44 days in Italy & Santorini Itinerary

44 days in Italy & Santorini Itinerary

Created using Inspirock Europe trip itinerary planner

Plan created by another user.Make it yours

Route & dates

1
Oia, Greece
— 6 nights
2
Salerno, Italy
— 5 nights
3
Positano, Italy
— 7 nights
4
Capri, Italy
— 5 nights
5
Naples, Italy
— 4 nights
6
Siena, Italy
— 4 nights
7
Pisa, Italy
— 3 nights
8
Cinque Terre, Italy
— 7 nights

6
nights
Oia, Greece

Oia ©
Every day hundreds of visitors come to Oia just to experience its sunsets.
Lioyerma Lounge Cafe Pool Bar has been added to your itinerary. Explore Oia's surroundings by going to Akrotiri (Akrotiri, La Ponta, &more), Kamari Beach (in Kamari) and Perissa Black Sand Beach (in Perissa). The adventure continues: contemplate the waterfront views at Amoudi Bay, make a trip to Wave, pause for some serene contemplation at Ekklisia Panagia Platsani, and stop by Aquamarine Jewelry.

For ratings and more tourist information, you can read our Oia trip maker site.

San Juan, Puerto Rico to Oia is an approximately 21.5-hour flight. Traveling from San Juan to Oia, you'll lose 6 hours due to the time zone difference. In August, daytime highs in Oia are °C, while nighttime lows are °C. Finish up your sightseeing early on the 15th (Sat) so you can travel to Salerno.

Things to do in Oia

Parks Outdoors Beaches

Side Trips

Akrotiri, Kamari Beach, Orthodox Metropolitan Cathedral, Panagia Theoskepasti Chapel, Perissa Black Sand Beach
Find places to stay Aug 9 — 15:
Highlights from your plan
Amoudi Bay ©
Amoudi Bay
Akrotiri ©
Akrotiri
Red Beach ©
Red Beach

5
nights
Salerno, Italy

Salerno ©
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.
Your day-by-day itinerary now includes Gran Caffe', Punto & Virgola, Negrito, and other attractions you added. Get out of town with these interesting Salerno side-trips: Chalet de Mar (in Minori), Ravello (Le Ville di Ravello & Convento Frati Minori Conventuali S.Francesco) and Paestum (Lido Mediterraneo Beach & Paestum Ruins). There's lots more to do: get outside with Cilento, browse for treasures at Libreria Antiquaria Vecchi Libri, don't miss a visit to Promenade Trieste, and pause for some serene contemplation at Duomo di Salerno.

To see traveler tips, ratings, other places to visit, and tourist information, refer to the Salerno online trip builder.

Traveling by flight from Oia to Salerno takes 7 hours. Alternatively, you can do a combination of car and ferry; or do a combination of taxi, ferry, and bus. The time zone difference moving from Eastern European Standard Time (EET) to Central European Standard Time (CET) is minus 1 hour. In August in Salerno, expect temperatures between °C during the day and °C at night. Wrap up your sightseeing on the 20th (Thu) to allow time to drive to Positano.

Things to do in Salerno

Outdoors Historic Sites Nightlife

Side Trips

Ravello, Paestum, Chalet de Mar, Arciconfraternita della Santissima Annunziata e del Santissimo Rosario
Find places to stay Aug 15 — 20:
Highlights from your plan
Cilento ©
Cilento
Paestum Ruins ©
Paestum Ruins
Speed Boats Tours

7
nights
Positano, Italy

Positano ©
Often referred to as the gem of the Amalfi Coast, Positano remains one of southern Italy's most sought-after vacation locales, thanks to its hillside location and picturesque, pastel buildings.
Venture out of the city with trips to Ravello (Belvedere Principessa di Piemonte, Villa Cimbrone Gardens, &more), Conca dei Marini (Grotta dello Smeraldo & Lido Capo di Conca) and Vicoli, scale e archi (in Atrani). There's still lots to do: enjoy the sand and surf at Fornillo, take in the exciting artwork at Art & Craft Gallery, take some stellar pictures from Il Sentiero Degli Dei, and take in the spiritual surroundings of Duomo di Sant'Andrea.

To find photos, maps, ratings, and more tourist information, read Positano travel planner.

You can drive from Salerno to Positano in 1.5 hours. Alternatively, you can ride a ferry; or do a combination of train and taxi. In August in Positano, expect temperatures between °C during the day and °C at night. Wrap up your sightseeing on the 27th (Thu) to allow time to ride a ferry to Capri.

Things to do in Positano

Outdoors Parks Beaches

Side Trips

Amalfi, Ravello, Praiano, Conca dei Marini, Vicoli, scale e archi
Find places to stay Aug 20 — 27:
Highlights from your plan
Fornillo ©
Fornillo
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei

5
nights
Capri, Italy

Capri ©
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
Capri is known for nature, parks, and historic sites. Your plan includes some of its best attractions: take some stellar pictures from Belvedere Cannone, take in panoramic vistas at Belvedere di Tragara, explore the striking landscape at I Faraglioni, and explore the historical opulence of Castiglione.

To find other places to visit and tourist information, use the Capri road trip planner.

Traveling by ferry from Positano to Capri takes 1.5 hours. Alternatively, you can do a combination of taxi and ferry; or do a combination of bus and ferry. August in Capri sees daily highs of °C and lows of °C at night. Finish your sightseeing early on the 1st (Tue) so you can ride a ferry to Naples.

Things to do in Capri

Parks Historic Sites Nature

Side Trip

Anacapri
Find places to stay Aug 27 — Sep 1:
Highlights from your plan
Monte Solaro ©
Monte Solaro
Belvedere Cannone ©
Belvedere Cannone
Belvedere di Tragara ©
Belvedere di Tragara

4
nights
Naples, Italy

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Step out of Naples with an excursion to Convento di Santa Maria a Castro in Praiano--about 1h 20 min away. And it doesn't end there: contemplate the long history of Pompeii Archaeological Park, examine the collection at Museo Archeologico Nazionale di Napoli, pause for some serene contemplation at Duomo di Napoli, and delve into the distant past at Parco Acheologico di Ercolano.

To see more things to do, where to stay, ratings, and other tourist information, you can read our Naples trip planning website.

Traveling by ferry from Capri to Naples takes 1.5 hours. Expect a daytime high around °C in September, and nighttime lows around °C. Cap off your sightseeing on the 5th (Sat) early enough to go by car to Siena.

Things to do in Naples

Historic Sites Museums

Side Trips

Convento di Santa Maria a Castro, Parco Acheologico di Ercolano, Pompeii Archaeological Park
Find places to stay Sep 1 — 5:
Highlights from your plan
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Parco Acheologico di Ercolano ©
Parco Acheologico di Ercolano
Museo Archeologico Nazionale di Napoli ©
Museo Archeologico Nazionale di Napoli

4
nights
Siena, Italy

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
You'll find plenty of places to visit near Siena: Museo della Porziuncola (in Santa Maria degli Angeli), Assisi (Eremo delle Carceri, Basilica Papale e Sacro Convento di San Francesco d'Assisi, &more) and San Gimignano (Historic Centre of San Gimignano & Torre Grossa). The adventure continues: don't miss a visit to Piazza del Campo, get lost in a book at Biblioteca Piccolomini, contemplate the long history of Cappella di Piazza, and pause for some serene contemplation at Duomo di Siena.

To find more things to do, photos, and more tourist information, use the Siena trip maker tool.

Getting from Naples to Siena by car takes about 4.5 hours. Other options: take a train; or take a bus. In September, daytime highs in Siena are °C, while nighttime lows are °C. Wrap up your sightseeing on the 9th (Wed) early enough to take a train to Pisa.

Things to do in Siena

Historic Sites Museums

Side Trips

Assisi, San Gimignano
Find places to stay Sep 5 — 9:
Highlights from your plan
Museo della Porziuncola ©
Museo della Porziuncola
Piazza del Campo ©
Piazza del Campo

3
nights
Pisa, Italy

Pisa ©
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
You'll find plenty of places to visit near Pisa: Lucca (San Michele in Foro, Torre Guinigi, &more). There's lots more to do: enjoy breathtaking views from Leaning Tower of Pisa, head outdoors with Il Pineto Parco Avventura, admire the landmark architecture of St Martin Cathedral, and don't miss a visit to Piazza dei Miracoli.

To find maps, traveler tips, where to stay, and more tourist information, refer to the Pisa holiday builder app.

Take a train from Siena to Pisa in 2 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around °C in September, and nighttime lows around °C. Finish your sightseeing early on the 12th (Sat) to allow enough time to take a train to Cinque Terre.

Things to do in Pisa

Historic Sites Outdoors Museums

Side Trip

Lucca
Find places to stay Sep 9 — 12:
Highlights from your plan
Leaning Tower of Pisa ©
Leaning Tower of Pisa
Piazza dei Miracoli ©
Piazza dei Miracoli
Le mura di Lucca ©
Le mura di Lucca

7
nights
Cinque Terre, Italy

Cinque Terre ©
Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Venture out of the city with trips to Genoa (House of Francesco Maria Balbi Piovera, Aquarium of Genoa, &more) and Sestri Levante (Creatini & Landriani Fine Art & Baia del Silenzio). There's still lots to do: appreciate the extensive heritage of Borgo Storico di Manarola, do a tasting at Buranco Agriturismo, trek along Cinque Terre Trails, and take some stellar pictures from Bar Terza Terra.

Plan a Cinque Terre trip in moments using our itinerary builder.

Getting from Pisa to Cinque Terre by train takes about 2 hours. Other options: drive; or take a bus. In September, daytime highs in Cinque Terre are °C, while nighttime lows are °C. Wrap up your sightseeing by early afternoon on the 19th (Sat) to allow enough time to travel back home.

Things to do in Cinque Terre

Parks Historic Sites Outdoors

Side Trips

Genoa, Sestri Levante
Find places to stay Sep 12 — 19:
Highlights from your plan
Footpath Monterosso - Vernazza ©
Footpath Monterosso - Vernazza
Aquarium of Genoa ©
Aquarium of Genoa
Parco Nazionale Cinque Terre ©
Parco Nazionale Cinque Terre

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