49 days in Italy Itinerary

49 days in Italy Itinerary

Created using Inspirock Europe itinerary planner

Make it your trip
Fly
1
Rome
— 3 nights
Train
2
Pompeii
— 1 day
Drive
3
Positano
— 3 nights
Ferry
4
Capri, Island of Capri
Ferry
5
Positano
— 4 nights
Drive
6
Montepulciano
— 2 nights
Drive
7
Pisa
Train
8
Cinque Terre
— 4 nights
Drive
9
Florence
— 3 nights
Train
10
Verona
— 2 nights
Drive
11
Venice
— 3 nights
Drive
12
San Gimignano
— 3 nights
Drive
13
Varenna
— 3 nights
Drive
14
Siena
— 13 nights
Train
15
Milan
— 2 nights
Fly

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Rome

— 3 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Kids will appreciate attractions like Colosseum and Trastevere. There's much more to do: contemplate the long history of St. Peter's Basilica, delve into the distant past at Palatine Hill, make a trip to Roman Forum, and pause for some serene contemplation at Santa Maria della Vittoria.

To find out how to plan a trip to Rome, use our trip itinerary maker.

Los Angeles, USA to Rome is an approximately 16-hour flight. The time zone difference when traveling from Los Angeles to Rome is 9 hours. In June, daytime highs in Rome are 84°F, while nighttime lows are 65°F. Cap off your sightseeing on the 17th (Fri) early enough to catch the train to Pompeii.

Things to do in Rome

Historic Sites · Neighborhoods

Side Trip

Find places to stay Jun 13 — 17:

Pompeii

— 1 day

Underground City

Pompeii has been a tourist destination for more than 250 years.
Kick off your visit on the 17th (Fri): explore the ancient world of Parco Acheologico di Ercolano, then explore the ancient world of Forum, then admire the striking features of Villa dei Misteri, and finally delve into the distant past at Pompeii Archaeological Park.

To see where to stay, photos, ratings, and other tourist information, use the Pompeii road trip website.

You can take a train from Rome to Pompeii in 2.5 hours. Other options are to drive; or take a bus. June in Pompeii sees daily highs of 82°F and lows of 66°F at night. Wrap up your sightseeing on the 17th (Fri) to allow time to drive to Positano.

Things to do in Pompeii

Historic Sites

Side Trip

Find places to stay Jun 17 — 18:

Positano

— 3 nights
Often referred to as the gem of the Amalfi Coast, Positano remains one of southern Italy's most sought-after vacation locales, thanks to its hillside location and picturesque, pastel buildings.
Start off your visit on the 18th (Sat): take some stellar pictures from Il Sentiero Degli Dei and then enjoy the sand and surf at Fornillo. Here are some ideas for day two: take a tour by water with Boat Tours & Water Sports.

For traveler tips, photos, reviews, and other tourist information, refer to the Positano trip itinerary builder app.

Drive from Pompeii to Positano in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 82°F in June, and nighttime lows around 68°F. You will leave for Capri on the 20th (Mon).

Things to do in Positano

Outdoors · Tours · Parks · Beaches
Find places to stay Jun 17 — 20:

Capri, Island of Capri

The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
On the 20th (Mon), explore the striking landscape at I Faraglioni, get outside with Via Krupp, then tour the pleasant surroundings at Monte Solaro, and finally don't miss a visit to Piazza Umberto I.

For more things to do, reviews, other places to visit, and more tourist information, read Capri trip planner.

Ride a ferry from Positano to Capri in 1.5 hours. Alternatively, you can do a combination of taxi and ferry; or do a combination of bus and ferry. In June in Capri, expect temperatures between 82°F during the day and 68°F at night. Cap off your sightseeing on the 20th (Mon) early enough to catch the ferry to Positano.

Things to do in Capri

Parks · Nature · Outdoors · Scenic Drive

Side Trip

Find places to stay Jun 20 — 21:

Positano

— 4 nights
Kids will enjoy Fornillo and Bagni d'Arienzo Beach Club, Positano. Enjoy Positano some more: Head underground at Grotte di Suppraiano, kick back and relax at Marina di Praia Beach, stroll through Spiaggia Grande, and let your taste buds guide you at a local gastronomic tour.

To find photos, ratings, and other tourist information, you can read our Positano trip website.

Traveling by ferry from Capri to Positano takes 1.5 hours. Alternatively, you can do a combination of ferry and taxi; or do a combination of ferry and bus. Wrap up your sightseeing on the 24th (Fri) to allow time to drive to Montepulciano.

Things to do in Positano

Parks · Beaches · Outdoors · Tours

Side Trip

Find places to stay Jun 20 — 24:

Montepulciano

— 2 nights

Pearl of the 16th Century

Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
Start off your visit on the 24th (Fri): take in the spiritual surroundings of Tempio di San Biagio, don't miss a visit to Terrazza Del Palazzo Comunale, then don't miss a visit to Piazza Grande a Montepulciano, and finally contemplate in the serene atmosphere at Dome of Montepulciano. Keep things going the next day: steep yourself in history at Val d'Orcia, look for all kinds of wild species at Fosso Bianco - Bagni San Filippo, then make a trip to Piazza Pio II, then examine the collection at Palazzo Piccolomini, and finally take in the spiritual surroundings of Eremo Le Celle.

To find reviews, where to stay, and other tourist information, go to the Montepulciano trip itinerary maker tool.

Traveling by car from Positano to Montepulciano takes 4.5 hours. Alternatively, you can do a combination of taxi and train; or take a bus. Traveling from Positano in June, plan for slightly colder nights in Montepulciano, with lows around 61°F. Finish your sightseeing early on the 26th (Sun) so you can drive to Pisa.

Things to do in Montepulciano

Historic Sites · Parks · Wildlife · Nature

Side Trips

Find places to stay Jun 24 — 26:

Pisa

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Start off your visit on the 26th (Sun): make a trip to Le mura di Lucca, admire the landmark architecture of St Martin Cathedral, then explore the different monuments and memorials at Camposanto, and finally take in panoramic vistas at Leaning Tower of Pisa.

For photos, other places to visit, more things to do, and more tourist information, use the Pisa trip itinerary builder site.

Drive from Montepulciano to Pisa in 2.5 hours. Alternatively, you can take a bus; or take a train. In June, plan for daily highs up to 81°F, and evening lows to 60°F. Wrap up your sightseeing on the 26th (Sun) early enough to take a train to Cinque Terre.

Things to do in Pisa

Historic Sites

Side Trip

Find places to stay Jun 26 — 27:

Cinque Terre

— 4 nights

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Bring the kids along to Footpath Monterosso - Vernazza and Oratorio della Cofradia dei Bianchi o de Santa Croce. Get out of town with these interesting Cinque Terre side-trips: Passeggiata Anita Garibaldi a Nervi (in Genoa), Porticato Brignardello (in Lavagna) and Sestri Levante (Chiesa di Santa Maria Immacolata & Baia del Silenzio). And it doesn't end there: see majestic marine mammals with 5 Terre Pelagos Boat Tours, pause for some serene contemplation at Santuario di Nostra Signora di Montenero, take a stroll around Vernazza, and hike along Cinque Terre Trails.

For traveler tips, more things to do, photos, and tourist information, read our Cinque Terre online tour itinerary planner.

Traveling by train from Pisa to Cinque Terre takes 2 hours. Alternatively, you can drive. June in Cinque Terre sees daily highs of 81°F and lows of 60°F at night. Finish your sightseeing early on the 30th (Thu) so you can drive to Florence.

Things to do in Cinque Terre

Parks · Outdoors · Nature · Historic Sites

Side Trips

Find places to stay Jun 26 — 30:

Florence

— 3 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Attractions like Florence Academy of Fine Arts and Piazzale Michelangelo make great kid-friendly stops. And it doesn't end there: take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, take in nature's colorful creations at The Boboli Gardens, take in the views from Ponte Vecchio, and savor the flavors at Food & Drink.

For where to stay, other places to visit, reviews, and more tourist information, use the Florence travel planner.

You can drive from Cinque Terre to Florence in 2.5 hours. Alternatively, you can take a train. Expect a daytime high around 83°F in June, and nighttime lows around 65°F. Cap off your sightseeing on the 3rd (Sun) early enough to catch the train to Verona.

Things to do in Florence

Historic Sites · Museums · Tours · Parks
Find places to stay Jun 30 — Jul 3:

Verona

— 2 nights

City of Romeo and Juliet

The famous setting for Shakespeare's star-crossed lovers, Romeo and Juliet, Verona is one of northern Italy's main tourist destinations, largely owing to its incredibly rich artistic heritage.
Start off your visit on the 4th (Mon): take in the spiritual surroundings of Basilica di San Zeno Maggiore, see the interesting displays at Casa di Giulietta, take in panoramic vistas at Torre dei Lamberti, make a trip to Piazza delle Erbe, then catch a live event at Arena di Verona, and finally don't miss a visit to Liston. Keep things going the next day: explore the different monuments and memorials at Cimitero di Guerra Tedesco, then explore the activities along Lago di Garda, and then head outdoors with La Rocca.

For ratings, maps, traveler tips, and tourist information, go to the Verona travel route builder website.

Traveling by train from Florence to Verona takes 2.5 hours. Alternatively, you can drive; or take a bus. July in Verona sees daily highs of 88°F and lows of 66°F at night. Cap off your sightseeing on the 5th (Tue) early enough to go by car to Venice.

Things to do in Verona

Historic Sites · Parks · Nature · Outdoors

Side Trips

Find places to stay Jul 3 — 5:

Venice

— 3 nights

City of Romance

Virtually unchanged for the last six centuries, Venice is actually a group of islands made famous by a series of canals, bridges, monuments, piazzas, and narrow pedestrian lanes.
You'll visit kid-friendly attractions like Canal Grande and Basilica di San Marco. The adventure continues: admire the landmark architecture of Doge's Palace, indulge in some culinary diversions at a local gastronomic tour, take in panoramic vistas at St Mark's Campanile, and get interesting insight from Like a Venetian.

To see reviews, where to stay, more things to do, and more tourist information, go to the Venice road trip planning website.

You can drive from Verona to Venice in 1.5 hours. Alternatively, you can take a shuttle; or take a bus. In July, daytime highs in Venice are 87°F, while nighttime lows are 67°F. Wrap up your sightseeing on the 9th (Sat) early enough to drive to San Gimignano.

Things to do in Venice

Historic Sites · Museums · Tours · Parks
Find places to stay Jul 5 — 9:

San Gimignano

— 3 nights

Town of Fine Towers

A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
You'll visit kid-friendly attractions like Duomo di San Gimignano and San Gimignano Bell Tower. Get out of town with these interesting San Gimignano side-trips: Museo Leonardiano di Vinci (in Vinci) and Teatro Del Silenzio (in Lajatico). And it doesn't end there: steep yourself in history at Historic Centre of San Gimignano, get engrossed in the history at Torre e Casa Campatelli, appreciate the extensive heritage of Piazza del Duomo, and browse the exhibits of San Gimignano 1300.

To find where to stay, ratings, other places to visit, and other tourist information, you can read our San Gimignano travel route planner.

Getting from Venice to San Gimignano by car takes about 3.5 hours. Other options: take a train; or do a combination of train and bus. In July, plan for daily highs up to 86°F, and evening lows to 65°F. Wrap up your sightseeing on the 12th (Tue) to allow time to drive to Varenna.

Things to do in San Gimignano

Historic Sites · Museums · Shopping · Childrens Museums

Side Trips

Find places to stay Jul 9 — 12:

Varenna

— 3 nights
Varenna is a comune (municipality) on Lake Como in the Province of Lecco in the Italian region Lombardy, located about 60km north of Milan and about 20km northwest of Lecco.Varenna was founded by local fishermen in 769, and was later allied of the commune of Milan. Explore the numerous day-trip ideas around Varenna: I Giardini di Villa Melzi (in Bellagio), Tremezzina (Villa del Balbianello & Villa Carlotta) and Abbazia Cluniacense di Santa Maria di Piona (in Colico). The adventure continues: get outside with Aero Club Monte Cornizzolo, step into the grandiose world of Castello di Vezio, view the masterpieces at Il Tornio, and admire the natural beauty at Il Giardino Botanico - Hotel Villa Cipressi.

To see other places to visit, maps, ratings, and other tourist information, read Varenna trip planner.

You can drive from San Gimignano to Varenna in 4.5 hours. Alternatively, you can take a train; or do a combination of bus and train. In July, plan for daily highs up to 85°F, and evening lows to 65°F. Finish your sightseeing early on the 15th (Fri) so you can drive to Siena.

Things to do in Varenna

Parks · Museums · Historic Sites · Outdoors

Side Trips

Find places to stay Jul 12 — 15:

Siena

— 13 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Family-friendly places like Piazza del Campo and Museo di Storia Naturale dell'Accademia dei Fisiocritici will thrill your kids. Change things up with these side-trips from Siena: Cala Martina (in Puntone), Marina di Grosseto (Ricci di Mare & Stabilimento Balneare Capri) and Scarlino (Cala Civette & Cala Violina). On the 23rd (Sat), give your taste buds a day to remember with a local gastronomic tour. There's lots more to do: pause for some serene contemplation at Duomo di Siena, kick back and relax at Bagno Capezzolo, steep yourself in history at Centro Storico di Siena, and stroll through Marina di Alberese.

To find where to stay, more things to do, reviews, and tourist information, use the Siena day trip planner.

Drive from Varenna to Siena in 5 hours. Alternatively, you can take a train; or fly. July in Siena sees daily highs of 89°F and lows of 67°F at night. Finish your sightseeing early on the 28th (Thu) so you can take a train to Milan.

Things to do in Siena

Historic Sites · Outdoors · Parks · Beaches

Side Trips

Find places to stay Jul 15 — 28:

Milan

— 2 nights

Fashion Capital of World

In many ways the most modern of Italian cities, Milan is a busy, elegant metropolis with an impressive list of grand palaces, fine churches, and important museums.
On the 29th (Fri), take in the spiritual surroundings of Il Cenacolo, don't miss a visit to Piazza del Duomo, then take in the architecture and atmosphere at Duomo di Milano, then take an in-depth tour of Galleria 92, and finally admire the striking features of Galleria Vittorio Emanuele II. On the next day, explore the historical opulence of Castello Sforzesco, get in on the family fun at Leolandia, and then explore the different monuments and memorials at Monumental Cemetery.

Ask Inspirock to suggest an itinerary and make planning a trip to Milan fast, fun, and easy.

Getting from Siena to Milan by train takes about 4 hours. Other options: drive; or take a bus. In July, plan for daily highs up to 85°F, and evening lows to 65°F. Finish your sightseeing early on the 30th (Sat) so you can travel back home.

Things to do in Milan

Historic Sites · Theme Parks · Shopping · Museums

Side Trip

Find places to stay Jul 28 — 30:

Italy travel guide

4.6
Landmarks · Ruins · Sacred & Religious Sites
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.

Tuscany travel guide

4.4
Landmarks · Art Museums · Sacred & Religious Sites
Birthplace of the Italian Renaissance
Known for its landscapes, traditions, and history, Tuscany possesses an unparalleled artistic legacy that continues to influence world culture. Regarded as the birthplace of the Italian Renaissance, the region boasts a lengthy list of attractions, including world-class museums, art galleries, and archeological sites. With a distinct culture and a very strong linguistic identity, this region is sometimes referred to as a nation within a nation. A land of picture-postcard areas, Tuscany contains plenty of places to visit on your holiday, with seven World Heritage Sites, including the historic town centers of Florence and Siena. With more than 120 protected nature preserves, Tuscany is not only a land of culture and historic monuments, but also a great place to discover and enjoy the Italian outdoors. Take it slowly here (as the locals do), and give yourself plenty of time to get to know the local culture and cuisine of Tuscany's medieval towns and ancient villages.

Lake Como travel guide

4.2
Gardens · Architectural Buildings · Churches
A favorite vacation spot for more than a century, Lake Como was once an exclusive retreat for local aristocrats and wealthy people. It is not only one of Europe's most beautiful lakes, but also one of the deepest at more than 400 m (1,300 ft). Surrounded by elegant villas, the lake has become a popular holiday destination for tourists because of its range of attractions, from landscapes, wildlife, and spas, to activities like sailing, windsurfing, and kite-surfing. The area has been an inspiration for artists since Roman times. English poet Percy Bysshe Shelley wrote, "This lake exceeds anything I ever beheld in beauty…It is long and narrow and has the appearance of a mighty river winding among the mountains and the forests."