Luxury women's food tour in Puglia: 7 days in Southern Italy
We run this trip for women only, in a small group, with our host leading every day of it. Some of our guests come with a friend. More than half come alone. By the second evening you would not be able to tell which is which.
Alberobello, Matera, Ostuni, Lecce, Bari and Polignano a Mare. A small group of women, a Puglian masseria, and a host who treats you like family from the first evening.
Close your eyes and picture the golden light coming down over an olive grove that has been worked by the same family for four hundred years. You are sitting outside with a glass of primitivo, the table is covered in burrata and bread still warm from the oven, and the woman beside you was a stranger four days ago.
That is the trip.
Puglia is the heel of Italy, and it is the part of the country most Americans have not been to yet. No queues at the Uffizi, no cruise crowds, no forty-minute wait for a photograph on a bridge. Instead you get whitewashed hill towns, cave dwellings carved into a ravine, a coastline the color of glass, and food that regional Italians travel for.
Upcoming departures
October 10 - 17, 2026 SOLD OUT
October 25 - November 1, 2026
April 30 - May 7, 2027
October 2 - 9, 2027
May 3 - 10, 2028 - SAVE THE DATE!
October 2 - 9, 2028 - SAVE THE DATE!
Every departure is capped at 16 women, which is the whole point. You will know everyone's name by the end of the first dinner.
Trips are hosted by either Melina or Kerry. Both are extraordinary, and you can read about each of our hosts further down this page.
Room options and pricing
All rooms are single occupancy. You are not sharing with a stranger, and there is no single supplement, because a room of your own is how we build this trip.
2026 trip registration closes September 9!
Pricing shown is for the October 25 to November 1, 2026 departure:
5 of 16 spots remain
Option 1
$7,995 USD
($11,295 CAD)
Per Person
Comfort Room (no terrace)
SOLD OUT!
Option 2
$8,495 USD
($11,895 CAD)
Per Person
Superior Room with a Private Terrace
4 ROOMS LEFT!
Option 3
$8,995 USD
($12,495 CAD)
Per Person
Superior Room with a Living Room
ONLY 1 ROOM!
$500 deposit - due upon acceptance to secure your place
September 9, 2026 - the final balance is due
April 30 - May 7, 2027
13 of 16 spots remain
Option 1
$8,495 USD
($11,895 CAD)
Per Person
Single Occupancy,
Comfort Room (no terrace)
4 ROOMS LEFT!
Option 2
$8,995 USD
($12,495 CAD)
Per Person
Single Occupancy,
Superior Room with a Private Terrace
9 ROOMS LEFT
$500 deposit - due upon acceptance to secure your place
October 1, 2026 - $3,995 second payment is due
January 1, 2027 - the final balance is due
October 2-9, 2027
12 of 16 spots remain
Option 1
$8,495 USD
($11,895 CAD)
Per Person
Single Occupancy,
Comfort Room (no terrace)
4 ROOMS LEFT!
Option 2
$8,995 USD
($12,495 CAD)
Per Person
Single Occupancy,
Superior Room with a Private Terrace
9 ROOMS LEFT
$500 deposit - due upon acceptance to secure your place
November 1, 2026 - $3,995 second payment is due
April 1, 2027 - the final balance is due
"It was not just a trip; it was a transformative experience that I'll cherish forever."
— Tracy B., past Puglia guest
What’s included
Included
Seven nights at a private masseria in the Puglian countryside
Your host with the group for the full duration of the trip
7 breakfasts, 6 lunches and 6 dinners
All tours, activities and entry fees per the itinerary
Private group motorcoach transportation to and from all activities unless stated otherwise
Not included
Airfare to and from Italy
Airport transfers in your departure city
Airport arrival and departure transfers in Bari, available at additional cost
Travel insurance, which we strongly recommend and can arrange for American travellers
Activities, food and beverages not listed in the itinerary
Items of a personal nature
Pre-paid guide and driver gratuities ($300 per person for 2026 departures and $400 per person for 2027 departures)
What the week holds
The towns
Alberobello is the one people have seen in photographs without knowing where it is. Whole streets of trulli, the conical stone houses built without mortar, stacked up a hillside. It is a UNESCO site and it deserves to be. We go with a guide who can tell you why they were built that way, which involves a genuinely good story about tax avoidance.
Matera is the day that stays with people. A city carved into a ravine, inhabited continuously for nine thousand years, abandoned in shame in the 1950s and now one of the most extraordinary places in Europe. We walk the sassi, the cave districts, and go into a cave dwelling preserved as it was.
Ostuni, the white city, sits on a hill above the olive plain and glows at sunset in a way that makes everyone stop talking.
Lecce is baroque architecture at a level that surprises people who thought they knew Italian baroque. Soft local limestone that carvers could work like wood, so every façade is extravagant.
Polignano a Mare is built on a cliff over the Adriatic, with a beach tucked into a cove between the rock walls. Bari gives you the old town, the pasta grandmothers making orecchiette in the street, and a working Italian port city that has not been prettied up for anyone.
The food
This is a foodie trip so the food is not a series of restaurant reservations. You cook. You go to the producers. You taste olive oil poured straight from the tank at the frantoio and understand for the first time why it matters.
Burrata at the caseificio where it was made that morning is a different food from burrata that has travelled. Orecchiette made by hand in front of you, then eaten twenty minutes later with cime di rapa, is the reason people book this trip twice.
Where you stay
A boutique masseria in the Puglian countryside.
Masserie are the fortified farmhouses of the region, and the good ones have been restored with the stone and the vaulted ceilings intact.
You will have a pool, olive groves, and a courtyard where the group ends up every evening whether or not anything is scheduled.
We stay in one property for the whole week. No packing and repacking every second night.
"This trip allows you to visit so many quaint towns, wineries seemingly in the middle of nowhere, and beautiful UNESCO sites without any of those worries."
— Jean K., past Puglia guest
Day-by-day
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Day 1
Arrival + Ostuni + Welcome Dinner
• Settle into your private country resort in the Pugliese countryside.
• A 90-minute guided tour of Ostuni’s luminous whitewashed streets.
• Aperitivo and a welcome dinner with the group.
• Return to the resort by 10:00 pm. -
Day 2
An Olive Oil Estate, a Countryside Picnic, a Cooking Class
• Depart at 9:45am
• Visit an enchanting olive oil estate for a private tour and tasting
• A rustic picnic lunch under the trees
• A hands-on focaccia and pasta cooking class
• Return to the resort by 10:00 pm -
Day 3
Lecce, Grottaglie Ceramics, a Butcher’s Dinner in Cisternino
• Depart at 8:45am
• A two-hour guided tour of Lecce, the “Florence of the South,” followed by free time to wander its ornate Baroque streets
• A tasting lunch featuring local specialties
• An afternoon in Grottaglie, one of Italy’s most celebrated ceramic towns
• Return to the resort for an hour before dinner
• A one-of-a-kind dining experience in Cisternino, famed for its barbecue-loving butchers
• Return by 9:30 pm -
Day 4
Mozzarella and Burrata, Alberobello, Folk Dancers
• Depart at 8:45am
• A guided walking tour of Alberobello, home to the iconic trulli, fairy-tale stone huts found nowhere else on earth
• Time to shop for unique local treasures
• Live demonstrations of mozzarella and burrata making, followed by a tasting lunch
• An exuberant cooking class featuring panzerotti, accompanied by traditional Pugliese folk dancers -
Day 5
Altamura’s Ancient Bread, UNESCO Matera
• Depart at 8:15am
• Visit a DOP bread producer in Altamura for an inside look at the ancient tradition
• A two-hour guided tour of Matera, one of the oldest continuously inhabited cities on earth and a UNESCO World Heritage Site
• Lunch at a local restaurant
• Return to the resort by 6:00 pm for an evening at leisure -
Day 6
Apulian Wines, Polignano a Mare
• Depart at 8:45am
• Tour a renowned Apulian winery and taste the wines alongside a beautiful spread of regional flavors
• A guided walk through the clifftop terraces of Polignano a Mare, gelato in hand
• Create a Puglian “luminaria,” a light installation with origins around the 1600s
• Time at leisure
• Group dinner at 7:00 pm
• Return to the resort by 10:30 pm -
Day 7
Bari, the Fish Market, a Farewell Feast
• Depart at 8:45am
• A guided walking tour of Bari, Puglia’s prosperous seaside capital
• Visit the fish market and taste a range of local specialty foods
• Return to the resort for relaxation and packing
• Farewell dinner at the resort. -
Day 8
Departure day
• A final breakfast and cappuccino at the resort
• Time at leisure before your transfer to the airport
Ready to join us in Puglia?
Tell me which departure you are looking at and I will walk you through the rest.
Who this trip is for
Women traveling solo.
More than half of every group arrives alone. This is the most common thing our guests worry about beforehand and the thing they mention least afterwards.
Women who want to combine Puglia with more of Italy
Since most international flights connect through Rome or another major Italian city, Puglia pairs beautifully with a longer Italian itinerary. You can easily add a few days in Rome, Florence, Venice, Milan, or another part of Italy before or after the tour, with excellent train connections making it easy to turn one trip into a much bigger Italian adventure.
Anyone who wants to eat properly.
Not restaurant tourism. Producers, kitchens, and a chef who explains what you are eating and why the region makes it that way.
Women who want the trip handled.
You book your flights. We do the rest. There is no one working out transport at 11pm, no decisions to make once you land.
Friends travelling together.
Bring someone and you both save. See the offers below.
"I made lifelong friends with fellow travelers, which was a delightful surprise. Everything was organized, so all I had to do was pay and show up."
— Tracy B., past Puglia guest
Meet your hosts
Every Puglia departure is led by one of two hosts. Both live the food culture of this region rather than reciting it, and both stay with the group from the first evening to the last morning. Which one you travel with is shown in the departures table above.
Our guests write to us about their host more than about anything else on the trip.
Melina
She is with the group every single day. Chef, guide, translator, and the person who knows which table at which restaurant, whose cousin has the best burrata, and when the group needs an unscheduled hour by the pool instead of another town.
Melina will be with you every single step of the way in Italy - your guide, your host, and your go-to person. From the morning cappuccino to the farewell dinner, she is your constant.
Melina was born in Australia to Italian parents from Calabria. At 19, she opened her first restaurant with her brother, the beginning of a lifelong love affair with food. At 22, she traveled to Italy for the first time and left her heart there. In 2009, she opened her cooking school, splitting her time between Australia and Italy until she moved back permanently in 2017.
Since then, Melina has been leading women's food tours across Southern Italy, welcoming travelers into her kitchen, her table, and the Italy her family has always known. She teaches the dishes that are specific to the region you're in, the ones most travelers never learn to make, the ones that aren't on any menu back home. She knows the olive oil producers, the mozzarella makers, the nonnas who still roll orecchiette by hand on wooden boards in their doorways.
And she knows how to make a group of women who arrived as strangers feel, by the end of the week, like they've always been family.
Kerry
Kerry's European adventure began over forty years ago, taking her from Virginia to the southeast of England, to the heart of Paris and the forests of Fontainebleau, and finally to Italy, where she made her home base with her former Italian husband and their two adult children, Eleonora and Lorenzo.
She grew up in a family of eleven where every meal was homecooked, and she learned early what food and time around a table do for people. That deepened over years living in Turin, Verona and Friuli. Her involvement with the Slow Food Movement, her Master's in Italian Cuisine and Oenology from ICIF, and her sommelier training with AIS all come from the same place. She also founded the English-Speaking Happy Hour in Verona, which grew into an international community that still nurtures friendships across the world.
As a host, she brings food and wine expertise, both American and Italian cultural depth, and a genuinely attentive personal touch. Whether that is a table set under two-thousand-year-old olive trees, the historic streets of Bari, or hunting for treasures in Ostuni, she leads with affection and attention, helping women step outside their comfort zone, find the joy in it, and build new friendships.
Kerry now divides her time between Italy and the United States, and she keeps doing what she has always done: creating experiences and connections that last.
"We came together not knowing each other and left as family."
— Carol F., past Puglia & Sicily guest
Book two trips and save $500. Bring a friend and you each save $250.
What’s included in your experience
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Accommodations
7 nights at a private masseria -
Tours & Activities
Tours, activities, & entry fees per itineraryTour leader for the duration of the trip
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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
Is this journey right for you?
Read through our frequently asked questions.
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Yes. Only women (she/her) are welcome to join.
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No. More than half of every group travels solo. The trip is built around that, from the way we structure meals to the pacing of the days.
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A reasonable level of fitness. There are uneven streets, stairs, long touring days, standing during guided visits, and the need to keep pace with the group.
Expect 10,000 or more steps a day on cobblestones, hilly paths and the beautifully uneven terrain Southern Italy is known for. The Matera day is the most demanding, with a lot of uphill and downhill walking through the sassi. If any day sounds like too much, you are welcome to enjoy a slow morning at the masseria instead. The itinerary balances guided experiences with free time on purpose.
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The group gathers at the masseria in Puglia on the first day of your chosen departure. Everyone books their own flights. We are happy to help you find airfare options, and we can plan an extension before or after the group journey, with any additional costs being yours.
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A boutique masseria, chosen because it feels personal rather than commercial. We stay in one property for the whole week rather than moving every couple of nights.
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No, but it is strongly recommended. We can arrange travel insurance for American travelers through Travel Guard and will quote it based on your specific trip cost.
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Our guests are typically 50+. What they have in common is more about outlook than age.
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Our Puglia departures sell out. Both 2026 dates are gone. For a 2027 date I would plan on booking ahead, particularly if you want a single room.
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Pre-paid guide and driver gratuities ($300 per person for 2026 departures and $400 per person for 2027 departures) will be collected
Ready to come to Puglia?
Every trip starts with a conversation. Tell me which dates you are looking at and what you are hoping for, and I will take it from there.
Moments from past Puglia journeys
Meet Anna
Anna Fishman is the founder of Olegana Travel Boutique, a luxury travel company specializing in bespoke European itineraries and women-only small group journeys.
With 33 countries explored and years spent building relationships with the finest local guides, chefs, and hoteliers across Europe, Anna designs travel experiences that feel personal, seamless, and impossible to replicate on your own. Her Puglia journeys have become a signature, with multiple departures selling out each year.
She lives in New Jersey, with her family and she cannot wait to welcome you on your next journey.