VIP Moms & Daughters:
Naples & Beyond
A Transformational Italian Journey for Generations
June 19–25, 2026 | Naples, Italy
VIP Moms & Daughters: Naples & Beyond
A Transformational Italian Journey for Generations
June 19–25, 2026 | Naples, Capri & Positano
Where Style, Bonding & Italian Beauty Meet
Naples isn’t just a destination it’s a living, breathing experience. A place where elegance and warmth meet in the streets, where history and modern style intertwine, and where every moment invites you to slow down and savor life more fully.
Over seven unforgettable days, you and your daughter (or mother, or grandmother) will experience Italy not as visitors, but as cherished insiders. With Rosa guiding the way, you’ll discover hidden boutiques, artisan studios, coastal towns, and family-run restaurants that reveal the true soul of Italy.
From curated shopping and breathtaking seaside views to laughter-filled meals and meaningful shared moments, you’ll step into a world where beauty, culture, and connection come alive.
This is more than a trip, it’s an invitation to experience Italian style, sophistication, and togetherness in its most authentic form. A week designed to deepen your bond, elevate your confidence, and leave you with memories you’ll carry long after you’ve returned home.
What Makes This Experience Unique
This is not a rushed group tour or a standard itinerary.
This is Rosa’s world — warm, carefully curated, and deeply personal.
You’ll enjoy:
Insider access to designers, ateliers, and boutiques Rosa has known for years
Shared moments designed to bring generations closer
Unforgettable meals, curated for connection and discovery
Guided shopping with Rosa, shaped around your personal style
The joy of exploring Naples, Capri & Positano like someone who belongs
It’s part girls’ weekend, part style retreat, part family love letter and all beautifully Italian.
Day 1: Friday, June 19
BENVENUTI A NAPOLI!
MORNING
When you arrive in Naples, you’ll settle into our four-star hotel - is an ideal home base for this Mother–Daughter experience, located in the heart of Naples’ most elegant district. Just steps from Piazza dei Martiri and the city’s iconic shopping streets - Via Calabritto, Via dei Mille, and Via Filangieri - the hotel places you within easy reach of prestigious boutiques, historic tailor shops, and some of Naples’ most beloved cafés and restaurants. It’s a setting that blends comfort, culture, and effortless access to the rhythms of everyday Neapolitan life.
EVENING
Our welcome dinner is about more than delicious Neapolitan food. Naples is a city where families still gather around long tables - rooted in connection, ritual, and shared moments. It’s a place where recipes are passed down like personal history, and where even the simplest dish carries meaning. Here, food isn’t just tasted; it’s felt. And it’s often how the most meaningful connections begin -making this first shared meal the perfect way to open our journey together.
Day 2: Saturday, June 20
HISTORIC NAPLES &
SHOPPING WITH ROSA
MORNING
We begin the day with a private guided walk through Naples’ historic center - a place where daily life unfolds against centuries of art, architecture, and storytelling. With a local guide, we’ll explore the layers that make Naples so expressive and alive, connecting its past to the rhythms of the present in a way that feels natural and engaging.
AFTERNOON
In the afternoon, I invite you to join me for a curated shopping experience through Naples - visiting boutiques and selected showrooms I know personally. This is shopping with intention: discovering beautifully made pieces, meeting local artisans, and finding items that feel authentic to both Naples and to you. There’s no rush and no expectation - just the pleasure of exploring, sharing opinions, and enjoying the experience together.
EVENING
That evening, we gathered for dinner in a charming palazzo courtyard - an elegant yet relaxed setting that pairs perfectly with classic Neapolitan flavors. Over food and conversation, the day winds down in the warm, effortless way Naples does best.
Day 3: Sunday, June 21
HISTORY, CRAFTSMANSHIP & THE JOY OF PIZZA
MORNING
This morning, I take you into the layers of Naples that continue to inspire me - beginning with the National Archaeological Museum, home to some of the most extraordinary artifacts from Pompeii and Herculaneum. It’s a powerful reminder of how deeply history lives here, not behind glass, but woven into everyday life. From there, we continue with a guided walk through the historic center, where centuries-old streets pulse with energy, conversation, and color.
AFTERNOON
We visit a historic landmark before stepping into a family-owned glove atelier founded in 1899 - a place that reflects Naples’ tradition of craftsmanship and pride in things made well and meant to last. Here, you’ll have the opportunity to shop for beautifully handmade leather gloves and accessories, each piece carrying a story of heritage and artistry passed down through generations.
EVENING
In the evening, we roll up our sleeves and step into one of Naples’ most beloved traditions. You’ll learn how to make authentic Neapolitan pizza, from shaping the dough to understanding what makes it so special. Once the pizzas are baked, we sit down to enjoy what we’ve created - a relaxed, joyful dinner that feels more like gathering in someone’s kitchen than dining out. The night ends the Neapolitan way, with gelato of course - and an easy stroll, savoring both the flavors and the moments shared.
Day 4: Monday, June 22
Capri: Sun, Style & La Dolce Vita
MORNING
Capri has a rhythm all its own - glamorous yet effortless, iconic yet deeply personal. This morning, we set sail on a private boat toward the island, letting the coastline unfold as we cross the water. Weather permitting, there’s time to pause, take in the sun, and enjoy a refreshing swim - the kind of moment that reminds you how good it feels to slow down and simply be present.
LUNCH
Lunch is enjoyed at one of Capri’s celebrated restaurants, chosen for its atmosphere as much as its cuisine. With sweeping views of the sea, it’s an unhurried moment to relax, connect, and savor the setting - the kind of lunch that lingers in memory long after the plates are cleared.
AFTERNOON
The afternoon is yours to enjoy Capri at an easy pace, wandering through its chic boutiques and artisan shops. I’ll guide you through a thoughtful mix of refined fashion and handcrafted finds - including the island’s famous made-to-measure sandals, created by local artisans who have been perfecting their craft for generations. It’s shopping that feels personal, joyful, and inspired rather than overwhelming..
EVENING
As the day winds down, we return to Naples in time for sunset. The evening concludes with dinner at a beloved Neapolitan restaurant - a relaxed, welcoming place where conversation flows easily and the day’s experiences naturally come together.
A personal note: Capri’s handmade sandals are a favorite among women who appreciate timeless style - even celebrity chef Giada De Laurentiis has shared that she and her daughter love having theirs made here. It’s one of those simple pleasures that feels both special and enduring.
Day 5: Tuesday, June 23
POSITANO: COASTAL BEAUTY & ITALIAN STYLE
MORNING
Positano is one of those places that feels almost unreal the first time you see it - cascading color, dramatic cliffs, and the sea stretching endlessly below. This morning, we take the ferry along one of Italy’s most breathtaking coastal routes.
Once ashore, I’ll guide you through Positano’s winding pathways and scenic terraces, offering a relaxed introduction to the village. This is a place best experienced on foot, moving slowly, pausing often, and letting the beauty reveal itself naturally as you explore.
LUNCH
Lunch is at one of Giorgia’s and my favorite restaurants - a place we return to for its warmth, amazing coastal flavors, and views that never fail to take our breath away.
AFTERNOON
The afternoon is dedicated to discovering Positano’s distinctive style. We’ll explore boutiques known for linen dresses, supple leather goods, and handcrafted sandals made by local artisans - pieces that feel effortless, wearable, and deeply connected to this place. Shopping here is about finding things that hold a memory, not chasing trends.
EVENING
As the light softens, we return to Naples in time for sunset. The evening concludes with a relaxed dinner, giving us space to reflect on the day and enjoy one another’s company.
Day 6: Wednesday, June 24
VOMERO, CULTURE & A BEAUTIFUL FINAL EVENING
MORNING & AFTERNOON
We begin the day in one of Naples’ most elegant neighborhoods - Vomero - with a visit to the Certosa di San Martino. Rich in history and art, it also offers sweeping views over the city and the bay. It’s a place that invites you to pause, take in the perspective, and appreciate Naples from a quieter, more reflective vantage point.
From there, we enjoy time for curated shopping and local discoveries, followed by a special lunch prepared by Tatto Chef - a local favorite known for his thoughtful approach to traditional flavors and warm hospitality.
AFTERNOON
The afternoon is intentionally left open, allowing you to experience Naples in your own way. Whether you choose to relax, revisit a favorite spot, enjoy the waterfront, or linger over coffee or gelato, this time is yours. I’m always happy to offer personalized suggestions if you’d like them.
EVENING
In the evening, we gather for our farewell dinner in Borgo Marinari - a waterfront enclave that feels timeless and welcoming. With the sea beside us and the city glowing nearby, it’s a setting that naturally invites reflection, gratitude, and celebration of the days shared together.
Day 7: Tuesday, June 25
CIAO NAPOLI: DEPARTING WITH STYLE & MEMORIES
MORNING
This morning begins slowly, with a final breakfast and one last Italian espresso. It’s a moment to reflect on the laughter, shared discoveries, and the meaningful time spent together - across generations - in a place that knows how to honor connection.
As you depart, you carry home more than memories or beautiful finds. You leave with moments that stay with you: walking historic streets side by side, lingering over meals, discovering places that revealed themselves gently, and sharing experiences that felt both special and deeply personal.
Naples has a way of leaving its mark - not loudly, but lastingly. Often described as the soul of Italy, it’s a place where life is felt deeply, shared openly, and remembered long after you return home. And as it always does, it welcomes you back whenever you’re ready.
What’s Included
4-star+ hotel in the main square of Naples (double occupancy, 6 nights)
Daily breakfast
4 dinners (welcome, traditional Neapolitan, “fun a la carte” evening, and farewell dinner)
3 curated lunches (pizza-making class, Positano, and Tatto Chef trattoria)
Private boat to Capri & ferry to Positano
All guided tours per itinerary and museum/monument entrance fees
Personalized shopping experiences with me (and Giorgia by my side)
In-city transfers during the tour
Pre-trip Zoom session for travel advice, packing guidance, and style planning
Gratuities for included services
What’s NOT Included
Flights
Meals and drinks not specified in the itinerary
Hotel incidentals (room service, laundry, bar tabs)
Personal expenses and additional activities
Travel insurance (PS: I personally recommend FAYE for their attentive service, intuitive app, and thoughtful support for travelers before and during their journey. Learn more.)
Airport transfers (available upon request)
Liability for changes beyond our control
How to Reserve
Naples Mothers & Daughters Tour
$5,997 per person (based on double occupancy)
Because this is a highly curated, boutique experience, only 5 spots are available.
To secure your place, a 30% non-refundable deposit is required at the time of booking.
Join us for this unforgettable week.
Ready to explore Naples & Beyond with your daughter (or mother, or granddaughter)?
Kind words from our client
Rosa helped create beautiful lifelong memories for my teenage daughter, my mother and myself during our trip to Naples in June. We were three generations of women exploring a new part of the world together, with Rosa as our personal Neapolitan guide. I wouldn’t have done it any other way. She catered to our varied interests and made sure we each experienced what was important to us. Historical walking tours and museum tours with knowledgeable local guides; delicious Neapolitan cuisine in neighborhood restaurants; casual strolls around charming
cobblestone streets and alleys near our centrally located hotel; excursions out of the big city to nearby Capri and Positano; and of course, shopping in one-of-a-kind boutiques, including a multi-generational family run leather glove and handbag manufacturer!
For my daughter, the trip was transformative. Although she has traveled abroad before, being able to experience a city and region with someone who is native to it made it more impactful. She has an interest in fashion and thoroughly enjoyed visiting the glove and handbag manufacturer. Seeing how their products are made with such care and talking with the owners (or as she said,
“the faces behind the products”) filled her with inspiration. In her words, the trip “will stay with me forever."
- Meg B
Terms and Conditions: Group Size, Payment, and Itinerary Policy
Minimum Group Size & Trip Confirmation:
This exclusive Naples journey requires a minimum of 5 participants to proceed, ensuring an intimate, highly personalized experience for all guests. Once the minimum group size is met, you will receive an official confirmation.
Reservation and Payment Terms:
Deposit Policy: A 30% non-refundable deposit is required to secure your spot.
Final Payment: The remaining balance must be paid in full 60 days prior to departure.
Accepted Payment Methods: You may choose to pay in full or in two parts using credit card (with a 2.25% processing fee), bank transfer, or check.
Pricing is based on a minimum of 5 participants.
Itinerary specifics are subject to change to enhance the experience or accommodate unforeseen circumstances.
Refunds and Cancellations:
If the trip is canceled by us due to not meeting the minimum group size, all participants will receive a full refund of payments made beyond the non-refundable deposit. Any credit card processing fees incurred will also be reimbursed, ensuring no out-of-pocket loss.
If a participant chooses to cancel their reservation, the deposit is non-refundable.
Cancellations made within 60 days of departure are non-refundable. Due to the nature of this exclusive experience, we are unable to offer refunds for cancellations at this stage.
To protect your investment, we strongly recommend purchasing comprehensive travel insurance that includes trip cancellation coverage in case of unforeseen circumstances.
Flight Bookings:
Direct flights are available from Philadelphia and New York City.
We recommend waiting to book flights until the trip is officially confirmed. Once the minimum group size is met, you will receive prompt confirmation so you can make travel arrangements with confidence.
Itinerary Flexibility:
The itinerary is carefully designed to provide a seamless, unforgettable experience. To ensure the highest level of quality and personalization, some itinerary elements may be subject to change. Any changes will be made with the goal of maintaining the highest level of quality and personalization.
By registering for this journey, you acknowledge and agree to these terms, which are designed to ensure a seamless and enriching travel experience. Our team is dedicated to supporting you through every step of your travel planning process.
For alternative payment methods or questions, contact: [email protected]
My Italian Lifestyle is part of The Rosa Group © 2026