21 days in Porto, Italy & Lisbon Itinerary

21 days in Porto, Italy & Lisbon Itinerary

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Route & dates

21 days in Porto, Italy & Lisbon Itinerary

Start: Sao Paulo, Brazil
Fly:  14​h
1
Porto, Portugal
— 1 day
Fly:  6​h
2
Milan, Italy
— 2 nights
Train:  2​h 30​min
3
Venice, Italy
— 1 night
Train:  2​h 15​min
4
Florence, Italy
— 1 night
Train:  1​h
5
Pisa, Italy
— Few hours
Drive:  1​h 30​min
6
San Gimignano, Italy
— Few hours
Drive:  1​h
7
Siena, Italy
— 2 nights
Drive:  2​h
8
Saturnia, Italy
— 1 night
Drive:  2​h 15​min
9
Rome, Italy
— 3 nights
Train:  1​h 15​min
10
Naples, Italy
— 2 nights
Bus:  15​min
11
Pompeii, Italy
— Few hours
Train:  45​min
12
Salerno, Italy
— Few hours
Ferry:  1​h 30​min
13
Positano, Italy
— 1 day
Drive:  3​h 15​min
14
Capri, Italy
— 1 night
Ferry + Drive:  3​h 15​min
15
Rome, Italy
— 2 nights
Fly:  6​h 15​min
16
Lisbon, Portugal
— 2 nights
Fly:  13​h 45​min
End: Sao Paulo, Brazil

1
day
Porto, Portugal

Called "Oporto" by many, the city of Porto along the Duoro River lent the country and Port wine their names. Portugal's second-largest metropolis dates back to the 4th century, representing both a rich cultural past and industrial present through its architecture and style.
On the 17th (Sun), pause for some photo ops at Monumento aos Herois da Guerra Peninsular, take in the views from Ponte de Dom Luis I, and then get the lay of the land with Walking tours.

To find maps, reviews, and tourist information, you can read our Porto tour planner .

Sao Paulo, Brazil to Porto is an approximately 14-hour flight. You can also do a combination of bus and flight; or do a combination of flight and train. The time zone difference when traveling from Sao Paulo to Porto is 3 hours. Traveling from Sao Paulo in May, things will get slightly colder in Porto: highs are around 23°C and lows about 13°C. Finish your sightseeing early on the 17th (Sun) so you can travel to Milan.

Things to do in Porto

Tours Historic Sites
Find places to stay May 17 — 18:
Highlights from your plan
Walking tours
Ponte de Dom Luis I ©
Ponte de Dom Luis I

2
nights
Milan, Italy

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.
Start off your visit on the 18th (Mon): don't miss a visit to Galleria Vittorio Emanuele II, then pause for some serene contemplation at Duomo di Milano, then get to know the fascinating history of Piazza del Duomo, and finally explore the historical opulence of Castello Sforzesco.

For maps, traveler tips, topicsMoreInfo.option.ratings, and tourist information, read Milan road trip planner.

Fly from Porto to Milan in 6 hours. Alternatively, you can do a combination of flight and train; or drive. You'll lose 1 hour traveling from Porto to Milan due to the time zone difference. May in Milan sees daily highs of 26°C and lows of 15°C at night. Wrap up your sightseeing on the 19th (Tue) early enough to take a train to Venice.

Things to do in Milan

Historic Sites Shopping
Find places to stay May 17 — 19:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Castello Sforzesco ©
Castello Sforzesco

1
night
Venice, Italy

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 19th (Tue), see the interesting displays at Doge's Palace, then snap pictures at Ponte dei Sospiri, then pause for some serene contemplation at Basilica di San Marco, and finally contemplate the waterfront views at Canal Grande.

To find maps, where to stay, other places to visit, and other tourist information, use the Venice online sightseeing planner .

Getting from Milan to Venice by train takes about 2.5 hours. Other options: drive; or do a combination of flight and train. In May in Venice, expect temperatures between 26°C during the day and 15°C at night. Wrap up your sightseeing on the 20th (Wed) to allow time to take a train to Florence.

Things to do in Venice

Historic Sites Nature Parks
Find places to stay May 19 — 20:
Highlights from your plan
Canal Grande ©
Canal Grande
Doge's Palace ©
Doge's Palace
Basilica di San Marco
Basilica di San Marco

1
night
Florence, Italy

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Start off your visit on the 20th (Wed): explore the world behind art at Academy Of Florence Art Gallery, explore the world behind art at Pitti Palace, don't miss a visit to Piazzale Michelangelo, then take in the views from Ponte Vecchio, and finally take in the spiritual surroundings of Cathedral of Santa Maria del Fiore.

To find topicsMoreInfo.option.ratings, traveler tips, other places to visit, and more tourist information, read Florence online driving holiday planner .

You can take a train from Venice to Florence in 2.5 hours. Other options are to drive; or take a bus. In May, daily temperatures in Florence can reach 25°C, while at night they dip to 13°C. Finish up your sightseeing early on the 21st (Thu) so you can catch the train to Pisa.

Things to do in Florence

Museums Historic Sites
Find places to stay May 20 — 21:
Highlights from your plan
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo
Cathedral of Santa Maria del Fiore ©

few
hours
Pisa, Italy

Pisa ©
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Start off your visit on the 21st (Thu): admire the striking features of Leaning Tower of Pisa.

For maps, where to stay, photos, and other tourist information, refer to the Pisa planning app .

Traveling by train from Florence to Pisa takes an hour. Alternatively, you can take a bus; or drive. May in Pisa sees daily highs of 25°C and lows of 13°C at night. You'll have a few hours on the 21st (Thu) to wrap things up before traveling to San Gimignano.
Find places to stay May 20 — 21:
Highlights from your plan
Leaning Tower of Pisa ©
Leaning Tower of Pisa

few
hours
San Gimignano, Italy

San Gimignano ©
A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
Start off your visit on the 21st (Thu): make a trip to San Gimignano Bell Tower and then learn about winemaking at Guardastelle Vineyard.

To find topicsMoreInfo.option.ratings, traveler tips, reviews, and other tourist information, you can read our San Gimignano journey builder tool .

Traveling by car from Pisa to San Gimignano takes 1.5 hours. Alternatively, you can take a train; or take a bus. In May, daily temperatures in San Gimignano can reach 25°C, while at night they dip to 13°C. Wrap up your sightseeing on the 21st (Thu) to allow time to drive to Siena.

Things to do in San Gimignano

Wineries
Find places to stay May 21 — 22:
Highlights from your plan
Guardastelle Vineyard ©
Guardastelle Vineyard
San Gimignano Bell Tower ©
San Gimignano Bell Tower

2
nights
Siena, Italy

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Start off your visit on the 22nd (Fri): savor the flavors at Food & Drink and then don't miss a visit to Piazza del Campo. Keep things going the next day: make a trip to Centro Storico di Siena, take in the architecture and atmosphere at Duomo di Siena, take in panoramic vistas at Torre del Mangia, then take in the spiritual surroundings of Battistero di San Giovanni, and finally look for gifts at Cravattificio di Siena.

To find more things to do, photos, topicsMoreInfo.option.ratings, and more tourist information, go to the Siena planner.

Drive from San Gimignano to Siena in an hour. Alternatively, you can take a bus; or do a combination of bus and train. Expect a daytime high around 27°C in May, and nighttime lows around 13°C. Cap off your sightseeing on the 23rd (Sat) early enough to go by car to Saturnia.

Things to do in Siena

Historic Sites Tours Shopping
Find places to stay May 21 — 23:
Highlights from your plan
Wine Tours & Tastings
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

1
night
Saturnia, Italy

Saturnia ©
Kick off your visit on the 24th (Sun): soothe aching muscles at Terme di Saturnia - Le Terme, then witness a stunning natural landmark at Cascate del Mulino, and then step into the grandiose world of Piazza del Castello di Montemerano.

To find where to stay, reviews, and more tourist information, read our Saturnia online trip planner .

You can drive from Siena to Saturnia in 2 hours. Alternatively, you can do a combination of train and taxi. Expect a daytime high around 27°C in May, and nighttime lows around 13°C. Wrap up your sightseeing on the 24th (Sun) early enough to drive to Rome.

Things to do in Saturnia

Nature Parks Spas

Side Trip

Piazza del Castello di Montemerano
Find places to stay May 23 — 24:
Highlights from your plan
Cascate del Mulino ©
Cascate del Mulino
Piazza del Castello di Montemerano ©
Terme di Saturnia - Le Terme
Terme di Saturnia - Le Terme

3
nights
Rome, Italy

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Explore Rome's surroundings by going to Tivoli (Villa Adriana & Villa d'Este). The adventure continues: delve into the distant past at Colosseum, make a trip to Piazza Navona, indulge your senses at some of the top wineries in the area, and take in the architecture and atmosphere at Pantheon.

For where to stay, more things to do, other places to visit, and tourist information, go to the Rome route builder site .

You can drive from Saturnia to Rome in 2.5 hours. Another option is to do a combination of taxi and train. 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 Naples.

Things to do in Rome

Historic Sites Tours Parks

Side Trips

Tivoli, St. Peter's Basilica
Find places to stay May 24 — 27:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
Trevi Fountain ©
Trevi Fountain

2
nights
Naples, Italy

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. On the 28th (Thu), appreciate the extensive heritage of Via Caracciolo e Lungomare di Napoli, then take in the spiritual surroundings of Museo Cappella Sansevero, then contemplate the long history of Underground Naples, and finally examine the collection at Museo Archeologico Nazionale di Napoli.

To see photos, reviews, maps, and other tourist information, you can read our Naples tour itinerary planner.

You can take a train from Rome to Naples in 1.5 hours. Other options are to drive; or take a bus. In May, daily temperatures in Naples can reach 27°C, while at night they dip to 17°C. Finish your sightseeing early on the 29th (Fri) so you can take a bus to Pompeii.

Things to do in Naples

Historic Sites Museums
Find places to stay May 27 — 29:
Highlights from your plan
Museo Cappella Sansevero ©
Museo Cappella Sansevero
Underground Naples ©
Underground Naples

few
hours
Pompeii, Italy

Pompeii ©
Pompeii has been a tourist destination for more than 250 years.
Start off your visit on the 29th (Fri): contemplate in the serene atmosphere at Pontificio Santuario della Beata Maria Vergine del Santo Rosario di Pompei, then delve into the distant past at Oplonti Villa di Poppea Ruins, then admire the landmark architecture of Villa dei Misteri, and finally explore the ancient world of Forum.

To find traveler tips, maps, more things to do, and more tourist information, go to the Pompeii road trip website .

Pompeii is just a stone's throw from Naples. May in Pompeii sees daily highs of 27°C and lows of 17°C at night. Wrap up your sightseeing on the 29th (Fri) to allow time to take a train to Salerno.

Things to do in Pompeii

Historic Sites

Side Trip

Oplonti Villa di Poppea Ruins
Find places to stay May 29 — 30:
Highlights from your plan
Villa dei Misteri ©
Villa dei Misteri
Forum ©
Forum

few
hours
Salerno, Italy

Salerno ©
While often overshadowed by the Amalfi Coast's array of quaint villages, Salerno has become one of the region's main areas for culture and entertainment, while remaining relatively unmarked by tourism.
On the 29th (Fri), pause for some serene contemplation at Duomo di Salerno.

For more things to do, photos, other places to visit, and other tourist information, go to the Salerno travel itinerary planner.

Take a train from Pompeii to Salerno in an hour. Alternatively, you can drive; or take a bus. Expect somewhat warmer evenings in Salerno when traveling from Pompeii in May, with lows around 21°C. Wrap up your sightseeing on the 29th (Fri) early enough to ride a ferry to Positano.

Things to do in Salerno

Historic Sites
Find places to stay May 29 — 30:
Highlights from your plan
Duomo di Salerno ©
Duomo di Salerno

1
day
Positano, Italy

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 30th (Sat): get great views at Il Sentiero Degli Dei, then tour the pleasant surroundings at Fornillo, and then go for a walk through Positano.

To see photos, more things to do, traveler tips, and tourist information, use the Positano trip builder tool .

Ride a ferry from Salerno to Positano in 1.5 hours. Alternatively, you can do a combination of train and taxi; or drive. Plan for a bit cooler nights when traveling from Salerno in May since evenings lows in Positano dip to 18°C. Wrap up your sightseeing on the 30th (Sat) to allow time to drive to Capri.

Things to do in Positano

Beaches Parks Outdoors
Find places to stay May 29 — 30:
Highlights from your plan
Fornillo ©
Fornillo
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei
Positano ©
Positano

1
night
Capri, Italy

Capri
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
To find where to stay, photos, maps, and more tourist information, use the Capri sightseeing app .

Drive from Positano to Capri in 3.5 hours. In May, plan for daily highs up to 27°C, and evening lows to 18°C. On the 31st (Sun), you're off to Rome.

Things to do in Capri

Tours Outdoors Transportation
Find places to stay May 30 — 31:

2
nights
Rome, Italy

See even more of Rome: admire the masterpieces at Galleria Borghese, contemplate in the serene atmosphere at Basilica Papale di Santa Maria Maggiore, make a trip to Roman Forum, and pause for some serene contemplation at Santa Maria in Trastevere.

To find topicsMoreInfo.option.ratings, maps, more things to do, and more tourist information, use the Rome road trip website .

You can do a combination of ferry and car from Capri to Rome in 3.5 hours. Other options are to do a combination of ferry and train; or do a combination of ferry, subway, and train. Finish your sightseeing early on the 2nd (Tue) to allow enough time to travel to Lisbon.

Things to do in Rome

Tours Museums Historic Sites
Find places to stay May 31 — Jun 2:
Highlights from your plan
Food Tours
Galleria Borghese
Galleria Borghese
Roman Forum ©
Roman Forum

2
nights
Lisbon, Portugal

Lisbon ©
Built on seven hills, Lisbon has experienced a renaissance in recent years, making it the cultural star of Portugal.
Kick off your visit on the 3rd (Wed): wander the streets of Alfama, then make a trip to Belém Tower, and then meet the residents at Lisbon Oceanarium. Here are some ideas for day two: make a trip to Elevador de Santa Justa, then don't miss a visit to Praca do Comercio (Terreiro do Paco), then take in the views from Ponte 25 de Abril, and finally stroll through Quinta da Regaleira.

For photos, other places to visit, where to stay, and more tourist information, read our Lisbon trip maker app .

Getting from Rome to Lisbon by flight takes about 6.5 hours. Other options: do a combination of train and flight; or drive. The time zone changes from Central European Time to Western European Time, which is usually a -1 hour difference. Traveling from Rome in June, plan for a bit cooler nights in Lisbon, with lows around 18°C. Finish up your sightseeing early on the 4th (Thu) so you can travel back home.

Things to do in Lisbon

Parks Neighborhoods Zoos & Aquariums

Side Trip

Quinta da Regaleira
Find places to stay Jun 2 — 4:
Highlights from your plan
Lisbon Oceanarium ©
Lisbon Oceanarium
Belém Tower ©
Belém Tower
Alfama ©
Alfama

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