16 days in Italy Itinerary

16 days in Italy Itinerary

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Route & dates

16 days in Italy Itinerary

Start: Boracay
+2
Ferry + Foot + Fly:  23 h 15 min
1
Rome
— 3 nights
Fly:  3 h
2
Lampedusa
— 2 nights
+3
Fly + Bus + Foot + Train:  3 h 45 min
3
Taormina, Sicily
— 2 nights
Fly + Bus:  7 h 15 min
4
San Teodoro, Sardinia
— 1 night
Bus + Fly:  4 h 15 min
5
Venice
— 2 nights
Train:  2 h 15 min
6
Florence
— 2 nights
+2
Fly + Foot + Ferry:  23 h
End: Boracay

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.
Explore hidden gems such as Fontana dei Quattro Fiumi and St. Clement Basilica. There's lots more to do: explore the ancient world of Colosseum, take in the architecture and atmosphere at St. Peter's Basilica, steep yourself in history at Palatine Hill, and don't miss a visit to Spanish Steps.

To see other places to visit, where to stay, photos, and tourist information, refer to the Rome online trip itinerary planner.

Boracay, Philippines to Rome is an approximately 23.5- hour combination of ferry and flight. You can also do a combination of ferry, bus, and flight; or do a combination of ferry, taxi, and flight. You'll gain 7 hours traveling from Boracay to Rome due to the time zone difference. Traveling from Boracay in September, Rome is slightly colder at night with lows of 18°C. Wrap up your sightseeing on the 29th (Tue) early enough to travel to Lampedusa.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trip

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

2
nights
Lampedusa

Italy's southernmost territory, Lampedusa, is known for its turquoise waters, white-sand beaches, and island charm.
Start off your visit on the 30th (Wed): get a new perspective on things with Boat Tours & Water Sports. On your second day here, kick back and relax at Cala Pulcino, then kick back and relax at Spiaggia dei Conigli, then enjoy the sand and surf at Cala Croce Beach, and finally identify plant and animal life at Centro di Recupero Tartarughe e Fauna Selvatica WWF.

To find reviews, ratings, other places to visit, and more tourist information, read Lampedusa day trip planning website.

Traveling by flight from Rome to Lampedusa takes 3 hours. Alternatively, you can do a combination of train, bus, and ferry; or do a combination of car and ferry. Traveling from Rome in September, expect a bit warmer with lows of 28°C in Lampedusa. Finish your sightseeing early on the 1st (Thu) so you can travel to Taormina.

Things to do in Lampedusa

Outdoors Parks Beaches
Highlights from your plan
Boat Tours & Water Sports
Spiaggia dei Conigli ©
Spiaggia dei Conigli
Cala Pulcino ©
Cala Pulcino

2
nights
Taormina, Sicily

Taormina ©
With its warm island weather and cliffside location overlooking the Ionion Sea, Taormina has been one of Sicily's most popular getaway destinations since the early 19th century.
Start off your visit on the 2nd (Fri): walk around Villa Comunale, don't miss a visit to Ancient Theatre of Taormina, step off the mainland to explore Isola Bella, then don't miss a visit to Corso Umberto, and finally go for a walk through Piazza IX Aprile. Get ready for a full day of sightseeing on the next day: don't miss a visit to Bell Tower and Astronomical Clock (Orologio Astronomico), then take in the architecture and atmosphere at Duomo di Messina, and then learn about winemaking at Gambino Vini.

For traveler tips, photos, reviews, and tourist information, refer to the Taormina holiday planner.

Traveling by combination of flight and train from Lampedusa to Taormina takes 4 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry, bus, and train. Expect slightly colder evenings in Taormina when traveling from Lampedusa in October, with lows around 20°C. Finish your sightseeing early on the 3rd (Sat) so you can travel to San Teodoro.

Things to do in Taormina

Historic Sites Parks Wineries

Side Trips

Messina, Gambino Vini
Highlights from your plan
Ancient Theatre of Taormina ©
Ancient Theatre of Taormina
Villa Comunale ©
Villa Comunale
Isola Bella ©
Isola Bella

1
night
San Teodoro, Sardinia

San Teodoro ©
A chance to sip cocktails at swanky beach bars by day and experience the vibrant club scene by night makes San Tedoro vacations extremely popular.
On the 4th (Sun), tour the pleasant surroundings at Spiaggia Berchida. On your second day here, kick back and relax at Spiaggia Isuledda, then enjoy the sand and surf at Spiaggia Capo Coda Cavallo, then enjoy the sand and surf at Lu Impostu Beach, and finally kick back and relax at Spiaggia La Cinta.

To find ratings, more things to do, where to stay, and more tourist information, read San Teodoro online trip itinerary maker.

You can fly from Taormina to San Teodoro in 7.5 hours. Other options are to do a combination of train and ferry; or do a combination of car and ferry. Traveling from Taormina in October, expect slightly colder with lows of 15°C in San Teodoro. Cap off your sightseeing on the 5th (Mon) early enough to travel to Venice.

Things to do in San Teodoro

Parks Outdoors Beaches

Side Trips

Spiaggia Berchida, Spiaggia Isuledda
Highlights from your plan
Spiaggia La Cinta ©
Spiaggia La Cinta
Lu Impostu Beach ©
Lu Impostu Beach
Spiaggia Berchida ©
Spiaggia Berchida

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.
Kick off your visit on the 6th (Tue): examine the collection at Doge's Palace, steep yourself in history at Ponte dei Sospiri, then admire the landmark architecture of Basilica di San Marco, and finally explore the activities along Canal Grande. On the 7th (Wed), you'll have a packed day of sightseeing: appreciate the history behind Punta della Dogana, admire the masterpieces at Peggy Guggenheim Collection, contemplate the long history of Basilica dei Santi Giovanni e Paolo, take in the views from Ponte di Rialto, then make a trip to Piazza San Marco, and finally enjoy breathtaking views from St Mark's Campanile.

To find photos, more things to do, where to stay, and tourist information, go to the Venice online holiday planner.

Traveling by flight from San Teodoro to Venice takes 4.5 hours. Alternatively, you can do a combination of flight and train; or do a combination of ferry and car. Traveling from San Teodoro in October, things will get little chillier in Venice: highs are around 22°C and lows about 12°C. Wrap up your sightseeing on the 7th (Wed) to allow time to take a train to Florence.

Things to do in Venice

Historic Sites Museums Parks
Highlights from your plan
Canal Grande ©
Canal Grande
Basilica di San Marco
Basilica di San Marco
Doge's Palace ©
Doge's Palace

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
On the 8th (Thu), appreciate the history behind Loggia dei Lanzi, get great views at Basilica San Miniato al Monte, don't miss a visit to Piazzale Michelangelo, then take in the views from Ponte Vecchio, then get to know the fascinating history of Piazza del Duomo, and finally contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore. Keep things going the next day: take in the spiritual surroundings of The Baptistery of St. John, don't miss a visit to Piazza della Signoria, get a sense of history and politics at Palazzo Vecchio, admire the landmark architecture of Church and Museum of Orsanmichele, then contemplate the long history of Basilica of Santa Croce, and finally admire the masterpieces at Academy Of Florence Art Gallery.

For maps, ratings, and more tourist information, refer to the Florence trip planner.

Getting from Venice to Florence by train takes about 2.5 hours. Other options: drive; or take a bus. In October in Florence, expect temperatures between 25°C during the day and 14°C at night. Wrap up your sightseeing on the 9th (Fri) to allow time to travel back home.

Things to do in Florence

Historic Sites Museums
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

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