59 days in Italy Itinerary

59 days in Italy Itinerary

Created using Inspirock Italy sightseeing planner

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Route & dates

59 days in Italy Itinerary

Start: Kabul
Fly + Drive:  17​h 45​min
1
Positano
— 7 nights
Drive:  3​h 15​min
2
Rome
— 9 nights
3
Assisi
— 7 nights
Drive:  2​h
4
Florence
— 8 nights
5
Venice
— 9 nights
bus:  1​h 15​min
6
Verona
— 6 nights
train:  1​h 30​min
7
Milan
— 6 nights
Drive:  1​h 15​min
8
Tremezzina
— 5 nights
Drive + Fly:  18​h
End: Kabul

7
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.
Attractions like Fornillo and Spiaggia Grande make great kid-friendly stops. Your inner history buff will appreciate Duomo di Ravello and Villa Cimbrone Gardens. Explore the numerous day-trip ideas around Positano: Minori (Spas & Wellness & Basilica di Santa Trofimena), Amalfi (Chiostro del Paradiso, Antichi Sapori d'Amalfi, & more) and Ravello (Ceramiche d'Arte Carmela, San Giovanni del Toro, & more). Spend a day of island exploring on the 6th (Sat) at Exclusive Cruises - Tours. There's much more to do: enjoy the sand and surf at Bagni d'Arienzo, take in the spiritual surroundings of San Lorenzo Cathedral, look for gifts at Ceramica Assunta, and hike along Sentiero degli dei (Path of the Gods).

For traveler tips, photos, ratings, and tourist information, read Positano visit planner.

Kabul, Afghanistan to Positano is an approximately 18-hour flight. The time zone changes from Afghanistan Time (AFT) to Central European Time (CET), which is usually a -3 hour difference. Expect somewhat warmer weather when traveling from Kabul in January: highs in Positano hover around 15°C, while lows dip to 10°C. Wrap up your sightseeing on the 8th (Mon) to allow time to drive to Rome.

Things to do in Positano

Outdoors Parks Historic Sites

Side Trips

Ravello, Amalfi, Duomo di Salerno, Cattedrale di San Lorenzo, Piccadilly
Find places to stay Jan 1 — 8:
Highlights from your plan
Le Vigne di Raito ©
Le Vigne di Raito
Duomo di Ravello ©
Duomo di Ravello
Fornillo ©
Fornillo

9
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
You'll visit kid-friendly attractions like Palatine Hill and Colosseum. Get some historical perspective at Piazza Navona and Vatican Museums. You'll find plenty of places to visit near Rome: Tivoli (Villa Adriana & Villa d'Este). And it doesn't end there: take in the architecture and atmosphere at Basilica di San Pietro, admire the striking features of Pantheon, admire the masterpieces at Sistine Chapel, and make a trip to Trevi Fountain.

To see maps, more things to do, ratings, and other tourist information, read Rome road trip planning site .

You can drive from Positano to Rome in 3.5 hours. Other options are to do a combination of bus and train; or take a bus. Expect slightly colder evenings in Rome when traveling from Positano in January, with lows around 3°C. Finish your sightseeing early on the 17th (Wed) so you can drive to Assisi.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trips

Vatican City, Tivoli
Find places to stay Jan 8 — 17:
Highlights from your plan
Trevi Fountain ©
Trevi Fountain
Pantheon ©
Pantheon
Colosseum ©
Colosseum

7
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Kids will enjoy Rocca Maggiore and Altamarea Beach Village. Your inner history buff will appreciate Basilica Papale San Francesco D'Assisi and Basilica di Santa Chiara. Change things up with these side-trips from Assisi: Piazza Grande (in Gubbio), Piazza Grande a Montepulciano (in Montepulciano) and Spas & Wellness (in Chianciano Terme). There's lots more to do: take in the spiritual surroundings of Eremo delle Carceri, do a tasting at Wineries & Vineyards, pause for some serene contemplation at Chiesa Santo Stefano, and appreciate the views at Piana di Castelluccio di Norcia.

To see more things to do, photos, reviews, and more tourist information, read our Assisi trip planning app .

You can drive from Rome to Assisi in 2.5 hours. Alternatively, you can take a train; or take a bus. When traveling from Rome in January, plan for a bit cooler days and about the same nights in Assisi: temperatures range from 10°C by day to 1°C at night. Cap off your sightseeing on the 24th (Wed) early enough to go by car to Florence.

Things to do in Assisi

Parks Historic Sites Nature

Side Trips

Orvieto, Cascata delle Marmore, Cascate del Mulino, Piazza Grande, Grotte di Frasassi
Find places to stay Jan 17 — 24:
Highlights from your plan
Decugnano dei Barbi ©
Decugnano dei Barbi
Eremo delle Carceri ©
Eremo delle Carceri

8
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Deepen your sense of the past at sights like Cathedral of Santa Maria del Fiore and Campanile di Giotto. Attractions like Piazza della Signoria and Easy Living - Spiaggia sull'Arno make great kid-friendly stops. Change things up with these side-trips from Florence: Castello del Trebbio (in Santa Brigida), Sovestro in Poggio vineyard (in San Gimignano) and Castello di Verrazzano (in Greve in Chianti). And it doesn't end there: see the interesting displays at Galleria dell'Accademia, admire the striking features of The Baptistery of St. John, make a trip to Piazzale Michelangelo, and appreciate the extensive heritage of Piazza del Duomo.

To see maps, ratings, traveler tips, and tourist information, refer to the Florence online road trip planner .

Traveling by car from Assisi to Florence takes 2 hours. Alternatively, you can take a train; or take a bus. In January, plan for daily highs up to 13°C, and evening lows to 3°C. Cap off your sightseeing on the 1st (Thu) early enough to catch the train to Venice.

Things to do in Florence

Wineries Historic Sites Tours

Side Trips

Greve in Chianti, Siena, Castello di Volpaia, Guardastelle Vineyard, Podere Il Cocco
Find places to stay Jan 24 — Feb 1:
Highlights from your plan
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi

9
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.
Kids will enjoy Porta della Carta and Punta della Dogana. Get some historical perspective at Basilica di San Marco and St. Mark's Square. Change things up with these side-trips from Venice: Padua (Basilica di Sant’Antonio - Basilica del Santo, Scrovegni Chapel, & more). There's much more to do: contemplate the waterfront views at Canal Grande, take in panoramic vistas at St Mark's Campanile, get to know the fascinating history of Campo del Ghetto, and admire the masterpieces at Gallerie dell'Accademia.

For other places to visit, reviews, traveler tips, and tourist information, you can read our Venice trip planning tool .

Traveling by train from Florence to Venice takes 2.5 hours. Alternatively, you can drive; or take a bus. In February in Venice, expect temperatures between 11°C during the day and 2°C at night. Cap off your sightseeing on the 10th (Sat) early enough to catch the train to Verona.

Things to do in Venice

Historic Sites Museums Tours

Side Trip

Padua
Find places to stay Feb 1 — 10:
Highlights from your plan
Piazza San Marco ©
Piazza San Marco
Doge's Palace ©
Doge's Palace
Basilica di San Marco
Basilica di San Marco

6
nights
Verona

Verona ©
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.
Get a sense of the local culture at Arena di Verona and Castelvecchio Museum. Get in touch with nature at Museo di Palazzo Ducale. and Lago di Molveno. Explore Verona's surroundings by going to Lago di Garda (in Garda), Palazzo Te (in Mantua) and Mountbaldo (in Malcesine). Pack the 16th (Fri) with family-friendly diversions at Gardaland Park. Next up on the itinerary: wander the streets of Piazza delle Erbe, explore the historical opulence of Piazzale Castel San Pietro, steep yourself in history at Castello Estense, and take in the architecture and atmosphere at Chiesa di Sant'Anastasia.

To see maps, traveler tips, reviews, and more tourist information, read our Verona trip tool .

Getting from Venice to Verona by train takes about 1.5 hours. Other options: drive; or take a bus. Expect a daytime high around 10°C in February, and nighttime lows around 0°C. Finish your sightseeing early on the 16th (Fri) so you can take a train to Milan.

Things to do in Verona

Parks Nature Historic Sites

Side Trips

Lago di Garda, Castello Estense, Lago di Molveno, Parco Natura Viva, MUSE - Museo delle Scienze
Find places to stay Feb 10 — 16:
Highlights from your plan
Lago di Garda ©
Lago di Garda
Arena di Verona ©
Arena di Verona
Museo di Castelvecchio ©
Museo di Castelvecchio

6
nights
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.
Get a sense of the local culture at Duomo di Milano and Tour delle Merlate - Castello Sforzesco. Kids will enjoy Galleria Vittorio Emanuele II and Melissa Beach. Change things up with these side-trips from Milan: La Citta Alta (in Bergamo), Faro voltiano (in Brunate) and Parco Faunistico le Cornelle (in Valbrembo). Plan for a day of cool, family-friendly fun on the 21st (Wed) at Acquaworld. Next up on the itinerary: explore the different monuments and memorials at Monumental Cemetery, admire the striking features of Chiesa di San Maurizio al Monastero Maggiore, wander the streets of Navigli District, and shop like a local with Brera District.

For traveler tips, photos, more things to do, and more tourist information, use the Milan trip itinerary planner .

Traveling by train from Verona to Milan takes 1.5 hours. Alternatively, you can drive; or take a shuttle. In February in Milan, expect temperatures between 10°C during the day and 1°C at night. Finish your sightseeing early on the 22nd (Thu) so you can drive to Tremezzina.

Things to do in Milan

Historic Sites Theme Parks Spas

Side Trips

Acquaworld, Faro voltiano, La Citta Alta, Melissa Beach, Parco Faunistico le Cornelle
Find places to stay Feb 16 — 22:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Castello Sforzesco ©
Castello Sforzesco
Monumental Cemetery ©
Monumental Cemetery

5
nights
Tremezzina

Tremezzina ©
The majestic Villa Carlotta is among the most popular places to visit in Tremezzina, its neoclassical architecture complimenting the lush, neatly maintained gardens and charming walkways.
Take a break from the city and head to Al Puunt-Snack Beach Bar and Lido di Faggeto Miamilaryo. Get a sense of the local culture at Enoteca Principessa and Castello di Corenno Plinio. Get out of town with these interesting Tremezzina side-trips: Lido di Moltrasio (in Moltrasio), Lido di Argegno (in Argegno) and Chiesa di San Giorgio (in Varenna).

To see more things to do and tourist information, read our Tremezzina online trip builder .

You can drive from Milan to Tremezzina in 1.5 hours. Another option is to do a combination of train and bus. Wrap up your sightseeing on the 27th (Tue) early enough to travel back home.

Things to do in Tremezzina

Outdoors Historic Sites Wineries

Side Trips

Bellagio, Menaggio & Cadenabbia Golf Club, Chiesa di San Giorgio, Enoteca Bianchi Bazzi, Lido di Argegno
Find places to stay Feb 22 — 27:
Highlights from your plan
Lido di Faggeto Miamilaryo ©
Lido di Faggeto Miamilaryo
Santuario Madonna del Soccorso ©
Santuario Madonna del Soccorso
Enoteca Principessa ©
Enoteca Principessa

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