19 days in Italy Itinerary

19 days in Italy Itinerary

Created using Inspirock Italy travel route planner

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

Route & dates

19 days in Italy Itinerary

Start: Chicago
Fly + Train:  15 h 45 min
1
Positano
— 3 nights
Drive:  3 h 15 min
2
Rome
— 4 nights
Train:  1 h 30 min
3
Florence
— 3 nights
Train:  2 h 45 min
4
Como
— 2 nights
Drive:  2 h
5
Verona
— 2 nights
Bus:  1 h 15 min
6
Venice
— 3 nights
Fly:  12 h
End: Chicago

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.
Head to Ceramica Assunta and Artigianato Rallofor some retail therapy. Explore Positano's surroundings by going to Vietri sul Mare (Le Vigne di Raito & Ceramica D'Urso Vietri), Ravello (Ceramiche Cosmolena di Margherita di Palma, Ceramiche d'Arte Carmela, & more) and Piccadilly (in Conca dei Marini). The adventure continues: tour the pleasant surroundings at Fornillo, stop by Theodora Moda Positano, kick back and relax at Spiaggia Grande, and do a tasting at Cantine Marisa Cuomo.

For where to stay, maps, reviews, and tourist information, read our Positano trip builder tool .

Chicago, USA to Positano is an approximately 16-hour combination of flight, train, subway, and bus. You'll lose 7 hours traveling from Chicago to Positano due to the time zone difference. When traveling from Chicago in December, plan for somewhat warmer days in Positano, with highs around 58°F, while nights are much warmer with lows around 51°F. Cap off your sightseeing on the 5th (Wed) early enough to go by car to Rome.

Things to do in Positano

Shopping Wineries Beaches

Side Trips

Ravello, Vietri sul Mare, Cantine Marisa Cuomo, Piccadilly
Highlights from your plan
Le Vigne di Raito ©
Le Vigne di Raito
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.
Head to Via Condotti and Porta Portesefor some retail therapy. There's much more to do: wander the streets of Trastevere, ponder the design of Trevi Fountain, make a trip to Spanish Steps, and admire the landmark architecture of Pantheon.

To see more things to do, other places to visit, reviews, and more tourist information, read our Rome tour itinerary planning website .

Traveling by car from Positano to Rome takes 3.5 hours. Alternatively, you can do a combination of bus, subway, and train; or take a bus. Traveling from Positano in December, plan for a bit cooler nights in Rome, with lows around 39°F. Finish your sightseeing early on the 9th (Sun) to allow enough time to take a train to Florence.

Things to do in Rome

Historic Sites Museums Shopping

Side Trip

Vatican City
Highlights from your plan
Trastevere ©
Trastevere
Pantheon ©
Pantheon
Trevi Fountain ©
Trevi Fountain

3
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Get out of town with these interesting Florence side-trips: Guardastelle Vineyard (in San Gimignano), Castello di Verrazzano (in Greve in Chianti) and Castello del Trebbio (in Santa Brigida). And it doesn't end there: admire the masterpieces at Uffizi Galleries, get great views at Piazzale Michelangelo, pause for some serene contemplation at Cathedral of Santa Maria del Fiore, and examine the collection at Galleria dell'Accademia.

To find more things to do, traveler tips, and other tourist information, refer to the Florence road trip planner.

You can take a train from Rome to Florence in 1.5 hours. Alternatively, you can drive; or fly. In December in Florence, expect temperatures between 55°F during the day and 39°F at night. Finish your sightseeing early on the 12th (Wed) so you can take a train to Como.

Things to do in Florence

Wineries Historic Sites Museums

Side Trips

Castello di Verrazzano, Guardastelle Vineyard, Castello del Trebbio
Highlights from your plan
Castello del Trebbio ©
Castello del Trebbio
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

2
nights
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 13th (Thu): stop by Bellagioseta, then stop by Profumeria Bellagio, then learn about winemaking at Enoteca Principessa, and finally admire the striking features of Galleria Vittorio Emanuele II. On your second day here, stop by L'Isola Che Non C'e', stop by Quelli Della Pelle, then look for gifts at Alimentari Da Caio, then look for gifts at Azalea - Silk of Como, and finally look for gifts at Dep Design Store.

To find where to stay, traveler tips, more things to do, and tourist information, read Como trip planner .

Traveling by train from Florence to Como takes 3 hours. Alternatively, you can drive; or do a combination of bus and train. Plan for little chillier temperatures traveling from Florence in December, with highs in Como at 45°F and lows at 30°F. Wrap up your sightseeing on the 14th (Fri) to allow time to drive to Verona.

Things to do in Como

Shopping Wineries

Side Trips

Bellagio, Galleria Vittorio Emanuele II
Highlights from your plan
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Enoteca Principessa ©
Enoteca Principessa
Azalea - Silk of Como ©
Azalea - Silk of Como

2
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.
Start off your visit on the 15th (Sat): see the grandeur of opera at Arena di Verona, look for gifts at Vivavino Wine Shop, learn about winemaking at Wine Shop Verona, take a stroll through Piazza delle Erbe, then stop by Baol Atelier Creativo, and finally look for gifts at Piacere Divino Enoteca E Vini Sfusi. Keep things going the next day: learn about winemaking at Villa Mosconi Bertani, stop by Diletta Sicilia, stop by The Merchant of Venice - Store Verona, then take a stroll through Via Mazzini, then look for gifts at Patrizia Prencipe, and finally stop by Cioccolateria Via Conventino.

To see photos, traveler tips, where to stay, and tourist information, read Verona trip itinerary planning site .

You can drive from Como to Verona in 2 hours. Other options are to take a train; or take a train. In December, daytime highs in Verona are 45°F, while nighttime lows are 31°F. Wrap up your sightseeing on the 16th (Sun) early enough to take a train to Venice.

Things to do in Verona

Shopping Wineries Neighborhoods
Highlights from your plan
Piazza delle Erbe ©
Piazza delle Erbe
Arena di Verona ©
Arena di Verona
Villa Mosconi Bertani ©
Villa Mosconi Bertani

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.
For shopping fun, head to I Tre Mercanti or Raggio Veneziano. Next up on the itinerary: contemplate the waterfront views at Canal Grande, take in the architecture and atmosphere at Basilica di San Marco, admire the landmark architecture of Doge's Palace, and snap pictures at Ponte di Rialto.

Plan my Venice trip by asking Inpirock to come up with tips and suggestions.

Traveling by train from Verona to Venice takes 1.5 hours. Alternatively, you can drive; or take a bus. In December, daytime highs in Venice are 49°F, while nighttime lows are 34°F. Cap off your sightseeing on the 19th (Wed) early enough to travel back home.

Things to do in Venice

Historic Sites Neighborhoods Museums
Highlights from your plan
Canal Grande ©
Canal Grande
Basilica di San Marco
Basilica di San Marco
Doge's Palace ©
Doge's Palace

Similar Plans

22 days in Italy BY A USER FROM NEW ZEALAND June, kids, culture, outdoors, relaxing, historic sites, museums, shopping, popular & hidden gems PREFERENCES: June, kids, culture, outdoors, relaxing, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 21 days in Italy BY A USER FROM UNITED STATES June, culture, outdoors, beaches, historic sites, wildlife, popular sights PREFERENCES: June, culture, outdoors, beaches, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 23 days in Italy BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, fast-paced, popular & hidden gems PREFERENCES: June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Fast-paced 20 days in Italy BY A USER FROM NEW ZEALAND October, culture, outdoors, historic sites, museums, shopping, popular & hidden gems PREFERENCES: October, culture, outdoors, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 20 days in Italy BY A USER FROM ITALY December, teens, kids, culture, relaxing, historic sites, museums, shopping, popular & hidden gems PREFERENCES: December, teens, kids, culture, relaxing, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 23 days in Italy BY A USER FROM UNITED STATES September, culture, outdoors, historic sites, museums, popular & hidden gems PREFERENCES: September, culture, outdoors, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Medium 20 days in Italy BY A USER FROM UNITED STATES October, culture, romantic, beaches, historic sites, museums, slow & easy, hidden gems PREFERENCES: October, culture, romantic, beaches, historic sites, museums ATTRACTION STYLE: Hidden gems PACE: Slow & easy 20 days in Italy BY A USER FROM COLOMBIA November, teens, culture, outdoors, relaxing, romantic, historic sites, museums, popular & hidden gems PREFERENCES: November, teens, culture, outdoors, relaxing, romantic, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Medium 21 days in Italy BY A USER FROM PAKISTAN October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 23 days in Italy BY A USER FROM NEW ZEALAND June, kids, culture, outdoors, relaxing, historic sites, museums, popular sights PREFERENCES: June, kids, culture, outdoors, relaxing, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 22 days in Italy BY A USER FROM AUSTRALIA May, culture, relaxing, beaches, historic sites, museums, popular & hidden gems PREFERENCES: May, culture, relaxing, beaches, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Medium 20 days in Italy BY A USER FROM SOUTH AFRICA April, culture, outdoors, relaxing, beaches, historic sites, shopping, hidden gems PREFERENCES: April, culture, outdoors, relaxing, beaches, historic sites, shopping ATTRACTION STYLE: Hidden gems PACE: Medium
See more plans