28 days in Italy Itinerary

28 days in Italy Itinerary

Created using Inspirock Italy visit planner

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Route & dates

28 days in Italy Itinerary

Start: Boston
Fly + train:  12​h 45​min
1
Salerno
— 3 nights
ferry:  1​h 30​min
2
Positano
— 4 nights
Drive:  3​h 15​min
3
Rome
— 4 nights
Drive:  2​h 15​min
4
Assisi
— 3 nights
Drive:  1​h 45​min
5
Siena
— 3 nights
bus:  1​h 15​min
6
Florence
— 4 nights
train:  2​h 15​min
7
Venice
— 5 nights
Fly:  12​h 30​min
End: Boston

3
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.
Venture out of the city with trips to Monte Finestra (in Tramonti), Chiesa di San Francesco (in Maiori) and Ravello (Ceramiche Cosmolena di Margherita di Palma, Cappella Sant'Angelo all'Ospedale, & more). There's still lots to do: contemplate the long history of Pompeii Archaeological Park, contemplate in the serene atmosphere at Arciconfraternita della Santissima Annunziata e del Santissimo Rosario, take in the architecture and atmosphere at Duomo di Salerno, and see the interesting displays at Pinacoteca Provinciale Salerno.

For other places to visit, ratings, photos, and tourist information, you can read our Salerno route planner .

Boston, USA to Salerno is an approximately 13-hour combination of flight and train. You can also fly. The time zone changes from Eastern Standard Time to Central European Time, which is usually a 6 hour difference. Expect somewhat warmer weather when traveling from Boston in November: highs in Salerno hover around 65°F, while lows dip to 58°F. Wrap up your sightseeing on the 18th (Mon) early enough to ride a ferry to Positano.

Things to do in Salerno

Historic Sites Outdoors Museums

Side Trips

Ravello, Pompeii Archaeological Park, Monte Finestra, Chiesa di San Francesco, Arciconfraternita della Santissima Annunziata e del Santissimo Rosario
Find places to stay Nov 14 — 18:
Highlights from your plan
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Monte Finestra ©
Monte Finestra

4
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.
You'll find plenty of places to visit near Positano: Amalfi (Wine Tours & Tastings & Duomo di Sant'Andrea) and Ravello (Belvedere Principessa di Piemonte, Duomo di Ravello, & more). And it doesn't end there: get great views at Il Sentiero Degli Dei, take in the spiritual surroundings of Cloister del Paradiso, get to know the fascinating history of Centro Storico, and kick back and relax at Fornillo.

For other places to visit, where to stay, maps, and tourist information, use the Positano trip itinerary maker tool .

You can ride a ferry from Salerno to Positano in 1.5 hours. Other options are to do a combination of train and taxi; or drive. In November, daytime highs in Positano are 64°F, while nighttime lows are 56°F. Cap off your sightseeing on the 22nd (Fri) early enough to go by car to Rome.

Things to do in Positano

Historic Sites Parks Beaches

Side Trips

Ravello, Amalfi, Praiano
Find places to stay Nov 18 — 22:
Highlights from your plan
Duomo di Ravello ©
Duomo di Ravello
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei
Fornillo ©
Fornillo

4
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: explore the ancient world of Colosseum, appreciate the extensive heritage of Piazza Navona, admire the masterpieces at Galleria Borghese, and make a trip to Roman Forum.

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

Drive from Positano to Rome in 3.5 hours. Alternatively, you can do a combination of subway and train; or take a bus. Traveling from Positano in November, expect slightly colder with lows of 47°F in Rome. Wrap up your sightseeing on the 26th (Tue) to allow time to drive to Assisi.

Things to do in Rome

Historic Sites Museums Tours

Side Trip

Vatican City
Find places to stay Nov 22 — 26:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

3
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Change things up with these side-trips from Assisi: Vineria del Carmine (in La Bruna) and Museo Cinema a Pennello (in Montecosaro). Next up on the itinerary: pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, contemplate in the serene atmosphere at San Damiano, see the interesting displays at Mostra Permanente degli Antichi Mestieri e della Civilta Contadina, and don't miss a visit to Eremo delle Carceri.

To see photos, ratings, reviews, and tourist information, read our Assisi journey planner.

You can drive from Rome to Assisi in 2.5 hours. Alternatively, you can take a train; or take a bus. Expect a bit cooler weather when traveling from Rome in November: highs in Assisi hover around 58°F, while lows dip to 44°F. Finish your sightseeing early on the 29th (Fri) to allow enough time to drive to Siena.

Things to do in Assisi

Wineries Historic Sites Museums

Side Trips

Vineria del Carmine, Museo Cinema a Pennello
Find places to stay Nov 26 — 29:
Highlights from your plan
Tili Vini Societa Agricola ©
Tili Vini Societa Agricola
Eremo delle Carceri ©
Eremo delle Carceri

3
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Go for a jaunt from Siena to San Gimignano to see Guardastelle Vineyard about 52 minutes away. Next up on the itinerary: make a trip to Piazza del Campo, let your taste buds guide you at a local gastronomic tour, pause for some serene contemplation at Duomo di Siena, and gain insight at Scuola di Cucina di Lella.

To find where to stay, other places to visit, traveler tips, and tourist information, read Siena visit planning app .

You can drive from Assisi to Siena in 2 hours. Alternatively, you can take a bus; or take a train. November in Siena sees daily highs of 63°F and lows of 48°F at night. Finish up your sightseeing early on the 2nd (Mon) so you can catcht the bus to Florence.

Things to do in Siena

Tours Historic Sites Wineries

Side Trip

Guardastelle Vineyard
Find places to stay Nov 29 — Dec 2:
Highlights from your plan
Wine Tours & Tastings
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

4
nights
Florence

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Go for a jaunt from Florence to Pisa to see Leaning Tower of Pisa about 1h 10 min away. The adventure continues: examine the collection at Academy Of Florence Art Gallery, take some stellar pictures from Piazzale Michelangelo, take in the views from Ponte Vecchio, and appreciate the extensive heritage of Piazza del Duomo.

To see other places to visit, reviews, where to stay, and more tourist information, you can read our Florence route tool .

You can take a bus from Siena to Florence in 1.5 hours. Alternatively, you can drive; or take a train. In December, plan for daily highs up to 55°F, and evening lows to 39°F. Cap off your sightseeing on the 6th (Fri) early enough to catch the train to Venice.

Things to do in Florence

Tours Historic Sites Museums

Side Trip

Leaning Tower of Pisa
Find places to stay Dec 2 — 6:
Highlights from your plan
Food Tours
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

5
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.
Venture out of the city with trips to Verona (Arena di Verona, Piazza delle Erbe, & more) and Padua (Scrovegni Chapel & Basilica di Sant’Antonio). Next up on the itinerary: contemplate the waterfront views at Canal Grande, admire the masterpieces at Gallerie dell'Accademia, browse the exhibits of Peggy Guggenheim Collection, and snap pictures at Ponte di Rialto.

To see more things to do, ratings, where to stay, and tourist information, read Venice trip itinerary planning app .

Getting from Florence to Venice by train takes about 2.5 hours. Other options: drive; or take a bus. Plan for little chillier temperatures traveling from Florence in December, with highs in Venice at 49°F and lows at 34°F. Cap off your sightseeing on the 11th (Wed) early enough to travel back home.

Things to do in Venice

Historic Sites Museums Parks

Side Trips

Verona, Padua
Find places to stay Dec 6 — 11:
Highlights from your plan
Canal Grande ©
Canal Grande
Basilica di San Marco
Basilica di San Marco
Doge's Palace ©
Doge's Palace

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