14 days in Italy Itinerary

14 days in Italy Itinerary

Created using Inspirock Italy sightseeing planner

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Route & dates

14 days in Italy Itinerary

Start: Singapore
Fly + train:  17​h 15​min
1
Pompeii
— 2 nights
Drive:  1​h 15​min
2
Positano
— 2 nights
Drive:  3​h 15​min
3
Rome
— 3 nights
train:  1​h 45​min
4
Florence
— 2 nights
5
Venice
— 2 nights
train:  2​h 30​min
6
Milan
— 2 nights
Fly:  15​h 30​min
End: Singapore

2
nights
Pompeii

Pompeii ©
Pompeii has been a tourist destination for more than 250 years.
Kick off your visit on the 21st (Thu): pause for some serene contemplation at Cappella Sant'Angelo all'Ospedale, kick back and relax at Otium Spa Costa d'Amalfi, and then explore the ancient world of Pompeii Archaeological Park. Get ready for a full day of sightseeing on the 22nd (Fri): do a tasting at Le Vigne di Raito, then enjoy the sand and surf at Spiaggia Lannio, then take in the spiritual surroundings of Duomo di Ravello, and finally contemplate in the serene atmosphere at San Giovanni del Toro.

For ratings, other places to visit, and tourist information, you can read our Pompeii route maker website .

Singapore, Singapore to Pompeii is an approximately 17.5-hour combination of flight and train. You can also fly; or do a combination of bus and flight. The time zone difference when traveling from Singapore to Pompeii is minus 7 hours. Traveling from Singapore in May, you will find days in Pompeii are little chillier (27°C), and nights are much colder (17°C). Finish up your sightseeing early on the 22nd (Fri) so you can go by car to Positano.

Things to do in Pompeii

Historic Sites Beaches Parks

Side Trips

Ravello, Spiaggia Lannio, Otium Spa Costa d'Amalfi, Le Vigne di Raito
Find places to stay May 20 — 22:
Highlights from your plan
Le Vigne di Raito ©
Le Vigne di Raito
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Duomo di Ravello ©
Duomo di Ravello

2
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.
Kick off your visit on the 23rd (Sat): admire the striking features of Villa Rufolo, tour the pleasant surroundings at Lido di Ravello, and then enjoy the sand and surf at Fornillo. On the 24th (Sun), you'll have a packed day of sightseeing: enjoy the sand and surf at Lido Capo di Conca, then take in the architecture and atmosphere at Duomo di Sant'Andrea, then get to know the fascinating history of Centro Storico, and finally admire the natural beauty at Villa Cimbrone Gardens.

To find other places to visit, traveler tips, and more tourist information, read Positano trip itinerary maker site .

Drive from Pompeii to Positano in 1.5 hours. Alternatively, you can take a bus; or do a combination of subway and bus. In May in Positano, expect temperatures between 27°C during the day and 18°C at night. Wrap up your sightseeing on the 24th (Sun) to allow time to drive to Rome.

Things to do in Positano

Parks Beaches Outdoors

Side Trips

Ravello, Amalfi, Lido Capo di Conca
Find places to stay May 22 — 24:
Highlights from your plan
Fornillo ©
Fornillo
Lido di Ravello ©
Lido di Ravello
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens

3
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Get some historical perspective at Colosseum and Piazza Navona. Bring the kids along to Trevi Fountain and Palatine Hill. There's lots more to do: contemplate the long history of St. Peter's Basilica, take a stroll through Trastevere, make a trip to Roman Forum, and take in the architecture and atmosphere at Church of St. Louis of the French.

To see ratings, traveler tips, reviews, and other tourist information, read our Rome day trip planning app .

Traveling by car from Positano to Rome takes 3.5 hours. Alternatively, you can do a combination of subway and train; or take a bus. In May, daily temperatures in Rome can reach 28°C, while at night they dip to 17°C. Finish up your sightseeing early on the 27th (Wed) so you can catch the train to Florence.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trip

Vatican City
Find places to stay May 24 — 27:
Highlights from your plan
Trevi Fountain ©
Trevi Fountain
Colosseum ©
Colosseum
Pantheon ©
Pantheon

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
On the 28th (Thu), admire the masterpieces at Gallerie Degli Uffizi, appreciate the extensive heritage of Piazza del Duomo, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, pause for some photo ops at Campanile di Giotto, then pause for some serene contemplation at Crypt of Santa Reparata, and finally examine the collection at Academy Of Florence Art Gallery. Get ready for a full day of sightseeing on the 29th (Fri): admire the masterpieces at Pitti Palace, take some stellar pictures from Piazzale Michelangelo, then snap pictures at Ponte Vecchio, then don't miss a visit to Piazza della Signoria, and finally contemplate in the serene atmosphere at The Baptistery of St. John.

For where to stay, reviews, ratings, and tourist information, refer to the Florence road trip planning site .

You can take a train from Rome to Florence in 2 hours. Other options are to drive; or fly. Plan for slightly colder nights when traveling from Rome in May since evenings lows in Florence dip to 13°C. Finish your sightseeing early on the 29th (Fri) to allow enough time to take a train to Venice.

Things to do in Florence

Museums Historic Sites
Find places to stay May 27 — 29:
Highlights from your plan
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Cathedral of Santa Maria del Fiore ©
The Baptistery of St. John ©
The Baptistery of St. John

2
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.
On the 30th (Sat), appreciate the extensive heritage of Piazza San Marco, then take in the views from Ponte di Rialto, then contemplate in the serene atmosphere at Santa Maria dei Miracoli, and finally contemplate the waterfront views at Canal Grande. Here are some ideas for day two: admire the striking features of Doge's Palace, take in the views from Ponte dei Sospiri, admire the landmark architecture of Basilica di San Marco, then explore the world behind art at Peggy Guggenheim Collection, and finally wander the streets of Campo del Ghetto.

To find reviews, traveler tips, other places to visit, and tourist information, refer to the Venice road trip tool .

You can take a train from Florence to Venice in 2.5 hours. Other options are to drive; or take a bus. In May, plan for daily highs up to 26°C, and evening lows to 15°C. Finish your sightseeing early on the 31st (Sun) so you can take a train to Milan.

Things to do in Venice

Historic Sites Museums Parks
Find places to stay May 29 — 31:
Highlights from your plan
Piazza San Marco ©
Piazza San Marco
Doge's Palace ©
Doge's Palace
Canal Grande ©
Canal Grande

2
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.
On the 1st (Mon), admire the striking features of Galleria Vittorio Emanuele II, then take in the spiritual surroundings of Duomo di Milano, and then step into the grandiose world of Castello Sforzesco.

For ratings, more things to do, maps, and more tourist information, read Milan sightseeing planning tool .

Traveling by train from Venice to Milan takes 2.5 hours. Alternatively, you can drive; or do a combination of train and flight. In May in Milan, expect temperatures between 26°C during the day and 15°C at night. Finish your sightseeing early on the 2nd (Tue) to allow enough time to travel back home.

Things to do in Milan

Historic Sites Shopping
Find places to stay May 31 — Jun 2:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Castello Sforzesco ©
Castello Sforzesco
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II

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