From sea to soul
A Private Journey Through Puglia to Italy’s Green Heart
With ENRICO CIOCCOLINI
June 13 – 21, 2026
From the sunlit coasts of Puglia to the timeless hills of Umbria
Step into a journey where landscapes, flavors, and stories unfold at their own rhythm. From the sun-drenched coasts of Puglia to the timeless hills of Umbria, this private road trip invites you to experience Italy in its most authentic and intimate form. Wander through ancient towns, taste the richness of regional cuisine, and immerse yourself in places where beauty feels both effortless and profound. Along the way, there will be moments – quiet, unexpected, and deeply personal – where a place may begin to feel less like a destination and more like something you could belong to.
This curated experience blends discovery, culture, and quiet moments of connection, offering a seamless balance between exploration and reflection. Guided with care and intention, this journey is more than a trip: it’s an invitation to slow down, reconnect, and gently explore what it might mean to create a different rhythm of life: one that feels truly your own, here in Italy.
From sea to soul: the highlights
Authentic Locations & Hidden Gems
Explore handpicked towns, countryside estates, and lesser-known places across Puglia and Umbria, where the true character of Italy reveals itself beyond the expected.
A Journey at Your Own Pace
Travel through ever-changing landscapes, from coastal roads to rolling hills, enjoying a seamless and comfortable experience designed around your rhythm.
Daily Winery Visits & Tastings
Each day includes a visit to a carefully selected winery, where you’ll meet passionate producers, explore their craft, and enjoy guided tastings that reflect the soul of each region.
Regional Flavors & Local Traditions
Savor the richness of Southern and Central Italian cuisine, from Puglian simplicity to Umbrian depth, with curated tastings and memorable dining moments.
Moments of Connection
Experience places not just as a visitor, but as someone who might belong. Quiet encounters and meaningful settings invite a deeper connection with each location.
Program Overview: A tentative Day-by-Day Itinerary
Day 1 – Saturday, June 13th
From Rome to Bari
Our journey begins in the South.
In the afternoon, we fly from Rome to Bari, where the air already carries the warmth of the Adriatic and the slower rhythm of Southern Italy. Upon arrival, we pick up the car and make our way into the heart of Bari Vecchia, where time seems to fold in on itself.
After settling into our accommodation, we step outside and immediately find ourselves immersed in a world of narrow alleys, open doors, and everyday life unfolding in the streets. Women prepare fresh pasta by hand, children play between stone walls, voices echo softly in the distance.
We visit the Basilica of Saint Nicholas, a place of deep history and quiet presence, before letting ourselves wander freely through the old town.
As the day softens into evening, we begin our journey with an aperitivo, followed by dinner in Bari Vecchia.
Highlights
Visit Bari Vecchia
Visit Saint Nicholas Basilica
Aperitif by the sea
Dinner in a typical restaurant
Day 2 – Sunday, June 14th
From Bari to the White City
We start the day slowly.
A quiet breakfast, either at the accommodation or in a local bar, where coffee is strong and mornings feel unhurried. Before leaving Bari, we take one last walk through its streets, letting the atmosphere settle in.
We then head south towards the coast, stopping in Polignano a Mare, suspended between sky and sea. We walk through its white streets, take in the views, and enjoy lunch overlooking the Adriatic.
After a coffee by the sea, we continue inland towards Ostuni.
The White City rises gently on the horizon, glowing in the afternoon light. After check-in, we explore its alleys, viewpoints, and hidden corners.
An aperitivo at sunset and dinner in town close the day.
As always, the day may include opportunities for informal wine tastings and encounters with local flavors.
Highlights
Breakfast in Bari Vecchia
Relaxed walking tour
Road trip by the coast
Lunch with sea view
Visit to a winery
Aperitif by the sea
Day 3 – Monday, June 15th
Flavors, Stone and Sea
The morning unfolds at our own pace in Ostuni.
After breakfast, we drive to Ceglie Messapica, a town deeply rooted in culinary tradition. We walk through its streets, step into small botteghe, and experience the authenticity of daily life.
Lunch is a highlight, at Cibus or Piaceri e Tradizioni, where cuisine expresses the richness of the land.
In the afternoon, we continue through a landscape of ancient olive trees and masserie, arriving in Carovigno. We visit the castle and take time to absorb the quiet character of the town.
Later, we reach Torre Guaceto, a protected natural reserve by the sea. A walk along the shore and an aperitivo at sunset create a moment of pure stillness.
We return to Ostuni for a relaxed dinner followed by an evening walk through the White City’s alleys and tiny, hidden squares.
Wine remains a constant presence throughout the day, whether structured or spontaneous.
Highlights
Breakfast in the White City
Drive through Puglia’s Countryside
Visit to Carovigno Castle
Wine Tastings Throughout the Day
Visit to a Natural Reserve
Sunset aperitif on the beach
Day 4 – Tuesday, June 16th
Baroque, Sea and Southern Soul
After another sumptuos breakfast in Ostuni, we begin our exploration of Salento.
After an optional stop in Mesagne, pearl of North Salento, we arrive in Lecce, a city of Baroque beauty and vibrant energy. We walk through Piazza Duomo and Santa Croce, then move through the streets, entering a library, an artisan workshop, a gallery. Lecce is not only to be seen, but to be lived.
A pause for a cappuccino allows us to simply observe the rhythm of the city.
After lunch, we then continue through the Salento, stopping in Galatina, known for its layered history and quiet elegance, and in Galatone, a more intimate and authentic village.
Depending on the moment, we explore either the Adriatic (San Cataldo or Torre dell’Orso) or Ionian coast (Porto Cesareo), allowing the landscape and light to guide us.
The journey naturally leads us to Gallipoli, where the old town opens onto the sea, offering a different perspective of the region.
Gallipoli is logically followed by a visit to a winery in the Manduria area, where we experience a tasting of Primitivo, one of the most expressive wines of Southern Italy (Agricola Felline, Soloperto, Cantolio, Museo Del Vino Primitivo).
We return to Ostuni for the evening.
Highlights
Breakfast in the White City
Drive through Salento's Countryside
Walking Tour of Lecce’s Baroque Center
Gourmet lunch
Exploration of Salento’s Coastline
Visits to Historic Salento Villages
Introduction to His Majesty, the Primitivo di Manduria
Sunset aperitif in Ostuni
Day 5 – Wednesday, June 17th
Into the Green Heart
A day of transition, yet rich in atmosphere.
After breakfast and check-out, we return to Bari and fly back to Rome. From Fiumicino Airport, we continue by car toward Umbria.
The landscape shifts gradually. The light softens, the rhythm slows, and a new chapter begins.
By mid-afternoon, we arrive in Orvieto, a town suspended above the valley. After check-in, we walk through its streets, visit the Duomo and/or the Pozzo di San Patrizio, and allow the timeless atmosphere to unfold.
An aperitivo along the corso, followed by dinner at Il Pozzo Etrusco, marks the beginning of our Umbrian experience.
Wine becomes more central here, offering deeper insight into the territory.
Highlights
Breakfast in the White City
flight from Bari to Rome
Scenic drive from Lazio into Umbria
Walking Tour of Orvieto
Visit to the Duomo and Pozzo di San Patrizio
Aperitif along the lively Corso
Dinner at il Pozzo Etrusco
Day 6 – Thursday, June 18th
Hills, Silence and Timeless Places
We begin the day gently in Orvieto, with a slow start and a final moment to take in its quiet, suspended atmosphere.
From here, we set off through the Umbrian countryside, heading first towards Titignano. The road unfolds through open landscapes and soft hills, until we reach this hidden hamlet overlooking the lake, where time seems to stand still. We pause, take in the views, and let the silence settle.
From Titignano, we continue to Decugnano dei Barbi, where a wine tasting awaits us. This becomes a natural aperitivo moment, an introduction to the wines and the identity of the Orvieto territory, experienced directly through the land and the people who shape it.
From there, we move to Civitella del Lago (my birthplace), a tiny medieval village perched on ancient castle walls, where we stop for lunch at Trattoria da Zio Cencio or Ristorante Trippini (both highly rated in the Michelin Guide). Here, the cuisine is deeply rooted, authentic, and expressive of the territory, with breathtaking views over the lake stretching toward Orvieto, Mount Amiata, and far beyond.
In the afternoon, we continue towards Monte Castello di Vibio, a perfectly preserved mediaeval village. We walk through its quiet streets and visit the Teatro della Concordia, the smallest theatre in the world, a place of surprising beauty and intimacy.
The journey then leads us to Todi, where we take time to explore the town, its alleys, and its viewpoints, absorbing its calm and balanced atmosphere.
From Todi, we continue towards Massa Martana, with the possibility of a stop at Villa Sobrano for an optional wine tasting, should we wish to extend the experience.
As the day draws to a close, we drive through the countryside towards Abbazia di Collemedio, where we arrive, settle in, and let the day gently come to rest.
Highlights
Breakfast in Orvieto
Scenic drive through the Umbrian hills
Wine Tasting at Decugnano dei Barbi
Lunch in Civitella del Lago
Visit to Montecastello di Vibio
Exploration of Todi
Discovering the Massa Martana Area
Evening and Stay at Abbazia di Collemedio
Day 7 – Friday, June 19th
Power, Art and the Soul of Sagrantino
This is the day we dedicate to the terroir of Sagrantino, one of the most powerful and distinctive expressions of Italian wine.
After breakfast, we pass through Bevagna for a quick stop to experience one of the most beautiful and well preserved medieval villages of Umbria. Then we drive to Montefalco, where we visit Arnaldo Caprai, the true pioneer of Sagrantino. Through vision, research, and dedication, Caprai has transformed this once obscure grape into one of the most respected wines in Italy. The visit and tasting offer a deep dive into both the wine and the story behind it, connecting us directly with the identity of the territory.
In the afternoon, we continue to Tenuta Carapace, a place where architecture, landscape, and wine come together in a truly unique way. The estate itself is a work of art by the worldwide famous Italian archistar Giò Pomodoro, perfectly integrated into the surrounding hills. Here, Sagrantino reaches one of its highest expressions, and this year stands as the leading wine of the appellation.
We then move through Foligno, letting the town unfold naturally along the way, before reaching Rasiglia, a small village shaped by water. We take a gentle walk through its streams and channels, where the sound of flowing water creates a calm and almost suspended atmosphere.
By late afternoon, we arrive in Perugia, a city layered with history, energy, and perspective. We walk through its streets, taking in its character and rhythm as the day begins to soften.
Dinner and overnight in Perugia.
Highlights
Breakfast at the Abbazia
Scenic drive through the Umbrian hills
Visit to Montefalco and Bevagna
Wine Tasting at Arnaldo Caprai
Wine tasting and Light Lunch at Tenuta Carapace
Visit to Foligno
Visit to Rasiglia
Dinner, evening and stay in Perugia
Day 8 – Saturday, June 20th
Where the Landscape Begins to Speak
Some places are not just seen, they are felt.
We begin the day in Perugia, leaving the city behind as we move towards Lake Trasimeno.
Our first stop is Passignano sul Trasimeno, where we walk along the lake, letting the landscape open and set the tone for what follows.
From there, we continue to Madrevite Winery for a tasting overlooking the lake, experiencing a side of Umbria shaped by light, water, and quiet balance.
After the tasting, we reach Castiglione del Lago, where we take time to walk through the town, absorb its elevated views and atmosphere and have lunch.
From here, the journey becomes more intentional.
We pass through Città della Pieve, stopping briefly for a cappuccino, but the real focus begins as we continue towards Monteleone d’Orvieto. The road unfolds through open countryside, gentle hills, vineyards, and scattered homes, this is where the landscape starts to speak in a different way.
In Monteleone d’Orvieto, we take time to walk through the village and its surroundings, allowing space to observe, imagine, and connect with the place.
We then continue through the countryside via Ficulle, as the landscape becomes quieter and more intimate.
By late afternoon, we arrive at Borgo San Faustino, where we settle in and let the day come to a natural close.
Highlights
Breakfast in Perugia
Scenic drive to Lake Trasimeno
Visit to Passignano sul Trasimeno
Wine Tasting at Madrevite Winery
Lunch in Castiglione del Lago
Visit to Città della Pieve
Discovering Monteleone d'Orvieto
Evening and Stay at Borgo San Faustino
Day 9 – Sunday, June 21st
A Different Kind of Ending
The final day carries a different energy.
After breakfast, we head to Narni, walking through the upper part of the town and absorbing its quiet presence.
We then reach the Marmore Falls, where the force of nature creates a moment of awe and stillness.
From there, we continue to Casteldilago for lunch at Osteria dello Sportello, a place suspended above the valley, where everything slows down.
In the afternoon, we drive through the countryside around Monteleone di Spoleto, with the possibility of a stop in Spoleto, before arriving in Assisi, where the journey gently comes to a close, leaving space for what comes next.
Highlights
Breakfast at Borgo San Faustino
Visit to Narni
Visit to Marmore Falls
Lunch in Casteldilago
Scenic drive through the Umbrian hills
Discovering Monteleone di Spoleto
Wine Tasting at Cantina Colle Uncinano
Arrival in Assisi
What’s Included
Domestic flights
Domestic flights within Italy are included as part of the journey, ensuring a smooth and time-efficient transition between regions. This includes the flight from Rome to Bari and from Bari to Rome, allowing us to move seamlessly from Rome to Puglia and then from Puglia to Umbria without interrupting the flow of the experience.
Private Transportation Throughout the Journey
All transportation is privately arranged and seamlessly integrated into the experience. Travel between all destinations is provided in a comfortable, fully equipped vehicle, with fuel, parking, tolls, and comprehensive insurance entirely covered. Each journey, from short local drives to longer scenic routes, is designed to be smooth and effortless, allowing you to remain fully present and engaged, without interruption or concern for logistics.
All Accommodations (including breakfast)
Stay in a curated selection of properties that reflect the character of each region, from the luminous landscapes of Puglia to the quiet elegance of Umbria. Each accommodation is chosen for its charm, comfort, and sense of place, offering restful, atmospheric settings that naturally become part of the journey itself.
Curated Dining Experiences Throughout the Journey
From breakfast to lunch, dinner, and aperitivo moments, all meals are seamlessly included throughout the journey. Each day unfolds through carefully curated dining experiences, from simple, authentic trattorias to refined restaurants rooted in local tradition. Every meal becomes an opportunity to connect with the land, its flavors, and its people, in settings that feel both intimate and memorable. Vegetarian cuisine is naturally embraced throughout the experience, with a focus on seasonal ingredients, regional specialties, and the richness of Italy’s plant-based culinary heritage.
All wine tastings
Wine accompanies the journey as both guide and expression of place. Each tasting is carefully curated to reflect the identity of the territory, from the sun-driven wines of Puglia to the depth and complexity of Umbria. These are not just tastings, but immersive moments that connect you directly with producers, landscapes, and traditions. Through wine, each place reveals itself more fully, offering insight, emotion, and a deeper sense of belonging.
What’s Not Included
Airfares
Flights to and from Italy are not covered.
Travel Insurance
Travel insurance is not included and is highly recommended. Participants are responsible for securing their own coverage to protect against unforeseen circumstances, including trip cancellations, medical emergencies, and lost or delayed baggage.
Pricing
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$11,400 (all included)
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$5,000 deposit at booking
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Balance due by May 13, 2026
Cancellation Policy
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Full refund minus 10% fee if canceled more than 30 days before the tour
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50% refund if canceled 15-29 days before the tour
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No refund if canceled 14 days or less before the tour
For full terms, visit our Cancellation Policy and General Terms.
Your journey is ready
Everything has been carefully designed, shaped around your rhythm, your interests, and the places that felt right along the way.
All that remains is to take the next step and let the experience begin.
Meet Enrico Cioccolini
Enrico is a multidisciplinary entrepreneur and creative strategist working at the intersection of hospitality, wine, and cultural experiences. With a background spanning music, events, restaurant management, digital systems, branding, and experiential travel, he designs and delivers projects that connect people to places in meaningful and authentic ways. As co-founder of Vinessance and co-creator of Faery Snail Tours, he curates immersive journeys across Italy, blending wine, art, and local culture into experiences that go far beyond tourism. Driven by a deep understanding of both operations and storytelling, Enrico transforms ideas into living concepts, where every detail contributes to a coherent and memorable whole.
Meet Faery Snail Tours
Faery Snail Tours offers immersive, slow-travel experiences that combine art, wine, culture, and lifestyle. Our programs are carefully crafted to allow you to connect deeply with the heart of Italy, savoring its beauty and traditions while engaging in creative workshops and curated wine tastings. We specialize in small groups, bespoke itineraries, and meaningful connections with the land, its people, and its stories. Enrico Cioccolini and Stefano Borelli are the visionaries behind Faery Snail Tours, a project born from their shared passion for art, wine, and immersive travel experiences. With years of expertise in hospitality, cultural tours, and wine education, they’ve crafted unique journeys that go beyond sightseeing. Together, they create spaces where travelers can connect deeply with Italy’s rich heritage, indulge in its finest flavors, and embrace the magic of authentic, soulful adventures.