World-famous cities, sandwiched between the azure coastline and dramatic glacial lakes, with a good helping of gelato, fresh pasta, and mozzarella-dripping pizza: yes, this is the beauty of Italy! This country really has it all, and with so much to do, you could easily stay for months on end. But don’t worry—if you’ve got just two weeks, you can still experience some of the country’s most stunning highlights. In this 2-week Italy itinerary, we’re sharing our favorite routes, hidden gems, and beautiful stays to help you plan the perfect trip.
Alternative Route: This 14-day Italy itinerary moves quickly throughout the country to cover the best spots. However, if you’re looking for something more slow-paced, we recommend eliminating the northern part of the trip (Como and Venice) and focusing more on the south.
Also have a look at our 7-day Italy itinerary!
Day 1-2 of Your Italy Itinerary: Rome
Start your trip in the capital of Italy: Rome. This city has an atmosphere like no other; it’s definitely the busiest place we visited, so it can sometimes feel a bit hectic, but this is what we love about it!
Spend the first part of your 14-day Italy itinerary wandering the streets of this ancient city, home to some of the world’s most popular tourist attractions. For example, you can visit the Colosseum, Vatican City, and the world-famous Trevi Fountain.
Top Tip: Don’t forget to toss a coin into the Trevi Fountain; legend says this will make your wishes come true! This famous spot gets very busy, so arrive here as early as possible to enjoy this moment for yourselves.
Arriving in Rome
Leonardo da Vinci–Fiumicino is a large international airport with flights arriving from all over the world. They’re also usually the most affordable, making Rome an excellent start location!
From the Airport
Jump on the Leonardo Express, a train that will bring you into the city center in just 35 minutes. Tickets cost 14 EUR each way, and to save you time at the airport, you can buy them in advance.
Alternatively, we found a more cost-effective option: the airport shuttle bus (book your tickets online).
Tip: If you’re planning on hiring a car, we recommend waiting until you finish your first few days in Rome. Like any big city, it can be hard to find parking (unless you book a hotel with parking included), and you won’t need a car to see the top sights in Rome.
We recommend to rent a car in Italy through Sunny Cars with free cancellation and insurance included. Book your rental car here.
Accommodation in Piazza Navona and San Lorenzo is ideal, as the central areas are within walking distance of many top attractions. However, hotels in San Lorenzo are slightly cheaper if you’re traveling on a budget.
Tip: We also really liked the look of hotels in Trastevere, a more authentic ‘Roman’ neighborhood by the river.
Day 3-4: Umbria
Next up on your epic 2-week Italy itinerary is the undiscovered region of Umbria. This is probably one of our favorite places in Italy! It felt very much like Tuscany, with the beautiful hilltop towns and nature but without the crowds. The only thing you’re missing is the coast, as it’s an inner region, but that’s made up for by the stunning lakes you can visit.
Spend your days kayaking on the great lake of Trasimeno, feeling the power of Marmore Waterfall (one of the highest waterfalls in Europe), immersing yourself in vibrant cultural festivals, or trying the region’s delicacy: truffle. There’s so much to see in Umbria (check out all our favorite things here)!
How to Get from Rome to Umbria
From Rome to Umbria, it’s a straightforward 2.5-hour drive north to the cities of Perugia or Assisi. You can set your route via Marmore Falls, which is an excellent way to break up the journey. Buy your entrance ticket to the falls here.
If you’re taking the train, there is a direct train from Rome to Foligno in Umbria (1 hour 45 minutes). From here, you can jump on connecting trains to Spello, Assisi, and Perugia.
Where to Stay in Umbria
While the ancient towns of Assisi, Spello, and Perugia are all great places to stay, most of the activities in Umbria center around nature. For that reason, we recommend staying in the countryside (we stayed at Borgobrufa in Brufa) and doing day trips in your Italian rental car. That’s what we did; our trips were never more than a 1-hour drive.
Day 5-7 in Tuscany: Best of Italy Itinerary (2 Weeks)
Tuscany is one of Italy’s most picturesque regions, with its rolling hills and vineyards. There’s also so much to do, from exploring the hilltop villages and thermal springs to wine tours and fantastic cooking classes.
Where you base yourself on this part of your itinerary is totally up to you. We had a car for our itinerary, so we chose to book an agriturismo in the Tuscan countryside and make day trips to explore the hilltop towns and bigger cities like Florence or Siena from there.
We recommend to rent a car in Italy through Sunny Cars with free cancellation and insurance included. Book your rental car here.
Note: If you don’t have a car, we recommend staying in Florence or Siena and joining organized tours or using public transport to reach some of the more hidden spots in Tuscany.
Option 1: Siena
Siena’s medieval city center has a great ambiance, with must-visit spots like Piazza Del Campo and the Cathedral Duomo di Siena. Cars are prohibited inside the old city center, making Siena a favorite on every Italy itinerary. Read more information about where to park your car here.
Restaurant Tip: Close off the day by having a delicious Italian dinner at Osteria Permalico. Here are some typical dishes from Siena you should try.
Visiting on a Wednesday morning? Don’t miss Siena’s vibrant weekly market (one of the biggest in Tuscany!). This is an authentic local experience, with residents shopping for ceramics, household goods, textiles, fresh fruit, and veg.
From Umbria: Using Perugia as a jumping-off point, it’s a quick 1 hour 30 minute drive to Siena. The route also takes you around the edge of Umbria’s famous Lago Trasimeno if you want to stop for a boat ride, take advantage of the cycle paths, or swim.
Where to Stay in Siena
If you’re only staying for one night in Siena, stick to the city center (around the Torre del Mangia), so you are close to all the historic landmarks, bars, and restaurants (this was our hotel).
Alternatively, if you want to get back on the road early the next day, book countryside accommodation within easy driving distance of the city.
Option 2: Florence
Welcome to Florence. Spend the next 24 hours wandering around this ancient city and discover the Cattedrale di Santa Maria del Fiore, one of the world’s biggest cathedrals, with a stunning, colorful marble exterior (book your tickets here). Afterward, admire it from a rooftop bar before heading to the city’s oldest bridge, Ponte Vecchio.
While you’re in Florence, don’t miss out on a foodie adventure. Hop between cafes and restaurants, trying delicious fresh pasta and finding the best gelato! Alternatively, book tickets for this popular food & drink tour.
From Umbria
If you’re visiting from Perugia and traveling to Florence directly, it’s a 2-hour journey that also hugs the edge of Lago Trasimano. This route also passes close to Cortona, a small hilltop town bordering the two regions.
Find out our top tips for Cortona in Italy
It also passes by Arezzo, where there is the ultimate food tour at Fattoria La Vialla, an eco-farm set amongst the rolling Tuscan hills. This was one of the most memorable experiences we’ve had in Italy! You’ll dine at a long table with other families and friends, enjoying up to 6 courses of delicious homemade pasta, bread, and salads. Send them a message to reserve your spot.
Where to Stay in Florence
Florence has many great accommodation options, from cute guesthouses and budget-friendly hostels to luxury hotels.
Santa Croce is the best area to stay in, with loads of small bars and walking distance from all the things to do in Florence.
Day 6 + Day 7: Tuscan Countryside
Day 6 and 7 of your 2-week Italy itinerary is about immersing yourself in Tuscany’s incredible nature. Drive through avenues of cypress trees, relax your muscles in thermal springs, or explore stunning medieval hilltop villages perched over sprawling valleys. Here are some of our favorite options to choose from:
- Saturnia: There’s no better way to start your day than a dip in this natural hot spring! Between 7-8 AM is the best time to visit; if you stay at this hotel, it is just a 5-minute walk.
- San Gimignano: Known as the ‘Manhattan of the Middle Ages’, this beautiful terracotta medieval town, home to multiple impressive towers, is an absolute must-see on your Italy itinerary.
- Pienza: This town’s stunning Renaissance architecture has given it UNESCO status. However, it’s also known for being the home of Pecorino cheese. As big cheese lovers, we couldn’t miss this town, and it absolutely lives up to expectations. If you’re visiting in September, there’s even a cheese-rolling competition! Here’s our list of the best things to do in Pienza.
- Montepulciano: The most famous wine town in Tuscany! Peruse the beautiful old-world streets before enjoying a wine tasting in one of Montepulciano’s underground cellars. (Book your tour here)
- Elsa Trail: Hike this picturesque trail that takes you through verdant greenery to some of the bluest water we’ve ever seen! There’s also a beautiful waterfall, which is perfect for a refreshing swim. Find out how to visit here.
Where to Stay in the Tuscan Countryside
The Tuscany region offers some fantastic accommodation options, whether rustic farmhouses, cozy city apartments, or budget hostels. Some of our favorite accommodations are based in around the towns of Pienza and Montepulciano:
Day 8-9: Cinque Terre (Coastal Gem on Your 14-Day Italy Itinerary)
Spend a couple of days in the magical Cinque Terre National Park. The dramatic cliffs are home to five incredibly picturesque villages painted in vibrant rainbow colors. Spend your days wandering the pretty streets, swimming in the crystal clear water at the foot of the cliffs, or making the most of the dramatic hiking routes along the coastline. (Discover the routes here)
Spend two nights in Riomaggiore, Monterosso, or La Spezia, which is right outside the national park. (Find the best train tickets here)
Note: You can visit all the villages within a single-day trip from Florence, but if you’re into hiking, spending two or more days in this area is worth it.
How to get from Florence to Cinque Terre
How you get to Cinque Terre will depend on which part of Tuscany you’re leaving from. However, for the purposes of this itinerary, we’re showing you the most straightforward route from Florence. It is 2.5 hours by car, through some beautiful villages, including the Renaissance city of Lucca.
By train: From Florence, there are multiple direct trains a day to La Spezia, which is just outside the Cinque Terre National Park. From here, you can easily get on a train to the main town of Monterosso. Book your tickets in advance here.
Our Top Tip: There’s also the option to take the train to La Spezia via Pisa. If you want to see the famous Leaning Tower, this is the perfect way to do so! See all our favorite things to do in Pisa, Italy.
Where to Stay in Cinque Terre
Accommodations inside Cinque Terre National Park are booked far in advance. Hotels are primarily available in Riomaggiore and Monterosso, but expect to pay way over your typical nightly budget.
A more affordable choice is to stay in La Spezia, where hotels start at 35 EUR a night. Alternatively, for the most budget-friendly option, search for a hostel in the area.
Day 10-11: Como (Optional)
While Lake Como is much further north on your Italy 2-week itinerary, it was well worth the trip for us. If you’d like to take your journey a bit slower, eliminate this part of the itinerary. You can always use it as an excuse to come back to Italy again!
You can also follow our 7-day Italy itinerary instead
This glacial lake is known for its luxury waterside living and known as a vacation spot for the rich and famous. However, there’s so much more than 5-star hotels and fine-dining restaurants. We loved exploring the pebbled coves by boat, stopping to swim whenever we wanted or for our 100th gelato of the day!
Tip: Explore the ‘golden triangle’, the three famous villages of Lake Como named Bellagio, Varenna, and Menaggio. You can travel between these villages by ferry, offering alternative views of the lake! See ferry timetable and tickets here.
Read: Lake Como, Italy (our favorite things to see, hotels, and restaurants)
How to get from Cinque Terre to Como
It’s a reasonably long car journey from Cinque Terre to Lake Como, ranging from 4 to 4.5 hours, depending on where you stay. The route passes through major cities, such as Genoa and Milan, so you can stop to eat here if you feel like spending a few hours in the city.
By Train: You can book a train from La Spezia or Monterosso directly to the Milan train station, where you’ll need to take trains to Lake Como. With the change, journey time can be upwards of 4 hours.
Where to Stay in Lake Como
Bellagio is the most popular option, and it has excellent connections by ferry to the other prominent villages on the lake.
However, we based ourselves in Brienno, a tranquil village on the western side (opposite Nesso). With just two restaurants and no supermarket or bakery, we spent our time taking day trips and relaxing at one of the many lakeside jetties. Bliss! See all hotels in Brienno.
Day 12-13: Venice
Welcome to the city where everything goes by boats and bridges (it’s actually built across 100+ small islands!). Venice is one of the world’s most unique cities and an absolute must-see when you travel to Italy. Spend your last days in the country strolling along the canals, floating along the water on a traditional gondola, or crossing bridges sipping Italian coffee.
Our Top Tip: We found the mornings or late afternoons to be the best times to stroll down the narrow streets of Venice, as the city center gets busy during midday and the day trippers arrive in the city. Make your trip even more peaceful by traveling in the shoulder seasons of Spring and Fall.
See the best things to do in Venice
How to get from Como to Venice
Travel from Como to Venice by car in 3.5 – 4 hours (However, remember that cars cannot enter the city). You’ll travel along the foothills of the Italian Alps and can stop on the way in the underrated gem of Bergamo. This was one of the most surprising cities we visited on our Italy itinerary!
Where to Stay in Venice
We stayed in the middle of the city but tucked away in a quiet street 5 minutes walking from San Marco Square at Novecento Boutique Hotel.
However, if you’re on a tight budget (or traveling during peak season), your best option is to stay outside Venice, in a city called ‘Mestre’ on the mainland. (See all hotels)
How to Visit Italy in 2 Weeks
Rome is a great place to start your itinerary as it’s the central flight hub. Alternatively, choose another airport and alter your itinerary to fit.
Italy Itinerary: Departure Day
You might book a flight from Venice rather than travel back to Rome. This is also a great option as the city is home to Marco Polo International Airport, which has plenty of cheap, affordable flights that leave for worldwide destinations.
However, if you need to travel back to Rome, it’s easy to take a direct train in under 4 hours. See all train tickets.
By car from Rome to Venice is a longer trip of 6 hours. If you want to break up this journey with an overnight stay, the route passes through Bologna and Florence. You can always create an alternative itinerary to include these stops.
Getting Around
Your 2-week Italy itinerary can be done by train or car. While the fastest and most affordable way to travel in Italy is by train, there’s nothing better than an Italian road trip. Particularly for the Umbria and Tuscany part of your itinerary, a car gets you to those scenic country roads and hidden rural spots.
Renting a Car in Italy
Driving is the best option for complete flexibility and to go off the beaten path. All major cities in Italy are well connected by train, but to visit Tuscany, Umbria, or the Dolomites, you need to rent a car. Avoid popular cities by car (such as Florence, Rome, or Milan), as parking costs are sometimes the price of a train ticket.
We recommend to rent a car in Italy through Sunny Cars with free cancellation and insurance included. Book your rental car here.
Note: Italian drivers have a ‘fast and furious’ reputation. This is easy to deal with on the country roads and highways, but driving in the big cities is definitely not for the faint of heart!
Travel by Train
Traveling around Italy by train is excellent. They are speedy (up to 350 km/h!), affordable, and much cleaner for the environment. Book the train tickets a few days in advance to secure your spot and soak up the views from the comfort of your seat.
Join a Tour
If you are basing yourself in one city and want to explore the surrounding countryside, the best option is to take day tours. Many tours leave from the bigger cities like Florence, Rome, and Venice and take you out into nature to explore wineries, hilltop towns, and lakes.
Our Favorite Places to Stay
There are many options when it comes to accommodation in Italy. From boutique hotels, beautiful beach resorts, or lively hostels, you’ll find it all. Below are our favorites per destination.
- Rome: Colosseum Palace Star, Casa Modelli, Sentho Roma
- Umbria: Borgobrufa, Relais Il Furioso
- Florence: Velona’s Jungle Luxury Suites, Santa Croce 14, Casa Botticelli
- Siena: Ca’ Bianca Tuscany Relais, Residenza d’Epoca Le Aquile, B&B Alle Due Porte
- Pienza: Castello di Spedaletto da Laura, La Chiocarella, Il Mastio di Spedaletto
- Montepulciano: Il Tosco, Lupaia, Agriturismo San Gallo
- Cinque Terre: Agriturismo Belvedere 9, Manuel’s Guest House, LA RIPA
- Lake Como: Locanda Alberti, Luxury Suites Rocapom
- Venice: Novecento Boutique Hotel, Giò and Giò Venice B&B, Casa Flora
Best Time to Visit Italy
Tourism in Italy is huge because it is one of the most visited countries worldwide, so it is recommended that tourists avoid the high season. Therefore, we always travel in the shoulder seasons (our favorite time is late September/October). During this time, the prices are lower, there are fewer crowds, and it’s not too hot — so you can enjoy some proper sightseeing!
Tip: If you want to travel during the summer months, we recommend booking your accommodation, tours, trains, and car rental well in advance to avoid disappointment. There are still ways to avoid crowds during these times; just choose more off-the-beaten-path locations like Umbria.
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