October 19 - 26, 2025

Fall 2025 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 relaxation—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

LOW $500 Deposit to Secure Your Spot

Last 2 rooms available!

Option 1

$6,995 USD

Per Person

Double Occupancy,
Junior Suite (no terrace)

Option 2

$8,495 USD

Per Person

Single Occupancy,
Junior Suite (no terrace)

June 30, 2025 - $3,995 payment is due

July 15, 2025 - the balance is due

The Trip at a Glance

  • Day 1 (Oct 19 - starting at 5 pm)

    Welcome to Italy! Rest + explore the masseria.

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

  • Day 2

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

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

  • Day 3

    Lecce, Grottaglie, ceramics, a local barbecue

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

  • Day 4

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

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

  • Day 5

    Altamura, traditional bread making, Matera, group dinner

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

  • Day 6

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

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

  • Day 7

    Bari walking tour, fish market, a tasting lunch!

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

  • Day 8 (Oct 26)

    Departure day

    Enjoy a breakfast and a cappuccino at the masseria
    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 trulli—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…

  • “Anna and her team in Italy did a fantastic job in making sure we had an amazing time visiting Puglia. There were so many “out 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

  • “I 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

  • “I 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.

  • Yes, only women (she/her) are welcome to join.

    • All activities, food and beverages not listed under the itinerary

    • All items of a personal nature and anything not expressly stated as included

    • Airfare to/from your arrival city and departure city

    • Airport transfers in your departure city

    • Airport arrival and departure transfers in Bari - can be arranged at extra cost

  • Insurance is strongly recommended. We can offer travel insurance for American travelers. Please let us know if you would like a quote for your travel insurance policy.

  • Yes, a decent level of fitness is highly recommended. We’ll be walking a lot—think 10,000+ steps a day—often on uneven cobblestone streets, hilly paths, stairs with no railings, and all the charming, ancient terrain Italy is famous for. You don’t need to be a triathlete, but comfortable walking for extended periods is key. Our day trip to Matera is the most physically demanding, with lots of uphill and downhill walking through the historic sassi.

    If that sounds like too much, you’re welcome to enjoy a relaxing day at the resort instead (poolside spritz, anyone?). We want you to have a beautiful, comfortable experience at your own pace.

  • The group will meet at the hotel in Italy on October 19, 2025. Everyone will be responsible for purchasing their own plane tickets to get to Italy. We are happy to help find the best airfare options and plan a trip extension before or after the group trip. The traveler will be responsible for any extra costs associated with that.

  • Each day is thoughtfully planned to make the most of your time in Puglia—whether it’s a market visit, a seaside lunch, or a private tasting in the countryside. Out of respect for the group, we kindly ask that all guests are ready on time each day.

    We stick to a schedule so we don’t miss reservations, guides, or that golden light on the olive groves.

    We promise to give gentle reminders… but we also can’t hold up the whole group—so please consider punctuality part of the adventure.

  • We thoughtfully select the meals for the group, so you can simply relax and enjoy.

    Every dish is chosen with care, giving you a true taste of Puglia’s most beloved flavors—from coastal seafood to rustic countryside specialties. We work closely with local chefs and restaurants to curate a delicious journey through the region, highlighting seasonal ingredients and traditional recipes.

    We encourage guests to come with open minds (and open appetites!). Italian meals are crafted with balance and intention—you may not see a salad at every sitting, but what you will find is a beautiful expression of the region’s culinary soul, one course at a time.

    All you have to do is bring your curiosity—and maybe a little room for dessert.

  • Each day in Puglia is designed to flow smoothly—whether we’re exploring whitewashed hill towns, tasting olive oil at a family estate, or watching the sun dip behind ancient trulli rooftops.

    If you’d rather skip an activity and unwind at the hotel, that’s totally fine—just give your tour host a heads-up in advance so we can plan accordingly.

    To keep things running smoothly and respect our local hosts, please be punctual. You’ll get a friendly nudge if needed, but the group can’t wait forever. And missing out on wine, burrata, and seaside magic? That’s not the kind of story you’ll want to tell later.

  • Guide and driver pre-paid gratuities of $300 per person will be collected approximately a week before the trip starts.

  • We will provide a packing list closer to travel dates with suggested attire and useful gadgets. The trip is very casual, so as long as you are comfortable, you will be fine.

  • No, this is an adults only group, for people 18 years old and older. If you’re under 50, don’t shy away - everyone is welcome! If you are interested in a family friendly adventure through Italy or any other country in Europe, we would be happy to create a custom trip for you. Please book a time on Anna's calendar here to discuss further.

Not sure if this trip is for you?

I hear it all the time - "I would love to come with you BUT..."

BUT I've never traveled alone!

This is a perfect option if you’re a solo traveler on a journey of self-discovery: you can be part of a larger group of women (usually 50+) that share your interests and have likely been in your shoes before, while going through a new stage of life like retirement, divorce or loss of a partner. Everyone is as excited to be on this trip as you are so you're not alone.

BUT I've never been to Europe!

That's ok - that's the beauty of travel and exploring new places! With our group, you don't have to worry about the logistics in an unfamiliar, new place. You're part of a small group that travels together with a professional, English-speaking guide and you get to know one another.

How amazing would you feel on the return flight home, knowing that you seized the chance to have a once-in-a-lifetime, authentic European experience and met some new friends along the way?

It’s time to feel that Italian sunset for yourself and learn into all Southern Italy has to offer!

P.S. This date doesn’t work for you?

Check out our 2026 trip to Puglia by clicking here.

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!

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Spring 2025 Foodie Adventure - Southern Italy

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Fall 2025: Wine, Chocolate & You in Sicily