21 days in Italy Itinerary

21 days in Italy Itinerary

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Route & dates

21 days in Italy Itinerary

Cairo
Fly:  7​h 30​min
Rome
— 2 nights
train:  1​h 45​min
Florence
— 2 nights
train:  2​h 15​min
Venice
— 3 nights
Fly:  3​h
Naples
— 2 nights
ferry:  45​min
Anacapri, Island of Capri
— 2 nights
ferry + shuttle + Fly:  4​h 45​min
Palermo, Sicily
— 2 nights
Drive:  3​h
Syracuse, Sicily
— 3 nights
Drive:  1​h 30​min
Taormina, Sicily
— 3 nights
Fly:  14​h
Cairo

2
days
Rome

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
On the 1st (Fri), wander the streets of Via del Corso, get answers to all your questions at Ostia Antica, and then make a trip to Piazza Venezia. Get ready for a full day of sightseeing on the next day: enjoy the sand and surf at Sabbianera Super Beach and then tour the pleasant surroundings at MOAI Beach.

To find ratings, traveler tips, reviews, and more tourist information, you can read our Rome itinerary builder.

Cairo, Egypt to Rome is an approximately 7.5-hour flight. Due to the time zone difference, you'll gain 1 hour traveling from Cairo to Rome. Traveling from Cairo in June, expect Rome to be slightly colder, temps between 33°C and 20°C. On the 3rd (Sun), wrap the sightseeing up by early afternoon so you can take a train to Florence.

Things to do in Rome

Sightseeing Beaches Parks

Side Trips

Ostia Antica, Sabbianera Super Beach, MOAI Beach
Accommodations
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Via del Corso
Ostia Antica
Piazza Venezia

2
days
Florence

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
On the 3rd (Sun), learn about winemaking at Castello di Monterinaldi. Get ready for a full day of sightseeing on the next day: take in the spiritual surroundings of Abbazia di San Miniato al Monte, then do a tasting at Tenuta Torciano Wine Tasting & Tours, and then steep yourself in history at Historic Centre of San Gimignano.

To see reviews, where to stay, and tourist information, refer to the Florence tour planner.

Traveling by train from Rome to Florence takes 2 hours. Alternatively, you can drive; or fly. June in Florence sees daily highs of 34°C and lows of 19°C at night. Wrap up your sightseeing by early afternoon on the 5th (Tue) to allow enough time to take a train to Venice.

Things to do in Florence

Sightseeing Historic Sites Wineries

Side Trips

Comune Di Certaldo, Tenuta Torciano, Castello di Monterinaldi, Pro Loco San Gimignano
Accommodations
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Pro Loco San Gimignano
Abbazia di San Miniato al Monte
Tenuta Torciano

2
days
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 5th (Tue), step off the mainland to explore La Giudecca. On the 6th (Wed), you'll have a packed day of sightseeing: pause for some serene contemplation at Basilica dei Frari, take in the spiritual surroundings of Campo del Ghetto, hunt for treasures at Mercati di Rialto, then take in the spiritual surroundings of Basilica dei Santi Giovanni e Paolo (San Zanipolo), then pause for some serene contemplation at Santa Maria dei Miracoli, and finally steep yourself in history at La Biennale di Venezia - Arsenale.

To find traveler tips, ratings, reviews, and tourist information, go to the Venice travel itinerary creator.

You can take a train from Florence to Venice in 2.5 hours. Alternatively, you can drive; or fly. Traveling from Florence in June, you will find days in Venice are little chillier (30°C), and nights are about the same (20°C). Wrap up your sightseeing on the 8th (Fri) early enough to travel to Naples.

Things to do in Venice

Parks Beaches Sightseeing

Side Trips

Eraclea Beach, Spiaggia di Levante
Accommodations
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La Giudecca
Campo del Ghetto

2
days
Naples

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy, after Rome and Milan. Kick off your visit on the 8th (Fri): don't miss a visit to Corso Italia, then browse the different shops at Centro Commerciale Campania, and then tour the pleasant surroundings at Lido Onde Blu. On your second day here, explore the ancient world of Parco Archeologico Pausilypon, then identify plant and animal life at Parco Sommerso di Gaiola Area Marina Protetta, and then explore the gorgeous colors at Posillipo.

To see reviews, traveler tips, photos, and tourist information, read our Naples travel itinerary planner.

You can fly from Venice to Naples in 3 hours. Alternatively, you can take a train; or drive. June in Naples sees daily highs of 32°C and lows of 21°C at night. On the 10th (Sun), you'll have the morning to explore before heading off to Anacapri.

Things to do in Naples

Parks Wildlife Areas Historic Sites

Side Trips

Lido Onde Blu, Corso Italia, Centro Commerciale Campania
Accommodations
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Lido Onde Blu
Parco Archeologico Pausilypon
San Lorenzo Maggiore

2
days
Anacapri, Island of Capri

Anacapri is a comune on the island of Capri, in the Metropolitan City of Naples, Italy. Kick off your visit on the 10th (Sun): don't miss a visit to Belvedere Cannone, stop by Carthusia, then Head underground at White Grotta, and finally explore the striking landscape at I Faraglioni. Get ready for a full day of sightseeing on the 11th (Mon): get great views at Monte Solaro Chairlift, contemplate the waterfront views at Marina Piccola, then stroll through Fortini Coastal Walk, and finally appreciate the extensive heritage of Scala Fenicia (Phoenician Steps).

To find more things to do, ratings, photos, and other tourist information, use the Anacapri travel planner.

Getting from Naples to Anacapri by ferry takes about an hour. In June, daytime highs in Anacapri are 32°C, while nighttime lows are 23°C. Finish your sightseeing early on the 12th (Tue) so you can travel to Palermo.

Things to do in Anacapri

Parks Sightseeing Nature

Side Trip

Capri
Accommodations
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White Grotta
I Faraglioni
Marina Piccola

2
days
Palermo, Sicily

The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
Start off your visit on the 12th (Tue): look for gifts at La Bottega nella Roccia, explore the historical opulence of Castello di Caccamo, and then contemplate the long history of Palazzo Chiaramonte. Keep things going the next day: explore the ancient world of Teatro, tour the pleasant surroundings at Spiaggia di Castellamare del Golfo, and then take in the spiritual surroundings of Santuario Santa Rosalia.

To see where to stay, more things to do, and tourist information, refer to the Palermo tour planner.

Traveling by combination of ferry and flight from Anacapri to Palermo takes 5 hours. Alternatively, you can ride a ferry. In June, plan for daily highs up to 30°C, and evening lows to 22°C. Finish your sightseeing early on the 14th (Thu) so you can drive to Syracuse.

Things to do in Palermo

Beaches Parks Historic Sites

Side Trips

Caccamo, Teatro, Spiaggia Guidaloca, Spiaggia di Castellamare del Golfo
Accommodations
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Castello di Caccamo
Teatro
Santuario Santa Rosalia

2
days
Syracuse, Sicily

Philosopher Cicero once described Syracuse as "the greatest Greek city and the most beautiful of them all." A powerful city-state of ancient Greece, Syracuse now is the capital of the eponymous Italian province on the eastern coast of Sicily.
Kick off your visit on the 15th (Fri): make a trip to Tonnara di Marzamemi, then kick back and relax at Agua Beach Resort, and then contemplate in the serene atmosphere at St. Nicholas Cathedral. Get ready for a full day of sightseeing on the 16th (Sat): look for gifts at Caseificio Borderi, then pause for some serene contemplation at Chiesa Santa Chiara, then step into the grandiose world of Palazzo Nicolaci, and finally enjoy the sand and surf at Spiaggia Pineta del Gelsomineto.

For traveler tips, other places to visit, reviews, and other tourist information, use the Syracuse itinerary builder.

Traveling by car from Palermo to Syracuse takes 3 hours. Alternatively, you can take a train; or take a bus. In June, daytime highs in Syracuse are 33°C, while nighttime lows are 23°C. Cap off your sightseeing on the 17th (Sun) early enough to go by car to Taormina.

Things to do in Syracuse

Beaches Parks Historic Sites

Side Trips

Noto, Tonnara di Marzamemi
Accommodations
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Agua Beach Resort
Chiesa Santa Chiara
Tonnara di Marzamemi

4
days
Taormina, Sicily

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.
Your inner history buff will appreciate Sanctuary of the Madonna di Tindari and Duomo di Messina. Get outdoors at Spiaggia libera - Santa Teresa di Riva and Gole Alcantara Terralcantara. Change things up with these side-trips from Taormina: Libreria Incantastorie (in Milazzo), Bronte (Pastificio Il Mattarello & Il Pistacchio) and Wine Tours & Tastings (in Linguaglossa). There's lots more to do: don't miss a visit to Piazza IX Aprile, browse the eclectic array of goods at A' Piscaria Mercato del Pesce, look for gifts at Il Laboratorio Dell'Arte, and view the masterpieces at Ceramiche Dell'Artigianato Siciliano Manago.

To see other places to visit, where to stay, reviews, and other tourist information, refer to the Taormina travel itinerary creator.

Traveling by car from Syracuse to Taormina takes 1.5 hours. Alternatively, you can drive; or take a train. Expect a daytime high around 33°C in June, and nighttime lows around 24°C. Wrap up your sightseeing on the 20th (Wed) to allow time to travel back home.

Things to do in Taormina

Parks Shopping Tours

Side Trips

Bronte, A' Piscaria Mercato del Pesce, Wine Tours & Tastings, Duomo di Messina, Spiaggia libera - Santa Teresa di Riva
Accommodations
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Highlights from your plan
Gole Alcantara Terralcantara
Duomo di Messina
Piazza IX Aprile

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