October in Puglia: La Dolce Vita, Salento Style!

Victoria De Maio of PostcardZ from Victoria has another one of her great small group tours in Puglia coming up. We’ve asked her to tell us the details.

Head Over HeelZ in Puglia! October 9 – 18, 2015

By Victoria De Maio

Here’s a daily itinerary of this awesome tour!*

Lecce, Puglia, Italy

Lecce, Italy

For the first 4 nights of your tour, you will stay in Lecce. Your boutique, an all-suite hotel is in the heart of Lecce’s historic center and walking distance from the very best that this Baroque jewel has to offer. Enjoy Lecce’s unique architecture and pedestrian center with its wine bars, museums, restaurants, shops, bookstores, and more.

Day 1 – Friday, October 9 – Benvenuti! Welcome to Puglia!

  • Arrive in Brindisi Airport.
  • Your private transfer will take you to your accommodation in Lecce.
  • Check in and welcome wine tasting.
  • Dinner to follow featuring traditional Pugliese cuisine at a local trattoria.

Day 2 – Saturday, October 10 – Lecce Lifestyle, “Florence of the South”


  • Walking tour of Lecce, the capital of Baroque. A guided walk in the historical center with its lavish, magnificent Baroque architecture and distinctive personality.
  • Visit a local artist and enjoy the cartapesta (papier-mâché) demonstration.
  • Lunch in a local renowned restaurant with traditional, regional delights.
  • Free afternoon in Lecce to explore and enjoy this lively, lovely town.
  • Late afternoon “Aperitivo Leccese” followed by dinner and wine in a local ristorante walking distance from your hotel.

Day 3 – Sunday, October 11 – Gallipoli, “Pearl of the Ionian” and Wine Tasting

Gallipoli, Italy - Photos by Victoria De Maio

Gallipoli, Italy – Photos by Victoria De Maio


  • On our way, let’s visit a local artisan in their pottery studio.
  • Visit the port of Gallipoli, “città bella” of fishermen.
  • Lunch by the sea at a local ristorante.
  • Walking tour of the old town of Gallipoli.
  • Gelato time! Stop for a gourmet gelato treat before heading home.
  • Return to Lecce to rest before dinner.
  • Another fabulous, traditional dinner of regional specialties.

Day 4 – Monday, October 12 – Food Artisans Experience!

Lecce Market - Photos by Victoria De Maio

Lecce Market – Photos by Victoria De Maio

  • After breakfast, embark on a food artisan tour (and a few samples!); visit to the Lecce food market, watch fresh mozzarella being made at the caccificio (cheese shop), and pasticciotto (Lecce’s favorite pastry) at the pasticceria (pastry shop).
  • Light lunch in a trendy enoteca in Lecce.
  • Caffè Experience: Taste different coffees and learn about coffee making.
  • Visit a pastificio (pasta shop) where we will make a very special wine pasta together.
  • Dinner at the pastificio.

For the second half of our stay, we will move to the nearby countryside among thousands and thousands of hectares of olive groves! Here we will stay at Masseria Provenzani, a charming and relaxing restored 16th-century farmhouse.

Masseria - Photos by Victoria De Maio

Masseria – Photos by Victoria De Maio


Here we will learn firsthand about “cucina povera”. Putting on our aprons, we’ll prepare and enjoy regional seasonal dishes with Mamma Giulia, explore more of the seductive Salento lifestyle, and learn firsthand about the exquisite local olive oil and vino (of course!).

Day 5 – Tuesday, October 13 – City to Country with Some Wine & Cooking Lessons Along the Way!

Cooking class in Puglia -- Photo by Victoria di Maio

Cooking class in Puglia — Photo by Victoria di Maio

  • After breakfast, we check out and head to a Salento winery where Primitivo, Negroamaro, and other local varietals are transformed into gorgeous wines!
  • Lunch at a traditional Masseria.
  • Check in to our new home for 5 nights, a traditional Salento style Masseria.
  • Time to unpack, relax, and practice some Italian with your hosts.
  • Grab your apron! It’s time to cook together! Learn about “cucina povera” and how to make culinary magic with very simple ingredients.
  • Dinner at the Masseria.


Day 6 – Wednesday, October 14 – It’s Olive Harvest! Time for a Picnic & the Pizzica!

  • Today we will harvest olives and make our own olive oil! Our olive oil expert will guide us through this beautiful experience!
  • Learn how to taste olive oil and enjoy a traditional picnic.
  • Let’s dance the Pizzica with locals to traditional Salento music.
  • Return to the Masseria for a private tutored wine tasting.
  • Mamma is in the kitchen tonight and she will demonstrate how to make the best risotto!
  • Dinner at the Masseria.
Olive harvest and tour of mill in Puglia - Photos by Victoria De Maio

Olive harvest and tour of mill in Puglia – Photos by Victoria De Maio


Day 7 – Thursday, October 15 – Explore “Grecia Salentina” and Pizza Making

  • Today we will explore the picturesque and historic “grecia salentina” or griko Salento.
  • Visit and enjoy guided walks in the town of Corigliano and the beautiful coastal city of Otranto, city of martyrs and mosaics (and great shopping!).
  • Lunch in a traditional trattoria.
  • On our way home, visit a farm where they make natural beauty products with aloe vera.
  • Return to the Masseria for pizza making and dinner.
Pizza Making - Photos by Victoria De Maio

Pizza Making – Photos by Victoria De Maio


Day 8 – Friday, October 16 – Visit to the Itria Valley for a Trulli Photo Safari!

  • Visit the famous Itria Valley and the famous white washed stone villages of Ostuni, Cisternino and Alberobello.
  • Enjoy walking tours of these picturesque trulli towns.
  • Guided stroll through Ostuni, “the white city”.
  • In Cisternino, famous for its tradition of butcher shops with annexed wooden ovens, you will choose the meat you want cooked for you “al Fornello”.
  • Free time in Alberobello to explore the many shops, wine bars, and gourmet food boutiques (and to take lots of photos!).
  • Return to the Masseria for another home traditional cooked dinner (with wine, of course!)
Towns of Puglia - Photos by Victoria De Maio

Towns of Puglia – Photos by Victoria De Maio


Day 9 – Saturday, October 17 – The Valle della Cupa Experience & Puglia Wine School

  • After breakfast, we go off the beaten track to the Valle della Cupa to visit more picture-perfect villages in Northern Salento.
  • Meet local artists and artisans.
  • Enjoy lunch in a local traditional trattoria.
  • Return to the Masseria to relax before our last evening together.
  • A special class at Puglia Wine School where we will learn how to pair food and wine.
  • Our last evening together will be celebrated with another special delicious dinner and wine.
Puglia tour group - Photo by Victoria De Maio

Puglia tour group – Photo by Victoria De Maio


Day 10 – Sunday, October 18 – Buon Viaggio!

  • Time to finish packing.
  • Enjoy breakfast and say our goodbyes.
  • Private transfer to Brindisi airport.

Arrivederci! Safe travels!

*Itinerary is subject to change due to weather and unforeseen schedule changes. However, all activities outlined will be included in your experience.

For more information and booking: Head Over HeelZ in Puglia

Photos courtesy of Victoria De Maio

About the author:
La dolce vita for me” sums up Victoria’s passion and love for all things Italian. An American (with deep Italian roots) living in California, her heart is always in Italy. Her book “Victoria’s Travel TipZ Italian Style” is a result of her love for Italy, all things Italian, and sincere desire to help others have a truly fabulous trip to Italy. As a travel consultant, writer, and blogger, Victoria loves sharing practical no-nonsense travel tips and insights as well as her own experiences from a personal and light-hearted point-of-view on her travel blog, PostcardZ from Victoria. Needless to say, her favorite subject is Italy! When she isn’t planning her next trip (or yours!), she loves being a regular contributing writer for Italian Notebook, Italian Talks, and L’Italo-Americano. She loves doing book signings and presentations and can also be found on Facebook, Twitter, YouTube, Pinterest, and Instagram as well as on blog radio, and doing guest posts and interviews.

Note: This post may contain affiliate links. If you make a purchase through these links, I will earn a commission at no extra cost to you. Thanks!

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