Formerly the main entrance to the city, the Porta Napoli (so named as it led to Naples) is still the most impressive entrance to the centro storico, although you will most likely enter it from Piazza Sant'Oronzo. The center of the city (new and old) is roughly centred on Sant'Oronzo and Piazza Mazzini - a newer, architecturally uninteresting square which is, however, important as it serves as an anchor for the shopping district running along Via Trinchese between the two squares. Hogan, SOCIETY, Max Mara, COIN, Henry Cottons, White7 (if you need a fix of Etro, Burberry's, or Aqua di Parma), Sephora, and numerous small boutiques (SMART for example, has a great selection of high-end menswear) provide significantly better selection than most towns of this size (and you didn't come to shop, or you would clearly be in Milan). Of note are De Salvatore (on the corner where via Templari turns into via Umberto I as you walk from Pza. Sant'Oronzo to Santa Croce), a small perfumerie carrying products from the wondrous Santa Maria Novella (Firenze) and Annick Goutal among others. For those who like such things, Lecce is also known for its papier mache (carta pesta) and there are a number of shops between Piazza Sant'Oronzo and Santa Croce, as well as a few on the Corso (e.g. next to Liberrima in the courtyard) As an aside, Ennio Capasa, the creator behind Costume Nationale, hails from Lecce.
Points you have to see include the epitome of barocco lecchese that is the Basilica Santa Croce (pictured) as well as the amphitheatre on Piazza Sant'Oronzo, the Duomo (with its campanile high enough to serve as a lookout for unfriendly ships approaching the Adriatic coast) and Corso Vittorio Emanuele II all the way to Porta Rudiae, not to mention the various other twisted streets, palazzi, churches, and of course cafes that crowd the centro storico. Lecce makes a good base to explore Salento from, or if you are staying in the countryside, to dip into if you want a bit more life. The train to Rome is convenient, and there is a shuttle bus that runs to the airport in Brindisi, a mere half hour away.
One warning - the siesta still exists here. Everything, and we mean everything, closes from around 1:30 to 4:30. Perfect for strolling around the old city to see the sites without the crowds, unless it is July or August, in which case you will understand why everything is shut - it is sweltering. Another warning - the festa patronale (from the 24th to 26th of August - yes, a three-day saint's day) is the most over the top crowded event ever seen (pick below). 2010 saw Sant'Oronzo celebrated with the ancient religious tome "Smoke on the Water". If you are afraid of crowds, or fireworks blasting from the main piazza, avoid town those days.
Eat, drink, and sleep - a bit of it all
As we are still exploring this charming area, this is only a first taste of what is on offer. Clearly, a gelato from Natale and an espressino (a shot of espresso with foamed milk, akin to a miniature cappuccino) at Cafe Alvino are must-dos. If you like traditional homemade pasta, or want to be exposed to la cucina povere, Nona Tetti and/or Le Zie should be on your list. More inventive Salentine dining could bring you to the bistro at personé (we dream of their interpretations of fish carpaccio), and of course to Osteria della Divina Providenza. Fifteen worthwhile minutes away from Lecce off Piazza Salandra in Nardó is the brilliant modern Italian kitchen at Modó, run by a couple whose backgrounds are perfect for merging design and taste (he is a chef, she is an architect).
Also known by some as "Via del Pub" the street running from Porta San Biaggio to Piazzetta Santa Chiara is packed from Thursday through Sunday nights (yes, Sunday is a big night out here). The entire stretch is covered in bars, cafes, and restaurants - and thus becomes a throng of young humanity overflowing when weather permits (i.e. almost all year). Places continually change, but if you are feeling the need to be in the midst of a crowd this is your best best, particularly if you are under 25. For those who find that a bit young, the wine bars on Via Umberto near the Basilica have an older, yet no less stylish, crowd.
P.zza V. Emmanuelle II, 8 (Piazzetta Santa Chiara)
+39 333 197 6161
One of our favorites all around spots in Lecce, "Headed South" is run by a team comprising 3 northern Italians and 2 Leccese, 4 of whom worked together in Dublin. The result is what might be called an Italian-esque gasto-pub, with emphasis on not only Salentine wines but also those of the north, as well as (thanks to Dublin) varied beers, ales, and stouts. The menu emphasizes fresh cheeses, cold cuts, and local produce. Aside from Mario at Shui 13, Domenico, Laura, Boris, and Ilaria are really the only staff in Lecce fully fluent in English. (Not that you needed any further incentive to drop by.)
Le Zie / Trattoria Cucina Casareccia
Via Colonnello Archimede Costadura, 19
+39 0832 245178
For some reason, everyone in Lecce calls this place "Le Zie" ("the Aunts") while the foreign guides all refer to it as Trattoria Casareccia. Who cares what it is called - this is the pinnacle of la cucina povere. Reservations are required, and when you arrive you ring the bell of what appears to be a house, and are then led into what looks like an old living room stuffed with dining tables. What you get, however, is several hours (yes, hours) of the absolute best traditional pugliese cuisine. Plan a long lunch here, a very long lunch.
Piazetta Regina Maria, 17
Traditional homemade Salentine pastas, with a menu that changes in accord with the seasonal offerings (pasta with sea urchins was the latest addition - and quite good!). Even more amazing is that a huge antipasti (order one antipasti misto per uno to share), wine, and the large pasta dishes and a couple can be amazing sated for under 30 Euros. Located just off Via Augusto Imperatore (La Movida).
via G.B. del Tufo, 16
+39 0832 242 091
Just at the beginning of La Movida in a small piazzetta is this restaurant which is highly recommended for its pizza - the rest of the menu is good, but the pizza is amazing. (Our favorite is the Tramp - no, not for the name, but as it it loaded with quickly fried aubergine, sundried tomatoes, and fior di latte). Pizza oven on only for dinner. Closed Mondays.
persone b&b, bistro, & cafe
via Umberto I, 9 (angolo Santa Croce)
+39 0832 246 302 infoline
Situated next to Santa Croce in the heart of the centro storico, persone is located just a few metres from Santa Croce, this cafe & restaurant attached to a similarly named B&B is highly recommended - either for a glass of wine, or even better, a meal starting with tuna tartare followed by polpito, or a brilliant "fan" of beef.
via Umberto I, 21
+39 0832 665 896
One of several wine bars/restaurants on the street just after Basilica Santa Croce; the staff are great at recommending excellent Salentine wines of all types. Mario speaks perfect English, and has yet to lead us astray in a wine suggestion.
Osteria della Divine Provvidenza
via Rubichi, 4c
+39 0832 179 2078
Brilliant food at this slightly more expensive (for Lecce) restaurant about a minute from Piazza Sant'Oronzo (head behind the Mayor's Office towards Porta Napoli). The mixed antipasti including seafood is amazing, their homemade pastas run from light and summery (e.g. the one with lemon) to heavy and filling (shrimp filled ravioli). Closed Mondays.
via Federico D'Aragona, 8
+39 0832 090 495
Ristorante/Pizzeria with a fairly broad selection, reasonable prices, and pleasantly stylish interior as well as outdoor seating on the piazetta out back. Not the best place in town, but as it is large you can usually get a seat and the food is still quite good. Located on the "pub street" running from SantOronzo to Porta San Biaggio.
Via Augusto Imperatore, 19 (off Piazza Sant'Oronzo)
+39 0832 246 311
If you like modern Italian architecture even when you are in the midst of a baroque palazzo, this hotel is for you. The location is stellar, and the roof terrace cafe only makes it better - the editor has the roof terrace in the next building. but don't worry they are both equally shielded from prying eyes.
via Trinchese (just off Piazza Sant'Oronzo heading towards Piazza Mazzini)
This may be the best ice cream to be found on the Adriatic (this and Alvino - below - are fighting for the title). Absolutely stellar gelato, not to mention pastries (you MUST try the pasticiotto - unique to the Lecce region), and the way they pack even simple purchases. The mandorlo (almond) and the fior di mandolo (almond flower) are the editor's two faves, but all are excellent.
Piazza Sant'Oronzo, 30
+39 0832 246748
Just across from the amphitheatre on Piazza Sant'Oronzo, Alvino may be the best known cafe in Lecce - everyone of every age goes there to see, be seen, and even to have excellent coffee, pastries, and ice cream (or just a prosecco). You haven't been to Salento if you haven't at least stopped by and had an espresso at the bar here - although some might say that unless you posed on one of the outdoor tables you haven't been to Alvino at all.
Liberrima Wine & Bookshop
Combined cafe on Corte dei Cicala, Italian bookstore, and next door (in a courtyard off Corso V. Emanuele II) the wine store with travel and foreign language books. Although the prices for wines are higher than in some other markets, the assistance from the staff, the packaging, and the assorted other Salentine food products make the prices worthwhile.
Temporary bike rental system with check-in/out automated stands in 7 convenient locations (including the train station, Piazza Sant'Oronzo, Piazza Mazzini, and the main parking at Carlo Pranzo). Useful if you want a bike for an hour or so - check the site for details and locations to get the cards activated - chances are your hotel is one of those spots.
Via XX Settembre 5/A
+39 0832 303832
Jazz bar and restaurant located just a few minutes walk from the centro storico (exiting Porta San Biago you go around the Piazza D'Italia and it is around the back on Via XX Settembre). Modern interior that fits well with the original vaulted ceilings, Svolta has been known to host such eccentric styles as Balkanic Jazz (was there, still not sure what it is) played by musicians from the region. Saturday night is boys' night - girls welcome, but don't expect to be flirted with.
Magnolia Art Sushi Bar
via Santa Maria del Paradiso (near Porta Rudiae in the centro storico)
+39 320 649 8712
Lecce has three sushi restaurants, of which Jeffrey's Guide has tried all and recommends two, one of which is Magnolia. With a great (but very small) interior and pleasant outside seating on a tiny piazzetta just off the Corso inside Porta Rudiae (look for the sign on the right as you come in from Rudiae), dinner for two with wine ran just at 60 Euros, which is pricey for Lecce but not when you think in terms of other places.
Viale Ugo Foscolo, 11/13
+39 0832 493085
Just outside the centro storico off the Piazza del Bastione at the northern entrance to Lecce from Brindisi, Fusion is the best Asian in Salento. Full stop. Check their menu on the website.