Because we have the VV Best hand selected Italian experts in place, I sometimes don’t go back and visit some of my favorite destinations, as I am always on the search for new locations and new experiences. I know my experts are constantly evaluating hotels and guides, but my serendipitous cooking class in Sicily led me to add Puglia to my travel schedule. This visit was a reminder of how much I adore Italy – picturesque landscapes, excellent food, warm and welcoming locals – Italy is definitely a repeat destination!

Meandering the chic heel of Italy through Puglia, an enchanting region of undiscovered towns, white sandy beaches, fields and fields of ancient olive trees, important ruins, and delicious food and wine. This is also an excellent area for bicycling.

Spend three or four nights in Lecce, Puglia’s cultural capital and one of Italy’s most enchanting towns. Our preferred Hotel La Fiermontina Urban Resort is charmingly attached to the ancient city wall and the refreshing and essential pool is situated amid a small grove of ancient olive trees. So many options besides touring, take a private cooking class in a former palace and learn the secrets of typical Puglian specialties. Tour with your expert private guide and wander through Lecce’s atmospheric narrow streets and visit prominent landmarks such as a Roman amphitheater, the Basilica di Santa Croce, and Baroque churches and palaces built of ornately carved Lecce stone, a distinctive colored limestone. Also visit Museo Faggiano, a unique archaeological museum featuring unearthed antiquities found under a private home.

From Lecce, enjoy day trips to the stunning white city of Ostuni, a genuine and charming example of whitewashed Mediterranean architecture. The town is a series of various levels, staircases, alleys and winding narrow roads, all very easy to navigate by foot. Reach the top of town for an impressive view of the sea, obligatory stop for a gelato near the rose window church.

Take a day trip to the seaside community of Otranto, where the azure Adriatic Sea meets the Ionian Sea; it is the eastern tip of Italy. Otranto occupies the site of the ancient Hydrus, a town of Greek origin, which, in the wars of Pyrrus, Hannibal sided against Rome. Walk the hilly streets to discover the Castello Aragonese and the Cathedral with a rose window. Do enjoy a traditional coffee in one of the many cafes. Fine handcrafts can be found in the small shops, take a lunch break for fresh fish at Laltro Baffo Ristorante, just steps from the Castle. Remember they enjoy a siesta here every day!

Spend a delightful afternoon at a vineyard and taste wine with the enthusiastic owners. Puglian wine in an ancient Masseria – the family has over 40 years of wine growing in Tuscany and in 1999 they began their adventure in Puglian wine. Masseria Li Veli has been selected among the 100 Italian Finest Wine Producers by Wine Spectator.

Move north on the coast to the small charming beach communities just south of Monopoli. There are several properties we like here – Borgo Egnazio is a bit larger property resembling an authentic village. This is a very kiddo centric property where you will see kiddy carts and bikes parked out side each villa, a great place for kids to safely roam. With three pools, there is room for adults and families – also several large villas on property. Looking for a smaller property, we would suggest Masseria Torre Coccaro – the small Puglia properties are rustic chic. Beach clubs to the properties are minutes away.

From here we will organize day trips to several appealing locations. Take a yacht excursion to the seaside town of Polignano a Mare where the massive white limestone cliffs host diving competitions. Take the skiff into the cobblestone streets of the tiny old town, cross through the Porta Vecchia gate to shop and enjoy lunch. If inclined, you can swim in the crystal clear Adriatic Sea on your transport back to the yacht. If you are of a certain age, you may fondly remember the old summer melody by Domenico Modugno, who wrote and sang the massive international hit, Volare (originally entitled Nel Blu Dipinto di Blu. His enormous bronze statute is proudly displayed near the sea wall. Volare, oh,oh… Cantare, oh,oh,oh,oh… Nel blu dipinto di blu… felice di stare lassù…”.

Imagine a typical Puglian feast and olive oil tasting at a renowned Olive Oil Masseria, which is home to many of the most ancient olive trees in Puglia, planted during Roman times. There is also a small underground museum here with original tools dating back centuries. Lunch under the massive Stone Pine tree with the summer symphony of cicadas serenading you while enjoying a traditional multi-course meal.

A visit to small hill town of Alberobello, where the streets are narrow and hilly – but again the charm lays in the gleaming whitewashed houses. Tour the alleyways and small streets lined with conical roofs crowning hundreds of limestone trulli—the traditional stone dwellings for which the town is known.

Visit Locorotondo and Cisternino, two of Puglia’s most historic and picturesque hilltop towns. We suggest exploring in the morning, stop for a fresh seafood lunch and return to your hotel for the afternoon siesta and swimming in the brilliant blue seas.

There will also be time to enjoy your luxury resort and its extensive facilities including a beach club, pool, spa and many fine dining options.

Visit Puglia and and add on Milan, Florence, the Amalfi coast, Tuscany or Rome. Italy has unlimited luxurious options – five star Villas and hotels. Staffing, guiding, drivers, biking!  Perché, No?