16 days in Italy Itinerary

16 days in Italy Itinerary

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Route & dates

16 days in Italy Itinerary

Start: Chicago
Fly:  9 h
1
Rome
— 2 nights
Train:  1 h 30 min
2
Florence
— 2 nights
train:  5 h
3
Cinque Terre
— 2 nights
Train:  7 h
4
Venice
— 3 nights
train:  4 h 30 min
5
Griante
— 4 nights
train:  1 h 30 min
6
Milan
— 1 night
Fly:  14 h 15 min
End: Chicago

2
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Start off your visit on the 23rd (Sat): take in the dramatic natural features at Passeggiata di Gianicolo, then enjoy the sand and surf at Acqua e Sale - Stabilimento Balneare, and then kick back and relax at Point Break. On the 24th (Sun), you'll have a packed day of sightseeing: delve into the distant past at Colosseum, enjoy the sand and surf at Oasi Naturista, then cool off at V Lounge Beach Club, and finally wander the streets of Via Condotti.

To find maps, traveler tips, more things to do, and other tourist information, you can read our Rome planner .

Chicago, USA to Rome is an approximately 13-hour flight. You can also do a combination of flight and train. You'll lose 7 hours traveling from Chicago to Rome due to the time zone difference. In June, daily temperatures in Rome can reach 84°F, while at night they dip to 65°F. Finish up your sightseeing early on the 25th (Mon) so you can catch the train to Florence.

Things to do in Rome

Parks Outdoors Beaches

Side Trips

Point Break, Oasi Naturista, Acqua e Sale - Stabilimento Balneare
Find places to stay Jun 23 — 25:
Highlights from your plan
Colosseum ©
Colosseum
Colle del Gianicolo ©
Colle del Gianicolo
Via Condotti ©
Via Condotti

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
On the 25th (Mon), relax in the rural setting at Castello di Verrazzano, then experience rural life at Chianti Cashmere Goat Farm, then get some fabulous bargains at The Mall, and finally take in the architecture and atmosphere at Cathedral of Santa Maria del Fiore. On the 26th (Tue), you'll have a packed day of sightseeing: look for gifts at L'Arte dei Ciompi, get great views at Basilica San Miniato al Monte, then enjoy the sand and surf at Easy Living - Spiaggia sull'Arno, then stop by Artesia Ceramica, and finally indulge your taste buds at Food & Drink.

For photos, ratings, traveler tips, and more tourist information, use the Florence online driving holiday planner .

Traveling by train from Rome to Florence takes 1.5 hours. Alternatively, you can drive; or fly. In June in Florence, expect temperatures between 83°F during the day and 65°F at night. Cap off your sightseeing on the 27th (Wed) early enough to go by car to Cinque Terre.

Things to do in Florence

Shopping Historic Sites Tours

Side Trips

Castello di Verrazzano, The Mall, Artesia Ceramica, Chianti Cashmere Goat Farm
Find places to stay Jun 25 — 27:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Basilica San Miniato al Monte
Basilica San Miniato al Monte
Castello di Verrazzano ©
Castello di Verrazzano

2
nights
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 27th (Wed), hike along Trail 531 Riomaggiore to Manarola, hike along Footpath Monterosso - Vernazza, and then get into the urban bustle at Vernazza. Get ready for a full day of sightseeing on the 28th (Thu): pause for some serene contemplation at Santa Margherita di Antiochia Church, explore the historical opulence of Castello Doria, enjoy the sand and surf at Beach Bar Stella Marina, then stroll through Spiaggia di Fegina, and finally pause for some serene contemplation at Convento dei Cappuccini e Chiesa di San Francesco.

To find maps, traveler tips, more things to do, and tourist information, use the Cinque Terre trip planner .

Getting from Florence to Cinque Terre by car takes about 2.5 hours. Other options: take a train. Traveling from Florence in June, expect slightly colder with lows of 60°F in Cinque Terre. Wrap up your sightseeing on the 29th (Fri) early enough to drive to Venice.

Things to do in Cinque Terre

Outdoors Parks Trails
Find places to stay Jun 27 — 29:
Highlights from your plan
Footpath Monterosso - Vernazza ©
Footpath Monterosso - Vernazza
Vernazza ©
Vernazza
Santa Margherita di Antiochia Church ©
Santa Margherita di Antiochia Church

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.
Doge's Palace and St. Mark's Square are good opportunities to explore the local culture. For shopping fun, head to I Tre Mercanti or Artigianato d'Arte di Vianello Mauro. There's much more to do: wander the streets of Cannaregio, pause for some serene contemplation at Basilica di Santa Maria della Salute, look for gifts at Raggio Veneziano, and contemplate in the serene atmosphere at Basilica Santa Maria Gloriosa dei Frari.

To find ratings, traveler tips, maps, and tourist information, read Venice trip maker app .

You can drive from Cinque Terre to Venice in 4.5 hours. Other options are to take a train; or take a bus. In June, daily temperatures in Venice can reach 81°F, while at night they dip to 63°F. Wrap up your sightseeing on the 2nd (Mon) early enough to travel to Griante.

Things to do in Venice

Shopping Historic Sites Neighborhoods
Find places to stay Jun 29 — Jul 2:
Highlights from your plan
Piazza San Marco ©
Piazza San Marco
Doge's Palace ©
Doge's Palace

4
nights
Griante

Griante ©
Griante is a comune (municipality) in the Province of Como in the Italian region Lombardy, located on the western shore of Lake Como about 25km northeast of Como between Menaggio (to the north) and Tremezzo. We've included these beaches for you: Spiaggia di Onno and Riva Bianca Beach. Deepen your sense of the past at sights like Castello di Vezio and Archeopark. Venture out of the city with trips to Spiaggia Parco Ulisse Guzzi (in Abbadia Lariana), Villa del Balbianello (in Tremezzina) and Isola Comacina (in Ossuccio). There's lots more to do: stroll through Spiaggia Tranquilla, let little ones run wild at Fattoria Didattica Sempreverde, stop by Fratelli Ciapponi, and look for all kinds of wild species at Riserva Naturale Val di Mello.

For photos, reviews, where to stay, and tourist information, read our Griante trip planning tool .

Drive from Venice to Griante in 4 hours. In July, daily temperatures in Griante can reach 85°F, while at night they dip to 65°F. Cap off your sightseeing on the 6th (Fri) early enough to travel to Milan.

Things to do in Griante

Parks Outdoors Beaches

Side Trips

Morbegno, Tremezzina, Isola Comacina, Archeopark, Spiaggia di Onno
Find places to stay Jul 2 — 6:
Highlights from your plan
Villa Carlotta ©
Villa Carlotta
Castello di Vezio ©
Castello di Vezio
Villa del Balbianello ©
Villa del Balbianello

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 6th (Fri): shop like a local with Brera District, then stroll through Ciclabile Alzaia Naviglio Pavese, and then head outdoors with Mediolanum Forum.

For photos, traveler tips, ratings, and more tourist information, you can read our Milan sightseeing planner .

You can drive from Griante to Milan in 1.5 hours. In July, plan for daily highs up to 85°F, and evening lows to 65°F. Finish your sightseeing early on the 7th (Sat) to allow enough time to travel back home.

Things to do in Milan

Neighborhoods Shopping Outdoors

Side Trip

Mediolanum Forum
Find places to stay Jul 6 — 7:
Highlights from your plan
Brera District ©
Brera District
Mediolanum Forum ©
Mediolanum Forum

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