21 days in Italy Itinerary

21 days in Italy Itinerary

Created using Inspirock Italy visit planner

This plan was created by another user. Make it your plan

Route & dates

21 days in Italy Itinerary

Start: San Diego
Fly:  17 h 15 min
1
Milan
— 1 day
Train:  45 min
2
Como
— 1 night
Drive:  3 h 30 min
3
Cinque Terre
— 1 night
Drive:  2 h 30 min
4
Florence
— 2 nights
Train:  2 h 45 min
5
Naples
— 2 nights
Bus:  15 min
6
Pompeii
— 1 night
Train:  30 min
7
Salerno
— 2 nights
Ferry:  45 min
8
Ravello
— 2 nights
Bus:  30 min
9
Positano
— 2 nights
Ferry:  30 min
10
Sorrento
— 1 night
Drive:  15 min
11
Capri
— 2 nights
+2
Ferry + Shuttle + Fly:  5 h
12
Venice
— 3 nights
Fly:  16 h 30 min
End: San Diego

1
day
Milan

Milan ©
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.
Kick off your visit on the 29th (Tue): admire the landmark architecture of Galleria Vittorio Emanuele II, then take in the architecture and atmosphere at Duomo di Milano, and then step into the grandiose world of Castello Sforzesco.

You can plan Milan trip in no time by asking Inspirock to help create your itinerary.

San Diego, USA to Milan is an approximately 17.5-hour flight. You can also do a combination of flight and train; or do a combination of train and flight. The time zone difference when traveling from San Diego to Milan is 9 hours. Plan for little chillier temperatures traveling from San Diego in October, with highs in Milan at 65°F and lows at 52°F. Wrap up your sightseeing on the 29th (Tue) early enough to take a train to Como.

Things to do in Milan

Historic Sites Shopping
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Castello Sforzesco ©
Castello Sforzesco
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II

1
night
Como

Como ©
Known for its idyllic location on the shores of Lake Como and at the foot of the Alps, Como is one of northern Italy's most popular tourist destinations.
Kick off your visit on the 30th (Wed): take in the spiritual surroundings of Basilica di Sant'Abbondio, then grab your bike and head to Sentiero 6 - Valbasca, then take in the architecture and atmosphere at Cathedral of Como (Duomo), and finally stop by Teatro del Gusto Como.

To see photos, maps, and tourist information, use the Como road trip app .

Take a train from Milan to Como in an hour. Alternatively, you can drive. In October, plan for daily highs up to 64°F, and evening lows to 49°F. Cap off your sightseeing on the 30th (Wed) early enough to go by car to Cinque Terre.

Things to do in Como

Historic Sites Wildlife Trails
Highlights from your plan
Cathedral of Como (Duomo) ©
Cathedral of Como (Duomo)
Basilica di Sant'Abbondio ©
Basilica di Sant'Abbondio
Teatro del Gusto Como ©
Teatro del Gusto Como

1
night
Cinque Terre

Cinque Terre ©
Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
On the 31st (Thu), explore the striking landscape of Sentiero 586 (ex n.6D) Volastra-Case Pianca, then trek along Footpath Monterosso - Vernazza, and then get into the urban bustle at Vernazza.

To find where to stay, reviews, maps, and other tourist information, go to the Cinque Terre road trip website .

You can drive from Como to Cinque Terre in 3.5 hours. Another option is to take a train. Traveling from Como in October, expect nights in Cinque Terre to be about the same, around 54°F, while days are somewhat warmer, around 71°F. Finish up your sightseeing early on the 31st (Thu) so you can go by car to Florence.

Things to do in Cinque Terre

Trails Outdoors Parks

Side Trip

Sentiero 586 (ex n.6D) Volastra-Case Pianca
Highlights from your plan
Footpath Monterosso - Vernazza ©
Footpath Monterosso - Vernazza
Vernazza ©
Vernazza

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Start off your visit on the 1st (Fri): take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, then explore the world behind art at Uffizi Galleries, then explore the world behind art at Pitti Palace, and finally get great views at Piazzale Michelangelo. Here are some ideas for day two: examine the collection at Academy Of Florence Art Gallery, then take an in-depth tour of Basilica di Santa Croce, then appreciate the extensive heritage of Centro Storico, and finally contemplate in the serene atmosphere at The Baptistery of St. John.

To find more things to do, reviews, and other tourist information, use the Florence trip builder site .

You can drive from Cinque Terre to Florence in 2.5 hours. Alternatively, you can take a train. In October, daytime highs in Florence are 71°F, while nighttime lows are 54°F. Wrap up your sightseeing on the 2nd (Sat) early enough to take a train to Naples.

Things to do in Florence

Historic Sites Museums
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Centro Storico ©
Centro Storico

2
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Start off your visit on the 3rd (Sun): brush up on your military savvy at Galleria Borbonica, then get to know the fascinating history of Via Caracciolo e Lungomare di Napoli, then see the interesting displays at National Archaeological Museum of Naples, and finally shop like a local with Keste. Keep things going the next day: take an in-depth tour of Museo Nazionale di Capodimonte, stroll the grounds of Catacombe di San Gennaro, explore the world behind art at Chiesa dei Santi Filippo e Giacomo - Complesso Museale dell'Arte della Seta, steep yourself in history at Underground Naples, then admire the masterpieces at Museo Cappella Sansevero, and finally pause for some serene contemplation at Duomo di Napoli.

To see more things to do, other places to visit, photos, and more tourist information, use the Naples day trip planning website .

Traveling by train from Florence to Naples takes 3 hours. Alternatively, you can do a combination of flight and train; or drive. In November, daytime highs in Naples are 66°F, while nighttime lows are 50°F. Cap off your sightseeing on the 4th (Mon) early enough to catcht the bus to Pompeii.

Things to do in Naples

Historic Sites Museums Nightlife
Highlights from your plan
Galleria Borbonica ©
Galleria Borbonica
Underground Naples ©
Underground Naples
Via Caracciolo e Lungomare di Napoli ©

1
night
Pompeii

Pompeii ©
Pompeii has been a tourist destination for more than 250 years.
Kick off your visit on the 5th (Tue): steep yourself in history at Ruins of Herculaneum and then steep yourself in history at Gli Scavi Archeologici di Pompei.

Plan my day in Pompeii using traveler tips and tourist information provided by Inspirock.

Pompeii is just a stone's throw from Naples. In November in Pompeii, expect temperatures between 66°F during the day and 50°F at night. Wrap up your sightseeing on the 5th (Tue) to allow time to drive to Salerno.

Things to do in Pompeii

Historic Sites

Side Trip

Parco Acheologico di Ercolano
Highlights from your plan
Parco Acheologico di Ercolano ©
Parco Acheologico di Ercolano
Pompeii Archaeological Park ©
Pompeii Archaeological Park

2
nights
Salerno

Salerno ©
While often overshadowed by the Amalfi Coast's array of quaint villages, Salerno has become one of the region's main areas for culture and entertainment, while remaining relatively unmarked by tourism.
On the 6th (Wed), shop like a local with Made In Salerno, pause for some serene contemplation at Chiesa di Sant'Agostino, do a tasting at Le Vigne di Raito, then shop like a local with Sol’Art Ceramiche, and finally explore the ancient world of Paestum Ruins. Here are some ideas for day two: stop by Ceramica D'Urso Vietri, kick back and relax at Spiaggia di Marina d'Albori, then tour the pleasant surroundings at Spiaggia Lannio, and finally get to know the fascinating history of Il Vecchio Centro Storico di Romagnano al Monte.

To see more things to do, reviews, and tourist information, go to the Salerno trip planner .

Salerno is just a short distance from Pompeii. Traveling from Pompeii in November, expect somewhat warmer with lows of 58°F in Salerno. Finish up your sightseeing early on the 7th (Thu) so you can go by car to Ravello.

Things to do in Salerno

Beaches Outdoors Parks

Side Trips

Vietri sul Mare, Paestum Ruins, Spiaggia Lannio
Highlights from your plan
Paestum Ruins ©
Paestum Ruins
Sol’Art Ceramiche ©
Sol’Art Ceramiche
Le Vigne di Raito ©
Le Vigne di Raito

2
nights
Ravello

Ravello ©
On the 8th (Fri), pause for some serene contemplation at Cappella Sant'Angelo all'Ospedale, enjoy the sand and surf at Spiaggia di castiglione, then get a taste of the local shopping with Ceramiche d'Arte Carmela, then steep yourself in history at Duomo di Ravello, and finally admire the striking features of Villa Rufolo. Get ready for a full day of sightseeing on the 9th (Sat): take in the spiritual surroundings of Parrocchia San Giovanni, take in the architecture and atmosphere at Duomo di Sant'Andrea, enjoy the sand and surf at Lido di Ravello, then stop by Ceramiche D'Arte Pascal, and finally view the masterpieces at Ravello Arte.

To see more things to do, where to stay, photos, and more tourist information, use the Ravello trip itinerary builder website .

Traveling by car from Salerno to Ravello takes an hour. Alternatively, you can ride a ferry; or take a bus. In November, plan for daily highs up to 65°F, and evening lows to 58°F. Wrap up your sightseeing on the 9th (Sat) to allow time to take a bus to Positano.

Things to do in Ravello

Beaches Outdoors Parks

Side Trips

Parrocchia San Giovanni, Duomo di Sant'Andrea
Highlights from your plan
Spiaggia di castiglione ©
Spiaggia di castiglione
Duomo di Ravello ©
Duomo di Ravello
Lido di Ravello ©
Lido di Ravello

2
nights
Positano

Positano ©
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.
Kick off your visit on the 10th (Sun): add some adventure to your tour with a kayaking and canoeing tour, take advantage of the amenities at Fornillo, then stop by Nana' Positano, and finally view the masterpieces at Miniaci Art Gallery. On your second day here, kick back and relax at Marina di Praia Beach, then enjoy the sand and surf at Bagni d'Arienzo, and then contemplate the long history of Chiesa di Santa Maria Assunta e Cripta Medievale.

To see where to stay, traveler tips, and more tourist information, read our Positano route maker tool .

Positano is just a stone's throw from Ravello. Expect a daytime high around 64°F in November, and nighttime lows around 56°F. Wrap up your sightseeing on the 11th (Mon) to allow time to drive to Sorrento.

Things to do in Positano

Outdoors Beaches Parks

Side Trip

Marina di Praia Beach
Highlights from your plan
Fornillo ©
Fornillo
Marina di Praia Beach ©
Marina di Praia Beach
Kayaking & Canoeing

1
night
Sorrento

A lovely town easily accessible from almost anywhere in the country, Sorrento overlooks the Bay of Naples and sits right on the Amalfi Drive.
Start off your visit on the 12th (Tue): race across the water with a speed boat tour.

To see reviews, other places to visit, where to stay, and tourist information, go to the Sorrento trip itinerary builder website .

Sorrento is just a short distance from Positano. In November, plan for daily highs up to 64°F, and evening lows to 56°F. Finish your sightseeing early on the 12th (Tue) so you can ride a ferry to Capri.

Things to do in Sorrento

Tours Outdoors
Highlights from your plan
Speed Boats Tours

2
nights
Capri

Capri ©
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
Kick off your visit on the 13th (Wed): tour the pleasant surroundings at Sentiero Del Passetiello Capri, get to know the fascinating history of Scala Fenicia (Phoenician Steps), take in nature's colorful creations at Giardini di Augusto, then stop by Carthusia, then explore the striking landscape at I Faraglioni, and finally examine the collection at La Bottega dell'Arte di Sergio Rubino. Get ready for a full day of sightseeing on the 14th (Thu): take in the architecture and atmosphere at Chiesa San Michele, enjoy the sea views from Punta Carena Lighthouse, tour the pleasant surroundings at Fortini Coastal Walk, then look for all kinds of wild species at Parco Astarita, and finally get engrossed in the history at Villa San Michele.

To see more things to do, photos, ratings, and more tourist information, read Capri trip planning tool .

Capri is very close to Sorrento. In November, plan for daily highs up to 64°F, and evening lows to 56°F. Wrap up your sightseeing on the 14th (Thu) to allow time to travel to Venice.

Things to do in Capri

Parks Trails Outdoors

Side Trips

Anacapri, Sentiero Del Passetiello Capri
Highlights from your plan
Villa San Michele ©
Villa San Michele
I Faraglioni
I Faraglioni
Fortini Coastal Walk ©
Fortini Coastal Walk

3
nights
Venice

Venice
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.
Museum-lovers will get to explore Peggy Guggenheim Collection and Ca' d'Oro. Your inner history buff will appreciate Basilica di San Marco and Basilica di Sant’Antonio. When in Venice, make a side trip to see Scrovegni Chapel in Padua, approximately 54 minutes away. And it doesn't end there: examine the collection at Doge's Palace, pause for some serene contemplation at San Giorgio Maggiore, steep yourself in history at Ponte dei Sospiri, and admire the striking features of St Mark's Campanile.

For maps, other places to visit, reviews, and more tourist information, use the Venice route planner.

Traveling by combination of ferry and flight from Capri to Venice takes 5 hours. Alternatively, you can do a combination of ferry, flight, and train; or do a combination of ferry and train. Traveling from Capri in November, expect Venice to be little chillier, temps between 56°F and 43°F. Finish your sightseeing early on the 17th (Sun) so you can travel back home.

Things to do in Venice

Historic Sites Museums Nature

Side Trip

Padua
Highlights from your plan
Basilica di San Marco
Basilica di San Marco
Doge's Palace ©
Doge's Palace
Piazza San Marco ©
Piazza San Marco

Similar Plans

24 days in Europe BY A USER FROM POLAND August, teens, kids, popular sights PREFERENCES: August, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 24 days in Italy & Croatia BY A USER FROM SWITZERLAND August, outdoors, beaches, wildlife, fast-paced, popular sights PREFERENCES: August, outdoors, beaches, wildlife ATTRACTION STYLE: Popular sights PACE: Fast-paced 29 days in Italy & Dubrovnik BY A USER FROM CANADA September, romantic, popular sights PREFERENCES: September, romantic ATTRACTION STYLE: Popular sights PACE: Medium 22 days in Milan BY A USER FROM BRAZIL December, culture, historic sites, museums, wildlife, slow & easy, popular sights PREFERENCES: December, culture, historic sites, museums, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 22 days in Europe BY A USER FROM HONG KONG July, kids, popular sights PREFERENCES: July, kids ATTRACTION STYLE: Popular sights PACE: Medium 22 days in Turkey & Milan BY A USER FROM ITALY July, kids, popular sights PREFERENCES: July, kids ATTRACTION STYLE: Popular sights PACE: Medium 25 days in Italy, Albania & Croatia BY A USER FROM GERMANY August, romantic, beaches, popular & hidden gems PREFERENCES: August, romantic, beaches ATTRACTION STYLE: Popular & hidden gems PACE: Medium 23 days in Milan BY A USER FROM IRELAND February, popular sights PREFERENCES: February ATTRACTION STYLE: Popular sights PACE: Medium 23 days in Italy BY A USER FROM UNITED STATES June, culture, outdoors, romantic, beaches, historic sites, fast-paced, popular sights PREFERENCES: June, culture, outdoors, romantic, beaches, historic sites ATTRACTION STYLE: Popular sights PACE: Fast-paced 26 days in Italy, Swindon & Ibiza BY A USER FROM CANADA August, popular sights PREFERENCES: August ATTRACTION STYLE: Popular sights PACE: Medium 23 days in Italy BY A USER FROM CANADA September, culture, relaxing, romantic, beaches, historic sites, shopping, slow & easy, popular sights PREFERENCES: September, culture, relaxing, romantic, beaches, historic sites, shopping ATTRACTION STYLE: Popular sights PACE: Slow & easy 22 days in Italy BY A USER FROM UNITED STATES April, popular sights PREFERENCES: April ATTRACTION STYLE: Popular sights PACE: Medium
See more plans