21 days in Italy Itinerary

Created using Inspirock Italy vacation builder
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Make it your trip
1
Lecce
— 2 nights
Drive
2
Otranto
— 2 nights
Drive
3
Ostuni
— 2 nights
Drive
4
Cisternino
— 2 nights
Drive
5
Alberobello
— 2 nights
Drive
6
Castellana Grotte
— 2 nights
Drive
7
Matera
— 1 night
Drive
8
Castel del Monte
— 1 night
Drive
9
Trani
— 2 nights
Drive
10
Polignano a Mare
— 4 nights

S M T W T F S
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24
25
26
27
28
29
30
31
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19

Lecce — 2 nights

Florence of the South

Known as the Florence of the South, Lecce is distinguished for its elaborate Baroque monuments.
Kick off your visit on the 29th (Sat): steep yourself in history at Basilica di Santa Croce, appreciate the extensive heritage of Piazza del Duomo, then take in the architecture and atmosphere at Duomo di Lecce, and finally make a trip to Centro Storico, Lecce. On the 30th (Sun), you'll have a packed day of sightseeing: take in the architecture and atmosphere at Basilica di Santa Caterina d'Alessandria, steep yourself in history at Centro Storico di Gallipoli, then cast your line with a fishing tour, and finally take an in-depth tour of Museo Faggiano.

To see where to stay, photos, other places to visit, and tourist information, you can read our Lecce road trip app.

If you are flying in from Romania, the closest major aiports are Brindisi Airport, Bari Karol Wojtyła Airport and Lamezia Terme Airport. Expect a daytime high around 26°C in October, and nighttime lows around 15°C. Wrap up your sightseeing on the 31st (Mon) early enough to drive to Otranto.
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Historic Sites · Tours · Wildlife · Museums
Side Trips

Otranto — 2 nights

Otranto is a town and comune in the province of Lecce (Apulia, Italy), in a fertile region once famous for its breed of horses.It is located on the east coast of the Salento peninsula. On the 31st (Mon), get outside with Maldive del Salento Pescoluse, look and learn at Sidereus, and then see some colorful creatures with a scuba or snorkeling tour. Keep things going the next day: explore the fascinating underground world of Grotta della Poesia, look for gifts at Roberta Risolo Art Jewels, contemplate the waterfront views at Cava di Bauxite, then take in the spiritual surroundings of Cattedrale Di Otranto, and finally get to know the fascinating history of Centro Storico Otranto.

For photos, where to stay, more things to do, and tourist information, go to the Otranto trip maker website.

You can drive from Lecce to Otranto in an hour. Alternatively, you can take a bus; or take a train. Expect a daytime high around 26°C in October, and nighttime lows around 15°C. Finish your sightseeing early on the 2nd (Wed) to allow enough time to drive to Ostuni.
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Outdoors · Nature · Historic Sites · Parks
Side Trips

Ostuni — 2 nights

Ostuni is a city and comune, located about 8 km from the coast, in the province of Brindisi, region of Apulia, Italy). Start off your visit on the 2nd (Wed): pause for some serene contemplation at Duomo di Ostuni, appreciate the extensive heritage of Centro Storico, then stop by Il Botteghino, then visit Mahi Sportfishing Puglia, and finally take an in-depth tour of Masseria Brancati. Get ready for a full day of sightseeing on the next day: get to know the fascinating history of Piazza della Liberta, then take in the architecture and atmosphere at Tempio di San Giovanni al Sepolcro, then don't miss a visit to Colonne Terminali della Via Appia, and finally identify plant and animal life at Torre Guaceto Marine Protected Area.

To see ratings, more things to do, other places to visit, and other tourist information, use the Ostuni trip planner.

Drive from Otranto to Ostuni in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. November in Ostuni sees daily highs of 21°C and lows of 13°C at night. Finish your sightseeing early on the 4th (Fri) so you can drive to Cisternino.
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Historic Sites · Wildlife · Tours · Museums
Side Trips

Cisternino — 2 nights

Cisternino is a comune in the province of Brindisi in Apulia, on the coast of south-eastern Italy, approximately 50km north-west of the city of Brindisi. Kick off your visit on the 4th (Fri): get to know the fascinating history of Centro Storico, look for all kinds of wild species at Valle d’itria e Dintorni, appreciate the views at Valle d'Itria, then take in the spiritual surroundings of Basilica di San Martino, and finally examine the collection at MuBa - Museo della Basilica di San Martino. On the 5th (Sat), you'll have a packed day of sightseeing: examine the collection at Palazzo Ducale, learn about winemaking at L'Acropoli di Puglia, awaken your taste buds at I Pastini, then pause for some serene contemplation at Chiesa Matrice di San Nicola Patara, and finally take a stroll around La Casbah della Valle d'Itria.

To see ratings, photos, and more tourist information, read Cisternino trip itinerary tool.

Cisternino is just a stone's throw from Ostuni. In November, daytime highs in Cisternino are 21°C, while nighttime lows are 13°C. Finish up your sightseeing early on the 6th (Sun) so you can go by car to Alberobello.
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Historic Sites · Parks · Wineries · Museums
Side Trip

Alberobello — 2 nights

Alberobello is a small town and comune of the Metropolitan City of Bari, Apulia, southern Italy. Kick off your visit on the 6th (Sun): visit Centro Storico Locorotondo, admire the striking features of I Trulli di Alberobello - World Heritage Site, then make a trip to Parrocchia Sant'Antonio di Padova, and finally browse the exhibits of Trullo Sovrano. Get ready for a full day of sightseeing on the next day: pause for some serene contemplation at Taranto Catherdral - Duomo of San Cataldo, then take an in-depth tour of Museo Nazionale Archeologico, then step into the grandiose world of Castello Aragonese, and finally snap pictures at Ponte Girevole.

For reviews, maps, photos, and more tourist information, refer to the Alberobello trip itinerary website.

Alberobello is just a stone's throw from Cisternino. Traveling from Cisternino in November, expect Alberobello to be slightly colder, temps between 18°C and 9°C. Finish your sightseeing early on the 8th (Tue) so you can drive to Castellana Grotte.
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Historic Sites · Museums · Neighborhoods
Side Trips

Castellana Grotte — 2 nights

Castellana Grotte is a town and comune in the province of Bari, Apulia, southern Italy. Start off your visit on the 8th (Tue): take in the spiritual surroundings of Chiesa di San Leone Magno, explore the striking landscape at Grotta del Trullo, see the interesting displays at Museo Speleologico Franco Anelli, then explore the fascinating underground world of Grotte di Castellana, and finally take in the spiritual surroundings of Santuario Madonna della Vetrana. On the next day, don't miss a visit to Bar Libreria Macondo, take in nature's colorful creations at Masseria del Barone, then examine the collection at Museo Nazionale Archeologico di Gioia del Colle, then delve into the distant past at Abbazia Madonna della Scala, and finally don't miss a visit to Centro Storico.

To find ratings, traveler tips, maps, and tourist information, go to the Castellana Grotte trip itinerary maker website.

Castellana Grotte is just a stone's throw from Alberobello. In November, plan for daily highs up to 18°C, and evening lows to 9°C. Cap off your sightseeing on the 10th (Thu) early enough to go by car to Matera.
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Parks · Historic Sites · Nature · Museums
Side Trips

Matera — 1 night

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.
Start off your visit on the 10th (Thu): capture your vacation like a pro with an inspiring photography tour, explore the fascinating underground world of Casa Grotta di Vico Solitario, and then appreciate the extensive heritage of Sassi di Matera. On the 11th (Fri), you'll have a packed day of sightseeing: contemplate the long history of Cripta del Peccato Originale, walk around Parco della Murgia Materana, then admire the striking features of Cattedrale di Matera, then don't miss a visit to Casa Noha, and finally explore the ancient world of Materasum Ipogeo.

To see ratings, where to stay, traveler tips, and other tourist information, go to the Matera trip builder app.

You can drive from Castellana Grotte to Matera in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In November, plan for daily highs up to 18°C, and evening lows to 9°C. Finish up your sightseeing early on the 11th (Fri) so you can go by car to Castel del Monte.
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Historic Sites · Parks · Tours · Nature

Castel del Monte — 1 night

Start off your visit on the 12th (Sat): take some stellar pictures from Santo Stefano di Sessanio.

To see ratings, other places to visit, photos, and more tourist information, refer to the Castel del Monte planner.

Traveling by car from Matera to Castel del Monte takes 5 hours. On the 12th (Sat), wrap the sightseeing up by early afternoon so you can drive to Trani.
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Historic Sites
Side Trip
Highlights from your trip

Trani — 2 nights

Trani is a seaport of Apulia, in southern Italy, on the Adriatic Sea, 40km by railway West-Northwest of Bari. Start off your visit on the 13th (Sun): pause for some serene contemplation at Cattedrale di Trani, then step into the grandiose world of Castello di Trani, then take a leisurely stroll along Porto di Trani, and finally don't miss a visit to La Maria del porto. On your second day here, make a trip to Villa Comunale, examine the collection at Museo del Confetto Mucci Giovanni, then take in the architecture and atmosphere at Chiesa Santa Maria Vetere di Andria, then step into the grandiose world of Castel del Monte, and finally contemplate in the serene atmosphere at Cattedrale di Ruvo di Puglia.

To see traveler tips, where to stay, other places to visit, and more tourist information, use the Trani driving holiday planner.

Getting from Castel del Monte to Trani by car takes about 4 hours. In November, daily temperatures in Trani can reach 20°C, while at night they dip to 9°C. Finish your sightseeing early on the 14th (Mon) to allow enough time to drive to Polignano a Mare.
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Historic Sites · Museums
Side Trips

Polignano a Mare — 4 nights

Polignano a Mare is a town and comune in the Metropolitan City of Bari, Apulia, southern Italy, located on the Adriatic Sea. Polignano a Mare is known for sightseeing, beaches, and outdoors. Your trip includes some of its best attractions: make a trip to Centro Storico di Polignano a Mare, get outside with Outdoor Activities, contemplate the long history of Piazza Dell'orologio, and explore the historical opulence of Il Castello di Santo Stefano.

To find more things to do, ratings, traveler tips, and tourist information, read Polignano a Mare tour itinerary planning tool.

Drive from Trani to Polignano a Mare in 1.5 hours. Alternatively, you can take a train; or take a bus. In November in Polignano a Mare, expect temperatures between 18°C during the day and 9°C at night.
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Historic Sites · Outdoors · Tours · Beaches
Side Trips

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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