61 days in Italy Itinerary

Created using Inspirock Italy trip planner
Make it your trip
Fly
1
Milan
— 3 nights
Train
2
Florence
— 5 nights
Drive
3
Monteriggioni
— 1 day
Drive
4
Siena
— 2 nights
Drive
5
Cortona
— 1 night
Drive
6
Montepulciano
— 2 nights
Drive
7
Pitigliano
— 2 nights
Drive
8
Saturnia
— 1 night
Drive
9
Rome
— 4 nights
Train
10
Naples
— 2 nights
Ferry
11
Ischia
— 2 nights
Ferry
12
Sorrento
— 5 nights
Fly
13
Palermo
— 1 night
Drive
14
Catania
— 4 nights
+2
Drive to Messina Marittima, Ferry to Villa San Giovanni, Drive to Tropea
15
Tropea
— 3 nights
Drive
16
Matera
— 3 nights
Drive
17
Alberobello
— 1 night
Drive
18
Torre dell'Orso
— 2 nights
Fly
19
Cagliari
— 4 nights
Fly
20
Cinque Terre
— 5 nights
Train
21
Pisa
— 1 night
Train
22
Verona
— 2 nights
Train
23
Venice
— 4 nights
Fly

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Milan — 3 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.
Your list of things to see and do now includes Duomo di Milano, Piazza del Duomo, Il Cenacolo, and other attractions.

To see where to stay, other places to visit, and more tourist information, go to the Milan trip maker tool.

Chur, Switzerland to Milan is an approximately 3-hour flight. You can also drive; or take a bus. In September, plan for daily highs up to 76°F, and evening lows to 57°F. Cap off your sightseeing on the 17th (Wed) early enough to catch the train to Florence.
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Parks · Historic Sites · Nature
Side Trips
Find places to stay Sep 14 — 17:

Florence — 5 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Your day by day itinerary now includes Parco Mediceo di Pratolino (Villa Demidoff) - World Heritage Site, Guido's Tours - Wine Tours in Tuscany, Fontana del Porcellino, and other attractions you added. There's more to do: take in the views from Ponte Vecchio.

To find maps, more things to do, where to stay, and tourist information, refer to the Florence journey app.

Take a train from Milan to Florence in 2.5 hours. Alternatively, you can drive; or take a bus. In September, daytime highs in Florence are 78°F, while nighttime lows are 59°F. Finish your sightseeing early on the 22nd (Mon) to allow enough time to drive to Monteriggioni.
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Tours · Wineries · Parks
Side Trip
Find places to stay Sep 17 — 22:

Monteriggioni — 1 day

Start off your visit on the 22nd (Mon): do a tasting at Sant'Agnese Farm, get to know the fascinating history of Centro storico di Monteriggioni, then contemplate in the serene atmosphere at Chiesa di Santa Maria Assunta, then explore the historical opulence of Castello di Monteriggioni, and finally learn about winemaking at Cantinetta di Monteriggioni.

To see ratings, where to stay, more things to do, and tourist information, go to the Monteriggioni trip site.

Traveling by car from Florence to Monteriggioni takes an hour. Alternatively, you can take a bus; or take a train. In September in Monteriggioni, expect temperatures between 81°F during the day and 61°F at night. Finish up your sightseeing early on the 22nd (Mon) so you can go by car to Siena.
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Wineries · Historic Sites · Shopping
Side Trip
Find places to stay Sep 22 — 23:

Siena — 2 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Torre del Mangia has been added to your itinerary.

To see where to stay, other places to visit, maps, and more tourist information, read our Siena tour itinerary maker app.

Siena is just a short distance from Monteriggioni. September in Siena sees daily highs of 81°F and lows of 61°F at night. You'll have a few hours on the 24th (Wed) to wrap things up before traveling to Cortona.
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Historic Sites
Find places to stay Sep 22 — 24:

Cortona — 1 night

City of Art

The hilltop town of Cortona gained international attention as the subject of the 2003 film "Under the Tuscan Sun." With the Chiana Valley and Lake Trasimeno as its backdrop, Cortona is one of Tuscany's hotspots for art and culture.
Kick off your visit on the 24th (Wed): take in the spiritual surroundings of Eremo Le Celle and then stop by DelBrenna Jewelry.

Plan a Cortona trip in moments using our itinerary builder.

You can drive from Siena to Cortona in 1.5 hours. Other options are to take a train; or do a combination of bus and train. Wrap up your sightseeing on the 25th (Thu) to allow time to drive to Montepulciano.
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Historic Sites · Shopping
Find places to stay Sep 24 — 25:

Montepulciano — 2 nights

Pearl of the 16th Century

Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
On the 26th (Fri), you'll have a packed day of sightseeing: contemplate in the serene atmosphere at Tempio di San Biagio, make a trip to Piazza Grande a Montepulciano, don't miss a visit to Terrazza Del Palazzo Comunale, then appreciate the extensive heritage of Via di Gracciano nel Corso, then learn about winemaking at Tenuta Valdipiatta, and finally do a tasting at Az. Agr. Poliziano.

To see more things to do, where to stay, reviews, and other tourist information, use the Montepulciano trip planner.

Traveling by car from Cortona to Montepulciano takes an hour. Alternatively, you can take a train; or take a bus. In September, daily temperatures in Montepulciano can reach 81°F, while at night they dip to 61°F. Wrap up your sightseeing on the 27th (Sat) to allow time to drive to Pitigliano.
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Wineries · Historic Sites
Find places to stay Sep 25 — 27:

Pitigliano — 2 nights

Pitigliano is a town in the province of Grosseto, located about 80km south-east of the city of Grosseto, in Italy. Your day by day itinerary now includes Sorano Centro Storico, Masso Leopoldino and Parco Archeologico Citta del Tufo. Start off your visit on the 27th (Sat): don't miss a visit to Via CAVA ETRUSCA SAN GIUSEPPE and then get to know the fascinating history of Pitigliano Centro Storico. Get ready for a full day of sightseeing on the 28th (Sun): stroll around Parco Archeologico Citta del Tufo, admire the striking features of Masso Leopoldino, and then appreciate the extensive heritage of Sorano Centro Storico.

For maps, reviews, ratings, and more tourist information, you can read our Pitigliano sightseeing planner.

You can drive from Montepulciano to Pitigliano in 1.5 hours. Alternatively, you can take a bus. In September in Pitigliano, expect temperatures between 78°F during the day and 59°F at night. Cap off your sightseeing on the 29th (Mon) early enough to go by car to Saturnia.
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Historic Sites · Parks
Side Trip
Find places to stay Sep 27 — 29:

Saturnia — 1 night

Start off your visit on the 29th (Mon): admire the sheer force of Cascate del Mulino and then take in the natural beauty of Terme di Saturnia - Parco Termale.

For reviews, other places to visit, more things to do, and other tourist information, refer to the Saturnia online travel planner.

Drive from Pitigliano to Saturnia in an hour. Alternatively, you can take a bus. In September, daily temperatures in Saturnia can reach 81°F, while at night they dip to 61°F. On the 30th (Tue), you'll have the morning to explore before heading off to Rome.
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Nature · Parks · Spas
Find places to stay Sep 29 — 30:

Rome — 4 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Your day by day itinerary now includes Isola Tiberina as well as St. Peter's Square. And it doesn't end there: explore the ancient world of Pantheon, get great views at Colle del Gianicolo, ponder the design of Trevi Fountain, and don't miss a visit to Spanish Steps.

To see reviews, traveler tips, photos, and other tourist information, you can read our Rome trip planner.

Traveling by car from Saturnia to Rome takes 2.5 hours. Alternatively, you can do a combination of taxi and train. In September, daytime highs in Rome are 81°F, while nighttime lows are 60°F. Cap off your sightseeing on the 4th (Sat) early enough to catch the train to Naples.
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Historic Sites · Nature · Parks · Neighborhoods
Side Trip
Find places to stay Sep 30 — Oct 4:

Naples — 2 nights

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Your day by day itinerary now includes Cimitero delle Fontanelle. Start off your visit on the 4th (Sat): get engrossed in the history at Galleria Borbonica. Get ready for a full day of sightseeing on the next day: explore the different monuments and memorials at Cimitero delle Fontanelle.

For more things to do, other places to visit, reviews, and more tourist information, refer to the Naples trip itinerary builder tool.

Getting from Rome to Naples by train takes about 2 hours. Other options: drive; or fly. October in Naples sees daily highs of 74°F and lows of 58°F at night. On the 6th (Mon), wrap the sightseeing up by early afternoon so you can ride a ferry to Ischia.
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Historic Sites · Museums
Find places to stay Oct 4 — 6:

Ischia — 2 nights

Ischia is a volcanic island in the Tyrrhenian Sea. On the 6th (Mon), explore the historical opulence of Castello Aragonese d'Ischia. Keep things going the next day: contemplate the waterfront views at Baia di San Montano and then admire the ancient design of Negombo.

To find maps, photos, other places to visit, and tourist information, go to the Ischia online road trip planner.

Ride a ferry from Naples to Ischia in 2 hours. Expect a daytime high around 72°F in October, and nighttime lows around 63°F. You'll have a few hours on the 8th (Wed) to wrap things up before traveling to Sorrento.
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Nature · Spas · Parks · Historic Sites
Side Trip
Find places to stay Oct 6 — 8:

Sorrento — 5 nights

Land of the Sirens

A lovely town easily accessible from almost anywhere in the country, Sorrento overlooks the Bay of Naples and sits right on the Amalfi Drive.
You've added I Giardini di Cataldo, Il Sentiero Degli Dei, Spiaggia Grande, and other attractions to your itinerary. Venture out of the city with trips to Pompeii (Pompeii Archaeological Park, Villa dei Misteri, &more) and Vesuvio National Park (in Ottaviano). The adventure continues: look for gifts at Fattoria Terranova Shop, appreciate the views at Il Vallone dei Mulini, and appreciate the extensive heritage of Corso Italia.

For where to stay, reviews, other places to visit, and tourist information, go to the Sorrento trip planning website.

You can ride a ferry from Ischia to Sorrento in 2 hours. In October, daily temperatures in Sorrento can reach 72°F, while at night they dip to 63°F. You'll set off for Palermo on the 13th (Mon).
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Parks · Historic Sites · Nature · Beaches
Side Trips
Find places to stay Oct 8 — 13:

Palermo — 1 night

The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
Kick off your visit on the 13th (Mon): don't miss a visit to Cattedrale di Palermo, then don't miss a visit to Quattro Canti, and then indulge in some culinary diversions at a local gastronomic tour.

To find reviews, ratings, traveler tips, and other tourist information, read our Palermo day trip planner.

You can fly from Sorrento to Palermo in 2.5 hours. Other options are to take a train; or ride a ferry. Wrap up your sightseeing on the 14th (Tue) to allow time to drive to Catania.
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Tours · Historic Sites
Find places to stay Oct 13 — 14:

Catania — 4 nights

Black Pearl of Ionian Sea

The landscape surrounding Catania, a medieval city on Sicily's eastern coast, is dominated by Mount Etna, the tallest active volcano in Europe.
Get out of town with these interesting Catania side-trips: Taormina (Corso Umberto, Ancient Theatre of Taormina, &more). And it doesn't end there: get impressive views of Mt Etna, see Off-Road Tours, and don't miss a visit to Piazza del Duomo.

To see other places to visit, photos, reviews, and tourist information, use the Catania vacation builder tool.

Drive from Palermo to Catania in 2.5 hours. Alternatively, you can take a bus; or take a train. October in Catania sees daily highs of 76°F and lows of 58°F at night. Finish up your sightseeing early on the 18th (Sat) so you can travel to Tropea.
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Parks · Nature · Tours · Outdoors
Side Trip
Find places to stay Oct 14 — 18:

Tropea — 3 nights

Tropea is a municipality located within the province of Vibo Valentia, in Calabria (southern Italy).The town is a famous bathing place, situated on a reef, in the gulf of St. Your day by day itinerary now includes Capo Vaticano as well as Blanca Beach Club Tropea. The adventure continues: tour the pleasant surroundings at Tropea Beach.

To find traveler tips, ratings, other places to visit, and other tourist information, you can read our Tropea day trip planner.

Traveling by combination of car and ferry from Catania to Tropea takes 3.5 hours. Alternatively, you can do a combination of bus and train; or take a train. In October, daytime highs in Tropea are 75°F, while nighttime lows are 57°F. On the 21st (Tue), you'll have the morning to explore before heading off to Matera.
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Outdoors · Parks · Beaches
Side Trip
Find places to stay Oct 18 — 21:

Matera — 3 nights

Subterranean City

Famous for its resemblance to the ancient settlements of Jerusalem and Cappadocia, Matera remains one of the oldest inhabited cities in the world.
Your day by day itinerary now includes Chiese rupestri Madonna delle Virtu e San Nicola dei Greci as well as Materasum Ipogeo. Step out of Matera to go to Castellana Grotte and see Grotte di Castellana, which is approximately 1h 15 min away. Next up on the itinerary: appreciate the extensive heritage of Sassi di Matera.

To see photos, ratings, where to stay, and more tourist information, use the Matera attractions site.

Traveling by car from Tropea to Matera takes 4 hours. Alternatively, you can do a combination of train and bus. Traveling from Tropea in October, you will find days in Matera are slightly colder (68°F), and nights are about the same (53°F). Wrap up your sightseeing by early afternoon on the 24th (Fri) to allow time for the car ride to Alberobello.
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Historic Sites · Nature · Parks
Side Trip
Find places to stay Oct 21 — 24:

Alberobello — 1 night

Alberobello is a small town and comune of the Metropolitan City of Bari, Apulia, southern Italy. Statua di Domenico Modugno has been added to your itinerary. On the 24th (Fri), don't miss a visit to Statua di Domenico Modugno and then don't miss a visit to Centro Storico di Polignano a Mare.

To see photos, reviews, traveler tips, and more tourist information, go to the Alberobello holiday planner.

Traveling by car from Matera to Alberobello takes 1.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. In October, daily temperatures in Alberobello can reach 68°F, while at night they dip to 53°F. On the 25th (Sat), you'll have the morning to explore before heading off to Torre dell'Orso.
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Find places to stay Oct 24 — 25:

Torre dell'Orso — 2 nights

Torre Sant'Andrea has been added to your itinerary.

To find more things to do, traveler tips, maps, and other tourist information, go to the Torre dell'Orso tour planner.

You can drive from Alberobello to Torre dell'Orso in 2 hours. Alternatively, you can do a combination of train and bus; or take a bus. In October, plan for daily highs up to 73°F, and evening lows to 55°F. You will have some time to spend on the 27th (Mon) before leaving for Cagliari.
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Nature · Parks
Side Trip
Find places to stay Oct 25 — 27:

Cagliari — 4 nights

City of Sun

The capital of Sardinia, Cagliari is spread out over seven hills and still bears the marks of its past conquerors, including the Phoenicians, Carthaginians, and Romans.
Your day by day itinerary now includes Poetto. Venture out of the city with trips to Area Archeologica di Nora (in Pula), Porto Flavia (in Iglesias) and Cala Domestica (in Buggerru).

For other places to visit, traveler tips, more things to do, and other tourist information, read our Cagliari route website.

You can fly from Torre dell'Orso to Cagliari in 3 hours. Alternatively, you can do a combination of bus, train, and ferry; or do a combination of bus and ferry. In October, plan for daily highs up to 77°F, and evening lows to 59°F. You'll have a few hours on the 31st (Fri) to wrap things up before traveling to Cinque Terre.
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Parks · Beaches · Outdoors · Historic Sites
Side Trips
Find places to stay Oct 27 — 31:

Cinque Terre — 5 nights

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
You've added Borgo Storico di Manarola, Via dell'Amore, Borgo Storico di Riomaggiore, and other attractions to your itinerary. You'll find plenty of places to visit near Cinque Terre: Porto Venere (Castello Doria, Palazzata a Mare, &more). There's much more to do: get into the urban bustle at Vernazza, step into the grandiose world of Castello di Riomaggiore, take a leisurely stroll along Passeggiata Lungomare, and appreciate the extensive heritage of Borgo Antico.

For maps, photos, more things to do, and other tourist information, read Cinque Terre trip site.

Fly from Cagliari to Cinque Terre in 3 hours. Alternatively, you can do a combination of bus, ferry, and train; or do a combination of train, bus, and ferry. In October, Cinque Terre is little chillier than Cagliari - with highs of 71°F and lows of 54°F. On the 5th (Wed), you'll have the morning to explore before heading off to Pisa.
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Historic Sites · Parks · Outdoors · Trails
Side Trip
Find places to stay Oct 31 — Nov 5:

Pisa — 1 night

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Your day by day itinerary now includes Duomo di Pisa, Ponte di Mezzo, Camposanto, and other attractions you added. Kick off your visit on the 5th (Wed): don't miss a visit to Piazza dei Miracoli, stroll the grounds of Camposanto, admire the landmark architecture of Leaning Tower of Pisa, take in the spiritual surroundings of Duomo di Pisa, then make a trip to Knights’ Square, and finally snap pictures at Ponte di Mezzo.

To find other places to visit, more things to do, photos, and other tourist information, read Pisa trip itinerary planning site.

Take a train from Cinque Terre to Pisa in 2 hours. Alternatively, you can drive. In November, daily temperatures in Pisa can reach 61°F, while at night they dip to 46°F. Finish up your sightseeing early on the 6th (Thu) so you can catch the train to Verona.
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Historic Sites
Find places to stay Nov 5 — 6:

Verona — 2 nights

City of Romeo and Juliet

The famous setting for Shakespeare's star-crossed lovers, Romeo and Juliet, Verona is one of northern Italy's main tourist destinations, largely owing to its incredibly rich artistic heritage.
Your day by day itinerary now includes Ponte Pietra, Teatro romano di Verona, Ponte Scaligero, and other attractions you added. Kick off your visit on the 6th (Thu): stop by Cioccolateria Via Conventino and then take a stroll through Quinzano. On your second day here, wander the streets of Piazza delle Erbe, admire the striking features of Domus Mercatorum, examine the collection at Casa di Giulietta, then don't miss a visit to Torre dei Lamberti, then explore the historical opulence of Piazzale Castel San Pietro, and finally see a show at Teatro romano di Verona.

To see maps, traveler tips, and other tourist information, go to the Verona trip itinerary planning app.

You can take a train from Pisa to Verona in 3 hours. Alternatively, you can drive; or take a bus. Expect slightly colder temperatures when traveling from Pisa in November; daily highs in Verona reach 54°F and lows reach 41°F. You will have some time to spend on the 8th (Sat) before leaving for Venice.
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Historic Sites · Neighborhoods · Shopping · Nightlife
Find places to stay Nov 6 — 8:

Venice — 4 nights

City of Romance

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.
Campo del Ghetto has been added to your itinerary. There's still lots to do: contemplate the waterfront views at Canal Grande, contemplate the long history of Squero di San Trovaso, take a stroll through Cannaregio, and make a trip to Torre dell'Orologio.

To find reviews, more things to do, and other tourist information, read Venice journey planning website.

Drive from Verona to Venice in 1.5 hours. Alternatively, you can take a shuttle; or take a train. Expect a daytime high around 56°F in November, and nighttime lows around 43°F. Wrap up your sightseeing on the 12th (Wed) early enough to fly back home.
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Nature · Parks · Historic Sites · Neighborhoods
Find places to stay Nov 8 — 12:

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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Isola d'Ischia travel guide

3.9
Thermal Spas · Castles · Beaches
Floating in the Bay of Naples, mountainous Isola d'Ischia boasts a 34 km (21 mi) long coastline. Nearly 6 million tourists vacation on this volcanic island every year, attracted by its famous thermal spas, beaches, and excellent food. The largest of its beachside towns, e Ischia, often called the Green Island, features a temperate climate allowing a range of Mediterranean plants to thrive in the fertile volcanic soil. On the southern side of the island, you'll see palms, cacti, and agave plants. Other places to visit include the almond groves, vineyards, and olive plantations that cover the northern side of Ischia. Farther away from the island's coastline, you can explore villas, gardens, and ancient towers.
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Province of Lecce travel guide

4
Beaches · Landmarks · Outdoor Activities
Lecce is a historic city of 94,766 inhabitants (2015) in southern Italy, the capital of the province of Lecce, the second province in the region by population, as well as one of the most important cities of Apulia. It is the main city of the Salentine Peninsula, a sub-peninsula at the heel of the Italian Peninsula and is over 2,000 years old.Because of the rich Baroque architectural monuments found in the city, Lecce is commonly nicknamed "The Florence of the South". The city also has a long traditional affinity with Greek culture going back to its foundation; the Messapii who founded the city are said to have been Cretans in Greek records. To this day, in the Grecìa Salentina, a group of towns not far from Lecce, the griko language is still spoken.In terms of industry, the "Lecce stone"—a particular kind of limestone—is one of the city's main exports, because it is very soft and workable, thus suitable for sculptures. Lecce is also an important agricultural centre, chiefly for its olive oil and wine production, as well as an industrial centre specializing in ceramic production.

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Sardinia travel guide

4.2
Beaches · Landmarks · Caves
Sardinia, with its Mediterranean atmosphere and charm, is loved by visitors looking for things to do outdoors on their holiday, like swimming, boating, windsurfing, hiking, climbing, and camping. Taking advantage of the island's near-perfect summer weather, visitors tend to overcrowd Sardinia's coastal areas. The inner life of the island, away from the most popular vacation spots, remains largely unblemished by mass tourism and commercialization. Sardinia is steeped in history and has a colorful character quite different from the rest of Italy. This is where the ancient Nuragic society, whose stone monuments still litter the land, flourished more than three millennia ago--predating the Etruscan civilization in mainland Italy by several hundred years. Sardinia's seaside resorts may be among the best in the world, but its quieter and more interesting countryside offers a greater array of attractions, including a patchwork of forests, citrus groves, and medieval villages.
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Veneto travel guide

4.2
Bodies of Water · Specialty Museums · Historic Walking Areas
An independent republic until Napoleon's invasion in 1797, Veneto is among the wealthiest and most developed regions in the country. The region has a bustling tourism industry, drawing nearly 70 million visitors annually to its historical, natural, artistic, cultural, musical, and culinary treasures. Though most tourists begin and end their Veneto holiday in Venice, the area has plenty more to offer. A range of attractions await beyond the capital city, including World Heritage-listed Palladian villas, seaside resorts, vineyards, lakes, beaches, thermal baths, lush parks, and imposing mountain ranges. Veneto's clubs, bars, and restaurants make for a lively nightlife in the region's thriving cities.
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