The first settlement was founded by the Messapians, the native population of Salento peninsula, probably with the name of Odra. It was then rebuilt by the Greeks that renamed it as Hydrus (Ὑδροῦς – meaning "water"), becoming one of the centres of Magna Graecia. After the Roman conquest the city was called Hydruntum and became soon an important commercial port, due to its location in the easternmost point of Italy.

During the 3rd century AD Hydruntum welcomed a Jewish community that contributed to the cultural growth of the city, in which one of the most relevant libraries of Europe was built. In the 12th century this community counted about 500 families, that continued to receive protection under the rule of Emperor Frederick II, who made the town capital of the justiciarate of Terra d'Otranto (Land of Otranto), part of the Kingdom of Sicily.

In 1480 Otranto was conquered by the Ottoman troops, that beheaded about 800 civilians who refused to deny their Christian faith. The siege lasted 13 months and concluded with the liberation of the city thanks to king Ferdinand I of Naples. Otranto had been reduced to a pile of rubble and its age of splendor definitely finished, leaving to Lecce the role of cultural centre of the area.

• 40.14514718.4906751 Tourist Information Office (Pro Loco Otranto), Via G. M. Laggetto, 30, ☏ +39 0836 806585, proloco.otranto@gmail.com. 09:00-13:00/17:00-21:00. 

• 40.65805617.9466671 Brindisi Airport (BDS ^IATA). It is the closest airport (95 km) and provides efficient connections through buses. (updated Jun 2018)

• Trainline. 
• 40.1494818.4816432 Otranto railway station, Via Stazione, 16. The town is served by the trains of Ferrovie del Sud Est (FSE), a regional railway company that provides a link to Lecce. (updated Jun 2018)

Reaching Otranto from the airport of Brindisi requires more or less an hour. Reach the freeway to bypass the center of Brindisi, then merge onto the , arrived in Lecce join the Tangenziale Ovest then follow the until the Adriatic sea.

If you want to visit the old town remember that it is a limited traffic zone (ZTL), so the best choice is to leave your car parked outside of it. Your vehicle will reveal useful to explore the coastline and countryside.

Definitely the best way to discover the colorful alleys and walk along the boardwalk or the medieval walls.

• 40.14454218.4923651 Aragonese Castle (Castello Aragonese), Piazza Castello, ☏ +39 0836 210094, castelloaragoneseotranto@gmail.com. M-F 10:00-19:00, Sa Su 10:00-20:00. A majestic fortress with three cylindrical towers and imposive rampants, deeply reinforced after the siege in 1481. You can visit the courtyard, various halls, the roof and even the dungeons. For detailed information about prices check the website.  

• 40.14583318.4911112 Cathedral (Duomo di Otranto), Piazza Basilica, ☏ +39 0836 801437. Jun - Sep: 07:00-12:00,15:00-19:00. An interesting church consecrated in 1088, and built on the remains of a Messapic village, a Roman domus and an early Christian temple. It represents an interesting mixture of Byzantine and Romanesque elements, and contains an enormous mosaic pavement, relics of the Martyrs, and a crypt resembling the Mezquita of Córdoba. Free.  
• 40.1455918.4926343 Church of San Pietro (Chiesa di San Pietro), Via San Pietro (in the historic center), ☏ +39 389 106 0055. Jun-Sep: 10:00-12:00, 16:30-20:30 (everyday). One of the most important examples of Byzantine art in the whole southern Italy. Free.  
• 40.14675618.4906344 Monument erected to the Heroes and Martyrs, Lungomare degli Eroi. It consists in a bronze statue of a woman holding the flag and the cross, symbol of the Christianity defended till the death by almost 800 citizens, killed by the Ottoman invaders in 1480. 
• 40.14641218.4902345 Porta Terra, Via Vittorio Emanuele/Largo Porta Alfonsina. Daily. The most ancient gate to the historic center, a sober arch high about 10 m (33 ft) tall, in the western side of the medieval walls. Free. (updated Jun 2018)
• 40.14647518.4906876 Porta Alfonsina, Largo Porta Alfonsina (in front of Porta Terra). Daily. The main gate of the town, between the two majestic towers "Ippolita" and "Duchessa", dedicated to king Alfonso II of Naples, liberator of the city from Turkish invaders. Free. (updated Jun 2018)
• 40.14551118.4906937 Museo Diocesano, Piazza Basilica (in front of the Cathedral), ☏ +39 0836 801133, museodiocesano.otranto@cslpuglia.net. Here you can admire treasures from the Cathedral and other churches of the Otranto diocese: church vestments, paintings, sculptures and remains of a 4th-century AD mosaic. It's inside Palazzo Lopez, built during the Spanish government period. (updated Jun 2018)

• 40.13230918.5006468 Bauxite quarry (Cava di bauxite), SP369, Contrada Orte (near the monument to pope John Paul II). Daily. A small lake grew into an abandoned bauxite quarry, characterised by an impressive red color of the ground, surrounded by Mediterranean scrubland. It has become a true must-see in the last years for all tourists. Free. (updated Jun 2018)
• 40.10742218.5198789 ^{[formerly dead link]} Punta Palascìa Lighthouse (Capo d'Otranto), Strada Provinciale 87 (under the Italian Navy base), ☏ +39 099 775 3782. 32 meters (105 ft) tall white cylindrical lighthouse located on the easternmost point of Italy. Walking along a path it's possible to climb over the 2-storey keeper’s house ad admiring the wonderful view of the Adriatic Sea. It is open to guided tours for visitors, particularly at New Year, when you can see the first dawn of the New Year.  
• Cave of San Giovanni. 
• Catacombs of Torre Pinta. 

• 40.14504618.4914691 LaltroBaffo, Via Cenobio Basiliano 23 (in the old town, on the road that runs between the castle and the duomo), ☏ +39 0836 801636, info@laltrobaffo.com. Tu-Su 12:30-14:00, 19:00-23:00, closed on Monday. Italian cooking, inventive without betraying its roots, in a very traditional setting. (updated Nov 2017)
• 40.14657718.4901332 La Bella Idrusa, Lungomare degli Eroi, 1, ☏ +39 0836 801475. 19:00-24:00. Pizza and Apulian cuisine in a homey restaurant under the historic center walls. (updated Jun 2018)