October 25 - November 1, 2026

Fall 2026: A Culinary Journey Through Southern Italy, Puglia

This is luxury small group travel for women who prefer substance over spectacle - immersive culinary travel through Southern Italy with no more than sixteen guests, every detail handled, and nothing left to chance. 

Luxury Women’s Group Tour to Puglia, Southern Italy

This trip is for women who are excited to taste what Puglia does best, from handmade pasta to olive oil, burrata, wine, and long regional meals shared around the table.

This is not a group tour of Italy. This is eight days in the sun-drenched heel of the boot, where every morning begins with espresso on a terrace overlooking ancient olive groves and every evening ends with wine, laughter, and the kind of conversation that only happens when the pace is right and the company is extraordinary.

You will make fresh pasta and focaccia alongside a local chef. You will taste burrata minutes after it is pulled. You will wander the whitewashed alleyways of Ostuni and stand inside the fairy-tale trulli of Alberobello. And between every experience, you will return to a private country resort that feels less like a hotel and more like the home of a very well-connected friend.

Two earlier 2026 Puglia departures are already sold out. This October departure is the final opening for 2026.

What makes this trip different

A typical group tour with other companies

  • 30–50 guests on a bus

  • Chain hotel near the highway

  • Factory lunch with a fixed tourist menu

  • A 20-minute photo stop in Alberobello

  • Mozzarella from the hotel buffet

  • A bus ride past Polignano a Mare

  • Eating alone at your hotel

This journey

  • No more than 16 women

  • A private country resort surrounded by olive groves

  • A hands-on cooking class with a local chef

  • A full morning in Alberobello with a local guide, time to shop, and burrata tasting

  • Watch mozzarella pulled by hand and taste it while it’s warm

  • Evenings that stretch into laughter, wine, & friendships that outlast the trip

Spring 2026 - SOLD OUT ⋆ Fall 2026 (Oct 10 departure) - SOLD OUT

⋆

Spring 2026 - SOLD OUT ⋆ Fall 2026 (Oct 10 departure) - SOLD OUT ⋆

⋆ Fall 2026 (October 25 departure) ⋆
7 of 16 spots remain

Your invitation to Puglia

ONLY $500 deposit to secure your place

Registration closes July 31!

Small group - 16 people maximum

Option 1

$7,995 USD

($11,295 CAD)

Per Person

Single Occupancy,
Comfort Room (no terrace)

SOLD OUT!

Option 2

$8,495 USD

($11,895 CAD)

Per Person

Single Occupancy,
Superior Room with a Private Terrace

6 ROOMS LEFT!

How it works

Submit a brief application and book a time on Anna’s calendar. After a short get-to-know-you call to confirm this trip is the right fit, you’ll receive an invoice for your $500 deposit to secure your place.

$500 deposit - due upon acceptance to secure your place
July 31, 2026 - the final balance is due

Option 3

$8,995 USD

($12,595 CAD)

Per Person

Single Occupancy,
Superior Room with a Living Room

ONLY 1 ROOM!


When you & a girlfriend book together, you each save $250

Book more than one Olegana trip & save $500


The trip at a glance

  • Day 1 (Oct 25 - start at 5 pm)

    Arrival + Ostuni + Welcome Dinner

    β€’ Settle into your private country resort in the Pugliese countryside.
    β€’ A 90-minute guided tour of Ostuni’s luminous whitewashed streets.
    β€’ Aperitivo and a welcome dinner with the group.
    β€’ Return to the resort by 10:00 pm.

  • Day 2

    An Olive Oil Estate, a Countryside Picnic, a Cooking Class

    β€’ Depart at 9:45am
    β€’ Visit an enchanting olive oil estate for a private tour and tasting
    β€’ A rustic picnic lunch under the trees
    β€’ A hands-on focaccia and pasta cooking class
    β€’ Return to the resort by 10:00 pm

  • Day 3

    Lecce, Grottaglie Ceramics, a Butcher’s Dinner in Cisternino

    β€’ Depart at 8:45am
    β€’ A two-hour guided tour of Lecce, the β€œFlorence of the South,” followed by free time to wander its ornate Baroque streets
    β€’ A tasting lunch featuring local specialties
    β€’ An afternoon in Grottaglie, one of Italy’s most celebrated ceramic towns
    β€’ Return to the resort for an hour before dinner
    β€’ A one-of-a-kind dining experience in Cisternino, famed for its barbecue-loving butchers
    β€’ Return by 9:30 pm

  • Day 4

    Mozzarella and Burrata, Alberobello, Folk Dancers

    β€’ Depart at 8:45am
    β€’ A guided walking tour of Alberobello, home to the iconic trulli, fairy-tale stone huts found nowhere else on earth
    β€’ Time to shop for unique local treasures
    β€’ Live demonstrations of mozzarella and burrata making, followed by a tasting lunch
    β€’ An exuberant cooking class featuring panzerotti, accompanied by traditional Pugliese folk dancers

  • Day 5

    Altamura’s Ancient Bread, UNESCO Matera

    β€’ Depart at 8:15am
    β€’ Visit a DOP bread producer in Altamura for an inside look at the ancient tradition
    β€’ A two-hour guided tour of Matera, one of the oldest continuously inhabited cities on earth and a UNESCO World Heritage Site
    β€’ Lunch at a local restaurant
    β€’ Return to the resort by 6:00 pm for an evening at leisure

  • Day 6

    Apulian Wines, Polignano a Mare

    β€’ Depart at 8:45am
    β€’ Tour a renowned Apulian winery and taste the wines alongside a beautiful spread of regional flavors
    β€’ A guided walk through the clifftop terraces of Polignano a Mare, gelato in hand
    β€’ Create a Puglian β€œluminaria,” a light installation with origins around the 1600s
    β€’ Time at leisure
    β€’ Group dinner at 7:00 pm
    β€’ Return to the resort by 10:30 pm

  • Day 7

    Bari, the Fish Market, a Farewell Feast

    β€’ Depart at 8:45am
    β€’ A guided walking tour of Bari, Puglia’s prosperous seaside capital
    β€’ Visit the fish market and taste a range of local specialty foods
    β€’ Return to the resort for relaxation and packing
    β€’ Farewell dinner at the resort.

  • Day 8 (Nov 1)

    Departure day

    β€’ A final breakfast and cappuccino at the resort
    β€’ Time at leisure before your transfer to the airport

This is luxury small group travel, thoughtfully designed

No large groups. No generic, overcrowded activities. Instead:

✨Carefully selected boutique accommodations at a private country resort

✨Private, immersive food and wine experiences you would not find on your own

✨Coastal views, ancient towns, and countryside corners most visitors never reach

✨A relaxed pace with time to truly savor each destination

✨A small group of like-minded women - evenings that stretch into laughter, wine, and conversation

An in-depth look at your trip

Cheese, trulli & the magic of Alberobello

  • Watch mozzarella and burrata come to life before your eyes and taste them both while they’re still warm

  • Wander the enchanting streets of Alberobello, home to the iconic trulli, fairy-tale stone huts found nowhere else on earth

  • An exuberant cooking class featuring panzerotti, with traditional Pugliese folk dancers setting the mood


Apulian wines, Polignano a Mare, luminaria & gelato!

  • Learn how to create a marvelous Puglian β€œluminaria,” a light installation whose origins date back to around the 1600s.

  • Tour a celebrated Apulian winery and taste the wines alongside a beautiful spread of regional flavors

  • Stroll the clifftop terraces of Polignano a Mare, with sweeping sea views and gelato in hand


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

Ostuni, an olive estate, a cooking class

  • Lose yourself in the luminous whitewashed alleyways of Ostuni, one of Southern Italy’s most beautiful hill towns

  • Visit an enchanting olive oil estate and discover the soul of Puglia’s most beloved ingredient

  • A hands-on focaccia and pasta cooking class in the heart of the countryside


From ancient bread to a UNESCO wonder - Altamura & Matera

  • Visit a DOP bread producer in Altamura for an inside look at the ancient tradition behind Italy’s most celebrated loaf

  • A guided tour of Matera, one of the oldest continuously inhabited cities on earth and a UNESCO World Heritage Site unlike anything you’ve ever seen


Lecce, ceramics & a butcher’s dinner in Cisternino

  • A guided tour of Lecce, the β€œFlorence of the South,” followed by free time to wander its ornate Baroque streets

  • An afternoon in Grottaglie, one of Italy’s most celebrated ceramic towns

  • Dinner at a traditional butcher’s restaurant in Cisternino, a one-of-a-kind Pugliese experience

Meet your host: Kerry

Kerry’s European adventure began over 40 years ago and took her from Virginia to the southeast of England, to the heart of Paris and the forests of Fontainebleau in France, and finally to Italy, where she established her home base with her former Italian husband and their two adult children, Eleonora and Lorenzo.

Growing up in a family of 11 where every meal was homecooked, she learned early the importance of food and time around the table with family and friends, a love that deepened through years living in Turin, Verona, and Friuli. Her involvement with the Slow Food Movement, Master’s in Italian Cuisine and Oenology from ICIF, and Sommelier training with AIS reflect her passion for regional foods, wines, and culture. Kerry founded the English-Speaking Happy Hour in Verona, creating a vibrant international community that still nurtures long-term friendships across the world.

As the host of this special tour to Puglia, she brings food-and-wine expertise, American and Italian cultural depth, and a caring, attentive personal touch. Whether sharing a table under 2,000-year-old olive trees, walking the historic streets of Bari, or searching for treasures in Ostuni, she leads with affection and attention, helping women step out of their comfort zone to embrace unique experiences, discover joy, and build new friendships.

Today, Kerry divides her time between Italy and the United States and continues to blend her love of travel, food, and community by creating meaningful experiences and lasting connections wherever she goes.

What’s included in your experience

  • A private masseria to stay in.

    Accommodations


    7 nights at a private masseria

  • Women join in on a class in Southern Italy.

    Tours & Activities


    Tours, activities, & entry fees per itinerary

    Tour leader for the duration of the trip

  • 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

Moments from past Puglia journeys

What 0ur guests say

  • 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

More than 40% of our guests return for a second journey.

Is this journey right for you?

This trip is designed for women who want more than a vacation.

  • You have been dreaming about Italy but you want someone to handle every detail so you can simply arrive and enjoy

  • You may be traveling on your own, but you want a sense of connection and community, not isolation

  • You appreciate refined accommodations, exceptional food, and experiences with depth and intention

  • You value a seamless, high-touch travel experience where nothing is left to chance

Many of our guests arrive on their own and leave with lasting friendships.

Read through our frequently asked questions.

What happens after you apply?

  1. Apply and book a call. Fill out a short application and schedule a time on Anna’s calendar. No commitment. No pressure.

  2. A personal call with Anna. This is your chance to ask questions, share what you’re looking for, and make sure this journey is the right fit. We’re selective about our groups β€” that’s what keeps the experience exceptional.

  3. Secure your place. Once we’ve confirmed the fit, you’ll receive an invoice for your $500 deposit. From there, you’ll get a welcome guide, packing list, and a direct line to Anna for anything you need before departure.

Ready to join us in Puglia?


Looking for a different style of adventure?

Our Summer 2027 Hidden Scotland trip trades sun-drenched coastlines for dramatic highlands, whisky distilleries, and the brooding beauty of the Scottish countryside. Or explore the UK Castles & Gardens journey through England’s stately homes and private gardens.

See How Much Fun We Have!

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.

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Spring 2027: Venice, Asolo & the Prosecco Hills