October 10 - 17, 2026 - SOLD OUT!

Fall 2026 Foodie Adventure in Southern Italy, Puglia

Close your eyes and imagine the golden glow of the Italian sunset, painting the sky with hues of orange and pink…

You and your best girlfriend are lounging in luxury, sipping on glasses of velvety wine, and soaking in the beauty of the moment.

But this trip is more than just relaxationβ€”it's an adventure off the beaten path, whisking you away from bustling metropolises and into the heart of authentic Southern Italian charm. Prepare to be enchanted as we explore the enchanting towns of Alberobello, Matera, Ostuni, Lecce, Bari, and Polignano a Mare.

Make Your Dream Come True

SOLD OUT!

Option 2

$7,995 USD

Per Person

Single Occupancy,
Comfort Room (no terrace)

Option 3

$8,495 USD

Per Person

Single Occupancy,
Superior Room with a Private Terrace

The Trip at a Glance

  • Day 1 (Oct 10 - starting at 5 pm)

    Welcome to Italy! Rest + explore the masseria.

    β€’ 1.5 hr Ostuni city tour
    β€’ Aperitivo & group dinner
    β€’ 10pm - return to the masseria

  • Day 2

    An olive tree estate, a rustic picnic, private cooking class

    β€’ 9:45am - departure
    β€’ Visit an enchanting olive oil estate
    β€’ Recharge with a rustic picnic lunch
    β€’ A hands-on focaccia and pasta cooking class
    β€’ 10pm - return to the masseria

  • Day 3

    Lecce, Grottaglie, ceramics, a local barbecue

    β€’ 8:45am - departure
    β€’ Lecce - 2-hr guided tour and free time
    β€’ A tasting lunch featuring local specialties
    β€’ Grottaglie, renowned for exquisite ceramics
    β€’ Return to the hotel for 1 hr before dinner
    β€’ A one-of-a-kind dining experience in Cisternino, famed for its barbecue-loving butchers!
    β€’ 9:30pm - return to the masseria

  • Day 4

    Mozzarella and burrata making, Alberobello & trulli houses, folk dancers

    β€’ 8:45am - departure
    β€’ Guided walking tour of Alberobello, famed for its trulli
    β€’ Shop for unique local treasures
    β€’ Live demonstrations of mozzarella and burrata making, followed by a tasting lunch
    β€’ An exciting cooking class featuring panzerotti, accompanied by a group of traditional folk dancers

  • Day 5

    Altamura, traditional bread making, Matera, group dinner

    β€’ 8:15am - departure
    β€’ Altamura, visit a DOP bread producer for an inside look at the traditional breads
    β€’ 2-hr guided tour of Matera, a UNESCO World Heritage Site
    β€’ A group lunch at a local restaurant
    β€’ 6pm - return to the masseria for an evening at leisure

  • Day 6

    Sea caves, Apulian wines, Polignano a Mare, gelato, group dinner

    β€’ 8:45am - departure
    β€’ Tour a renowned winery
    β€’ A guided walk in Polignano a Mare + gelato
    β€’ Weather permitting, set sail on a modern skiff to explore sea caves
    β€’ Time at leisure
    β€’ 7 pm - group dinner
    β€’ 10:30pm - return to the masseria

  • Day 7

    Bari walking tour, fish market, a tasting lunch!

    β€’ 8:45am - departure
    β€’ A guided walking tour of Bari
    β€’ Visit the fish market
    β€’ Taste a range of local specialty foods
    β€’ Return to the masseria for relaxation and packing to prepare for departure
    β€’ Farewell dinner at the masseria

  • Day 8 (Oct 17)

    Departure day

    β€’ Enjoy a breakfast and a cappuccino at the masseria
    β€’ Enjoy some time at leisure before it’s time to transfer back to the airport for your flight home

An In-Depth Look at Your Trip

Cheese Fiesta & Trulli Houses

  • Live demonstrations of mozzarella and burrata making at a local cheesemaker

  • Visit Alberobello, famed for its fairy-tale trulliβ€”traditional stone huts

  • Shop for unique local treasures


Women travel by boat an explore the sea caves near Polignano a Mare.

Sea caves, Apulian wines, Polignano a Mare & gelato!

  • Explore the awe-inspiring sea caves, channeling the spirit of ancient smugglers

  • Tour a winery and sample fine wines and a mouthwatering spread of regional delights

  • Visit Polignano a Mare - a guided walk along the seaside terraces & panoramas


Women take a focaccia and pasta cooking class in Southern Italy.

Ostuni, an olive tree estate, a cooking class, & folk dancers!

  • Walk the dazzling alleys of the old town of Ostuni

  • Visit an enchanting olive oil estate

  • Enjoy a rustic picnic lunch in the olive grove

  • A hands-on focaccia and pasta cooking class with a master chef!

"In every tour, in every class, in every meal prepared in my
restaurant, my goal is always the same, to teach my guests to learn to live like an Italian, to love like an Italian .. learn to BE Italian.”

Meet Your Host:
Chef Melina

Melina was born and raised in Australia by Italian immigrant
parents from Calabria, located in the south of Italy. At the age
of 19, she opened her first restaurant in Australia with her
brother, which was the beginning of her love affair with food.
At 22, Melina went to Italy for the first time and that's where
she left her heart. In 2009, Melina opened her cooking school,
traveling between both countries before transferring to Italy
indefinitely in 2017.

Melina began escorted food tours after realizing that the
story behind each dish, each plate is what it truly makes it
special. Her love for Italy, her love for food, and her passion for
sharing that is evident after spending just 5 minutes with her.

"Cooking is my biggest love but sharing
is my biggest joy."

Melina is the host of Olegana Travel Boutique’s women-only
group tours to Puglia and Sicily, where she happily shares her
love for Italy with other women.

What’s Included in Your Experience of a Lifetime

  • A private masseria to stay in.

    Accommodations

    7 nights at a private masseria

    Tour leader for the duration of the trip

  • Women join in on a class in Southern Italy.

    Tours & Activities

    Tours & activities per itinerary

    Entry fees for all activities listed under Itinerary

  • Cuisine from Southern Italy, including mozerella, tomatoes and cucumbers.

    Food & Beverages

    7 Breakfasts, 6 Lunches, and 6 Dinners

  • Transportation in Southern Italy.

    Transportation

    Private group motorcoach/bus transportation to/from all activities unless stated otherwise

What Guests Said About Past Trips…

  • β€œAnna and her team in Italy did a fantastic job in making sure we had an amazing time visiting Puglia. There were so many β€œout of the box” experiences that made this trip unique & wonderful.

    The group of women brought together by Anna made the trip fantastic! Thank you for a memorable trip!"

    - MJ

  • β€œI can't say enough about Anna and Olegana Travel
    Boutique!!! What an awesome trip first off, and the ladies I met OMG!!! 

    She helped me plan an AMAZING and PERFECT itinerary. 

    This will not be my last trip with this Boutique.”

    - Lucia

  • β€œI went on the incredible Spain trip in the fall of 2023 and I was very impressed with the high quality of the tours, the guides and the accommodations. 

    Anna did a great job, and I wouldn’t hesitate to book another tour with her company."

    - Lin

You Might Be Wondering…

Read through our frequently asked questions.

See How Much Fun We Have!

Meet Anna

Hi - I’m Anna Fishman, the proud mastermind behind Olegana Travel Boutique, your go-to hub for unforgettable journeys.

I live for family adventures with my travel-loving husband and our little jetsetters in training. With 31 countries under my belt, I’ve combined my personal globetrotting escapades with the expertise of local destination gurus. Together, we craft personalized itineraries that are perfect for you to reconnect with your inner self, to discover the world, and to make new friends.

I can’t wait to meet you on our next group trip for incredible women!

Next
Next

Fall 2026 Secret Spain: Discover Andalusia