19 days in Italy Itinerary

19 days in Italy Itinerary

Created using Inspirock Italy trip itinerary planner

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Route & dates

19 days in Italy Itinerary

Start: San Juan, Puerto Rico
Fly + Drive:  19​h 30​min
1
Carloforte, Sardinia
— 2 nights
+2
Drive + Fly + Drive:  7​h
2
Capri, Island of Capri
— 1 night
Ferry + Drive:  3​h 15​min
3
Rome
— 3 nights
Drive:  2​h 15​min
4
Assisi
— 3 nights
Drive:  2​h 15​min
5
Florence
— 3 nights
Train:  2​h 15​min
6
Venice
— 4 nights
Fly:  15​h 15​min
End: San Juan, Puerto Rico

2
nights
Carloforte, Sardinia

Carloforte ©
Carloforte is a fishing and resort town of located on Isola di San Pietro, approximately 7km off the southwestern coast of Sardinia, in southern Sardinia, Italy.HistoryAccording to a legend, a local church was founded in the early 14th century in honour of hundreds of participants to the so-called Children's Crusade of 1212 who perished in a shipwreck just off the island on their way to North Africa during a gale. Escape the urban bustle at La Conca and Punta Delle Colonne. You'll get in some beach time at Cala Ferraglione and Spiaggia di Cala Fico. Next up on the itinerary: enjoy the sand and surf at Cape Sandalo and stroll through Spiaggia del Giunco Isola di San Pietro.

To find other places to visit, more things to do, and more tourist information, go to the Carloforte trip itinerary planning tool .

San Juan, Puerto Rico to Carloforte is an approximately 19.5-hour flight. The time zone changes from Atlantic Standard Time to Central European Time, which is usually a 5 hour difference. When traveling from San Juan in May, plan for little chillier days in Carloforte, with highs around 30°C, while nights are much colder with lows around 14°C. Wrap up your sightseeing on the 6th (Mon) early enough to travel to Capri.

Things to do in Carloforte

Outdoors Beaches Parks

Side Trip

Cala Ferraglione
Highlights from your plan
Cape Sandalo ©
Cape Sandalo
Spiaggia di Girin ©
Spiaggia di Girin

1
night
Capri, Island of Capri

Capri
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
On the 7th (Tue), look for all kinds of wild species at Parco Astarita, take in the dramatic natural features at I Faraglioni, take in nature's colorful creations at Giardini di Augusto, then stroll through Fortini Coastal Walk, and finally see the interesting displays at La Bottega dell'Arte di Sergio Rubino. On the 8th (Wed), you'll have a packed day of sightseeing: take in the spiritual surroundings of Chiesa San Michele, delve into the distant past at Villa del Damecuta, appreciate the extensive heritage of Scala Fenicia (Phoenician Steps), visit a coastal fixture at Punta Carena Lighthouse, then take an in-depth tour of Villa San Michele, and finally hike along Sentiero Del Passetiello Capri.

To see reviews, traveler tips, other places to visit, and more tourist information, go to the Capri travel route builder .

The Route module can help you plan travel from Carloforte to Capri. Traveling from Carloforte in May, you can expect nighttime temperatures to be somewhat warmer in Capri, with lows of 18°C. Cap off your sightseeing on the 8th (Wed) early enough to travel to Rome.

Things to do in Capri

Parks Outdoors Trails

Side Trips

Anacapri, Sentiero Del Passetiello Capri
Highlights from your plan
I Faraglioni
I Faraglioni
Villa San Michele ©
Villa San Michele
Giardini di Augusto ©
Giardini di Augusto

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.
Appreciate the collections at Vatican Museums and Sistine Chapel. Visit Palatine Hill and St. Peter's Basilica for their historical value. Next up on the itinerary: admire the landmark architecture of Pantheon, admire the masterpieces at Galleria Borghese, wander the streets of Trastevere, and steep yourself in history at Roman Forum.

To see photos, more things to do, ratings, and tourist information, use the Rome day trip app .

You can do a combination of ferry and car from Capri to Rome in 3.5 hours. Alternatively, you can do a combination of ferry and train; or do a combination of ferry, subway, and train. In May in Rome, expect temperatures between 28°C during the day and 17°C at night. Finish up your sightseeing early on the 11th (Sat) so you can go by car to Assisi.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trip

Vatican City
Highlights from your plan
St. Peter's Basilica ©
St. Peter's Basilica
Vatican Museums
Vatican Museums
Pantheon ©
Pantheon

3
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Popular historic sites such as Civita di Bagnoregio and Basilica di Santa Maria degli Angeli - Porziuncola are in your itinerary. Get a sense of the local culture at Duomo di Orvieto and Basilica di Santa Chiara. Take a break from Assisi with a short trip to Pozzo di San Patrizio in Orvieto, about 1h 25 min away. And it doesn't end there: take in the architecture and atmosphere at Basilica inferiore di San Francesco d'Assisi, see the interesting displays at Museo della Porziuncola, step into the grandiose world of Rocca Paolina, and appreciate the extensive heritage of Centro Storico.

Start your trip to Assisi by creating a personalized itinerary on Inspirock.

You can drive from Rome to Assisi in 2.5 hours. Other options are to take a train; or take a bus. Traveling from Rome in May, Assisi is a bit cooler at night with lows of 13°C. Finish your sightseeing early on the 14th (Tue) to allow enough time to drive to Florence.

Things to do in Assisi

Historic Sites Neighborhoods Museums

Side Trips

Orvieto, Civita di Bagnoregio, Rocca Paolina
Highlights from your plan
Civita di Bagnoregio ©
Civita di Bagnoregio
Museo della Porziuncola ©
Museo della Porziuncola

3
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Explore hidden gems such as Centro Storico and Basilica San Miniato al Monte. Appreciate the collections at Pitti Palace and Basilica di Santa Croce. There's lots more to do: admire the masterpieces at Uffizi Galleries, explore the historical opulence of Palazzo Vecchio, examine the collection at Academy Of Florence Art Gallery, and take in the spiritual surroundings of The Baptistery of St. John.

To see photos, where to stay, and other tourist information, you can read our Florence trip itinerary app .

Traveling by car from Assisi to Florence takes 2.5 hours. Alternatively, you can take a train. Expect a daytime high around 25°C in May, and nighttime lows around 13°C. Wrap up your sightseeing on the 17th (Fri) to allow time to take a train to Venice.

Things to do in Florence

Historic Sites Museums Shopping
Highlights from your plan
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Cathedral of Santa Maria del Fiore ©

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.
Popular historic sites such as Peggy Guggenheim Collection and St. Mark's Square are in your itinerary. Basilica di San Marco and Doge's Palace are good opportunities to explore the local culture. You'll find plenty of places to visit near Venice: Padua (Basilica di Sant’Antonio & Scrovegni Chapel). There's still lots to do: explore the activities along Canal Grande, wander the streets of Campo del Ghetto, snap pictures at Ponte di Rialto, and enjoy breathtaking views from St Mark's Campanile.

To find other places to visit, more things to do, and other tourist information, use the Venice road trip planner .

You can take a train from Florence to Venice in 2.5 hours. Alternatively, you can drive; or take a bus. May in Venice sees daily highs of 26°C and lows of 15°C at night. Wrap up your sightseeing by early afternoon on the 21st (Tue) to allow time for travel back home.

Things to do in Venice

Historic Sites Museums Neighborhoods

Side Trip

Padua
Highlights from your plan
Peggy Guggenheim Collection ©
Peggy Guggenheim Collection
Doge's Palace ©
Doge's Palace
Piazza San Marco ©
Piazza San Marco

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