World-famous cities, sandwiched between the coastline and dramatic glacial lakes, with a good helping of gelato, fresh pasta, and mozzarella-dripping pizza: yes, this is Italy! This country has so much to do that you could easily stay for months on end. But don’t worry—in just two weeks, we still experienced some of the 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, skip the northern part of the trip (Como and Venice) and focus 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. The 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 past some of the world’s most popular tourist attractions like 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.
Where to stay? Rome has some incredible hostels, bnbs, and hotels downtown. We chose accommodation in Piazza Navona, which is within walking distance of the top attractions. But, a hotel in San Lorenzo (slightly cheaper) or Trastevere (authentic) is also a great option!
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 feels very much like Tuscany, with the beautiful hilltop towns and nature, but without the crowds. The only thing you’re missing is the coast, 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). You can get your entrance ticket to the falls here.
- Immersing yourself in vibrant cultural festivals, or trying the region’s delicacy: truffles.
Getting from Rome to Umbria: It’s a 2.5-hour drive north to the cities of Perugia or Assisi. We set the route via Marmore Falls to break up the journey. There’s also 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. Browse tickets here.
Where to Stay? The ancient towns of Assisi, Spello, and Perugia are all great places to stay, but we recommend staying in the countryside (we stayed at Borgobrufa in Brufa) and doing day trips in your 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 Tuscany’s more hidden spots.
Option 1: Siena
This medieval city has a great ambiance, with must-visit spots like Piazza Del Campo and the Duomo. Cars can’t enter the old center, making it a favorite on this Italy itinerary. (Here’s where to park) Restaurant tip: We had a delicious Italian dinner at Osteria Permalico.
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: From Perugia, it’s a 1-hour 30-minute drive to Siena. The route 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? For just one night, stick to the city center (around the Torre del Mangia). This was our hotel. Alternatively, book countryside accommodation within easy driving distance of the city.
Option 2: Florence
Welcome to Florence! Here you can:
- 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).
- Admire the cathedral from a rooftop bar afterward
- Head to the city’s oldest bridge, Ponte Vecchio.
- Hop between cafes and restaurants, trying delicious fresh pasta and finding the best gelato! We found this popular food & drink tour.
From Umbria: It’s about a 2-hour journey that hugs the edge of Lago Trasimano. This route also passes close to Cortona, a small hilltop town bordering the two regions.
Top tip: The route also passes by Arezzo, where there is the farm-to-table tour at Fattoria La Vialla 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: 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 within walking distance of the things to do in Florence.
Day 6 + Day 7: Tuscan Countryside
Days 6 and 7 of your 2-week Italy itinerary are about immersing yourself in Tuscany’s incredible nature. 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 and 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 stunning Renaissance town is known for being the home of Pecorino cheese. As big cheese lovers, we couldn’t miss it, and it absolutely lives up to expectations. If you’re visiting in September, there’s even a cheese-rolling competition!
- 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
There are so many accommodation options in Tuscany, from rustic farmhouses to cozy city apartments or budget hostels. Some of our favorite accommodations are based around the towns of Pienza and Montepulciano:
Day 8-9: Cinque Terre (Gem on Your 14-Day Italy Itinerary)
Spend a couple of days in Cinque Terre National Park. The dramatic cliffs are home to five incredibly picturesque villages painted in vibrant rainbow colors. We spent our days wandering the pretty streets, swimming in the clear water at the foot of the cliffs, and hiking along the coastline. (Discover the routes here)
We recommend 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.
Getting from Florence to Cinque Terre: It is 2.5 hours by car, through some beautiful villages, including the Renaissance city of Lucca. By train, there are multiple a day to La Spezia. 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 the 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. We chose to stay in La Spezia, which is much cheaper. (Or browse hostels here)
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 is 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)
Getting from Cinque Terre to Como: It’s long, about 4-4.5 hours, depending on where you stay. Drive or book a train from La Spezia/Monterosso to Milan, then on to Lake Como.
Where to stay? Bellagio is the most popular option, and it has ferry connections to the other villages on the lake. However, we based ourselves in Brienno, a village on the western side with just two restaurants and no supermarket or bakery. We spent our time taking day trips and relaxing at the many lakeside jetties. Bliss!
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.
Getting from Como to Venice: 3.5-4 hours by car or train (but remember that cars cannot enter the city). By car, 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?
We stayed at Novecento Boutique Hotel, tucked away in a quiet street in the middle of the city, a 5-minute walk from San Marco Square. However, if you’re on a tight budget (or traveling during peak season), 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.
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).
- Renting a car? We got one after the first few days in Rome. You won’t need a car to see the top sights in the city.
Italy Itinerary: Departure Day
You might book a flight from Venice rather than travel back to Rome. The city is home to Marco Polo International Airport, which offers plenty of affordable flights to destinations worldwide.
However, if you need to travel back to Rome:
- Take a direct train in under 4 hours. See all train tickets.
- Or, a drive from Venice to Rome in 6 hours. If you want to break up this journey, you can always create an alternative itinerary to include stops like Bologna and Florence.
Getting Around
We like to travel in Italy by car, and did the same on this 2-week itinerary. Though by train is the fastest and most affordable (browse your ticket options here), there’s nothing better than a road trip. Particularly in Umbria and Tuscany, a car gets you to those scenic country roads and hidden rural spots.
Renting a Car in Italy: Best to visit Tuscany, Umbria, or the Dolomites. However, avoid popular cities by car (such as Florence, Rome, or Milan), as parking costs can be as high as 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!
Join a tour: Many tours depart from larger cities like Florence, Rome, and Venice and take you into nature to explore wineries, hilltop towns, and lakes. (Browse all tours in Italy)
Our Favorite Places to Stay
There are many options for 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
As tourism in Italy is huge (!), we always travel in the shoulder seasons (our favorite is late September/October). During this time, prices are lower, crowds are fewer, and it’s not too hot!
- Traveling in summer? We recommend booking your accommodation, tours, trains, and car rental well in advance to avoid disappointment. You can still avoid crowds during these times; just choose more off-the-beaten-path locations like Umbria.
By purchasing through our links, you support us at no additional cost.
Thank you for your support. ♥️
- Find Hotels via Booking.com
- Find a Rental Car via Sunny Cars
- Find Flights to Italy via Skyscanner
- Get a Travel Insurance via Heymondo
- Book Tours & Attractions via GetYourGuide
- Book a Bus/Train/Transfer via 12Go
Looking for more travel information? Plan a chat with us for personalised travel advice or get an answer from the Salt in our Hair Travel Community on Facebook.