2 Weeks in Italy: The Ultimate Itinerary for First-Timers

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Planning your first trip to Italy? I know it can seem overwhelming. We got you. This itinerary covers Rome, The Amalfi Coast, Florence, Cinque Terre, and Venice. It is packed with highlights, don’t miss items, and best of all- no fluff.

Italy will always hold a special place in our hearts. It’s truly the place that opened our eyes to the beauty of travel. Unique culture, amazing food, stunning views, epic history- Italy has it all.

Italy was our first real international trip- I’m talking long haul flights, changing cities, multiple hotels, and public transportation. It was incredibly overwhelming and we had absolutely no clue where to begin. 

What we did know, was that there were a handful of cities we had always dreamed of visiting. No real hidden gems, but the big cities that scream ITALY. So, that is how this itinerary was born- we were essentially wanting to hit the highlights. 

Are you planning your first trip to Italy? Let us take the stress of planning away and follow this epic itinerary for your two- week intro to Italy.

Why Visit Italy for 2 Weeks?

Ah, Italy. The little boot, food heaven, a place where many of us Americans proudly claim to have ancestors. Italy is comprised of 20 regions, each with its own unique blend of history, culture, and, most importantly, food. We’ve been going to Italy every summer for the past few years and still haven’t made our way through each region. You could probably spend years here, but most of us don’t have a few years PTO built up. Two weeks is ideal because it will get you to see most of the “highlights”, without rushing around too much. However, if you have less time, don’t write off visiting Italy, see our article here for what to do with limited time.

Who this itinerary is for?

This itinerary is perfect for anyone who loves culture, food, and getting their steps in. Our days are packed with things to do, but not leave you needing a vacation at the end of your vacation. We prioritize local culture and things we feel are actually worth recommending, no extra fluff You won’t find us recommend visiting every church or museum in the city (although, you can if you want to), just the highlights.

Here is the itinerary breakdown:

• Rome: 3 days
• Amalfi Coast: 4 days
• Florence: 3 days
• Cinque Terre: 2 days
• Venice: 2 days

When to Visit Italy

If you’re wanting fewer crowds and cheaper prices (but still decent weather), May and September are for you. We personally choose to visit Italy every summer in June and while it is still crowded, we love the weather and don’t find the crowds to be too much to manage. Places like Rome and the Amalfi Coast do tend to experience more mild winters (with average highs in the mid 50’s Fahrenheit), but you would certainly have to plan accordingly.

Essential Italy Travel Tips

Italy uses type C electrical outlets, which have two round pins. If coming from the US, make sure to back your electrical outlet adapter.

Our go-to app recommendations:

In most major cities, you will likely do a lot of walking. We always recommend downloading the google maps for your planned cities ahead of time. This will allow you to have directions, even in areas with poor reception (plus you won’t be using all your data).

If Italian isn’t your spoken language, download the offline version of google translate for help with communication. We’ve had plenty of full conversations using google translate!

👉🏻Pro tip: you can use the camera feature for help reading the menu. Just be aware that somethings don’t translate well, so leave room for error.

How to Travel Italy by Train: Tips for First-Timers

It is very easy to travel to most large cities in Italy via train. Here is our Step-by-step on how to plan your route with trains:

1. Use Google Maps to plan your route. Google maps is an excellent resource to see the distance between your accommodations and attractions. It will help you establish a realistic sense of travel time.
   1. Use the google maps date & time feature to get accurate train schedules. Tap the departure time to adjust for your time and date preferences. We love this feature for planning as you go.
   1. Click routes to find operator information. Once you’ve selected your route, day, and time, click to see the details of the operating company (usually Trenitalia or Italo)
   1. Book in advance. If you can, it’s best to book in advance (especially for those long routes). Ideal booking time is about 2-3 months prior to your trip, especially during peak season.
   1. Pay attention to booking options. Both Trenitalia and Italo offer different booking classes and inclusions (Standard, Premium, Business, Quiet zones). If you’ve got a long trip planned, you’re probably going to want to book an outlet seat so plan in advance.

Tickets can also be purchased at a kiosk or ticket office. Look for “biglietto” which means tickets.

Trains run on time in Italy, so give yourself leeway to make sure you don’t miss it.

Make sure that you validate your ticket prior to boarding, otherwise you could receive a fine. Validation stations are the tan & green machines found on the platforms.

ALWAYS have your ticket with you. They will check. If you don’t have a ticket, you will be fined.

Italian Food Etiquette

Dinner is typically served very late in Italy. Standard dinner time is 8pm-10pm. Most restaurants will close for a small window prior to opening for dinner service. Make sure to plan accordingly.

Italy’s food is very region specific. Each region is known for specific dishes and pasta shapes. You can find things outside of that, but it is most common to find regional dishes. Except pizza, pizza is a universal love language (although the crust varies by region). Don’t go to Rome expecting to get lasagna- can you find it? Yes. But you are more likely to find Cacio e pepe or Carbonara. 

Types of Restaurants in Italy

Pasticceria’s are bakeries. Typically, they serve espresso and have cases filled with pastries. The selection varies by region, but there are a few popular goodies that can be found throughout Italy. This is Joc’s favorite place to frequent.

A bar is typically more of a coffee shop or café. Expect to find pastries, coffee, and maybe even gelato during the day. In the evening, they may start to serve alcoholic drinks & aperitivo. Bars are our favorite place to grab a little treat.

Enoteca’s are a wine shop or a place that serves regional wines.

Ristorantes are standard restaurants. You can expect to be seated and have table service. There is usually a “coperto” or cover charge per person which covers the table service. It is usually 1-5 euros. Tips or gratuity are not expected and you will likely need to ask for the check.

Trattoria’s are less formal than Ristorantes, typically family-run eateries serving regional dishes. Usually cheaper prices (and in our opinion, better food).

Osteria’s are very similar to trarrorias. Cheaper food, less formal atmosphere. Some wine and small plates are common, but others serve full meals. 

Is Italy safe?

Currently the US department of state has Italy listed at a level 2 (exercise increased caution). However, we have never felt unsafe in Italy. Italy is known for petty type crime, such as pick-pocketing or scams. In fact, if you are purchasing a train ticket at a kiosk, they warn you during the process to be aware of pickpocketing. 

Here are a few tips we use to stay vigilant against pick-pockets:

• Leave all flashy things out of sight (in fact, if you don’t need it, don’t even bring it).
• Never leave your bags unattended.
• Pay attention to your surroundings.
• Bring antitheft bags or backpacks
• If someone “bumps” into you, it’s usually not an accident. Take note.

Rome: Days 1-3

Rome will always be our favorite city in Italy. It’s the perfect blend of ancient history and city. It’s also important to note that, in our opinion, Rome has the best food. So that obviously moves it up to #1 for foodies like us.

If you’re looking for ALL the tips for Rome, checkout our detailed 3 day guide to Rome.

Getting to Rome:

We started our trip in Rome. One excellent argument for starting an Italy trip here is that Rome Fiumicino Airport (FCO) is a major international airport and Rome itself is relatively centrally located in Italy. From Rome, most places can be accessed by taking a train. We recommend taking the Leonardo Express train from the airport into the main train station, Roma Termini.

Where to Stay in Rome:

For a 5 star colosseum view, we recommend this hotel.

For an excellent mid-range hotel near Roma Termini, we recommend this hotel.

For a slightly less expensive option, but still excellent location, we recommend this hotel.

Day 1

• Colosseum, Roman Forum & Palatine Hill

Arguably the most famous sights to see in all of history, it seems only natural to put this first. Make sure to book a tour because tickets do sell out and you will learn so much more having someone guide you through this ancient wonder. Book your tour here:

• Piazza Venezia &Altare della Patria, and Trastevere

Altare della Patria is also known as the “wedding cake building”. Book a ticket in advance and head to the panoramic terrace- the view is a dream. 

Spend the evening in Trastevere, enjoying carb heaven with some fresh carbonara. 

Day 2:

• Spanish Steps, Trevi Fountain, Pantheon, Campo dei Fiori & Piazza Navona

Start early at the Trevi, a new cue is in place for this 2025 year, but heading there before 8 am will get you in before the cue begins. The Spanish steps, Pantheon, Piazza Navona are all in walkable distance from each other. It’s a perfect way to spend the afternoon wondering around with a gelato in hand.

• Castel Sant’Angelo, Piazza del Popolo & Villa Borghese

Enjoy views of the Taber River at Castel Sant’Angelo. The Villa Borghese is a little slice of heaven in Rome. Visit the pond, rent a bike, or enjoy a walk in the shade with gelato in hand.

If you’re looking to get less steps or interested in a unique take on todays itinerary, we definitely recommend checking out one of these tours:

Day 3

• Vatican Museums & Chapel Sistine

Marvel at the Vatican & Chapel Sistine, but make sure to have your tickets purchased ahead of time or risk the long cue. Fair warning: it’s always crowded, so be mentally prepared. Tours can be purchased here.

• St Peter’s Square and St Peter’s Basilica

Purchase tickets to climb the dome for epic views of the basilica from above. Don’t forget to wear clothing that covers your knees and shoulders because the dress code is strictly enforced.

Amalfi Coast: Days 4-7

The Amalfi Coast is Italy’s glittering coastline where iconic charm and Italian vacation vibe together harmoniously. Beautiful seaside villages, winding roads, history, lemon flavored… everything. The Amalfi Coast is a post-card picture place to relax in the Italian sun.  

We recommend basing yourself in Positano for its central location and using ferries or the SITA bus system to move around.

Getting to Positano:

From Roma Termini you will need to purchase tickets for Napoli Centrale. Tickets should be purchased in advance here for the best possible price.

Exit the Napoli Centrale station and walk towards signs for Piazza Garibaldi. When you arrive, look for the look EVA S.R.L. trains (Ente Autonomo Volturno) bound for Sorrento and purchase tickets for Sorento or Meta.

Tickets can be purchased at the ticket counter. These are local trains with multiple stops so make sure to get off at Meta or Sorento.

In Sorrento or Meta use the SITA bus station to purchase tickets for SITA bus. When purchasing the tickets for Positano, they will let you know the bus number. These buses make multiple stops so make sure you get off at Pasitano.

👉🏼Pro tip: You can also confirm the bus number with google maps.

Where to Stay in Positano:

If you’re looking for the ultimate bucket-list luxury stay, we recommend this hotel.

For an excellent mid-range option, we recommend staying here.

For another wonderful mid-range option, we recommend this hotel.

Day 4: Positano

• Explore Positano. This small, seaside town packs a punch with charm and views. Spend some time wondering around the small shops.
• Want to be a beach bum for the day? Rent an umbrella and set up shop. This a place where locals and tourist love to get the best souvenir- an Italian tan.
• Try a ceramics class! It’s the best way to stay out of the sun, but have a blast. We recommend this one:
• Enjoy the iconic sunset on a sunset cruise. Perfect time to get that Instagram photo. Book your cruise here: 

Day 5: Amalfi town & Ravello

• Visit a lemon farm and learn all about the famous Amalfi lemon. Bonus: limoncello is included. Book here:
• Wonder around Amalfi town- don’t forget to stop into the Nino & friends for some chocolate samples (plus some chocolate to bring home too).
• Take the winding roads up to Ravello and get lost in the Villa Cimbrone Gardens
• Stop for Gelato at at Baffone Gelateria Artigianale– it was seriously one of the best Gelatos we had in Italy.

Day 6: Pompeii & Mount Vesuvius

Getting to Pompeii

Purchase tickets for SITA bus to Sorrento or Meta or Sant’ Angelo.

Once there, make your way the EVA S.R.L. (Ente Autonomo Volturno) train station and purchase tickets for Pompeii Scavi Villa Dei Misteri from the ticket counter.

Look for trains bound for Napoli Porta Nolana and make sure to get off at Pompeii Scavi Villa Dei Misteri.

• You can’t visit this region without taking a trip to Pompeii. Booking a tour is the best way to experience this area and bonus point, you can visit Mount Vesuvius too!
• Try the Eat, Pray, Love pizza experience in Naples. This pizza was made famous by Julia Roberts and honestly, it’s worth the hype.

Day 7: Capri 

Getting to Capri

From Positano, purchase ferry tickets for Capri. We used Pasitano Jet and had no issues. You can book your tickets in advance here to save time.

• Visit Anacapri and take the Monte Solaro chairlift to the top for the best views of the Faraglioni.
• Anacapri town is full of little shops and places to grab a bite (or some gelato), so spend some time here exploring. 
• Take the bus to Capri for some high-end shopping and celebrity spotting in the Piazza. 
• Hike up to Belvedere Tragara for a quiet ecape with some epic views.

If you’re looking for an easy way to see Capri, you can definitely consider a tour. Here are some great options.

Florence & Tuscany (days 8-10)

After all that sun, it’s time to head to Italy’s art capital. Florence is an incredibly walkable city filled with Renaissance culture, artsy vibes, and incredibly rare steak. Rather than recommending you do endless museum marathons, we’re mixing art, nature, and epic views to show you the best of this region in 3 days.

Getting to Florence:

If you are following this itinerary exactly, you will be coming from Positano. You will need to purchase tickets for the SITA bus heading to Sorrento, Meta, or Sant’ Angelo. Confirm the bus stop number with google maps.

After exiting your bus, walk to the EVA S.R.L. (Ente Autonomo Volturno) train station and purchase tickets on the local metro for Piazza Garibaldi. You need to take the train bound for Napoli Porta Nolana and get off at Piazza Garibaldi.

Walk out of Piazza Garibaldi terminal and look for signs for Napoli Centrale, there you will purchase tickets for Firenze Santa Maria Novella. Take the train to Firenze Santa Maria Novella.

👉🏼 Pro-tip: tickets should be purchased in advance here in order to get the best possible price.

Where to Stay in Florence

If you’re looking for a high-end feeling hotel, right near the train station, we definitely recommend staying here.

For a mid-range hotel near the train station, with a duomo view, we recommend staying here.

For a budget option, that feels like a modern hotel, we recommend staying here.

Day 8: Exploring Florence

Since you will likely be arriving on this day from Amalfi, we have only included a few things to do. No need to rush around, you will have plenty of time.

• Visit Ponte Vecchio, Florence’s ancient bridge. The only pre-modern medieval bridge remaining over the Arno river in Florence. Bring some cash because there is plenty of shopping.
• Experience sunset at the Piazzale Michelangelo viewpoint. In our opinion, this is the best view of Florence. You will definitely be able to spot the duomo.

If you’re interested in seeing the city with a guide, here is a fantastic option:

Day 9: Getting Artsy 🎨

Morning:

• Visit the Galleria dell’Accademia to see the famous Statue of David by Michelangelo.  You need to book your ticket in advance. You can do this as part of a tour; here is a great tour option:
• Try the famous All’Antico Vinaio sandwiches. They’re famous on social media and definitely worth the hype.
• See the duomo! It’s kinda a big deal here (pun intended). Climb the tower if you wish, but make sure to grab your tickets in advance.
• Try the Bistecca alla Fiorentina (Florence steak). This steak is a specialty known to the Florence area. Warning: it’s going to come rare. Make a reservation in advance.

Day 10: Tuscany road trip.

• Drive from Florence to the Val D’Orcia region. Val D’Orcia is a region in Tuscany where you will find those dreamy picturesque rolling hills vibes. Spend a few hours getting lost in the best way.
• Visit Sienna and stroll the Piazza del Campo.
• Stop for lunch at II Bocconcino.  Honestly, these were the best sandwiches we had in all of Italy. We dream about these sandwiches. Please go get one, for us.
• Climb the 300 steps of the Torre del Mangia for the best views in Sienna.

If driving is too scary, here are some fantastic tour options

Cinque Terre (days 11-12)

Are you missing the sun? Perfect because its back to the coast we go! Cinque Terra, 5 old fishing villages dotted along the coastline. You can explore the villages by foot by hiking the coastline trail or by train.

To be honest, although Cinque Terre is worth visiting and incredibly picturesque, we didn’t find there to be much to do, so we were glad to spend our days hiking. Because of this, 2 days is the optimal time to see all the towns without feeling bored. If you want to go at a more relaxed pace or spend more time having beach days, feel free to adjust accordingly.

If you plan on hike, due to landslides or natural disasters, part of the trail can sometimes be closed, which is why this itinerary is written the way it is. Always be sure to check prior to heading out. Updated information can be found here.

Getting to Cinque Terre:

From Firenze Santa Maria Novella station, purchase tickets for Pisa Centrale or La Spezia Centrale. These are local trains, so make sure to get off at either Pisa Centrale or La Spezia Centrale stop.

Once at Pisa Centrale or La Spezia Centrale, purchase tickets to Monterosso using the Cinque Terre Express.

Where to stay in Cinque Terre

Because these are five tiny towns, hotel accommodations are quite limited. Therefore, here are a few recommendations we can make if you’re looking to stay as close to the villages as possible.

For a stunning stay in Riomaggiore, we recommend booking here.

Another more budget friendly accommodation in Riomaggiore is this hotel.

Day 11

Today is a shorter day due to travel time, but we still managed to make time to get a hike in and explore 2 of the 5 towns.

If you’re not staying in Cinque Terre (or even if you are, but don’t feel like hiking), then take the Cinque Terre Express train to Riomaggiore and begin exploring.

Spend some time exploring in the town grab some of the famed fried fish in a cone and then take the blue trail hike over to Manarola. It’s will take approximately 1 hour to get over to Manorala and it is definitely worth the views. End your evening sampling some of the local wines, taking a boat tour, or just watching an epic beach sunset.

If relaxing and doing a tour seems less overwhelming than hiking (or if the weather just isn’t on your side), here are some options for you.

Day 12

Begin in Monterosso, the biggest village. Depending on where you are coming from, you may need to take the Cinque Terre express to get here. In Monterosso you will find beaches, shopping, stunning views.

Hike from Monterosso to Vernazza. A beautiful scenic pathway which takes approximately 2 hours. Make sure to pack sunscreen & start early because shade is limited. 

Vernazza, is the colorful village with vibes similar to Positano. Once here, you can explore the town, take a dip in the ocean to cool off, or grab some stunning Instagram worthy selfies.

Next you will hike from Vernazza to Corniglia. This hike takes about 1.5 hours. Once in Corniglia, you can kayak at sea, explore the local village, and be sure to try some local Cinque Terre wine.

Venice (Days 13-14):

Venice, the magical floating city with more dead ends than a corn maze. Built upon 118 islands and connected by over 400 bridges, this beautiful city is sure to test your sense of direction.

At this point in your two-week itinerary, your feet are probably hurting and you are likely craving a break. Good news! Venice is a fairly small territory to cover compared to other areas like Rome and the Amalfi Coast. These next two days will have you cover the highlights with time to enjoy an Aperol spritz in the afternoon.

Getting to Venice:

If you are following this itinerary directly, you will need to head to the Monterosso station and purchase tickets for Pisa Centrale or La Spezia Centrale. These are local trains, so make sure to get off at either Pisa Centrale or La Spezia Centrale.

Once at Pisa Centrale or La Spezia Centrale, purchase tickets for Firenze Santa Maria Novella. Take the train to Firenze Santa Maria Novella.

Once you arrive at Firenze Santa Maria Novella purchase your tickets for Venezia Santa Lucia.

Where to Stay in Venice

For a luxury stay, look no further than this stunning hotel

For an excellent mid-range option, we recommend staying here.

For a budget option, this would be a fantastic choice.

Day 13

Since you’re likely going to have a day of travel today, we are recommending a less full itinerary. No rushing around today. 

Visit the Basilica Santa Maria Della Salute. This beautiful church stands out among the typical Venetian façade- that alone piqued our interest enough to make a stop.

Take a Gondola Ride. It’s pricey, but absolutely a core-memory. Go before 7pm to avoid an even steeper price.

Ponte Di Rialto. Walk across the iconic bridge, visit the shops, but go in the evening for a stunning view of the canals (and less crowds).

Day 14:

Piazza San Marco. Grab a pizza, listen to the music, and just enjoy the venetian vibes in this beautiful Piazza.

Doges palace: a place of stunning beauty and important history. We recommend taking. A tour. We listed a few tour options below.

Bridge of sighs. You will likely walk across this bridge during your Doges Palace tour, but make sure to see it from the outside too for a change or perspective.

Visit Saint Marks Basilica. This stunning Basilica stands out in all the best ways. Make sure to climb the bell tower for the best views of Venice.

If you’re looking for more Venice info, visit our detailed post on how to see the best of Venice in 2 days.

Getting Home

From Venice, you can either catch a flight out of Venice Marco Polo Airport (VCE), or make your way back to Rome Fiumicino Airport (FCO). We personally chose to fly out of VCE due to time constraints, but you can easily hop on a train back to Rome to make a flight there.

Final thoughts

Whew! A two week trip to Italy will leave you feeling exhausted, but yearning for more. There’s something so charming about each of these towns (and all the small towns in between). We are sure that you will be returning home with a full heart, heaps of memories, and a desire to return again.