20 days in Italy Itinerary

20 days in Italy Itinerary

Created using Inspirock Italy trip planner

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

Route & dates

20 days in Italy Itinerary

Start: Charlotte
Fly:  14​h 30​min
1
Venice
— 1 night
2
Canazei
— 1 night
Drive:  4​h 15​min
3
Bellagio
— 2 nights
train:  1​h 15​min
4
Milan
— 1 night
train:  3​h
5
Cinque Terre
— 1 night
train:  1​h 30​min
6
Pisa
— 1 night
train:  1​h 45​min
7
Siena
— 1 night
bus:  1​h
8
Florence
— 2 nights
train:  1​h 30​min
9
Rome
— 3 nights
Drive + ferry:  3​h
10
Capri, Island of Capri
— 1 night
Drive:  30​min
11
Sorrento
— 1 night
ferry:  30​min
12
Positano
— 3 nights
train + Fly:  15​h 45​min
End: Charlotte


Learn more about your trip

1
night
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.
Kick off your visit on the 5th (Fri): contemplate the waterfront views at Canal Grande, examine the collection at Museo Ebraico di Venezia, take a stroll through Campo del Ghetto, then explore the world behind art at Peggy Guggenheim Collection, and finally steep yourself in history at Squero di San Trovaso. Keep things going the next day: admire the landmark architecture of Basilica di San Marco, take in the views from Ponte dei Sospiri, admire the striking features of Doge's Palace, then make a trip to St. Mark's Square, and finally admire the landmark architecture of Scala Contarini del Bovolo.

To find ratings, more things to do, traveler tips, and more tourist information, you can read our Venice trip app .

Charlotte, USA to Venice is an approximately 14.5-hour flight. You can also do a combination of flight and train; or do a combination of flight and shuttle. You'll lose 6 hours traveling from Charlotte to Venice due to the time zone difference. Traveling from Charlotte in October, expect nights in Venice to be about the same, around 51°F, while days are little chillier, around 66°F. Finish your sightseeing early on the 6th (Sat) to allow enough time to drive to Canazei.

Things to do in Venice

Historic Sites Museums Nature
Find places to stay Oct 5 — 6:
Highlights from your plan
Canal Grande ©
Canal Grande
Piazza San Marco ©
Piazza San Marco
Doge's Palace ©
Doge's Palace

1
night
Canazei

Canazei ©
Canazei is a comune (municipality) in Trentino in the northern Italian region Trentino-Alto Adige/Südtirol, located in the upper part of the Val di Fassa, about 110km northeast of Trento. On the 7th (Sun), head outdoors with La Terrazza delle Dolomiti and then hike along Sass Pordoi.

To see where to stay, traveler tips, more things to do, and tourist information, you can read our Canazei trip planner .

You can drive from Venice to Canazei in 2.5 hours. Alternatively, you can take a bus. In October in Canazei, expect temperatures between 66°F during the day and 47°F at night. Cap off your sightseeing on the 7th (Sun) early enough to go by car to Bellagio.

Things to do in Canazei

Outdoors Trails Parks
Find places to stay Oct 6 — 7:
Highlights from your plan
Sass Pordoi ©
Sass Pordoi
La Terrazza delle Dolomiti ©
La Terrazza delle Dolomiti

2
nights
Bellagio

Bellagio ©
Known as the pearl of Lake Como for its luxury accommodations, high-end shops, and fine dining options, Bellagio serves as the lake's premiere resort town.
Kick off your visit on the 8th (Mon): do a tasting at Enoteca Principessa, then take in the architecture and atmosphere at Chiesa di S. Leonardo, then explore the historical opulence of Castello di Vezio, and finally examine the collection at Museo Etnografico E Naturalistico Val Sanagra. On the next day, take in the architecture and atmosphere at Chiesa Di S. Sisinnio, then tour the water at your own pace with Turati Centro Nautico Lario, and then tour the water at your own pace with AC Boat.

To find traveler tips, reviews, and other tourist information, go to the Bellagio tour itinerary builder .

Traveling by car from Canazei to Bellagio takes 4.5 hours. Alternatively, you can do a combination of taxi and train; or do a combination of bus and train. October in Bellagio sees daily highs of 64°F and lows of 49°F at night. Finish your sightseeing early on the 9th (Tue) to allow enough time to drive to Milan.

Things to do in Bellagio

Tours Outdoors Transportation

Side Trips

Museo Etnografico E Naturalistico Val Sanagra, Castello di Vezio, AC Boat, Chiesa di S. Leonardo, Turati Centro Nautico Lario
Find places to stay Oct 7 — 9:
Highlights from your plan
Turati Centro Nautico Lario ©
Turati Centro Nautico Lario
AC Boat ©
AC Boat

1
night
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 10th (Wed): admire the masterpieces at Pinacoteca Ambrosiana, pause for some serene contemplation at Basilica di Sant'Ambrogio, then take in the architecture and atmosphere at Duomo di Milano, and finally admire the landmark architecture of Galleria Vittorio Emanuele II.

To find maps, where to stay, and other tourist information, refer to the Milan day trip site .

Traveling by car from Bellagio to Milan takes 1.5 hours. Alternatively, you can take a train; or do a combination of bus and train. In October, daytime highs in Milan are 65°F, while nighttime lows are 52°F. Cap off your sightseeing on the 10th (Wed) early enough to catch the train to Cinque Terre.

Things to do in Milan

Museums Historic Sites Shopping
Find places to stay Oct 9 — 10:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana
Basilica di Sant'Ambrogio ©
Basilica di Sant'Ambrogio

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 11th (Thu), get to know the fascinating history of Borgo Storico di Corniglia, then tour the pleasant surroundings at Cinque Terre Trails, then do a tasting at Terra di Bargon, and finally hike along Footpath Monterosso - Vernazza.

For reviews, where to stay, photos, and tourist information, go to the Cinque Terre online travel planner .

Traveling by train from Milan to Cinque Terre takes 3 hours. Alternatively, you can drive. Traveling from Milan in October, you will find days in Cinque Terre are somewhat warmer (71°F), and nights are about the same (54°F). Wrap up your sightseeing on the 11th (Thu) to allow time to take a train to Pisa.

Things to do in Cinque Terre

Trails Outdoors Parks
Find places to stay Oct 10 — 11:
Highlights from your plan
Cinque Terre Trails ©
Cinque Terre Trails
Footpath Monterosso - Vernazza ©
Footpath Monterosso - Vernazza
Borgo Storico di Corniglia ©
Borgo Storico di Corniglia

1
night
Pisa

Pisa ©
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
On the 12th (Fri), contemplate the long history of St Martin Cathedral, contemplate the long history of Le mura di Lucca, and then make a trip to Torre di Pisa.

To find more things to do, photos, traveler tips, and other tourist information, read our Pisa trip itinerary planning app .

Traveling by train from Cinque Terre to Pisa takes 1.5 hours. Alternatively, you can drive; or take a bus. In October, daytime highs in Pisa are 71°F, while nighttime lows are 54°F. Wrap up your sightseeing by early afternoon on the 12th (Fri) to allow enough time to drive to Siena.

Things to do in Pisa

Historic Sites

Side Trip

Lucca
Find places to stay Oct 11 — 12:
Highlights from your plan
St Martin Cathedral ©
St Martin Cathedral
Leaning Tower of Pisa ©
Leaning Tower of Pisa
Le mura di Lucca ©
Le mura di Lucca

1
night
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Kick off your visit on the 13th (Sat): do a tasting at Take Me Out in Tuscany, then take in the architecture and atmosphere at Siena Cathedral, then make a trip to Piazza del Campo, and finally explore the galleries of Palazzo Pubblico and Museo Civico.

To find reviews, photos, traveler tips, and tourist information, use the Siena trip planner .

Traveling by car from Pisa to Siena takes 2 hours. Alternatively, you can take a train; or take a bus. In October, daytime highs in Siena are 73°F, while nighttime lows are 56°F. Cap off your sightseeing on the 13th (Sat) early enough to catcht the bus to Florence.

Things to do in Siena

Classes Tours Transportation
Find places to stay Oct 12 — 13:
Highlights from your plan
Duomo di Siena ©
Duomo di Siena
Palazzo Pubblico and Museo Civico ©
Palazzo Pubblico and Museo Civico
Piazza del Campo ©
Piazza del Campo

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 14th (Sun): appreciate the extensive heritage of Piazza del Duomo, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, explore the world behind art at Uffizi Galleries, then take an in-depth tour of Basilica di Santa Croce, and finally see the interesting displays at Galleria dell'Accademia. Keep things going the next day: take in the views from Ponte Vecchio, get great views at Piazzale Michelangelo, then explore the world behind art at Pitti Palace, then don't miss a visit to Piazza della Signoria, and finally take in the spiritual surroundings of The Baptistery of St. John.

For photos, traveler tips, other places to visit, and other tourist information, go to the Florence day trip tool .

Traveling by bus from Siena to Florence takes an hour. Alternatively, you can drive; or take a train. October in Florence sees daily highs of 71°F and lows of 54°F at night. Finish your sightseeing early on the 15th (Mon) so you can take a train to Rome.

Things to do in Florence

Museums Historic Sites
Find places to stay Oct 13 — 15:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

3
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Appreciate the collections at Vatican Museums and Sistine Chapel. Your inner history buff will appreciate Palatine Hill and Colosseum. And it doesn't end there: admire the landmark architecture of Pantheon, explore the world behind art at Galleria Borghese, take in the spiritual surroundings of Chiesa di Sant'Ignazio di Loyola, and make a trip to St. Peter's Basilica.

To find maps, photos, ratings, and tourist information, read Rome trip planner.

Take a train from Florence to Rome in 1.5 hours. Alternatively, you can drive; or fly. In October, daily temperatures in Rome can reach 73°F, while at night they dip to 55°F. Wrap up your sightseeing on the 18th (Thu) to allow time to travel to Capri.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trip

Vatican City
Find places to stay Oct 15 — 18:
Highlights from your plan
St. Peter's Basilica ©
St. Peter's Basilica
Vatican Museums
Vatican Museums
Pantheon ©
Pantheon

1
night
Capri, Island of 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 19th (Fri): enjoy the sand and surf at Marina Grande, then contemplate the waterfront views at Marina Piccola, then Head underground at Blue Grotto, and finally take in the awesome beauty at Monte Solaro.

To find other places to visit, ratings, more things to do, and other tourist information, you can read our Capri itinerary planning site .

Do a combination of train and ferry from Rome to Capri in 3 hours. Alternatively, you can do a combination of car and ferry; or do a combination of flight and ferry. Traveling from Rome in October, you can expect nighttime temperatures to be somewhat warmer in Capri, with lows of 63°F. Finish up your sightseeing early on the 19th (Fri) so you can catch the ferry to Sorrento.

Things to do in Capri

Parks Beaches Outdoors

Side Trip

Anacapri
Find places to stay Oct 18 — 19:
Highlights from your plan
Marina Piccola
Marina Piccola
Monte Solaro ©
Monte Solaro
Blue Grotto ©
Blue Grotto

1
night
Sorrento

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.
On the 20th (Sat), kick back and relax at Villa di Pollio Felice - Bagni della Regina Giovanna, then explore the activities along Marina di Puolo, and then tour the pleasant surroundings at La Solara.

For where to stay, maps, traveler tips, and other tourist information, refer to the Sorrento sightseeing planner.

Sorrento is just a stone's throw from Capri. In October in Sorrento, expect temperatures between 72°F during the day and 63°F at night. Wrap up your sightseeing on the 20th (Sat) early enough to drive to Positano.

Things to do in Sorrento

Beaches Outdoors Parks
Find places to stay Oct 19 — 20:
Highlights from your plan
La Solara ©
La Solara
Marina di Puolo ©
Marina di Puolo

3
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.
On the 21st (Sun), take in the architecture and atmosphere at Duomo di Sant'Andrea, then enjoy the sand and surf at Lido di Ravello, and then enjoy the sand and surf at Fornillo. Keep things going the next day: take in the spiritual surroundings of Duomo di Ravello, admire the landmark architecture of Villa Rufolo, then enjoy the sand and surf at Spiaggia Lannio, and finally learn about winemaking at Le Vigne di Raito.

To see ratings, traveler tips, reviews, and more tourist information, refer to the Positano itinerary maker tool .

Positano is just a short distance from Sorrento. Expect a daytime high around 72°F in October, and nighttime lows around 63°F. Wrap up your sightseeing by early afternoon on the 23rd (Tue) to allow enough time to travel back home.

Things to do in Positano

Beaches Outdoors Parks

Side Trips

Ravello, Le Vigne di Raito, Spiaggia Lannio, Duomo di Sant'Andrea
Find places to stay Oct 20 — 23:
Highlights from your plan
Le Vigne di Raito ©
Le Vigne di Raito
Duomo di Ravello ©
Duomo di Ravello
Duomo di Sant'Andrea ©
Duomo di Sant'Andrea

Similar Plans

22 days in Italy BY A USER FROM UNITED STATES August, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, slow & easy, popular sights PREFERENCES: August, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 21 days in Italy BY A USER FROM AUSTRALIA September, beaches, historic sites, museums, shopping, hidden gems PREFERENCES: September, beaches, historic sites, museums, shopping ATTRACTION STYLE: Hidden gems PACE: Medium 23 days in Italy BY A USER FROM UNITED STATES August, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: August, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 22 days in Italy BY A USER FROM SAUDI ARABIA July, teens, kids, popular sights PREFERENCES: July, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 23 days in Italy BY A USER FROM COLOMBIA July, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife, slow & easy, popular & hidden gems PREFERENCES: July, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 22 days in Asia & Europe BY A USER FROM INDIA February, relaxing, romantic, beaches, popular & hidden gems PREFERENCES: February, relaxing, romantic, beaches ATTRACTION STYLE: Popular & hidden gems PACE: Medium 21 days in Europe BY A USER FROM SAUDI ARABIA January, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular sights PREFERENCES: January, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Fast-paced 22 days in Europe & Asia BY A USER FROM INDIA February, relaxing, romantic, beaches, popular & hidden gems PREFERENCES: February, relaxing, romantic, beaches ATTRACTION STYLE: Popular & hidden gems PACE: Medium 22 days in Italy BY A USER FROM UNITED KINGDOM July, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, popular & hidden gems PREFERENCES: July, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 22 days in Italy BY A USER FROM ARGENTINA July, popular & hidden gems PREFERENCES: July ATTRACTION STYLE: Popular & hidden gems PACE: Medium 24 days in Italy BY A USER FROM AUSTRALIA September, popular & hidden gems PREFERENCES: September ATTRACTION STYLE: Popular & hidden gems PACE: Medium 22 days in Italy BY A USER FROM UNITED KINGDOM July, culture, outdoors, relaxing, romantic, beaches, shopping, popular & hidden gems PREFERENCES: July, culture, outdoors, relaxing, romantic, beaches, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium
View more plans