Girl's Trip: Puglia & Matera's Dolce Vita

Girl's Trip: Puglia & Matera's Dolce Vita

Hosted By:

Jenn Hilchey

For this Girls’ Trip, I’m taking you south to Apulia, where food is a reason to gather, wine comes with a story, and centuries-old olive groves lead to little towns and a beautiful coastline.

We’ll stay in a historic masseria, wander among Alberobello’s trulli, explore sea caves by boat, and spend time in Matera, with its ancient stone streets and cave dwellings. There’s wine to taste, local traditions to experience, and plenty to look forward to around the table.

Come on your own or bring a friend—I’ll be there hosting, with the details taken care of so you can enjoy the week and the company.

VIEW THE FULL ITINERARY HERE

Itinerary

BENVENUTI IN PUGLIA
1

BENVENUTI IN PUGLIA

Arrival + Welcome Dinner

Arrive in Puglia, where your private transfer will bring you to our beautiful 5-star masseria near Monopoli. Settle in among the olive groves before we come together for a multi-course welcome dinner with regional wine—our first toast to the week ahead.

THE FLAVORS OF VALLE D’ITRIA
2

THE FLAVORS OF VALLE D’ITRIA

Alberobello + Burrata Experience

We’ll venture into the Valle d’Itria, where whitewashed villages, vineyards, olive groves and Puglia’s famous trulli fill the countryside. Explore iconic Alberobello, taste the flavors of the region and get hands-on during a traditional burrata-making experience.

PUGLIA FROM THE SEA
3

PUGLIA FROM THE SEA

Private Boat Day in Polignano a Mare


A full day on the Adriatic awaits. Cruise the dramatic coastline of Polignano a Mare by private boat, discovering sea caves, hidden coves and limestone cliffs accessible only from the water. Lunch is served onboard as we spend the day soaking up one of Puglia’s most beautiful stretches of coastline.

The evening is yours to relax at the masseria or head into Monopoli for dinner and a night in the historic center.

THE WINES OF PUGLIA
4

THE WINES OF PUGLIA

Vineyards, Cellars & the Wines of Puglia

Today is dedicated to Puglia’s wine country. We’ll visit three distinctive wineries, meet local producers and taste native varieties including Primitivo, Negroamaro, Susumaniello and Nero di Troia, with lunch included along the way.

Tonight, enjoy another evening at leisure or join an optional dinner in the heart of Monopoli.

FROM PUGLIA TO MATERA
5

FROM PUGLIA TO MATERA

A New Chapter in Basilicata

After breakfast, we’ll leave the Puglian countryside behind and travel privately to Matera, where we’ll check into our luxury boutique hotel in the heart of the ancient Sassi.

The rest of the day is yours. Wander Matera’s stone streets, browse artisan shops, find a terrace for an aperitivo, or simply take in the extraordinary surroundings.

THE ANCIENT SASSI
6

THE ANCIENT SASSI

Private Matera Experience + Sunset Aperidinner

Discover the fascinating story of Matera with a private local guide as we explore its ancient cave dwellings, rock-hewn churches and remarkable Sassi neighborhoods.

After free time in the afternoon, we’ll come back together at sunset for an aperidinner overlooking the Sassi, complete with local wine and specialties as Matera begins to glow for the evening.

WINE COUNTRY OF BASILICATA
7

WINE COUNTRY OF BASILICATA

Aglianico del Vulture + Farewell Dinner

Our final full day takes us into northern Basilicata in search of Aglianico del Vulture, one of Southern Italy’s most celebrated wines. Visit two wineries, taste approximately six labels and enjoy lunch while discovering a wine region many travelers never experience.

Back in Matera, we’ll gather for our farewell dinner and raise one final glass to our week together.

ARRIVEDERCI
8

ARRIVEDERCI

Departure to Bari

After breakfast and check-out, we’ll travel together by private transportation to Bari Airport.

Seven nights, two remarkable regions, five wineries, a private boat day, incredible food, and plenty of time to actually enjoy where we are—not just rush from one stop to the next.

VIEW THE FULL ITINERARY HERE
Girl's Trip: Puglia & Matera's Dolce Vita Price

Trip Deposit & Payment Schedule

Final Payment Due:
June 8, 2027.

€5,810 pp Double Occupancy 

€6,610 pp Single Occupancy

Non-Refundable Deposit: €1,000

  • 50% of the remaining balance due 120 days before departure
  • Final balance due 90 days before departure


For guests booking together: Double occupancy pricing is based on two guests sharing a room. If one guest cancels, the remaining guest may find another traveler to take their place or, if available, be paired with another solo traveler. If neither option is available, the single occupancy rate will apply, as accommodations are priced per room rather than per person.

Included In Price

  • 7 nights of luxury accommodations 
  • Daily breakfast plus 6 included dining experiences
  • Private transportation throughout the journey 
  • Two dedicated wine experiences across Puglia and Basilicata — including visits and guided tastings at five wineries.
  • A private boat day along the Polignano a Mare coastline, exploring Puglia’s famous sea caves with lunch served onboard.
  • All scheduled excursions and cultural experiences — including Alberobello and the Valle d’Itria, a hands-on burrata workshop, a privately guided exploration of Matera’s ancient Sassi and cave dwellings.
  • Pre-travel planning, concierge support & on-site hosting
  • A personally hosted small-group experience limited to no more than 12 guests, allowing for a more intimate and relaxed way to experience Southern Italy.
  • Gratuities for drivers, guides, and included experiences — Additional gratuities for exceptional service are always at your discretion, but never expected.

Excluded In Price

  • International flights: I’m happy to assist with flight recommendations based on the trip’s arrival and departure schedule.
  • Travel insurance (required): I can assist you in securing a policy appropriate for your trip.
  • Visa or entry fees (if applicable)
  • Meals and beverages during scheduled leisure time that are not specifically listed as included in the itinerary
  • Taxis or transportation for personal leisure outside of scheduled group transportation
  • Optional activities, spa treatments, and excursions not specifically listed as included in the itinerary
  • Local city/tourist taxes: Approximately €8–€10 per person, per day, payable directly to the hotels by cash or credit card.
  • Personal expenses, including shopping, souvenirs, laundry, and other incidental purchases
  • Additional food, wine, or alcoholic beverages ordered outside of the included meals, tastings, and experiences
Our Stay: Masseria Il Melograno | Monopoli

Our Stay: Masseria Il Melograno | Monopoli

Our home in Puglia is Masseria Il Melograno, a 5-star historic masseria surrounded by centuries-old olive trees just outside Monopoli. 

Originally a 17th-century fortified farmhouse, the property has been beautifully restored while preserving the whitewashed stone, peaceful courtyards and gardens that give Puglia’s masserie their unmistakable character. Between our adventures, there’s time to slow down by the pool, enjoy the grounds, or take advantage of the masseria’s private beach club along the Adriatic during seasonal operating dates.

It’s a peaceful countryside base for our days exploring Puglia’s coastal towns, vineyards, food and wine—while still being just a short drive from the historic center of Monopoli.

Our Stay: Palazzo del Duca | Matera

Our Stay: Palazzo del Duca | Matera

For the second half of our journey, we’ll move into the heart of Matera’s ancient Sassi for a completely different experience at Palazzo del Duca.

This luxury boutique hotel is spread across beautifully restored historic spaces built into Matera’s centuries-old stone landscape. Individual rooms incorporate original architectural details, exposed rock and vaulted ceilings, blending the history of the Sassi with an elegant, contemporary stay.

Step outside and you’re already in the historic center, surrounded by Matera’s winding stone streets, restaurants, artisan shops and extraordinary viewpoints. It’s the kind of location that allows you to experience Matera beyond our scheduled activities—simply walk out the door and explore.

Cancellation Policy

Cancellation Policy

All payments are non-refundable unless we cancel the trip, including if the minimum group size is not met by May 9, 2027. In that case, all trip payments will be refunded. Reservation transfers may be considered on a case-by-case basis, subject to availability, supplier approval, and any applicable fees. Travel insurance is required; cancellation claims must be filed directly with your insurer and are subject to policy coverage. 

Full Terms & Conditions.

Your Host

Your Host

Hi, I’m Jenn Hilchey, a Tampa-based travel advisor and small-group host with more than 15 years of experience in hospitality. I’ve hosted group journeys throughout Italy, Spain, and France, and creating an environment where everyone feels welcomed, supported, and genuinely included is one of my favorite parts of what I do.

My trips are designed for women who want to relax and actually enjoy where they are without worrying about all the details behind the scenes. I’m very intentional about creating a balance between culturally immersive experiences, incredible food and wine, beautiful places to stay, and enough leisure time to wander, shop, have a glass of wine, or simply slow down.

I absoutely love watching a group of women who may arrive as strangers leave with new friendships. Whether you come with a friend or completely on your own, you’ll be welcomed into a small group of women who share a love of travel, culture, good wine, and experiencing somewhere new. I’ll be there throughout the journey to host, support you, and take care of the details so you can settle in and enjoy the experience. Come as you are, relax, and let me take care of the rest!

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FAQ’s

The trip is €5,810 per person for double occupancy or €6,610 for single occupancy. A €1,000 non-refundable deposit is required to secure your spot, with the remaining balance divided into two payments: 50% of the remaining balance: due 120 days before departure Final balance: due 90 days before departure

Yes, it is.

All adult ages are welcome! Past groups have typically ranged from their 30s-50s.

All payments are non-refundable unless we cancel the trip, including if the minimum group size is not met by May 9, 2027. In that case, all trip payments will be refunded. Reservation transfers may be considered on a case-by-case basis, subject to availability, supplier approval, and any applicable fees. Travel insurance is required; cancellation claims must be filed directly with your insurer and are subject to policy coverage.

Travel insurance is required for all travelers. It helps protect your investment and gives you peace of mind in the event of unexpected changes, delays, or emergencies. Please plan to purchase your travel insurance within 7 days of your deposit to take advantage of the best possible coverage options. Proof of travel insurance must be submitted no later than 90 days prior to departure. The Travel Box International is happy to assist you with this—I’ll send over a quote link from our trusted partner, TravelSafe Insurance, right after your deposit is processed.

10-12 Guests Only!

Airfare is NOT included. We’re happy to assist with flight recommendations based on your arrival and departure.

13 meals are included: 7 breakfasts, 3 lunches, 2 dinners, and 1 sunset aperidinner—plus wine or beverages with included dining experiences as specified throughout the itinerary. You’ll also enjoy additional food and wine tastings along the way, including our burrata experience and winery visits.

Complete the registration form, and I’ll be in touch to confirm availability, answer any questions, and send your deposit payment form. Your spot is officially confirmed once availability has been verified and your €1,000 non-refundable deposit has been received.

Embrace the freedom of solo travel and join a supportive, vibrant community! This trip is designed to warmly welcome and embrace solo adventurers. We believe traveling solo on a group trip is an incredible way to build confidence, make new friends, and create truly personal memories.

Yes! Dietary restrictions and allergies can be accommodated. Please include any dietary needs when registering.

Bari Karol Wojtyła Airport (BRI) is the recommended airport for this trip. Private arrival transportation from Bari Airport and our group departure transfer back to Bari Airport are included. Brindisi Airport (BDS) is another option; however, transfers to and from Brindisi are not included in the trip price. I’m happy to assist with arranging private transportation if you choose to fly through Brindisi.

For cancellations outside of insurance coverage, please review the standard cancellation policy HERE. Itinerary subject to change.

Make Your Reservation Now!