53 days in Italy & Santorini Itinerary

53 days in Italy & Santorini Itinerary

Created using Inspirock Europe trip itinerary builder
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Fly
1
Fira, Greece
— 7 nights
Taxi
2
Oia, Greece
— 6 nights
Bus to Santorini, Fly to Florence
3
Florence, Italy
— 6 nights
Drive
4
Siena, Italy
— 4 nights
Taxi to Piombino, Ferry to Portoferraio
5
Portoferraio, Italy
— 3 nights
Ferry to Piombino, Drive to Massa
6
Massa, Italy
— 6 nights
Train
7
Cinque Terre, Italy
— 7 nights
Drive
8
Milan, Italy
— 12 nights
Fly

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Fira, Greece — 7 nights

Fira, the busy capital of Santorini, sits on the very edge of a volcanic caldera.
Step off the beaten path and head to Wine Tours & Tastings and Spas. And it doesn't end there: see the world from above with a helicopter tour, tour the pleasant surroundings at Vlychada Beach, do a tasting at Santo Winery, and get impressive views of Santorini Volcano.

Discover how to plan a Fira trip in just a few steps with Inspirock's itinerary builder.

Sydney, Australia to Fira is an approximately 24.5-hour flight. You'll gain 8 hours traveling from Sydney to Fira due to the time zone difference. Prepare for a bit warmer weather when traveling from Sydney in June: high temperatures in Fira hover around 32°C and lows are around 24°C. Finish your sightseeing early on the 16th (Fri) so you can drive to Oia.
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Outdoors · Parks · Wineries · Tours
Side Trips
Find places to stay Jun 9 — 16:

Oia, Greece — 6 nights

Every day hundreds of visitors come to Oia just to experience its sunsets.
You'll discover tucked-away gems like Amoudi Bay and Safowi. And it doesn't end there: race across the water with a speed boat tour, enjoy the sand and surf at Katharos Beach, tour the pleasant surroundings at Baxedes Beach, and make a trip to Sunset in Oia.

To find more things to do, traveler tips, and tourist information, go to the Oia trip itinerary app.

Oia is just a short distance from Fira. In June, daytime highs in Oia are 32°C, while nighttime lows are 24°C. Finish up your sightseeing early on the 22nd (Thu) so you can travel to Florence.
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Tours · Parks · Outdoors · Wineries
Find places to stay Jun 16 — 22:

Florence, Italy — 6 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
You'll explore the less-touristy side of things at Food Tours and Museo Galileo - Institute and Museum of the History of Science. You'll find plenty of places to visit near Florence: A Solatio Organic Farm (in Certaldo) and Castello del Trebbio (in Santa Brigida). The adventure continues: explore the world behind art at Florence Academy of Fine Arts, appreciate the extensive heritage of Piazza del Duomo, see the interesting displays at Pitti Palace, and snap pictures at Ponte Vecchio.

To see maps, photos, more things to do, and other tourist information, use the Florence route tool.

Do a combination of bus and flight from Oia to Florence in 6.5 hours. Alternatively, you can do a combination of car and ferry; or do a combination of taxi, ferry, bus, and train. Due to the time zone difference, you'll gain 1 hour traveling from Oia to Florence. Traveling from Oia in June, expect little chillier with lows of 21°C in Florence. Finish your sightseeing early on the 28th (Wed) so you can drive to Siena.
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Historic Sites · Museums · Tours · Wineries
Side Trips
Find places to stay Jun 22 — 28:

Siena, Italy — 4 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Explore hidden gems such as Food Tours and Cascate del Mulino. Venture out of the city with trips to Abbazia di San Galgano (in Chiusdino), Abbazia di Sant'Antimo (in Castelnuovo dell'Abate) and Giardino dei Tarocchi (in Pescia Fiorentina). And it doesn't end there: steep yourself in history at Centro Storico di Siena, don't miss a visit to Piazza Grande a Montepulciano, take in the architecture and atmosphere at Basilica Cateriniana San Domenico, and admire the masterpieces at Museo dell'Opera Metropolitana.

To find ratings, traveler tips, and other tourist information, read our Siena trip itinerary app.

Traveling by car from Florence to Siena takes 1.5 hours. Alternatively, you can take a bus; or take a train. In June, daytime highs in Siena are 34°C, while nighttime lows are 19°C. Finish your sightseeing early on the 2nd (Sun) to allow enough time to travel to Portoferraio.
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Tours · Historic Sites · Parks · Museums
Side Trips
Find places to stay Jun 28 — Jul 2:

Portoferraio, Italy — 3 nights

Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. Step off the beaten path and head to Spiaggia Di Sansone and Spiaggia di Capo Bianco. Explore the numerous day-trip ideas around Portoferraio: Dolphin & Whale Watching (in Marina di Campo), Spiaggia di Cavoli (in Seccheto) and Monte Capanne (in Marciana). The adventure continues: stroll through Spiaggia di Barabarca, enjoy the sand and surf at Spiaggia delle Ghiaie, immerse yourself in nature at Percorso dell'Enfola, and take in the awesome beauty at Monte Calamita.

For ratings, maps, more things to do, and more tourist information, refer to the Portoferraio travel planner.

You can do a combination of taxi and ferry from Siena to Portoferraio in 3.5 hours. Other options are to do a combination of train and ferry; or do a combination of bus, train, and ferry. When traveling from Siena in July, plan for little chillier days in Portoferraio, with highs around 33°C, while nights are about the same with lows around 24°C. Finish your sightseeing early on the 5th (Wed) so you can travel to Massa.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Jul 2 — 5:

Massa, Italy — 6 nights

Massa is a town and comune in Tuscany, central Italy, the administrative centre of the province of Massa and Carrara. Explore hidden gems such as Grotta Turistica Antro del Corchia and Duomo di Pisa. Change things up with these side-trips from Massa: Pisa (Knights’ Square, Leaning Tower of Pisa, &more), CavallinoMatto (in Marina di Castagneto Carducci) and Lucca (San Michele in Foro, Torre delle Ore, &more). There's lots more to do: contemplate in the serene atmosphere at Santuario di Nostra Signora di Montallegro, pause for some serene contemplation at Oratorio della Santissima Trinita, steep yourself in history at Abbazia di San Fruttuoso, and get to know the fascinating history of Centro Storico del Paese di Tellaro.

For traveler tips, photos, where to stay, and tourist information, refer to the Massa holiday app.

Getting from Portoferraio to Massa by combination of ferry and car takes about 3.5 hours. Other options: do a combination of ferry and train. In July, plan for daily highs up to 35°C, and evening lows to 21°C. Wrap up your sightseeing on the 11th (Tue) to allow time to take a train to Cinque Terre.
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Historic Sites · Parks · Theme Parks · Outdoors
Side Trips
Find places to stay Jul 5 — 11:

Cinque Terre, Italy — 7 nights

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Discover out-of-the-way places like Angelo's Boat Tours - Cinque Terre Boat Tours and Footpath Monterosso - Vernazza. Change things up with these side-trips from Cinque Terre: Genoa (Chiesa di Santo Stefano, Piazza De Ferrari, &more), La Spezia (Enoteca la Civilta del Bere e Altro, Ponte Thaon di Revel, &more) and Porto Venere (San Pietro Church & Portovenere). Next up on the itinerary: explore the striking landscape of Parco Nazionale Cinque Terre, take a stroll around Vernazza, take in the spiritual surroundings of Chiesa Di San Pietro, and make a trip to Lungomare Vittorio Veneto.

To find photos, where to stay, reviews, and tourist information, refer to the Cinque Terre travel route builder.

Take a train from Massa to Cinque Terre in 1.5 hours. Alternatively, you can drive. In July, plan for daily highs up to 35°C, and evening lows to 21°C. Wrap up your sightseeing on the 18th (Tue) early enough to drive to Milan.
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Parks · Historic Sites · Outdoors · Wildlife
Side Trips
Find places to stay Jul 11 — 18:

Milan, Italy — 12 nights

Fashion Capital of World

In many ways the most modern of Italian cities, Milan is a busy, elegant metropolis with an impressive list of grand palaces, fine churches, and important museums.
Step off the beaten path and head to Villa del Balbianello and Dialogo nel Buio. Change things up with these side-trips from Milan: Turin (Chiesa di Santa Maria del Monte dei Cappuccini, Parco del Valentino, &more), Verona (Basilica di San Zeno Maggiore, Piazza Bra, &more) and Orta San Giulio (Lake Orta, Sacro Monte di Orta, &more). There's much more to do: pause for some serene contemplation at Duomo di Milano, stroll around Sempione Park, take in nature's colorful creations at Botanical Gardens Of Villa Taranto, and get in on the family fun at Leolandia.

To see other places to visit, more things to do, traveler tips, and tourist information, read Milan vacation app.

Traveling by car from Cinque Terre to Milan takes 3 hours. Alternatively, you can take a train. In July, plan for daily highs up to 34°C, and evening lows to 21°C. Wrap up your sightseeing by early afternoon on the 30th (Sun) to allow time for the flight back home.
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Historic Sites · Parks · Museums · Nature
Side Trips
Find places to stay Jul 18 — 30:

Santorini travel guide

4.1
Beaches · Landmarks · Ruins
Wine Island
Known for dramatic views and romantic sunsets, the island of Santorini draws visitors with its long string of black, white, and red beaches. The largest and most significant of a small group of volcanic islands located just 200 km (120 mi) southeast of Greece's mainland, Santorini boasts just over 15,000 permanent residents. Created by a massive volcanic eruption that likely destroyed a single large island, the archipelago still features an active volcano, which saw its last eruption in the 1950s. The easiest way to explore Santorini's craggy coastline is on foot. Start by visiting the archaeological sites on the island's southwestern side, which offer a chance to discover the area's ancient past with unobstructed views of the famed volcano.
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Italy travel guide

4.6
Landmarks · Ruins · Beaches
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.
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