April 27 - May 4, 2026
Luxury Couples Trip: Foodie Adventure in Puglia, Italy
Close your eyes and imagine the golden glow of an Italian sunset lighting up the sky in fiery shades of orange and pink...
You and your partner are wrapped in luxury, glasses of rich, velvety wine in hand, as laughter echoes and the magic of the moment sinks in.
Forget the usual tourist trail—this adventure takes you deep into the heart of Southern Italy, where every cobblestone street, every bite of handmade pasta, and every hidden piazza tells a story.
Wander through the fairytale trulli homes of Alberobello, explore the ancient cave city of Matera, and get lost in the beauty of Ostuni. Feel the passion of Lecce’s baroque flair, dive into the dramatic cliffside charm of Polignano a Mare, and soak up the seaside vibrance of Bari.
This is not just a getaway—it’s an unforgettable journey of discovery, connection, and romance that stays with you long after you return home.
The Trip at a Glance
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Day 1 (Apr 27)
Welcome to Italy! Rest + explore the masseria.
• Ostuni city tour
• Aperitivo & group pizza dinner -
Day 2
An olive tree estate, a rustic picnic, private cooking class
• Visit an enchanting olive oil estate
• Recharge with a rustic picnic lunch
• A hands-on focaccia and pasta cooking class -
Day 3
Lecce, Grottaglie, ceramics, a local barbecue
• Lecce - 2-hr guided tour and free time
• A tasting lunch featuring local specialties
• Grottaglie, renowned for exquisite ceramics
• A one-of-a-kind dining experience in Cisternino, famed for its barbecue-loving butchers! -
Day 4
Mozzarella and burrata, Alberobello & trulli houses, group dinner
• 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
• Afternoon at leisure
• 3-course group dinner -
Day 5
Altamura, traditional bread making, Matera, group dinner
• Altamura, visit a DOP bread producer for an inside look at the traditional breads
• Matera, a UNESCO World Heritage Site
• A group lunch at a cave restaurant
• An evening at leisure -
Day 6
Sea caves, Apulian wines, Polignano a Mare, gelato, group dinner
• Tour a renowned winery
• A guided walk in Polignano a Mare
• Weather permitting, set sail on a modern skiff to explore sea caves
• A 3-course feast at a charming seafood spot -
Day 7
Bari, fish market, cooking class, and folk dancers!
• A guided walking tour of Bari
• Visit the fish market & sample raw seafood
• A tasting lunch at a cozy home restaurant
• An exciting cooking class featuring panzerotti, accompanied by a group of traditional folk dancers
• A farewell dinner -
Day 8 (May 4)
Departure day
• Enjoy breakfast and 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
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
Enjoy a rustic picnic lunch in the olive grove
A hands-on focaccia and pasta cooking class with a master chef!
Make Your Dream Come True
LOW $500 Deposit to Secure Your Spot
$ USD
Per Person
Double Occupancy,
Junior Suite (no terrace)
September 1, 2025 - $3,995 payment is due
June 1, 2026 - the final balance is due
What’s included in your experience of a lifetime
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Accommodations
7 nights at a private masseria
Tour leader for the duration of the trip
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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
You Might Be Wondering…
Read through our frequently asked questions.
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This trip is only for couples - we have other women-only groups you 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 April 27, 2026. 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.
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!