Italy – Done Right

The Art of Italian Living

14 nights
15 days
September 1, 2027
-
September 1, 2027

A journey through the food, wine and rhythms of Italian life.

Hosted by Josh of WEKA, experience the Italy he came to know through 17 years of living there -through its people, regional traditions and the relationships that reveal a place from the inside.

Begin in the volcanic hills of the Castelli Romani, before travelling south to Sorrento and the Amalfi Coast. Continue to Castello di Potentino in Tuscany, then into the vineyards and olive groves of Umbria at Roccafiore Wine Resort & Spa.

Across four distinctive regions, share tables, meet local makers and experience the care, pride and craftsmanship woven into everyday Italian life.

This is Italy beyond the familiar highlights personal, generous and deeply connected to place.

Meet your hosts

Josh Loughnan
Josh Loughnan, founder of WEKA, has spent nearly two decades creating journeys shaped by food, culture and people. Warm, curious and deeply connected to Bali, Josh’s relationships with local chefs, growers and hosts open the door to experiences that feel personal, generous and impossible to replicate.
Ali Ward
With a senior qualification in international cuisine and experience cooking in places as far-flung as Antarctica, Ali brings a natural connection to the culinary heart of the journey. Alongside Josh, her designer’s eye, warmth and attention to detail help create a relaxed group dynamic where every guest feels welcomed and beautifully looked after.

Your Journey

Your Journey

Day 1: Arrive in Italy | Welcome to Castelli Romani

Arrive in Rome, where you’ll be met and transferred into the hills of Castelli Romani. Just beyond the capital, this landscape of historic villages, volcanic lakes and vineyards offers a gentler introduction to Italian life.

Settle into your accommodation in Frascati before joining your host and fellow guests for a relaxed welcome aperitivo and dinner, introducing the wines, flavours and traditions of the region.

Frascati, Castelli Romani

Day 2: Castelli Romani | Hidden Villages & Historic Cellars

Explore Marino and Castel Gandolfo alongside a local host, discovering historic streets, traditional food shops and the underground wine cellars hidden beneath the villages.

Continue towards Lake Nemi, known for its tiny wild strawberries, before gathering for a leisurely lunch showcasing regional produce. The afternoon allows time to wander, meet local people and experience the pace of village life.

Frascati, Castelli Romani

Day 3: Castelli Romani | From the Market to the Table

Join a local chef to select seasonal ingredients, meet producers and learn about the culinary traditions of the region.

Continue to a privately hosted winery, where you’ll meet the winemaker and cook together before settling around the table for a long lunch accompanied by estate wines. Personal, generous and unhurried, this is far more than a conventional cooking class – it is an invitation into local life.

Frascati, Castelli Romani

Day 4: Rome, Your Way | Or a Slower Day in Frascati

Today is yours to shape.

Spend the day exploring Rome independently from its historic landmarks and museums to neighbourhood restaurants, markets and quiet streets or remain in Frascati for a slower day among its cafés, wine bars and local shops.

Frascati, Castelli Romani

Day 5: Castelli Romani to Sorrento | Journey South

Leave the hills outside Rome and travel south towards Sorrento, your base for three nights on the Amalfi Coast.

Settle into your coastal accommodation, with time to explore the surrounding village or simply pause and take in the Mediterranean views. This evening, gather for dinner and the beginning of a more coastal rhythm.

Sorrento, Amalfi Coast

Day 6: Capri | A Private Day on the Water

Spend the day exploring the coastline and the island of Capri aboard a private boat.

Cruise beneath dramatic cliffs and past hidden coves and the Faraglioni rock formations, stopping to swim when conditions allow. Step ashore to explore Capri and enjoy a leisurely seaside lunch, with the flexibility to let the day unfold at its own pace.

Sorrento, Amalfi Coast

Day 7: Pompeii with a Specialist | Or the Coast at Leisure

Choose between a privately guided visit to Pompeii with a specialist archaeologist or an unhurried day on the coast.

At Pompeii, walk through the remarkably preserved streets and homes of the ancient Roman city, gaining a deeper understanding of everyday life beneath Mount Vesuvius. Alternatively, remain on the coast to explore nearby villages, visit local artisans, relax by the water or simply enjoy the surroundings.

This evening is relaxed, with the option to come together for dinner.

Sorrento, Amalfi Coast

Day 8: Sorrento to Tuscany | North to Castello di Potentino

Depart Sorrento and begin the journey north, combining rail and private transfers where appropriate to make the day as comfortable as possible.

Arrive at Castello di Potentino, an historic castle and wine estate near Monte Amiata. Settle in for three nights immersed in the vineyards, olive groves and slower rhythms of rural Tuscany.

Castello di Potentino, Tuscany

Day 9: Tuscany | A Day in the Life of a Wine Estate

Spend the day with the people of Potentino, discovering the vineyards, the winemaking process and daily life on this historic estate.

If the timing of the harvest allows, join the grape picking and experience traditional grape stomping by foot. Local cheesemakers will share their craft, inviting guests to take part before everyone gathers around the table for a long lunch featuring estate wines and local produce.

This is a day built around participation, conversation and the people whose care for the land shapes everything produced here.

Castello di Potentino, Tuscany

Day 10: Tuscany, Your Way | Florence, Siena or the Castle

Choose an optional excursion to Florence or Siena, or remain at Potentino and enjoy a day with very little planned.

Walk through the countryside, read beneath the trees, spend time around the estate or simply settle into the pleasure of being somewhere beautiful without needing to rush elsewhere.

Castello di Potentino, Tuscany

Day 11: Civita di Bagnoregio & Orvieto | Into Umbria

Leave Tuscany and travel towards Umbria, stopping first at Civita di Bagnoregio. Reached on foot across a long bridge, this extraordinary medieval village rises above the surrounding valleys.

Continue to Orvieto to explore its historic centre and the underground network of tunnels, caves and ancient cellars hidden beneath the hill town.

Later, arrive at Roccafiore Wine Resort & Spa near Todi, your final home for four nights among the vineyards and olive groves of Umbria.

Roccafiore Wine Resort & Spa, Umbria

Day 12: Umbria | Truffles & the Flavours of the Land

Venture into the countryside with a local truffle hunter and trained dog in search of one of Umbria’s most celebrated ingredients.

Return for a special lunch shaped around the day’s discoveries and seasonal local produce, with an opportunity to learn how truffles are prepared and used in traditional Umbrian cooking.

Roccafiore Wine Resort & Spa, Umbria

Day 13: Todi | Vineyards, Winemaking & Village Life

Explore Todi, one of Umbria’s beautiful historic hill towns, with time to discover its streets, cafés, local shops and artisan producers.

Later, return to Roccafiore for a hosted tasting, learning about the estate’s vineyards, wines and approach to winemaking while looking across the surrounding Umbrian countryside.

Roccafiore Wine Resort & Spa, Umbria

Day 14: Umbria | The Pleasure of Doing Very Little

The final full day is deliberately unhurried.

Enjoy the pool, book an optional spa treatment, walk through the estate or simply take in the quiet of the Umbrian countryside.

This evening, gather for a memorable farewell dinner celebrating the food, wine, people and friendships shared over the past two weeks.

Roccafiore Wine Resort & Spa, Umbria

Day 15: Depart Italy | Arrivederci

Enjoy a final breakfast before your onward transfer.

Depart Italy with a deeper appreciation for the people, traditions and landscapes encountered along the way and for the care and craftsmanship woven into everyday Italian life.

Roccafiore Wine Resort & Spa
A refined wine resort set among the vineyards and olive groves of the Umbrian countryside, with views towards the medieval hill town of Todi. Warm, natural interiors, an exceptional spa and cuisine grounded in estate-grown produce create a deeply restorative final chapter.
Castello di Potentino
An historic castle and working wine estate in an undiscovered corner of Tuscany, where staying feels more like being welcomed into a private home. Surrounded by vineyards and olive groves, Potentino brings together centuries of history, estate wines and the unhurried rhythms of rural life.
Inclusions
Private arrival and departure airport transfers at the designated times
14 nights’ accommodation in double or twin-share rooms
Daily breakfast
Welcome dinner, selected long lunches and farewell dinner
All included culinary and cultural experiences detailed in the itinerary
Exclusions
International and domestic flights
Travel insurance
Visas and entry requirements
Optional excursions, spa treatments and activities not specified as included
Meals and beverages not specified in the final itinerary
Personal expenses

Signature Moments

From Market to a Private Table
-Selecting seasonal ingredients alongside a local chef before cooking and sharing a long lunch with the winemaker at a privately hosted estate
Capri, On Our Own Time
-Exploring Capri by private boat, with hidden coves, time to swim and a leisurely seaside lunch reached from the water
A Castle Becomes Home
-Spending three nights at Castello di Potentino, welcomed into the rhythms of a private Tuscan home, vineyard and olive estate
The Harvest, by Hand
-Picking grapes, traditional foot-stomping and learning alongside local cheesemakers before gathering for a long estate lunch, harvest permitting
Beneath the Hill Towns
-Descending into the historic wine cellars of Castelli Romani and the ancient tunnels and caves hidden beneath Orvieto
In Search of the Truffle
-Joining a local truffle hunter and trained dog in the Umbrian countryside before sharing a seasonal lunch shaped around the day’s discoveries
The weka list

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