THE DAY-BY-DAY GUIDE TO THE HIGHLIGHTS OF ITALY - ROME, FLORENCE, VENICE, & MORE 🇮🇹
I've been fortunate enough to visit Italy multiple times and even more fortunate to have been guided by true Italian friends. Here, I take all that I've learned from those travels and distill it into one perfect itinerary that hits the big highlights.
This itinerary is a great fit for first-timers since it'll take you to the absolute must-see spots in Italy. You certainly won't see all the boot has to offer (just plan on coming back for future trips, plural, to make that happen), but you'll see the most iconic places at a reasonable, enjoyable pace. You'll be able to soak up all the history, food, wine, and dolce vita these cities have to offer. After this first taste, you'll be dying to come back for more!
🗺️ Main Itinerary Stops:
- Rome | 2 full days / 3 nights
- Orvieto | Pit stop
- Tuscany // Montalcino | 2 full days / 3 nights
- Siena | Pit stop
- Florence | 2 full days / 3 nights
- Tivoli | Pit stop
- Rome | Overnight for return flight
🗺️ Optional Extension Stops:
- Pisa | Day trip (+ extra night in Florence)
- Bologna | Pit stop
- Venice | 2 full days / 3 nights
- Modena | 1 full day / 1 night here or nearby
Get an idea for what to expect with stats including: trip length, ideal season, trip speed, physicality, trip themes, who this trip is best for, cost, and how to get around
Stop-by-Stop Overview
Stop-by-stop trip structure, including number of days at each destination and number of activities, restaurants, and hotels included in the full version of this guide
Example Itinerary Day
An example day from the full version of this itinerary, so you can see the level of detail and travel style you can expect!
BONUS: Hotel Recommendations
Hotel recommendations for this itinerary! Consider supporting my work by booking through the links provided - it’s much appreciated!
Scroll down to the FREE GUIDE header to dive in!
Full Intinerary Features
If you like this free sneak peek, check out this complete version of this itinerary! The full version includes:
🗺️ A full itinerary covering 4 overnight destinations & 6 day-trips or pit-stops
Late Spring or early Autumn for fewer crowds and pleasant weather
⏱️ Trip speed
On-the-go with time for gelato or apertivo! Some slow days built-in
💪🏻 Physicality
Lots of walking!
🧳 Trip themes
History | Religion | Architecture | Local Eats | Fine Food & Wine | Romance
🎯 Best for
Couples | Honeymooners | Small groups | Families | Multi-generational
💵 Cost
$$$ - Moderately expensive
🗺️ Getting around
This trip is designed for you to drive via car. You could also do this trip via train, but some of the day trips / pit stops will be more difficult or impossible without a car.
STOP-BY-STOP OVERVIEW
All the stops you'll discover in the complete itinerary and how long you'll spend in each. Get a sense for the level of detail you can expect from my guide based on the number of recommendations at each stop!
Rome is nicknamed the Eternal City, and for good reason. It's obviously one of the oldest cities in the world, which is reason enough for a visit. But, Rome is unique in that it has renewed itself consistently throughout its extensive life, always finding a starring role in the historical narrative. Rome has been center stage at some of history's biggest moments: the ancient world, the rise of Papal power, the Renaissance, World War II, and more. This makes Rome one of the best tourist cities in the world. There's the sheer magnitude of history to soak in, but that history has great breadth. Whether you like art, architecture, war, politics, or religion there is something here for you.
While it may not be as well known as some other cities in Italy, the charming hilltop town of Orvieto is well worth a stop. Its crown jewel is its frescoed Gothic Cathedral, but you can also explore its famous well and its Etruscan underground or simply catch the beautiful views from atop the volcanic tuff.
Tuscany is actually a sweeping region that includes Florence, Pisa, Siena, and other cities, but when most tourists say they are going to Tuscany they are likely referring to staying in the countryside to explore hilltop medieval villages, drive winding cypress-lined roads, and sample wine at the region’s countless estates.
Siena is one of the most beautiful towns in Tuscany. It is famous for the twice annual Palio, a cut-throat, bareback horse race in the town square dating back to medieval times where each of the city's Contrata, or neighborhoods, sponsors a competitor.
Today Florence is the capital of Tuscany. Back in time, this was the Birthplace of the Renaissance. You'll find treasures of the city's heritage throughout Florence - from the architecture of Brunelleschi and the scientific achievements of Galileo to the sculpture of Michelangelo and the paintings of Botticelli and so much more.
Today this city is best known for the engineering folly of its Cathedral’s bell tower, but Pisa also has a rich history as a maritime republic that once rivaled Genoa and Venice. It is considered a hub of education with multiple prestigious universities. It also has famous museums, city architecture, monasteries, and more.
Bologna is the capital city of the Emilia-Romagna Region. It’s known for being the home of the world’s oldest university. The city also has distinct architecture, fantastic museums and libraries, and is an excellent place to try the outstanding local dishes and agricultural products of Italy’s Food Valley.
Venice is one of the most unique - and romantic - cities in the world. Its 126 islands are interwoven with canals and bridges and navigated by iconic gondolas and sleek speedboats. The power of this maritime republic led to a city that is filled with art and culture and comes especially alive each year during the sumptuous Carnevale Festival.
Modena is a town most tourists don’t know much about - that is unless you are a car fan or a major foodie. You can explore the Ferrari factory and museum or dine at the Massimo Bottura’s world-famous restaurant here. The town also flaunts a World Heritage Site, Pavarotti’s birthplace, and excellent balsamic vinegar.
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🗓️ 1 full day / 1 night (here, in Bologna, or near Florence)
Tivoli is a small but ultra-scenic suburb of Rome situated in the rolling landscape of the Sabine Hills. The town is known for two UNESCO World Heritage Site villas, one dating to Ancient Rome and the other to the 16th century. Millennials might also recognize this town’s cameo in the Lizzie McGuire Movie.
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🗓️ Stop en route to Rome
📍 2 hand-picked experiences & sights to see
🍽️ 2 of the best places to dine & drink
EXAMPLE DAY FROM THIS ITINERARY:
Below you'll find an example day from the full version of this itinerary, so you can see the level of detail and travel style you can expect!
DAY 1: Roman Icons
Take a guided tour to bring the excitement & history of Ancient Rome alive at the Forum and Colosseum. After lunch, take a walking tour through the historic center, stopping at some of the most classic Roman sights.
Morning
Book these morning activities with a tour guide. Not only will they help bring Ancient Rome to life, but they also have special privileges that will let you truly skip the line and make the most of your day. I highly recommend the Colosseum Underground Tour (this also includes the wedding cake exterior and a tour of the Forum).
Altare della Patria
⏳ Fly-by (enough time for a photo-op)
💡 Tip: You have a big day ahead of you, so just grab some quick shots of this famous "Wedding Cake"
This colossal monument to Italy’s first King, Victor Emmanuel II, is known as the wedding cake for its opulent white exterior.
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🚶♀️ Walk about 10 minutes
Roman Forum
⏳ Half-day (with the Colosseum)
💡 Tip: A guide can really help bring the Forum to life. I also highly recommend looking up before and after photos to help visualize what life was once like in this bustling place.
Once a hub for Roman life, the forum is still alive and abuzz today (now with tourists). Gone are the markets and public speeches, but the history is still palpable as you walk among the ruins of temples, palaces, and government buildings.
💡 Tip: A guide can really help bring the Forum to life. I also highly recommend looking up before and after photos to help visualize what life was once like in this bustling place.
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🚶♀️ Walk about 10 minutes
The Colosseum
⏳ Half-day (with the Forum)
💡 Tip: Lines at the Colosseum can be very long, and "skip the line" tickets only help so much. A guide is the only real way to skip to the front. Bring water for while you wait, especially at midday or in the summer.
Lions and Tigers and Gladiators! The Colosseum is one of the must see stops in Rome. Men and beasts once fought here in what was not only the largest ancient amphitheater, but a feat of engineering that has survived since its grand opening in 80 AD.
💡 Tip: Lines at the Colosseum can be very long, and "skip the line" tickets only help so much. A guide is the only real way to skip to the front. Bring water for while you wait, especially at midday or in the summer.
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Midday
Stop and take a break for lunch! Check out some nearby options.
DELI & ROMAN CLASSICS IN CENTRO STORICO
Known for having some of the world’s best Carbonara and Amatriciana Pastas as well as Cacio e Pepe and a strong cocktail program.
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Afternoon
This afternoon schedule looks busy, especially since I usually campaign for picking one morning and one afternoon activity each day so you don't overbook. But, I promise this is doable. All of these spots are in very close walking distance, and you won't spend a ton of time at any one of them - the Pantheon you'll want to go inside, but the others are pretty easy stroll around & photo-op type places.
Also, note that you can flip this and start at the Spanish Steps. Either way works perfectly fine, just consider when you book your Pantheon time slot and where you want to have lunch and dinner so you can avoid extra walking.
Come stroll & check out the street artists. The Piazza was once an ancient Circus. Now it's baroque, headlined by Bernini's Four Rivers Fountain, which depicts the then Christian world's main rivers (Nile, Danube, Ganges, & Rio della Plata).
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🚶♀️ Walk about 6 minutes
The Pantheon
⏳ Quick (about an hour)
💡 Tip: Make sure you reserve a timeslot in advance!
As impressive today as it was when it was built (~128 AD), the record-setting concrete dome of the pantheon has inspired architects and artists a world over - Michaelangelo, Bernini, Brunelleschi, and Thomas Jefferson among them.
💡 Tip: Make sure you reserve a timeslot in advance!
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🚶♀️ Walk about 8 minutes
Trevi Fountain
⏳ Very quick (less than an hour)
💡 Tip: Whether you throw 1, 2, or 3 coins each has a different superstition. Most just throw one over their shoulder to "guarantee" their future return to Rome!
Toss a coin (or three) in the fountain and you'll guarantee your return to Rome (or that you'll find a spouse) - at least according to Three Coins in the Fountain. Yeah it's touristy, but it's big, it's beautiful, and it's a must when you're in Rome.
💡 Tip: Whether you throw 1, 2, or 3 coins each has a different superstition. Most just throw one over their shoulder to "guarantee" their future return to Rome!
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🚶♀️ Walk about 8 minutes
Spanish Steps
⏳ Fly-by (enough time for a photo-op)
💡 Tip: You can’t sit on the steps anymore! Check out the azaleas in late April to May.
Admittedly, the history here is a little lacking, unless you count their appearance in Roman Holiday. But, the steps are beautiful, especially when the azaleas are in bloom, and a quick and easy stop when you're in the city center.
💡 Tip: You can’t sit on the steps anymore! Check out the azaleas in late April to May.
MODERN ITALIAN IN CENTRO STORICO
This moody spot serves updated Italian dishes with modern gastronomic twists. Our concierge asked us if we were okay going somewhere owned by the French - there are definitely influences in the food here. A great spot to shake up the mainstay Roman dishes.
GELATO IN CENTRO STORICO
We asked our waiters for their favorite gelato in Rome, and we have to admit we were very skeptical when multiple people suggested a place known for having so many flavors. We did a head to head with Giolitti and suddenly understood why it was a locals’ favorite.
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🛎️ Leading Hotels of the World & Anantara
Not only is this a beautiful hotel with an extremely rare rooftop pool, it's in a great location with easy access to places in Rome and the train for when you want to explore more of Italy!
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🏆 Forbes 5-star
🛎️ Dorchester Collection
Absolute luxury with panoramic views from one of the best locations in Rome - between the Spanish Steps and the Borghese Gardens!
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🏆 Forbes 5-star
🛎️ Rocco Forte
Check out the chic, secluded walled-garden restaurant and bar at this luxury hotel near the Spanish Steps and Villa Borghese.
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🛎️ Relais & Chateaux
📍 Near Montalcino
This Tuscan town turned resort not only has a beautiful, amenity-rich hotel and Michelin-starred restaurant, but also an on-site winery with impressive wines, balsamic vinegar, and grappas and a tour to match.
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🏆 Forbes 5-star
📍 Near Montalcino
With ties to famous names like Ferragamo and Tom Weiskopf and a prime location in the Val d’Orica, it’s no wonder this village turned resort is one of the Tuscan countryside’s splashiest. Tour the winery, take a cooking class, play 18, explore the landscape, or simply relax at the pool.
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🏆 Forbes 4-star
📍 Near Siena
This hotel is full of history - including a tower from 998 and an ancient amphitheater- but it’s been updated into a luxurious resort with an infinity pool, a spa in the old wine cellar, cooking classes, and more.
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🛎️ Leading Hotels of the World
📍 Near Siena
This hotel was once an 11th century village, then a monastery, then the residence of several noble families, and it hasn’t lost an ounce of its authentic Tuscan charm. Come here for wine tastings, truffle hunting, Ferrari rentals, cooking classes, hot air ballooning, and so much more.
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🛎️ Leading Hotels of the World
This hotel is a stunner, inside and out. Here you’ll be able to enjoy the highlights of Tuscany - intimate seclusion (since the resort only has 22 rooms) and excellent cuisine (thanks to multiple farm-to-table dining concepts on site).
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📍 Near Siena
The hills here are the perfect setting for an e-bike excursion or a dip in the glittering pool. If that’s not relaxing enough, take a trip to the health club with a second indoor pool, jacuzzi Turkish bath, and more.
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🛎️ Relais & Chateaux
📍 Near Arezzo
This vast Ferragamo-owned estate is hard to wrap your head around with its acres and acres of organic agriculture (that you’ll enjoy exploring, in your glass, and on your plate) and wealth of activities ranging from cooking and art classes to horseback riding to truffle hunting to hot air ballooning and more.
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🏆 Forbes 4-star
🛎️ Marriott Bonvoy
This 15th century palazzo, originally designed by Brunelleschi, exudes Florentine style, especially thanks to its spot on the banks of the Arno.
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🛎️ Marriott Bonvoy
This historic palace is right in the heart of Florence - plus its rooftop overlooking the Arno has some of the best views in the city.
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🏆 Forbes 5-star
You’ll feel like you’re staying in one of Florence’s famous museums or palazzos at this ornate hotel on the edge of the city. Embrace the royal treatment at the city’s largest private garden or the hotel’s outdoor pool.
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🏆 Forbes Recommended
🛎️ Marriott Bonvoy
This hotel is just far enough off the beaten path to feel a world away from the bustle of the city (especially thanks to its rare outdoor pool and garden) while still being convenient for sightseeing.
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🏆 Forbes 4-star
🛎️ Small Luxury Hotels of the World
This boutique by the Ferragamos of fashion fame couldn’t be much more chic or better located - right in the city center, on the bank of the Arno, overlooking Ponte Vecchio.
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This hotel isn’t technically in Florence but it’s an exquisite escape just 15 minutes away, perched on a hill with spectacular views. It’s a former monastery designed by Michelangelo so of course it’s a masterpiece of art and architecture; it also has all the amenities you could want, like a gorgeous outdoor pool.
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COMING SOON | Collegio alla Querce, Auberge Resorts Collection
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🏆 Forbes 5-star
This iconic Venice hotel is tucked away from the tourist buzz on Giudecca Island but is still a quick hop across the Grand Canal from Venice's top sights. It has enough space to unwind in the pristine gardens or by the heated pool. It's also famous for its legendary bar where the Bellini was invented.
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🏆 Forbes 4-star
🛎️ Marriott Bonvoy
This palazzo on the Grand Canal has welcomed guests since the 17th century, but a recent renovation in 2022 has the icon feeling fresh. Chic waterfront gardens and rooftop terraces are the perfect base to watch the gondolas go by. The resort also has a history with artists including Monet, Sargent, and others - you can make your own art at on-site mask making and jewelry workshops.
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The Gritti Palace, a Luxury Collection Hotel, Venice
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🏆 Forbes 4-star
🛎️ Marriott Bonvoy
Immerse yourself in Venice at this historic hotel. The over-the-top decor harkens to the hotel's roots as a noble palace from the 15th century. The hotel also has an excellent location for hitting Venice's hot-spots; it sits on a stretch of the Grand Canal and just steps away from St. Mark's Square.
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🏆 Forbes Recommended
🛎️ Marriott Bonvoy
If Venice's ornate, gilded accommodations aren't your cup of tea, this clean, modern hotel might be a better fit. The resort is also off in its own little bubble on an island beyond the main city of Venice. This means it has plenty of space for pools, spacious suites, and spa facilities. But, the complimentary water shuttle can have you at St. Mark's in 20 minutes.
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🏆 Forbes Recommended
🛎️ Leading Hotels of the World
If you want to escape the bustle of Venice but still feel like you're living in its history, this could be the pick for you. The Kempinski is a former monastery set on a 15-acre private island. It comes with expansive gardens, a heated pool, spacious suites, and more that's all just 10 minutes away on the resort's complimentary boat shuttle.
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If you liked these hotel recommendations or this free preview, upgrade to my complete 9-14 Day Italian Highlights Itinerary for all the details on things to see, places to eat, and how to string it all together!
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I build out guides here on Thatch, but also check out ptotravelpro.com where I go into even more detail about what to do, where to stay, and how to string it all together in jam-packed destination guides!
Recent travels include:
🇫🇷 France | Paris, Loire Valley, & Normandy
🇸🇬 Singapore
🇰🇭 Cambodia | Siem Reap
🇹🇭 Thailand | Bangkok & Phuket
🇬🇧UK | London & Stonehenge
🇭🇷Croatia | Split & Dubrovnik
🇹🇿Tanzania | Arusha & Serengeti
🇰🇪Kenya | Maasai Mara, Chyulu Hills, & Nairobi
🇸🇨Seychelles | Mahe & La Digue
🇮🇹Italy | Rome, Tuscany, Florence, & more
🇺🇸USA | NYC, New England, Texas, Florida Keys, DC, Charleston, California, Las Vegas, and more
Planned travels include:
🇺🇸 USA | Denver, Seattle, & St. Louis
