16 days in Italy Itinerary
Created using Inspirock Italy route planner
Start: Chicago
Fly
1
Florence
— 3 nights
Fly
2
San Vito lo Capo, Sicily
— 2 nights
Drive
3
Palermo, Sicily
— 1 night
Drive
4
Cefalu, Sicily
— 1 night
Drive
5
Agrigento, Sicily
— 1 night
Drive
6
Catania, Sicily
— 1 night
Drive
7
Taormina, Sicily
— 2 nights
Fly
8
Rome
— 4 nights
Fly
End: Chicago
Mon, Jun 19 - Tue, Jul 4
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View full calendar
Florence — 3 nights

Birthplace of the Italian Renaissance
Florence is known for sightseeing, museums, and historic sites. Your trip includes some of its best attractions: explore the world behind art at Florence Academy of Fine Arts, take in nature's colorful creations at The Boboli Gardens, take in panoramic vistas at Campanile di Giotto, and see the interesting displays at Pitti Palace.
To find reviews, photos, where to stay, and other tourist information, go to the Florence online trip builder.
Chicago, USA to Florence is an approximately 14-hour flight. Traveling from Chicago to Florence, you'll lose 7 hours due to the time zone difference. June in Florence sees daily highs of 83°F and lows of 65°F at night. Finish your sightseeing early on the 22nd (Thu) to allow enough time to fly to San Vito lo Capo.
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To find reviews, photos, where to stay, and other tourist information, go to the Florence online trip builder.
Chicago, USA to Florence is an approximately 14-hour flight. Traveling from Chicago to Florence, you'll lose 7 hours due to the time zone difference. June in Florence sees daily highs of 83°F and lows of 65°F at night. Finish your sightseeing early on the 22nd (Thu) to allow enough time to fly to San Vito lo Capo.
Find places to stay Jun 19 — 22:
Highlights from your trip
San Vito lo Capo, Sicily — 2 nights

Start off your visit on the 23rd (Fri): identify plant and animal life at Riserva Naturale Dello Zingaro and then kick back and relax at Caletta del Bue Marino. On the 24th (Sat), you'll have a packed day of sightseeing: see what you can catch with a fishing tour and then enjoy the sand and surf at Spiaggia di San Vito lo Capo.
For maps, more things to do, ratings, and other tourist information, use the San Vito lo Capo trip planner.
Getting from Florence to San Vito lo Capo by flight takes about 3 hours. Other options: do a combination of train, ferry, and bus; or do a combination of train and taxi. While traveling from Florence, expect little chillier days and about the same nights in San Vito lo Capo, ranging from highs of 78°F to lows of 67°F. Finish your sightseeing early on the 24th (Sat) so you can drive to Palermo.
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For maps, more things to do, ratings, and other tourist information, use the San Vito lo Capo trip planner.
Getting from Florence to San Vito lo Capo by flight takes about 3 hours. Other options: do a combination of train, ferry, and bus; or do a combination of train and taxi. While traveling from Florence, expect little chillier days and about the same nights in San Vito lo Capo, ranging from highs of 78°F to lows of 67°F. Finish your sightseeing early on the 24th (Sat) so you can drive to Palermo.
Side Trip
Find places to stay Jun 22 — 24:
Highlights from your trip
Palermo, Sicily — 1 night

On the 25th (Sun), take in the architecture and atmosphere at Chiesa Inferiore, pause for some serene contemplation at Cattedrale di Palermo, and then indulge your taste buds at Food & Drink.
To find maps, traveler tips, photos, and tourist information, refer to the Palermo online travel planner.
You can drive from San Vito lo Capo to Palermo in 2 hours. Other options are to do a combination of taxi and train; or take a bus. Finish your sightseeing early on the 25th (Sun) to allow enough time to drive to Cefalu.
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To find maps, traveler tips, photos, and tourist information, refer to the Palermo online travel planner.
You can drive from San Vito lo Capo to Palermo in 2 hours. Other options are to do a combination of taxi and train; or take a bus. Finish your sightseeing early on the 25th (Sun) to allow enough time to drive to Cefalu.
Find places to stay Jun 24 — 25:
Highlights from your trip
Cefalu, Sicily — 1 night
Kick off your visit on the 26th (Mon): get up close to creatures of the deep with a dolphin and whale watching tour, stop by L'Albero delle Cose, take in the spiritual surroundings of Oratorio del Santissimo Sacramento, then steep yourself in history at Duomo di Cefalu, and finally contemplate the long history of Piazza del Duomo.
For more things to do, traveler tips, maps, and tourist information, you can read our Cefalu holiday maker website.
You can drive from Palermo to Cefalu in 1.5 hours. Alternatively, you can take a train; or take a bus. Cap off your sightseeing on the 26th (Mon) early enough to go by car to Agrigento.
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For more things to do, traveler tips, maps, and tourist information, you can read our Cefalu holiday maker website.
You can drive from Palermo to Cefalu in 1.5 hours. Alternatively, you can take a train; or take a bus. Cap off your sightseeing on the 26th (Mon) early enough to go by car to Agrigento.
Find places to stay Jun 25 — 26:
Highlights from your trip
Agrigento, Sicily — 1 night

Valley of the Temples
On the 27th (Tue), contemplate in the serene atmosphere at Valle dei Templi, then contemplate in the serene atmosphere at Chiesa San Nicola, then take in the dramatic natural features at Scala dei Turchi, and finally relax and rejuvenate at Seta Spa and Wellness.
For photos, reviews, other places to visit, and more tourist information, you can read our Agrigento online tour itinerary planner.
Drive from Cefalu to Agrigento in 2 hours. Alternatively, you can take a train; or take a bus. June in Agrigento sees daily highs of 78°F and lows of 68°F at night. Finish your sightseeing early on the 27th (Tue) so you can drive to Catania.
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For photos, reviews, other places to visit, and more tourist information, you can read our Agrigento online tour itinerary planner.
Drive from Cefalu to Agrigento in 2 hours. Alternatively, you can take a train; or take a bus. June in Agrigento sees daily highs of 78°F and lows of 68°F at night. Finish your sightseeing early on the 27th (Tue) so you can drive to Catania.
Side Trip
Find places to stay Jun 26 — 27:
Highlights from your trip
Catania, Sicily — 1 night
Black Pearl of Ionian Sea
Start off your visit on the 28th (Wed): discover the deep blue sea with Trigone Diving School, make a trip to Piazza Alonzo di Benedetto, and then head outdoors with Outdoor Activities.
For where to stay, maps, traveler tips, and other tourist information, refer to the Catania visit planner.
Getting from Agrigento to Catania by car takes about 2 hours. Other options: take a bus; or take a train. Finish up your sightseeing early on the 28th (Wed) so you can go by car to Taormina.
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For where to stay, maps, traveler tips, and other tourist information, refer to the Catania visit planner.
Getting from Agrigento to Catania by car takes about 2 hours. Other options: take a bus; or take a train. Finish up your sightseeing early on the 28th (Wed) so you can go by car to Taormina.
Find places to stay Jun 27 — 28:
Highlights from your trip
Taormina, Sicily — 2 nights

Start off your visit on the 29th (Thu): get a dose of the wild on Etna Wild, enjoy the sand and surf at Isola Bella, then get a new perspective on things with Blue Sea Diving Center, then don't miss a visit to Corso Umberto, and finally contemplate in the serene atmosphere at Chiesa del Varo. Here are some ideas for day two: walk around Villa Comunale, then explore the ancient world of Ancient Theatre of Taormina, then look for gifts at Sicilian Store, and finally relax and rejuvenate at Bagni Arabi.
To see reviews, where to stay, other places to visit, and tourist information, read Taormina travel site.
Getting from Catania to Taormina by car takes about an hour. Other options: take a bus; or take a train. In June, daily temperatures in Taormina can reach 82°F, while at night they dip to 69°F. Finish your sightseeing early on the 30th (Fri) to allow enough time to fly to Rome.
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To see reviews, where to stay, other places to visit, and tourist information, read Taormina travel site.
Getting from Catania to Taormina by car takes about an hour. Other options: take a bus; or take a train. In June, daily temperatures in Taormina can reach 82°F, while at night they dip to 69°F. Finish your sightseeing early on the 30th (Fri) to allow enough time to fly to Rome.
Side Trips
Find places to stay Jun 28 — 30:
Highlights from your trip
Rome — 4 nights

Eternal City
Rome is known for historic sites, sightseeing, and nightlife. Your trip includes some of its best attractions: contemplate the long history of Colosseum, make a trip to St. Peter's Basilica, get to know the fascinating history of Piazza Navona, and delve into the distant past at Palatine Hill.
To find out how to plan a trip to Rome, use our trip itinerary maker.
You can fly from Taormina to Rome in 3 hours. Other options are to do a combination of train and ferry; or do a combination of car and ferry. In June, daily temperatures in Rome can reach 84°F, while at night they dip to 65°F. Wrap up your sightseeing on the 4th (Tue) to allow time to fly back home.
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To find out how to plan a trip to Rome, use our trip itinerary maker.
You can fly from Taormina to Rome in 3 hours. Other options are to do a combination of train and ferry; or do a combination of car and ferry. In June, daily temperatures in Rome can reach 84°F, while at night they dip to 65°F. Wrap up your sightseeing on the 4th (Tue) to allow time to fly back home.
Side Trip
Find places to stay Jun 30 — Jul 4:
Highlights from your trip
Italy travel guide
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.
Sicily travel guide
The largest island in the Mediterranean Sea, Sicily is a ruggedly attractive land. The island has a long history of foreign domination and has been controlled by the Greeks, Romans, Arabs, and Normans. The result is a distinct culture blending elements from all of those areas and featuring an intriguing dialect. This is a huge island with plenty of small villages to tour, each with its own treasures. Beyond the popular coastal areas, Sicily's inland attractions include an unspoiled landscape of mountains, hills, and villages that sometimes seem frozen in time. While the natural environment is its biggest draw, Sicily's greatest asset may be its people. They are proud of their traditions and incredibly hospitable to visitors.