18 days in Italy & Santorini Itinerary

18 days in Italy & Santorini Itinerary

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Route & dates

18 days in Italy & Santorini Itinerary

Start: Chicago, United States
Fly:  12​h
1
Venice, Italy
— 3 nights
Fly:  6​h
2
Fira, Greece
— 3 nights
bus:  30​min
3
Perissa, Greece
— 4 nights
Fly:  6​h 15​min
4
Naples, Italy
— 1 night
bus:  30​min
5
Salerno, Italy
— 4 nights
Fly:  4​h 45​min
6
Venice, Italy
— 1 night
Fly:  12​h 30​min
End: Chicago, United States

3
nights
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.
Step out of Venice with an excursion to Scrovegni Chapel in Padua--about 54 minutes away. There's much more to do: admire the landmark architecture of Doge's Palace, steep yourself in history at Ponte dei Sospiri, pause for some serene contemplation at Basilica dei Santi Giovanni e Paolo (San Zanipolo), and don't miss a visit to Basilica di San Marco.

To see ratings, traveler tips, and more tourist information, refer to the Venice road trip planning website .

Chicago, USA to Venice is an approximately 12.5-hour flight. You can also do a combination of flight and train; or do a combination of train and flight. Traveling from Chicago to Venice, you'll lose 7 hours due to the time zone difference. In May in Venice, expect temperatures between 72°F during the day and 55°F at night. Wrap up your sightseeing by early afternoon on the 17th (Sun) to allow enough time to travel to Fira.

Things to do in Venice

Historic Sites Museums Nature

Side Trip

Scrovegni Chapel
Find places to stay May 14 — 17:
Highlights from your plan
Canal Grande ©
Canal Grande
Doge's Palace ©
Doge's Palace
Basilica di San Marco
Basilica di San Marco

3
nights
Fira, Greece

Fira, the busy capital of Santorini, sits on the very edge of a volcanic caldera.
Fira is known for nightlife, museums, spas, historic sites, and wildlife. Your plan includes some of its best attractions: indulge your taste buds at Food & Drink, pause for some serene contemplation at Cathedral of Saint John the Baptist, delve into the distant past at Ancient Thera, and hike along Ekklisia Theoskepasti hiking trail.

For more things to do, maps, where to stay, and more tourist information, read Fira journey website .

Traveling by flight from Venice to Fira takes 6 hours. Alternatively, you can do a combination of train and flight; or do a combination of ferry and car. The time zone changes from Central European Time to Eastern European Time, which is usually a 1 hour difference. Traveling from Venice in May, expect somewhat warmer with lows of 63°F in Fira. On the 20th (Wed), wrap the sightseeing up by early afternoon so you can take a bus to Perissa.

Things to do in Fira

Parks Outdoors Tours

Side Trips

Kamari, Amoudi Bay, Ekklisia Theoskepasti hiking trail
Find places to stay May 17 — 20:
Highlights from your plan
Wine Tours & Tastings
Amoudi Bay ©
Amoudi Bay
Ekklisia Theoskepasti hiking trail ©

4
nights
Perissa, Greece

Perissa ©
One of Santorini's seaside treasures, Perissa provides travelers with a lively restaurant scene and easy access to several archaeological sites.
Step out of Perissa with an excursion to Speed Boats Tours in Oia--about 38 minutes away. There's much more to do: explore the ancient world of Akrotiri, do a tasting at Boutari, J., & Son Wineries S.A., explore by horseback at Santo Horse Riding, and identify plant and animal life at Wildlife Areas.

For maps, ratings, and tourist information, read our Perissa day trip tool .

Perissa is very close to Fira. In May, daily temperatures in Perissa can reach 75°F, while at night they dip to 63°F. Finish your sightseeing early on the 24th (Sun) so you can travel to Naples.

Things to do in Perissa

Outdoors Parks Wildlife

Side Trips

Akrotiri, Vlychada, Boutari, J., & Son Wineries S.A., Megalochori - Traditional Village
Find places to stay May 20 — 24:
Highlights from your plan
Santo Horse Riding ©
Santo Horse Riding
Akrotiri ©
Akrotiri
Red Beach ©
Red Beach

1
night
Naples, Italy

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 24th (Sun): steep yourself in history at Underground Naples, examine the collection at Museo Archeologico Nazionale di Napoli, and then make a trip to Pompeii Archaeological Park.

To find more things to do, other places to visit, and tourist information, use the Naples online sightseeing planner .

Getting from Perissa to Naples by flight takes about 6.5 hours. Other options: do a combination of flight and train; or do a combination of ferry and car. The time zone changes from Eastern European Time (EET) to Central European Time (CET), which is usually a -1 hour difference. Traveling from Perissa in May, expect little chillier with lows of 58°F in Naples. Wrap up your sightseeing on the 25th (Mon) early enough to take a bus to Salerno.

Things to do in Naples

Historic Sites Museums

Side Trip

Pompeii Archaeological Park
Find places to stay May 24 — 25:
Highlights from your plan
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Museo Archeologico Nazionale di Napoli ©
Underground Naples ©
Underground Naples

4
nights
Salerno, Italy

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.
You'll find plenty of places to visit near Salerno: Ravello (Duomo di Ravello, Villa Rufolo, & more), Paestum Ruins (in Paestum) and Amalfi (Duomo di Sant'Andrea & Wine Tours & Tastings). There's lots more to do: learn about winemaking at Le Vigne di Raito, get a taste of the local shopping with Sol’Art Ceramiche, get a new perspective on things with Boat Tours & Water Sports, and get to know the fascinating history of Il Vecchio Centro Storico di Romagnano al Monte.

For maps, where to stay, photos, and tourist information, use the Salerno trip itinerary website .

Salerno is just a short distance from Naples. Traveling from Naples in May, expect a bit warmer with lows of 65°F in Salerno. Finish your sightseeing early on the 29th (Fri) so you can travel to Venice.

Things to do in Salerno

Tours Historic Sites Outdoors

Side Trips

Ravello, Amalfi, Vietri sul Mare, Paestum Ruins
Find places to stay May 25 — 29:
Highlights from your plan
Wine Tours & Tastings
Le Vigne di Raito ©
Le Vigne di Raito
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens

1
night
Venice, Italy

Venice
To see ratings, photos, reviews, and more tourist information, read our Venice trip planner .

Getting from Salerno to Venice by flight takes about 5 hours. Other options: do a combination of train and flight; or drive. Traveling from Salerno in May, expect slightly colder with lows of 55°F in Venice. On the 30th (Sat), you're off tohome.

Things to do in Venice

Historic Sites Nightlife Outdoors
Find places to stay May 29 — 30:

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