THE DAY-BY-DAY GUIDE TO THE HIGHLIGHTS OF ITALY ROME, FLORENCE, VENICE, & MORE
OVERVIEW
2-WEEK ITALIAN HIGHLIGHTS ITINERARY
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 all the 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!
CHECK OUT THESE DESTINATION GUIDES TO HELP YOU PLAN YOUR TRIP:
INTERACTIVE JOURNEY MAP
BUILT ON THATCH
This free map shows the main stops of this itinerary along with hotels. I also offer a premium version with a step-by-step plan for this itinerary - it includes 150 suggestions for experiences, hotels, restaurants, and more.
CHECK OUT THE FREE INTERACTIVE MAP ON THATCH:
IF YOU LIKE THE FREE VERSION, CHECK OUT THIS STEP-BY-STEP PREMIUM VERSION:
STOP 1: ROME
3 NIGHTS
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.
Where we've stayed: Palazzo Naidi & Hotel Eden
See my free guide on Thatch for an interactive map with even more hotel options.
CHECK OUT THIS DESTINATION GUIDE:
DAY 0: Arrive in Rome
Land from your flight and get adjusted to the time change. Grab a traditional Roman pasta and some gelato before you rest up for your first full day in the Eternal City.
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 including Piazza Navona, the Pantheon, the Trevi Fountain, and the Spanish Steps.
DAY 2: Vatican City
Today your jaw will drop - no joke. Book an early-entry tour to see the Sistine Chapel with few(er) crowds. Spend the rest of your time gawking in the museums and Basilica. Be sure to climb the dome! End with a walk around Trastevere, a charming neighborhood where you can also grab a bite to eat - it'll be plenty for one day!
DAY 3: Rome to Tuscany via Orvieto
Venture into wine country with a stop in the Umbrian town of Orvieto. Situated on a volcanic tuff, Orvieto has sweeping views of the countryside. You can also explore the Duomo, former papal palaces, and a deep well with impressive engineering including a double-helix staircase.
See even more experiences, hotels, and restaurants in my step-by-step itinerary:
STOP 2: TUSCANY
3 NIGHTS
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.
Where we stayed: Castello Banfi Il Borgo
See my free guide on Thatch for an interactive map with even more hotel options.
DAY 4: In the Vineyards
Start of your time in Tuscany with a tour of a winery (or several) to discover how the historic beverage is made, and of course to taste a few glasses!
DAY 5: Dealer's Choice in Tuscany
You can easily book a repeat of day 4, tasting wines and relaxing at the resort, but if you're looking to get out and explore, there are plenty of options to discover the beautiful scenery and charming towns of Tuscany!
DAY 6: Tuscany to Florence via Siena
Head to Florence, the capital of Tuscany, with a stop at one of its former rivals. The former Republic of Siena is steeped in tradition (plan to come back for a bucket list trip to the Palio). Siena is exactly what you imagine for a medieval Italian city - check out the tower-topped town square and the decadent Duomo di Siena.
See even more experiences, hotels, and restaurants in my step-by-step itinerary:
STOP 3: FLORENCE
4 NIGHTS
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.
Where we've stayed: St. Regis Florence & Westin Excelsior Florence
See my free guide on Thatch for an interactive map with even more hotel options.
DAY 7: Art of the Medicis
Explore the art and history of the Medicis at the world-famous and jam-packed Uffizi Galleries and in the former residence of the Medicis, the Palazzo Vecchio. Top off your day with a visit to Florence's iconic Ponte Vecchio.
DAY 8: Duomo & David
Admire the architecture of the Duomo of Florence and the art of Michelangelo’s David, two of the most impressive and iconic achievements of the Italian Renaissance. Then catch a sunset looking out over the gorgeous city skyline.
DAY 9: Daytrip to Pisa
Take a daytrip to one of the most famous monuments in all of Italy if not the world. Take some time for wacky tourist photos, but also make sure to appreciate the beauty of the tower, baptistery, and cathedral.
DAY 10: Florence to Venice via Bologna
Head to the final leg of Italy's Big Three, but first make a stop in the heart of Italy's Food Valley. Not only can you enjoy excellent Emilian cuisine, but you can also enjoy the unique city of Bologna - home of the world's oldest continuously operating university.
See even more experiences, hotels, and restaurants in my step-by-step itinerary:
STOP 4: VENICE
3 NIGHTS
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.
Bucket list hotel: Hotel Cipriani, a Belmond Hotel
See my free guide on Thatch for an interactive map with even more hotel options.
DAY 11: Canals, Cathedrals, & Carnevale
Introduce yourself to the city of Venice, which is famous for - you guessed it - cathedrals, canals, and Carnevale. This day plan will have you seeing plenty of the first two. Since you likely won't be here during Carnevale season, drop into one of the many mask-making shops for a taste of the Venetian tradition.
DAY 12: Glassmakers & Gondoliers
In addition to cathedrals, canals, and Carnevale, Venice is also famous for its glassmakers and gondoliers. Spend the morning with a mini day trip to nearby Murano to see the incredible craftsmanship of glassmaking, then spend a lazy afternoon being serenaded by a gondolier to see the canals from a new perspective.
DAY 13: Venice to Emilia-Romagna or Florence via Modena
Fast car fans and foodies rejoice! This day is for you. Spend the day at the Ferrari Museum learning about both man and machine. Then prepare yourself for culinary magic as you sit down for dinner at one of the world's most celebrated restaurants.
See even more experiences, hotels, and restaurants in my step-by-step itinerary:
STOP 5: EMILIA-ROMAGNA
1 NIGHT
Depending on personal preference, you could stay in either Modena or Bologna in the region of Emilia-Romagna or return to Florence for an additional night. Here are quick overviews of both Modena and Bologna.
MODENA
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.
BOLOGNA
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.
Bucket list hotel: Casa Maria Luigia
See my free guide on Thatch for an interactive map with even more hotel options.
DAY 14: Emilia-Romagna to Rome via Tivoli
Enjoy your final full day in the hills of Tivoli. This respite outside Rome has been a favorite of Emperors and Cardinals alike for centuries, and today you can explore the elaborate villas they built here at Villa Adriana or Villa d'Este.
See even more experiences, hotels, and restaurants in my step-by-step itinerary:
STOP 6: ROME
1 NIGHT
Return to the Eternal City for one final night to complete your trip. Fly home from Italy full of great food and new memories after your two-week trip to some of the country's most incredible highlights.
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