Italy, with its art, history, stunning landscapes, and delicious cuisine, is a dream destination for many. If you’re planning an unforgettable Italian adventure, this itinerary will guide you through five major destinations: Milan, Florence, Rome, Naples, and Sorrento. Along the way, we’ll provide suggestions for day trips and the most efficient route to travel by train and ferry to optimize your time. This itinerary is based on our own travel experiences in the country.
Since we were traveling in Spring (mid to late April), we chose Italy for its mild and comfortable climate— warm enough to enjoy sightseeing without the intense summer heat. While we did experience a few rainy days, the weather overall was pleasant.
Summer is great for beach lovers, but it can be scorching hot and much busier. Travel tip: If you’re visiting in the summer, stay well-hydrated, wear hats and sunglasses, dress in light, breathable clothing, and plan outdoor activities for early mornings or late afternoons / evenings to avoid the peak heat.
Here’s a suggested travel route with transportation options for each leg of the journey. This will help you make the most of your time while traveling between destinations.
Start your journey by flying into Milan, then make your way through Italy’s iconic historic cities —Florence, Rome, and Naples. Afterward, unwind and soak in the scenic beauty and relaxed charm of the Amalfi Coast.
Milan → Florence → Rome → Naples → Amalfi Coast
1️⃣ Milan → Florence
- Option 1: High-speed train (~2 hours, fast & scenic).
- Option 2: Flight (~1 hour, but consider the extra time needed for airport check-in and security).
2️⃣ Florence → Rome
- Option 1: High-speed train (~1.5 hours, quick & easy).
- Option 2: Bus (~3.5 hours, cheaper but slower).
3️⃣ Rome → Naples
- Option 1: High-speed train (~1 hour, quick & easy).
- Option 2: Bus (~2 hours, cheaper but slower).
4️⃣ Naples → Sorrento
- Option 1: Ferry (~45 minutes, scenic option).
- Option 2: Circumvesuviana train (~1 hour).
5️⃣ Sorrento → Naples or Rome (to fly out)
- Option 1: Sorrento → Naples → Flight
- Travel back to Naples by ferry or train to catch your flight out.
- Option 2: Sorrento → Naples → Rome → Flight
- Travel back to Naples by ferry or train, then switch to a high-speed train to Rome. From here, get to the airport to catch your flight out.
- While it’s a bit longer, the high-speed train between Naples and Rome is comfortable and efficient.
Here’s a suggested jam-packed two-week itinerary, but feel free to adjust it to suit your schedule and budget. If you like to travel at a relaxed pace, consider skipping destinations or extend your stays in places that appeal to you more.
Milan (Day 1-3)
Accommodation: We stayed close to the Milano Centrale train station in an Airbnb. It was a last minute booking so it wasn’t the best but it was spacious and located just a few meters away from the station making it very convenient for us.
Commuting: Most of our commuting was using their public transport and the rest was on-foot. Travel Tip: for a unique experience, commute on one of their historic trams that’ll take you back in time.
Things to do in Milan
If this is your first time in Milan, here are our suggested things to do, which are do-able in 2 days. For your third day, you can keep it relaxed or take a day trip to Lake Como.
🚌 Take a Hop-on, Hop-off Bus Tour – A great way to get a quick overview of the city and its major attractions, especially on your first day.
🕍 Visit the Duomo di Milano – Admire the stunning structure from the outside. Or climb to the rooftop for panoramic city views and admire the intricate Gothic spires up close.
🛍 Galleria Vittorio Emanuele II – Stroll through one of Italy’s oldest shopping gallery with high-end boutiques and elegant cafes.
🏰 Explore Sforza Castle – Wander the courtyards and museums of this Renaissance-era fortress.
🎨 See Da Vinci’s The Last Supper – If you’re an art lover, then book tickets in advance to view this world-renowned masterpiece at Santa Maria delle Grazie.
—- Day Trip from Milan —-
Take a day trip to Lake Como, just an hour north of Milan by train. Visit the picturesque towns of Bellagio, Varenna, or Como itself. You can also take a boat tour on the lake to see the beautiful villas and enjoy the stunning alpine scenery.
Florence (Day 4-6)
Accommodation: We stayed in the city centre (Centro Storico) in this apartment we booked through booking.com. The location was very convenient and we just walked to most places of interest. Having stayed there though, we can say that this stay is not suitable for families. If you’re a couple though, it’s okay for the price.
Commuting: Florence is a compact, walkable town and we went walking to most places of interest.
Things to do in Florence
Here are our suggested things to do which are do-able in 2 days. For the third day, you may keep it low-key or take a day trip to one or more destinations we’ve shared further down.
⛪ Florence Cathedral and Brunelleschi’s Dome – Start your day with a visit to Piazza del Duomo, home to the stunning Florence Cathedral and its famous dome designed by Brunelleschi. For sweeping views over the city, consider tackling the 463 steps of the iconic cathedral dome.
🌉 Walk across Ponte Vecchio – Browse goldsmiths’ shops on this historic bridge spanning the Arno River.
🌄 Views from Piazzale Michelangelo – A stunning panoramic viewpoint over Florence—especially magical at dusk.
🎨 Tour the Uffizi Gallery – Marvel at works by Botticelli, Michelangelo, and Leonardo da Vinci.
🖼 Visit the Accademia Gallery – Home to Michelangelo’s David, a must-see in Florence for art lovers.
🍽 Visit Mercato Centrale – Sample authentic Tuscan and Italian dishes from dozens of food stalls, perfect for lunch or a casual dinner.
👜 Shop for Leather Goods – Florence is renowned for its high-quality leather products. Explore local markets and boutiques to find handcrafted bags, jackets, and accessories.
🍽 Bonus: City views from a rooftop cafe / bar – If you want to sit back, relax and enjoy beautiful views of the dome and the city, while sipping coffee or some wine, head to Tosca & Nino. It can be accessed from within a shopping centre and is a great spot to unwind. Tip: To avoid waiting time, arrive bright and early to enjoy some breakfast.
🚗 Bonus to-do: Take a Vintage Fiat 500 City Tour with Platinum Tours – Experience Florence in a beautifully restored electric Fiat 500 from the 1980s. Cruise through the heart of the city, discovering hidden gems and learning interesting facts and anecdotes with your driver/guide.
—- Day Trips from Florence —-
There are quite a few day trip options from Florence. We’ve listed the ones we personally shortlisted, but there are others worth exploring too, such as Bologna and Siena.
Pisa (~1 hour by train)
Visit the world-famous Leaning Tower of Pisa, along with the Cathedral and Baptistery in the stunning Piazza dei Miracoli. Climb the tower (advance booking recommended) and stroll through Pisa’s old town before heading back.
Lucca (~1.5 hours by train)
A hidden gem with Renaissance-era city walls, a charming historic center, and bike-friendly streets. Rent a bike and ride along the tree-lined city walls, then relax with a coffee in Piazza dell’Anfiteatro.
San Gimignano (~1.5 hours by bus or car)
Known for its skyline of towers, this UNESCO town offers charming streets, artisanal shops, and gelato that’s won world championships. Climb Torre Grossa for stunning views over the Tuscan hills.
Chianti Wine Region (~1 hour by car or guided tour)
Rolling vineyards, olive groves, and historic wineries. Perfect for wine tasting, especially Chianti Classico. Join a small group or private wine tasting tour that includes lunch in a countryside estate.
Rome (Day 7- 9)
Accommodation: We stayed in this charming hotel, close to the centre of Rome.
Commuting: Most of our commuting was using their public transport and the rest was on-foot.
Things to do in Rome
🚌 Take a Hop-on, Hop-off Bus Tour – A convenient way to cover the city’s highlights and get oriented.
🏛 Explore the Colosseum and Roman Forum – Step back into ancient history with a tour of Rome’s most famous ruins. Tip: The colosseum and Roman Forum are next to each other so plan to visit it together for better use of your time.
🪙 Toss a coin in the Trevi Fountain – A Roman tradition said to ensure your return to the city.
🍝 Dine in Trastevere – A charming neighborhood filled with cobbled streets, family-run osterias, and vibrant nightlife.
🕍 Visit the Vatican Museums and Sistine Chapel – See Michelangelo’s frescoes and the treasures of the Catholic Church.
⛪ St. Peter’s Basilica – One of the world’s largest churches, with an optional dome climb for epic views.
Travel Tip: Plan an entire day to visit The Vatican city as queues can be long just to enter the museums and basilica. Book tickets online in advance and arrive bright and early to maximise your time.
Naples (Day 10 – 11)
Accommodation: We stayed in an Airbnb in the Chiaia neighbourhood. This area was less busy, neat and clean and we felt quite safe here. It was also walking distance to the promenade by the sea.
Commuting: Most of our commuting was using their public transport and the rest was on-foot. We did take a local taxi a couple of times to get to the port and back, which was affordable.
Things to do in Naples
🌊 Stroll the Naples Waterfront – Walk along Lungomare with views of the bay and Mount Vesuvius.
🕍 Explore Spaccanapoli – A narrow, bustling street cutting through Naples’ historic center.
🏘 Wander the Spanish Quarter – Discover authentic street life, local eateries, and colorful murals in this vibrant neighborhood.
🍕 Eat Authentic Neapolitan Pizza – Try the one at Sorbillo or another historic pizzeria.
—- Day Trips from Naples —-
Mount Vesuvius (~1 hour by bus or car)
Hike to the crater of one of Europe’s most famous volcanoes for dramatic views of the Bay of Naples. Combine this with a trip to Pompeii for a full day of history and adventure.
Pompeii (~40 minutes by train)
Explore the remarkably preserved ruins of an ancient Roman city frozen in time by the eruption of Mount Vesuvius in 79 AD. Hire a guide or use an audio tour to fully appreciate the site’s history and layout.
Herculaneum (~20 minutes by train)
Smaller and better preserved than Pompeii, Herculaneum offers an intimate look at daily Roman life. Less crowded than Pompeii, it’s perfect if you want a quieter, more manageable archaeological experience.
Amalfi Coast towns / villages (~45 mins to 2 hours)
If you didn’t already know, you can take day trips to several Amalfi coast towns from Naples. The time it takes depends on which town you travel to and can vary between 45 mins to 2 hours. We, however, decided to head out of Naples to spend more time along the coast and fully soak in its beauty and laid-back atmosphere.
Sorrento (Day 12 – 14)
We chose to make Sorrento as our base location and took day trips to visit other destinations on the coast.
Accommodation: We stayed in this very cute Airbnb right at the port, with a view of the bay. The apartment had a large balcony to hang out as well, from where we could enjoy watching sunsets too.
Commuting: within Sorrento it was all on-foot. To get to the main city, we took a lift which took us from the port to the town perched on top of the cliffs. It was a paid lift and costed €2.40 for a round trip.
Travel Tip: If you want to avoid repeatedly using the lift to reach the town, look for accommodation within the main city area. We opted to stay near the port since we planned to visit other coastal towns by ferry. It turned out to be a convenient and stress-free way to travel, especially compared to driving, which, while scenic, is often plagued by traffic jams and navigating challenging, narrow roads.
—- Day Trips from Sorrento —-
Capri (~30 minutes by ferry)
Discover the island’s glamorous appeal, with highlights like the Blue Grotto, Villa San Michele, and Monte Solaro. Take the chairlift in Anacapri for stunning panoramic views, and avoid peak crowds by leaving early.
Positano (~45 minutes by ferry or ~1 hour drive)
Famous for its colorful cliffside homes, chic boutiques, and beach clubs. Tip: Wear comfortable shoes—Positano is full of steep steps and winding lanes.
Amalfi & Ravello (~1.5 hours by ferry or car)
Amalfi offers historic charm with its cathedral and seaside vibe, while Ravello provides breathtaking views and elegant gardens like Villa Cimbrone and Villa Rufolo.
Here are a few more Travel Tips to help you plan better:
- Paywave / Digital Payments like Apple Pay work in most stores so you do not need to carry too much cash with you.
- Digital Payments and credit/debit cards work on their public transport as well, so you don’t need a separate transport card.
- For trains and attractions, e-tickets/digital tickets are acceptable.
- Italy is a cycle / scooter friendly country and several places offer cycles / e-scooter sharing at several spots around towns.
Hopefully this post gives you a starting point when planning your own trip. And if you have any questions, leave them in the comments – and we’ll try our best to answer them. Happy travels folks!
