16 days in Italy Itinerary

16 days in Italy Itinerary

Created using Inspirock Italy trip planner

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Route & dates

16 days in Italy Itinerary

Start: San Francisco
Fly:  16​h
1
Milan
— 1 day
train:  2​h 30​min
2
Venice
— 2 nights
3
Florence
— 3 nights
Drive:  2​h 15​min
4
Assisi
— 1 night
Drive:  4​h 45​min
5
Positano
— 3 nights
ferry:  1​h 30​min
6
Salerno
— 2 nights
7
Rome
— 3 nights
Fly:  15​h 45​min
End: San Francisco

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.
On the 9th (Wed), admire the striking features of Galleria Vittorio Emanuele II and then contemplate in the serene atmosphere at Duomo di Milano.

For photos, more things to do, where to stay, and other tourist information, use the Milan itinerary maker site .

San Francisco, USA to Milan is an approximately 16-hour flight. You can also do a combination of flight and train; or do a combination of train and flight. The time zone difference moving from Pacific Standard Time to Central European Time is 9 hours. In September, daily temperatures in Milan can reach 76°F, while at night they dip to 57°F. Wrap up your sightseeing on the 9th (Wed) early enough to take a train to Venice.

Things to do in Milan

Historic Sites Shopping
Find places to stay Sep 9 — 10:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II

2
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.
On the 10th (Thu), admire the landmark architecture of St Mark's Campanile, admire the landmark architecture of Basilica di San Marco, take in the views from Ponte di Rialto, then contemplate in the serene atmosphere at Santa Maria dei Miracoli, and finally contemplate the waterfront views at Canal Grande. Get ready for a full day of sightseeing on the next day: admire the masterpieces at Ca' d'Oro, explore the galleries of Peggy Guggenheim Collection, then take in the views from Ponte dei Sospiri, then get to know the fascinating history of Piazza San Marco, and finally browse the exhibits of Doge's Palace.

To see traveler tips, ratings, and tourist information, read Venice trip planner .

Traveling by train from Milan to Venice takes 2.5 hours. Alternatively, you can drive; or do a combination of flight and train. September in Venice sees daily highs of 77°F and lows of 59°F at night. Wrap up your sightseeing on the 11th (Fri) to allow time to take a train to Florence.

Things to do in Venice

Historic Sites Museums Nature
Find places to stay Sep 9 — 11:
Highlights from your plan
Canal Grande ©
Canal Grande
Piazza San Marco ©
Piazza San Marco
Basilica di San Marco
Basilica di San Marco

3
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Step out of Florence with an excursion to Leaning Tower of Pisa in Pisa--about 1h 10 min away. The adventure continues: explore the world behind art at Gallerie Degli Uffizi, snap pictures at Ponte Vecchio, see the interesting displays at Pitti Palace, and take in the spiritual surroundings of Cathedral of Santa Maria del Fiore.

For photos, more things to do, and more tourist information, you can read our Florence trip site .

You can take a train from Venice to Florence in 2.5 hours. Other options are to drive; or take a bus. In September, daily temperatures in Florence can reach 78°F, while at night they dip to 59°F. Wrap up your sightseeing on the 14th (Mon) to allow time to drive to Assisi.

Things to do in Florence

Museums Historic Sites Parks

Side Trip

Leaning Tower of Pisa
Find places to stay Sep 11 — 14:
Highlights from your plan
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

1
night
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
On the 15th (Tue), pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, learn about winemaking at Azienda Agraria Saio, learn about winemaking at Tili Vini Societa Agricola, then learn about winemaking at Bibenda Assisi, and finally make a trip to Eremo delle Carceri.

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

Traveling by car from Florence to Assisi takes 2.5 hours. Alternatively, you can take a train. In September, daytime highs in Assisi are 78°F, while nighttime lows are 57°F. Finish your sightseeing early on the 15th (Tue) so you can drive to Positano.

Things to do in Assisi

Wineries Historic Sites
Find places to stay Sep 14 — 15:
Highlights from your plan

3
nights
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.
You'll find plenty of places to visit near Positano: Amalfi (Wine Tours & Tastings & Duomo di Sant'Andrea), Ravello (Villa Rufolo, Duomo di Ravello, & more) and Lido di Ravello (in Castiglione). There's still lots to do: kick back and relax at Fornillo, head outdoors with I Suoni degli Dei - Pelagos, contemplate in the serene atmosphere at Cloister del Paradiso, and go for a walk through Positano.

To see reviews, more things to do, maps, and other tourist information, you can read our Positano tour builder website .

Getting from Assisi to Positano by car takes about 5 hours. Other options: do a combination of train and subway; or take a bus. Traveling from Assisi in September, Positano is a bit warmer at night with lows of 68°F. Finish your sightseeing early on the 18th (Fri) so you can ride a ferry to Salerno.

Things to do in Positano

Outdoors Parks Tours

Side Trips

Ravello, Amalfi, I Suoni degli Dei - Pelagos
Find places to stay Sep 15 — 18:
Highlights from your plan
Wine Tours & Tastings
Fornillo ©
Fornillo
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei

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.
Start off your visit on the 19th (Sat): don't miss a visit to Pompeii Archaeological Park, then take in the architecture and atmosphere at Cappella Sant'Angelo all'Ospedale, then take in the exciting artwork at Ceramiche Cosmolena di Margherita di Palma, and finally get outside with Monte Finestra. Here are some ideas for day two: kick back and relax at Marina Di Vietri, then kick back and relax at Spiaggia di castiglione, and then learn about winemaking at Le Vigne di Raito.

For reviews, ratings, other places to visit, and tourist information, read our Salerno tour planner.

Ride a ferry from Positano to Salerno in 1.5 hours. Alternatively, you can do a combination of taxi and train; or drive. In September, daily temperatures in Salerno can reach 79°F, while at night they dip to 70°F. Finish your sightseeing early on the 20th (Sun) to allow enough time to take a train to Rome.

Things to do in Salerno

Outdoors Parks Beaches

Side Trips

Ravello, Monte Finestra, Pompeii Archaeological Park, Le Vigne di Raito
Find places to stay Sep 18 — 20:
Highlights from your plan
Le Vigne di Raito ©
Le Vigne di Raito
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Spiaggia di castiglione ©
Spiaggia di castiglione

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.
Rome is known for historic sites, nightlife, museums, classes, and shopping. Your plan includes some of its best attractions: delve into the distant past at Colosseum, admire the landmark architecture of Pantheon, contemplate the long history of St. Peter's Basilica, and admire the local landmark of Trevi Fountain.

To see maps, photos, where to stay, and more tourist information, read Rome tour itinerary builder app .

You can take a train from Salerno to Rome in 2 hours. Other options are to drive; or take a bus. Traveling from Salerno in September, plan for a bit cooler nights in Rome, with lows around 60°F. Finish your sightseeing early on the 23rd (Wed) so you can travel back home.

Things to do in Rome

Historic Sites Museums

Side Trip

Vatican City
Find places to stay Sep 20 — 23:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

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