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

A fully curated food and wine journey through Puglia that’s designed exclusively for women who want depth, not a checklist.

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, stand inside the fairy-tale trulli of Alberobello, and sail past sea caves that glow turquoise in the late-afternoon light. 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

  • 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

  • A boat along the Adriatic coast, sailing past sea caves carved into the cliffs

  • 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) ⋆
13 of 16 spots remain

Your invitation to Puglia

ONLY $500 deposit to secure your place

Small group - 16 people maximum

Option 1

$7,995 USD

($11,295 CAD)

Per Person

Single Occupancy,
Deluxe Room (no terrace)

ONLY 3 ROOMS!

Option 2

$8,495 USD

($11,895 CAD)

Per Person

Single Occupancy,
Superior Room with a Private Terrace

ONLY 7 ROOMS!

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
May 1, 2026 - $3,995 second payment is due
July 1, 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 2 ROOMS!


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

    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

    Sea Caves, 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
    Weather permitting, set sail on a modern skiff to explore ancient sea caves carved into the Adriatic cliffs
    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 (Nov 1)

    Departure day

    A final breakfast and cappuccino at the resort
    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


Women travel by boat an explore the sea caves near Polignano a Mare.

Sea caves, Apulian wines, Polignano a Mare & gelato!

  • Set sail to explore ancient sea caves carved into the Adriatic cliffs - dramatic, otherworldly, and completely unforgettable

  • 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 “Florence 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

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

  • “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

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.

  • Yes, this journey is exclusively for women (she/her). And yes, most of our guests join on their own. By the end of the week, it rarely feels that way. The experience is designed to feel welcoming, comfortable, and genuinely connected from the very first evening.

  • Just your airfare. From the moment you arrive, every accommodation, experience, meal, and transfer is handled for you. We are happy to help you find the best flight options and can arrange airport transfers in Bari at additional cost.

    • Activities, food, and beverages not listed in the itinerary.

    • Items of a personal nature.

    • Airfare to and from Italy.

    • Airport transfers in your departure city.

    • Airport arrival and departure transfers in Bari (available at additional cost).

  • Strongly recommended. We can arrange travel insurance for American travelers - let us know if you would like a quote.

  • A reasonable level of fitness is recommended. Expect 10,000+ steps a day on cobblestone streets, hilly paths, and the beautifully uneven terrain Southern Italy is known for. Our day in Matera is the most physically demanding, with plenty of uphill and downhill walking through the historic sassi.

    If that sounds like too much on a particular day, you are welcome to enjoy a leisurely morning at the resort instead.

    The itinerary is designed to balance guided experiences with free time.

  • The group gathers at the resort in Puglia on October 25, 2026. Everyone is responsible for booking their own flights to Italy. We are happy to help find airfare options and can plan a trip extension before or after the group journey - any additional costs would be the traveler’s responsibility.

  • We focus on boutique, high-quality accommodations and curated experiences that feel personal rather than commercial. Think of it as the kind of trip a very well-connected friend in Puglia would design for you - elevated, thoughtful, and never generic.

  • 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 our local hosts and guides, we kindly ask that all guests are ready on time each day. We will give gentle reminders, but punctuality is part of what keeps the experience seamless for everyone.

  • Every meal is thoughtfully selected to give 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. Come with an open mind and a generous appetite. 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.

  • If you’d prefer to skip an activity and unwind at the resort, that’s completely fine - just give your tour host advance notice so we can plan accordingly.

  • Pre-paid guide and driver gratuities of $300 per person will be collected approximately one week before departure.

  • We will provide a detailed packing list closer to the travel dates with suggested attire and useful items. The trip is comfortably casual - dress for warm days, cool evenings, and a great deal of walking.

  • This is an adults-only journey for guests 18 and older. If you’re under 50, please don’t hesitate — all ages are welcome. If you’re interested in a family adventure through Italy or another European destination, we would be happy to design a custom trip for you.

  • Absolutely. Many of our guests add a few days in Rome, the Amalfi Coast, or elsewhere in Italy before or after the group journey. Anna can help you plan the perfect extension.

  • Most group tours in Italy move 30–50 people through the same crowded stops on a fixed schedule. This journey is limited to 16 guests, led by local guides who know every back street and family-run restaurant, and designed around private experiences (cooking classes, estate visits, tastings) that you simply cannot access on a standard tour.

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 — 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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