16 days in Italy Itinerary

16 days in Italy Itinerary

Created using Inspirock Italy attractions planner

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Route & dates

16 days in Italy Itinerary

Start: Lynchburg
Drive + Fly:  22 h 30 min
1
Milan
— Few hours
Drive:  4 h
2
Cinque Terre
— 2 nights
Drive:  2 h 30 min
3
Florence
— 2 nights
Train:  1 h 45 min
4
Rome
— 2 nights
Drive:  2 h 15 min
5
Naples
— 1 night
Bus:  1 h 30 min
6
Positano
— 1 night
+5
Bus + Subway + Foot + Bus + Foot + Fly:  6 h 30 min
7
Venice
— 4 nights
Train:  2 h 30 min
8
Milan
— 1 night
Fly + Drive:  22 h 30 min
End: Lynchburg

few
hours
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.
To plan Milan vacation without wasting time, ask Inspirock to design an itinerary.

Lynchburg, USA to Milan is an approximately 22.5-hour combination of car and flight. Due to the time zone difference, you'll lose 6 hours traveling from Lynchburg to Milan. In May, daily temperatures in Milan can reach 73°F, while at night they dip to 55°F. You'll set off for Cinque Terre on the 16th (Sat).

Things to do in Milan

Nightlife Historic Sites Outdoors
Find places to stay May 15 — 16:

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 16th (Sat), tour the pleasant surroundings at Cinque Terre footpaths, contemplate in the serene atmosphere at Chiesa Di San Pietro, take in the architecture and atmosphere at Santa Margherita di Antiochia Church, then hike along Footpath Monterosso - Vernazza, and finally get into the urban bustle at Vernazza. Get ready for a full day of sightseeing on the 17th (Sun): take in the architecture and atmosphere at Santuario di Nostra Signora di Montenero, stroll through Cinque Terre Trails, take in the spiritual surroundings of Oratorio di Santa Maria Assunta, trek along Il Sentiero da Levanto a Monterosso, then get great views at View Point Corniglia, and finally get great views at Bar Terza Terra.

For photos, where to stay, and more tourist information, read Cinque Terre road trip planner.

Lynchburg, USA to Cinque Terre is an approximately 24-hour combination of car and flight. Traveling from Lynchburg to Cinque Terre, you'll lose 6 hours due to the time zone difference. Traveling from Lynchburg in May, expect nights in Cinque Terre to be about the same, around 52°F, while days are slightly colder, around 71°F. Cap off your sightseeing on the 18th (Mon) early enough to go by car to Florence.

Things to do in Cinque Terre

Trails Parks Historic Sites
Find places to stay May 16 — 18:
Highlights from your plan
Footpath Monterosso - Vernazza ©
Footpath Monterosso - Vernazza
Santa Margherita di Antiochia Church ©
Vernazza ©
Vernazza

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Your day-by-day itinerary now includes Taste Florence as well as Wine Tours & Tastings. On the 18th (Mon), take in nature's colorful creations at The Boboli Gardens, indulge your senses at Taste Florence, make a trip to Piazzale Michelangelo, then take in the views from Ponte Vecchio, and finally savor the flavors at Food & Drink. Get ready for a full day of sightseeing on the next day: admire the masterpieces at Pitti Palace, contemplate in the serene atmosphere at The Baptistery of St. John, get to know the fascinating history of Piazza della Signoria, appreciate the extensive heritage of Piazza del Duomo, then steep yourself in history at Cathedral of Santa Maria del Fiore, and finally take in panoramic vistas at Campanile di Giotto.

Plan my day in Florence using traveler tips and tourist information provided by Inspirock.

Getting from Cinque Terre to Florence by car takes about 2.5 hours. Other options: take a train. In May, daily temperatures in Florence can reach 71°F, while at night they dip to 52°F. On the 20th (Wed), you're off to Rome.

Things to do in Florence

Tours Historic Sites Museums
Find places to stay May 18 — 20:
Highlights from your plan
Taste Florence ©
Taste Florence
Piazzale Michelangelo ©
Piazzale Michelangelo
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore

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.
Kick off your visit on the 20th (Wed): explore the ancient world of Palatine Hill and then delve into the distant past at Colosseum. Here are some ideas for day two: make a trip to Spanish Steps, ponder the design of Trevi Fountain, then explore the ancient world of Pantheon, then contemplate the long history of St. Peter's Basilica, and finally appreciate the extensive heritage of Piazza Navona.

For photos, more things to do, ratings, and other tourist information, go to the Rome trip itinerary app.

Traveling by train from Florence to Rome takes 2 hours. Alternatively, you can drive; or fly. Traveling from Florence in May, Rome is a bit warmer at night with lows of 58°F. You will have some time to spend on the 22nd (Fri) before leaving for Naples.

Things to do in Rome

Historic Sites

Side Trip

St. Peter's Basilica
Find places to stay May 20 — 22:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
Trevi Fountain ©
Trevi Fountain

1
night
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Start off your visit on the 22nd (Fri): examine the collection at Museo Archeologico Nazionale di Napoli and then admire the masterpieces at Museo e Real Bosco di Capodimonte.

For maps, more things to do, reviews, and tourist information, use the Naples trip itinerary planning site.

Getting from Rome to Naples by train takes about 1.5 hours. Other options: drive; or take a bus. Expect a daytime high around 74°F in May, and nighttime lows around 58°F. You will have some time to spend on the 23rd (Sat) before leaving for Positano.

Things to do in Naples

Museums Historic Sites
Find places to stay May 22 — 23:
Highlights from your plan
Museo Archeologico Nazionale di Napoli ©
Museo e Real Bosco di Capodimonte ©
Museo e Real Bosco di Capodimonte
Via San Gregorio Armeno ©
Via San Gregorio Armeno

1
night
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.
Fornillo has been added to your itinerary. On the 23rd (Sat), get great views at Il Sentiero Degli Dei.

Use Inspirock's suggestions to plan your Positano trip and find the best activities and attractions for your vacation.

Take a bus from Naples to Positano in 1.5 hours. Alternatively, you can drive; or do a combination of subway and bus. In May, daily temperatures in Positano can reach 74°F, while at night they dip to 60°F. Cap off your sightseeing on the 24th (Sun) early enough to travel to Venice.

Things to do in Positano

Outdoors Beaches Parks
Find places to stay May 23 — 24:
Highlights from your plan
Fornillo ©
Fornillo
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei
Boat Tours & Water Sports

4
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.
Explore Venice's surroundings by going to Padua (Oratorio di San Rocco & Scrovegni Chapel). And it doesn't end there: explore the activities along Canal Grande, explore the world behind art at Gallerie dell'Accademia, make a trip to Piazza San Marco, and contemplate the long history of Peggy Guggenheim Collection.

To find maps, ratings, where to stay, and more tourist information, you can read our Venice road trip planner.

You can do a combination of subway and flight from Positano to Venice in 6.5 hours. Other options are to do a combination of subway, train, and flight; or drive. Expect a bit cooler evenings in Venice when traveling from Positano in May, with lows around 55°F. Finish up your sightseeing early on the 28th (Thu) so you can catch the train to Milan.

Things to do in Venice

Historic Sites Museums Tours

Side Trip

Padua
Find places to stay May 24 — 28:
Highlights from your plan
Canal Grande ©
Canal Grande
Doge's Palace ©
Doge's Palace
Basilica di San Marco
Basilica di San Marco

1
night
Milan

Milan ©
Start off your visit on the 29th (Fri): shop like a local with Galleria Vittorio Emanuele II.

For traveler tips, more things to do, photos, and other tourist information, read our Milan tour builder site.

Traveling by train from Venice to Milan takes 2.5 hours. Alternatively, you can drive; or do a combination of train and flight. On the 29th (Fri), you'll have the morning to explore before heading off to Ottaviano.

Things to do in Milan

Shopping
Find places to stay May 28 — 29:
Highlights from your plan
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II

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