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Southern Italy: A Road Less Traveled

Southern Italy: A Road Less Traveled

April 11-19, 2022



Minimum 6 travelers

Experience the Southern Italy lifestyle with a small group of women travelers! We will visit the heel of the boot of Southern Italy, a region known as Puglia. This distinctive and delightful region, with its crystal blue seas, beautiful countryside and endless sunshine is a land of natural beauty, warm hospitality and amazing food and wine.

Recognized as the heel of the boot, (Yes, Italy is shaped like a boot!), this region looks and feels like nowhere else in Italy.

 As we make our way through dramatic mountains,we will visit Byzantine churches and wander through sun-baked olive groves.  Our time in Puglia is just the beginning of your love affair with Southern Italy!

This beautiful coastline is evidence of the diverse influences of the many conquering invaders of centuries past: the Normans, the Spanish, the Turks, the Swabians and the Greeks.

Let’s discover the eclectic history of Puglia and how the intermingling of the diverse cultures forms the basis of their signature cuisine. We will have a over a week filled with exquisite food and wine tastings, historic towns, and a lot of art and history.

We will meet the most charming local people who are passionate about their lifestyle, their region and the region’s many offerings: Barocco (architecture), farmhouses, red earth, olive groves, uncontaminated countryside, Mediterranean aromas, an incredible cultural heritage and architecture are only part of what this southern Italy region has to offer. 

Puglia is truly an outstanding unknown amongst many travelers. This dream vacation is a real lifestyle immersion to understand deeply the most authentic personality of this southern Italian gem. It will be a pleasure to have you join me in this beautiful region where I once attended school as a teenager.

Day 1

images-2Welcome to Puglia! You will arrive in Bari/Brindisi where you will be met by our private driver who will bring you to our charming Salento Masseria where we will be staying 3 nights.

Once settled in, we will gather for a welcome celebration and get to know more about the Puglia region, its lifestyle and the other fabulous women travelers.

Lecce, city of Baroque

Polignano_a_Mare_-_panoramio_-_Carlo_PelagalliDay 2

After breakfast, we will enjoy a splendid guided tour of Lecce discovering the beauty of its cobblestones, streets, baroque palaces, and churches.

We will explore on foot with our personal tour guide and enjoy a lunch featuring cucina povera and local delights.

The afternoon will be spent at the Masseria for some relaxing time by the pool and an urlafternoon cooking class.

It will be an afternoon of learning to prepare some traditional recipes.

Our dinner will be based on our creations with an informal wine tasting. Andiamo a mangiare!        


Galatina and Gallipoli

Day 3

imagesAfter breakfast, we head south on the Ionian coast to Gallipoli, a small island characterized by a mix of converging alleys and little streets. The walls, the embankments and the towers that have defended the city for centuries from invaders, give the city a unique charm, leading travelers here from faraway places.

We will enjoy lunch with a seafood menu and an amazing sea view. On our way back to our Masseria, we will visit Galatina, another refined example of Barocco Salentino: this architecture features ornate Baroque balconies and doorways which we will see on the Palazzo del Concerto and the Palazzo Scrimeri. The church of Saint Peter and Saint Paul, known as the ‘mother church’ is a pretty church in Baroque style made of the local pale golden stone.

However, Galatina‘s most impressive monument is the 14th century Romanesque church of Santa Caterina d’Alessandria with frescoes by Francesco d’Arezzo from the 15th century.  


Corigliano d’Otranto, Otranto, Maglie

Day 4

After breakfast, our first stop is Maglie to visit of one of the oldest and best known Pastificio’s in the region.

A pasta factory!

After our fun time in the pasta factory, we will visit is Otranto: this town lies in an inlet on the western coast of the Otranto channel.

The Ancient Hydruntum was founded by the Greeks. During the Middle Ages, Otranto became even more important as a mercantile port, but the mid- fifteenth century marked the beginning of a long period of decline with the violent Turkish intrusions.

We will visit an amazing Cathedral, founded at the end of the eleventh century. Featuring a majestic interior  with an exceptional mosaic floor and precious historic works including the splendid Tree of life, the “Martiri” chapel commemorates the massacre perpetrated in 1480 by Turks.

We will then stop in Corigliano d’Otranto, one of the 11 towns of the Grecia Salentina that have retained the Greek heritage of the Byzantine period including the Griko dialect. It is a small town with a fascinating medieval castle.

For The Love of Food and Wine

Day 5

imgres-6After breakfast, we will visit a premium local winery and an olive oil farm.

Today’s lunch will be a picnic in the olive grove with traditional Pizzica Music and Dance.  

After lunch, we will make our way to Lecce where we will settle in  for the next two days.

How fun for a chic tour in a classic car before we share an aperitivo in a lovely venue.

Dinner will be on our own as we discover our own favorites in Lecce.

Foodie Tour in Lecce        

Day 6


This morning we will have a beautiful crafted food tour of Lecce: there will be tastings and more tastings!

Our guide will be available to make recommendations on the goodies you may wish to bring home.

The afternoon will be yours to relax and immerse in the local lifestyle and devote time for additional last minute shopping. Tonight we will have our dinner in one of Lecce’s most fabulous award winning restaurants.

Day 7- This will be Easter Sunday

images-6The white washed stone villages of Ostuni, Cisternino and Alberobello

After breakfast, we head north to the famous white and trulli villages where we will start with a stroll through Ostuni and enjoy lunch in Cisternino .

We will then discover Alberobello, the trulli district with its many shops, wine bars and gourmet food boutiques. 

Day 8

Lifestyle Puglia: Bari, Polignano a Mare, Locorotondo

imgres-5Today we explore the secrets of the medieval Bari Vecchia, the old town of Bari, a buzzing maze of tight alley ways and small piazzas adjacent to the city’s port.

We will wander the narrow lanes of southern Italy soaking up the vibrant southern life. In the afternoon, we will indulge ourselves with a photography tour inspired by the “Scenes from Polignano a Mare‟,  a medieval town perched precariously on a sheer cliff facing the bright blue Adriatic sea.

Mesmerizing will be the picturesque narrow ancient buildings and vivid colors. Along the way we will visit a winery which produces Puglia’s classics wines.

In the evening, we will have our farewell dinner in a small traditional restaurant in the heart of the old town. It is never easy saying goodbye.      


Day 9

Buon viaggio, Arrivederci

After breakfast, we’ll be transferred back to Bari, where we will depart either by air, rail or road to the rest…



Join us for this ultimate dream vacation as we discover Southern Italy! Tantalize your taste buds, immerse yourself in local culture, enjoy hands on cooking with the locals, drink fabulous wines and luxuriate in some of the most authentic Masserries and boutique hotels in Puglia.


Two roads diverged in a wood, and I —
I took the one less traveled by,
And that has made all the difference.

– Robert Frost



NO SINGLE SUPPLEMENTS. We believe all women deserve their own space and privacy.  Her Dream Vacation tour price includes private single room in boutique hotels or similar private accommodations, meals and tours where indicated, private transportation and more.

This particular dream vacation is limited to 10 women. Minimum booking is 6. In the event, we do not meet the minimum capacity for travel, you will have the option to pay a supplemental fee for a private customized tour.  This decision will be made with your approval and receipt of supplemental payment.

Early reservations are advised and a non refundable deposit of $800.00 is required at the time of your reservation. You will receive a confirmation with travel details and an invoice for balance due. Full payment is due 120 days prior to commencement of trip.

If you are making your reservation, less than 90 days of departure, the entire amount of the trip must be paid in full at the time of reservation. Please contact us and you will be invoiced. 

Tour Cost:  $5695.00 

Does Not Include: International flight or mandatory all inclusive travel insurance. Tips for guides, drivers, meals not indicated, alcoholic beverages, & personal spending or taxes.

*Itinerary is subject to change based upon weather and unknown events. Final itinerary with listed hotel accommodations, contact information, and transfer schedule will be sent prior to departure.*

THIS IS NOT A BUS TOUR. We will be traveling using private transportation, trains and ferries. After final payment, you will be sent additional information with travel and packing tips, final day to day itinerary, logistics and needed details from you to help you with ease of travel.

Our small group women’s tours include many extras that you may not be expecting. Because we are a small women’s group tour, we have the luxury of flexibility including necessary changes. We stop when we want to, we add in an extra site and we start our day when it makes sense. Some days are easier than others but you do have some free time built in. It is important to us that you take care of YOU. Do you want to get a massage? Go shopping? Or just chill in your room with a good book? Please do so with being mindful and respectful to your tour companions and traveling concierge.

We have expert guides and drivers who answer questions one on one, with transportation that is typically a luxurious touring van. We immerse with the locals and there is a lot of serendipity! We visit the “planned by us” but unknown to you and surprises along the way are built in. Please join us!

***Note: Easter Sunday is


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