
My Favorite Spot on the Tour: Museo Cappella Sansevero, a chapel that is adorned with a number of intricate sculptures, including two life-size figures of chained sinners. The most impressive sculpture is “The Veiled Christ,” a marble statue of Christ shrouded in a thin layer of transparent marble, which is in one word “heavenly”.
Day 3: A Trip to Pompeii
So don’t repeat my mistake and go to Pompeii without a guided tour, paying only for the entrance ticket and boring audio guide; you’ll end up tuning out anyway. It will be like walking through history blind – beautiful and intriguing, but you’ll be lacking the depth, story, and impact.
👉 If I was to do this day again, this is how I would think about it: Rome to Pompeii Day Trip: The Smart Way vs. The Hard Way.
Day 4: Arrive on the Amalfi Coast
Grab the ferry from Napoli to Amalfi (2 hours for about $30) and head out in the morning. The town of Amalfi is absolutely picturesque and small, easy to explore in one day.
A little secret from locals and travelers alike is that the best way to see the Amalfi Coast is from the sea. So once you arrive and settle in, grab some lunch, head to the harbor again, and get a boat for the afternoon.
➡️ This is the Amalfi Coast Boat Rental I got so I didn’t have to spend extra money on a skipper – zero regrets!
Where to Stay
📍 Albergo L’Antico in the Town of Amalfi
This will be your home base for the next four days. I got a little room close to the main square and Cathedral, more expensive than Naples but within walking distance of everything. Because the AirBnBs are expensive and a little run down in the town of Amalfi, my favorite part about this hotel is that it was central, and felt super Italian in its decor.
Day 5: Explore Ravello
Ravello is a town in Italy that sits high above the Amalfi Coast. Though it’s small, there’s plenty to see and do – the main attraction being Villa Rufolo. It sits atop a cliff with incredible views of the coastline and has a beautiful garden. And some nights, live shows!
Day 6: Explore Positano
Positano is one of the most beautiful places in Italy, and it’s easy to see why. The colors are absolutely breathtaking, and the views are simply WOW!
Although it is a popular tourist destination, there are still plenty of hidden gems to be found.
➡️ This was one of my favorite days on the trip because I took the road less traveled and hiked from Amalfi to Nocelle in Positano via the Path of the Gods Hike.
Day 7: A Day on the Island of Capri
A day trip to the island of Capri is a must for this itinerary. The island is known for celebrity vacations, crystal-clear water, and picturesque towns.
You can take a boat around Capri from Amalfi, and then spend the rest of the day on the island soaking in the Mediterranean vibe.
➡️ This is the Private Boat Tour of Capri I took to capture the picture below – I liked it so much that I actually did it again on a separate trip back to the little island!
Here are a few highlights you can’t miss:
- Giardini di Augusto – Get ready for the most stunning views of the sea and Via Krupp.
- Arco Naturale – My favorite lookout point, an easy walk/hike from Giardini di Augusto.
- Marina Piccola – Swim in the azure waters of Marina Piccola, overlooking the famous Faraglioni rocks.
- Explore the many quaint shops and restaurants in the town of Capri.
❌ Do NOT take the fancy-looking taxis on Capri, as they are expensive.
The best way to get around Capri is the little funicular from Marina Grande to the town of Capri, from which you can walk to all of the recommendations I outlined above.
There is also a bus if time allows you to go further to Marina Piccola or Anacapri.
Day 8: Relax in Maratea
After all the boogie-ness of the Amalfi coast, I headed south by train to Maratea in the region of Basilicata. This is a sleepy little town along the coast of Italy (in the Basilicata region) known for its dramatic coastline.
The Church of San Biagio is a beautiful example of Baroque architecture, and the views from the bell tower are not to be missed.
Not only that, there are a number of excellent restaurants serving fresh seafood, and the town is surrounded by olive groves and vineyards. Go for dinner at HOST di Viceconte Antonio and try the ravioli!
Where to Stay
📍Villa Venezuela (1 night)
A night of relaxation and a stunning sunset in Villa Venezuela. Book ahead of time! As a peek, this is the view from the room!
Day 9: Onward to Sicily
From Maratea to Taormina, today is a travel day, by train to ferry to train again. This was enough to have me questioning my itinerary – the silver lining was the beautiful views the train gives as it makes its way down the beautiful coastline.
I did have this thought …. should I just go back up the coast or keep going south – Which is Better: The Amalfi Coast or Sicily? Bottom line, Sicily is the place to be if you’re looking for an authentic south Italian experience.
Where to Stay
📍 Terra Rosa Residences near Isola Bella
I stayed a little outside of Taormina near the beach of Isola Bella for 2 days at the most beautiful residence: Terra Rosa. The town was a lovely 15-minute walk up the stairs. The sunrises, sunsets, and views of Isola Bella along the path took my breath away.
Day 10: Explore Taormina
This picturesque town is located on a cliff overlooking the Mediterranean Sea. From here, you can enjoy stunning views of Isola Bella, explore the ancient Greek theatre, and sample some of Sicily’s best gelato and cannoli.
It is worth mentioning that I quite seriously ate my way through Taormina. That being said, here are some quick hitters for a self-guided walking tour:
- Teatro Antico di Taormina – Great for sunset with views of Mt. Etna.
- Villa Comunale di Taormina – For quiet walks and naps in the park.
- Piazza IX Aprile – cafe central!
Day 11: A Beach Day on Isola Bella
From my little residence at Terra Rosa, I walked down the stairs to Isola Bella and spent the day relaxing on the beach, drinking granitas, and snacking on fruit.
I met fellow travelers in the sun, and we ended up chatting and going out in Taormina the whole night. I went to bed at sunrise – perfection!
Day 12: Explore Isola Ortigia
Grab the train further south to Ortigia (thankfully, trains are a great place to nap). This little island is located in the city of Syracuse on the southeastern coast of Sicily. Although it is only about a kilometer in size, Ortigia is packed with history and culture.
Once the center of Greek civilization, its ancient ruins are now a UNESCO World Heritage Site. Today, the island’s streets are lined with shops and cafes, making it the perfect place to spend an afternoon exploring.
Day 13: A Day in Noto
A quick train ride from Ortigia, Noto is the best place to spend a day in Sicily. The entire town is a UNESCO world heritage site, and it’s easy to see why.
The town was rebuilt in the 18th century after a devastating earthquake, and the resulting baroque architecture is simply stunning.
Start your morning with a stroll down Corso Vittorio Emanuele, the main drag, which is lined with cafes and shops. Then visit the Noto Cathedral, followed by all the other churches and palaces that line the streets, each more beautiful than the last.
Finish up with a stroll through the picturesque gardens of Villa Comunale, and head home to Ortigia for dinner!
Day 14: Time to Fly Home!
And that wraps up what I hope will be many more itineraries to explore La Dolce Vita of the Italian coast. Take the train to Catania Airport, and connect to wherever you call home. Don’t forget to send postcards before you go!
2 Weeks in Italy Map
This is the route I took for the trip. I flew into Naples and flew home from Catania, Sicily.
If you have MORE than 2 Weeks in Italy
If you have a couple more days, here are a few more spots and adjustments to the itinerary I would make:
✅ Spend a few more days in Capri.
On another trip, I ended up spending a long weekend on the island of Capri itself (lodging in Anacapri) and treated myself to a solo relaxation holiday!
✅ Spend more time in Sicily.
On yet another Italy trip, I spent a whole two weeks exploring Sicily. Here are the best of the best recs:
- Palermo – The capital of Sicily, this is a full-on immersion into Sicilian everything – from the churches to the food, to the impossibly winding tiny streets of the old town. Just amazing!
- Isola di Favignana – Take the ferry from Trapani and rent a bike to wander this beautiful little island for a day or two!
- Erice – A gorgeous historic town on top of a mountain, this is a great day trip from Palermo on the way to Scopello!
- Scopello – Find your way to this little retreat beach – Cala Mazzo di Sciacca.
- Cefalu – Also found on many postcards from Sicily, this little town rounds up some of my favorite northern spots in Sicily!
If you have LESS time in Italy
If you have less than 14 days in Italy, try not to be sad. Just promise you’ll be back! Jokes aside, here are a few adjustments you can make to this itinerary:
✅ Skip Maratea and focus on the Amalfi Coast & Sicily. I would start the trip with a roundtrip flight from Naples to Sicily (flying into Catania Airport near Taormina). And of course, there is the ferry from Naples to the Amalfi for the second portion of your trip.
✅ Spend only two days on the Amalfi Coast, prioritizing a day trip to Capri and seeing Positano from the sea (check out the recommendations I made in the itinerary to save money on boat rentals).
However you customize your trip, something about Italy just makes you feel alive. The food, the wine, the history, and the culture all come together to create a magical place that I couldn’t help but fall in love with.
Travel Tips Before You “Andiamo!”
There are a few frequently asked questions I’d like to get out of the way.
Can I tour Italy in 2 weeks?
While 14 days in Italy may seem short for some (or their entire vacation time for Americans), it’s actually the perfect amount of time to explore the major cities and 1 to 2 regions without feeling rushed.
As an aside, I loosely split Italy into three regions:
- The North – Think mountains, skiing, Lake Como, Milan, Venice.
- The South – Naples on down to Sicily, including Pompeii and the Amalfi Coast
- The Chunky Middle – The capital of Rome, the Vatican, the rolling hills of Tuscany
Hiking in the Italian Dolomites & Swiss Alps
If the mountains are more your calling, consider heading to North Italy for some of the most epic hiking of your life. This is my favorite region of Italy, and I say this very seriously because I know how pretty the Amalfi Coast and Sicily are!
How long do I need on the Amalfi Coast?
The Amalfi coastline is one of the most popular tourist destinations in Italy, because, yes, it really does look like the pictures – dramatic cliffs and turquoise waters galore.
I think a long weekend will give you plenty of time to relax on the beach, take day trips to nearby islands, and explore the charming villages, like Positano and Ravello, that dot the coast.
Do I need travel insurance for this trip?
Yes, if you’re planning to stay in Italy for an extended time OR you’re going to be hiking and driving long distances, you should consider reviewing the 5 Best Medical Insurance Policies for traveling in Europe, because shit happens.
This is what I use
▶️ Check Prices for SAFETYWING Insurance! ◀️
The idea is that if something does go wrong, you’ll have peace of mind knowing that you’re covered.
How much does it cost to stay in Italy for 2 weeks?
I was worried 14 days in Italy would break the bank – especially with the Amalfi Coast and Taormina on my itinerary – but it didn’t!
There are a number of ways to save money while traveling, such as staying in hostels or AirBnB rather than hotels, eating at local restaurants rather than tourist traps, and taking advantage of free activities such as walking tours – all of which I did.
Here is the price breakdown for my 14-day stay in Italy, which totaled around $1,500 (sans flights because I use credit card points for this).
- Transportation: $100/week (ferries, trains, Uber – still cheaper than renting a car)
- Housing: $40-100/night (places like Maratea will be less expensive, Amalfi on the more expensive end)
- Meals: $15-30 for some of the best pasta, seafood, and desserts of your life
- Wine: $3 a glass for amazing Italian wines (and the Italians always pour a little extra every time... bless them!)
When should I visit Italy?
While that depends on what you want to see and do, I went on this trip in June!
That said, spring or fall is ideal if you’re interested in exploring the country’s major cities. The weather is pleasant, and there are fewer crowds compared to the summer months.
If you’re more interested in spending time outdoors, then summer is the best time to visit. Italy is also a great destination for winter sports, as the Dolomites offer some of the best skiing in Europe.
What should I pack?
First and foremost, the Italian sun can be incredibly strong, especially during summer.
You’ll want to pack light, comfortable clothing that can be easily layered – firstly because the temperatures can vary widely, and secondly because you’re traveling by public transport most of the time. Minimalism is key!
I’ve put together a quick checklist of Comfy Road Trip Outfits for this itinerary- pay special attention to the summer capsule wardrobe for Italy.
Conclusion: 2 Weeks in Italy from Napoli to Sicily
Planning a trip to Italy can be a big task, as this country has so much to see and do.
I went for a whole month, journeying from Rome all the way down to Bari and Sicily, one gelato cup at a time, living the “dolce far niete“, meaning “the sweetness of doing nothing” before writing this little guide.
To be fair, I think even if I went a thousand times, there is still more to see. All that said, with a little careful planning, it is possible to get a good sampling of Italy in just 14 days.
