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
Option 1
$6,995 USD
Per Person
Double Occupancy,
Junior Suite (no terrace)
Option 2
$7,695 USD
Per Person
Single Occupancy,
Deluxe Room (no terrace)
Option 3
$7,995 USD
Per Person
Single Occupancy,
Superior Room with a Private Terrace
January 15, 2025 - first payment of $1,995 is due
February 15, 2025 - $2,995 payment is due
June 1, 2025 - the balance is due
The Trip at a Glance
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Day 1 (Oct 19)
Welcome to Italy! Rest + explore the masseria. Group dinner
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Day 2
Mozzarella and burrata making, Alberobello & trulli houses, group dinner
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Day 3
Sea caves, Apulian wines, Polignano a Mare, gelato.
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Day 4
Ostuni, an olive tree estate, Monopoli, a private cooking class, folk dancers.
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Day 5
Altamura, traditional bread making Matera, a cave restaurant.
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Day 6
Lecce, Grottaglie, a private museum, a local barbecue.
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Day 7
Bari walking tour, a seaside promenade, fish market and specialty foods, cooking class.
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Day 8 (Oct 26)
Departure day
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
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
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
Explore Monopoli, a seaside jewel
A hands-on focaccia and pasta cooking class with a master chef!
What’s Included in Your Experience of a Lifetime
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Accommodations
7 nights at a private masseria
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Tours & Activities
Tours & activities per itinerary
Entry fees for all activities listed under Itinerary
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Food & Beverages
7 Breakfasts, 6 Lunches, and 6 Dinners
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Transportation
Private group motorcoach/bus transportation to/from all activities unless stated otherwise
What Guests Said About Past Trips…
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“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
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“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
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“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.
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Yes, only women (she/her) are welcome to join.
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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
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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.
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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.
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Guide and driver pre-paid gratuities of $300 per person will be collected approximately a week before the trip starts.
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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.
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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 other trip to Puglia in 2025 by clicking here.
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!