Sample Itinerary · Italy

Italy Wine Tour
with Castles

Piedmont · Emilia Romagna · Tuscany

Duration
10 Days · 9 Nights
Accommodations
Castle + Estate Hotels
Transport
Private Transfers
Best For
Luxury · Wine Enthusiasts · Castle Stays

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This is a sample itinerary — for inspiration only. Every Juniper trip is designed from scratch around you. Many clients travel a very similar route — if this resonates, book a free consultation and an Italy specialist will build something just like it (or better) specifically for your travel style, dates, and group.

1
Day One

Arrive in Piedmont

Turin & Langhe

Your wine journey begins in Piedmont, the noble wine region of northwest Italy. A private driver meets you at Turin or Milan airport and takes you into the Langhe hills — a UNESCO World Heritage landscape of rolling vineyards, medieval towers, and mist-shrouded valleys. Check into your first castle hotel, a converted medieval fortress surrounded by Nebbiolo vines.

This evening, a welcome dinner in the castle dining room: local agnolotti pasta, vitello tonnato, and your first glass of Barolo — the King of Italian wines, produced from the very hills outside your window.

Private airport transfer
Castle hotel check-in
Welcome dinner

Overnight: Castle Hotel, Langhe

2
Day Two

Barolo & the Langhe Hills

Barolo & La Morra

A full day in the heart of Barolo country. Visit the village of Barolo itself, where the Museo del Vino traces the history of Piedmont winemaking through centuries. Then a private tasting at one of the region’s legendary estates — the winemaker walking you through five vintages, explaining how Nebbiolo expresses differently on every hillside.

Lunch in La Morra at a restaurant overlooking the entire Langhe valley — handmade tajarin pasta with butter and white truffle (in season), paired with a Barolo Riserva. Afternoon, visit a second estate with a completely different philosophy — traditional versus modern Barolo, the great debate of Piedmont, tasted side by side.

Barolo village & museum
Private estate tasting
La Morra lunch

Overnight: Castle Hotel, Langhe

3
Day Three

Alba, Truffles & Barbaresco

Alba & Barbaresco

Morning in Alba, the truffle capital of Italy. Walk the arcaded streets, visit the Saturday market (if timing allows), and join a truffle-focused tasting — white truffle butter, truffle honey, truffle-shaved eggs. Alba during truffle season (October-December) is one of the great food experiences in Europe.

Afternoon, cross into Barbaresco territory — Barolo’s elegant sibling. A private tasting at a family-run cantina reveals why Barbaresco is increasingly sought after: the same Nebbiolo grape but a different expression — more approachable, more perfumed, equally profound. Return to your castle as the sun sets behind the Langhe ridgeline.

Alba truffle market
Truffle tasting
Barbaresco estate visit

Overnight: Castle Hotel, Langhe

4
Day Four

Piedmont to Emilia Romagna

Transfer & Arrival

After breakfast, your driver takes you east through the Po Valley into Emilia Romagna — Italy’s undisputed food capital. The landscape shifts from hillside vineyards to flat, fertile plains that produce Parmigiano-Reggiano, Prosciutto di Parma, balsamic vinegar, and Lambrusco.

Arrive at your estate accommodation near Parma and settle in. Late afternoon, a private visit to a Parmigiano-Reggiano dairy where wheels of cheese age for 24 months in cathedral-like warehouses. The cutting ceremony — splitting a 40-kilogram wheel with traditional tools — is theatrical and the fresh-cut cheese, still warm, is extraordinary. Dinner at a local trattoria with fresh tortellini in brodo.

Private transfer east
Parmigiano dairy visit
Cheese aging caves

Overnight: Estate Hotel, Emilia Romagna

5
Day Five

Parma & the Food Valley

Parma & Langhirano

A day in Italy’s food heartland. Morning, visit a traditional prosciuttificio in Langhirano where legs of pork cure in mountain air for 18 months. The simplicity of the process — salt, air, time — produces one of the world’s great cured meats. Tasting is revelatory: paper-thin slices, a glass of Lambrusco, the sweetness of the fat against the sparkling wine.

Lunch in Parma city center, then a private visit to a traditional balsamic vinegar acetaia where the Trebbiano grape must ages for 12 to 25 years in progressively smaller barrels. A single tablespoon of aged balsamic costs more than most bottles of wine, and tasting the 25-year-old directly from the barrel explains why.

Prosciutto factory visit
Traditional balsamic acetaia
Lambrusco tasting

Overnight: Estate Hotel, Emilia Romagna

6
Day Six

Bologna — La Grassa

Bologna

Drive to Bologna, known as La Grassa (The Fat One) for its extraordinary food culture. A guided food tour through the Quadrilatero market district reveals stall after stall of mortadella, fresh tortellini, ragù, and crescentine. This is where Italian food traditions run deepest.

Afternoon, a hands-on pasta workshop in a traditional Bolognese kitchen — learn to make tortellini by hand, the tiny parcels of pasta that Bologna considers its sacred dish. The filling, the folding technique, the broth — every detail matters and takes years to master. You’ll leave with a skill you’ll use for life. Evening free to explore Bologna’s porticoed streets and aperitivo culture.

Bologna food tour
Quadrilatero market
Tortellini workshop

Overnight: Estate Hotel, Emilia Romagna

7
Day Seven

Emilia Romagna to Tuscany

Transfer & Castle Arrival

After breakfast, your driver takes you south over the Apennines and into Tuscany. The landscape transforms dramatically — from Emilia’s plains to Tuscany’s rolling hills, cypress-lined roads, and medieval hilltop towns. Your destination is a castle estate in the heart of the Brunello di Montalcino zone.

Check into your castle — a 12th-century fortress with panoramic views across the Val d’Orcia. Many of these properties have their own vineyards producing Brunello or Rosso di Montalcino. Afternoon at leisure: swim, walk the grounds, or simply sit on the terrace with a glass of Rosso and watch the light change across the hills. Estate dinner this evening.

Private transfer to Tuscany
Castle estate check-in
Estate dinner

Overnight: Castle Hotel, Montalcino

8
Day Eight

Brunello di Montalcino

Montalcino & Sant’Antimo

A day dedicated to one of Italy’s greatest wines. Morning, visit a prestigious Brunello estate for a vertical tasting — five vintages spanning a decade, each showing how the Sangiovese Grosso grape evolves with time. The winemaker explains the ageing requirements: five years minimum, two in oak, before a Brunello can be released.

Walk the hilltop town of Montalcino itself, with its 14th-century fortress and panoramic walls. Visit the Romanesque Abbey of Sant’Antimo in the valley below — Gregorian chant still echoes here daily. Lunch at a vineyard restaurant: bistecca alla fiorentina, pici cacio e pepe, and a Brunello Riserva that justifies its reputation. Return to your castle for a final Tuscan sunset.

Brunello vertical tasting
Montalcino fortress
Abbey of Sant’Antimo

Overnight: Castle Hotel, Montalcino

9
Day Nine

Chianti Classico & Siena

Chianti & Siena

Drive north through the Chianti Classico heartland — the black rooster territory, where Sangiovese has been cultivated since Etruscan times. Visit a historic Chianti producer for a private cellar tour and tasting, comparing Chianti Classico, Riserva, and Gran Selezione — the hierarchy of Tuscan winemaking explained through the glass.

Afternoon in Siena: the Piazza del Campo, the striped marble cathedral, the narrow medieval streets that have barely changed in 700 years. Your guide connects the wine to the city — how Siena’s banking families funded the vineyards, how the Palio horse race still defines neighborhood identity. Farewell dinner at a Chianti estate — the perfect ending to your wine journey through Italy.

Chianti Classico estate
Siena guided tour
Farewell estate dinner

Overnight: Castle Hotel, Chianti

10
Day Ten

Departure

Florence or Rome

A final Italian breakfast at your castle — fresh bread, local honey, estate olive oil, espresso in the courtyard. Your private driver takes you to Florence or Rome for your departure flight.

You leave carrying Italy’s wine country in your memory: the fog lifting off Barolo vineyards at dawn, the scent of aging Parmigiano, the purple stain of Brunello on your lips, the medieval walls of your castle silhouetted against a Tuscan sunset. Ten days, three regions, centuries of winemaking tradition — and a cellar list that will never look the same again.

Private transfer to airport
App support throughout

Overnight: Depart from Florence/Rome

Love this itinerary? Make it yours.

This is a sample luxury custom route — a starting point, not a fixed package. Many clients travel something very close to this, customized for their travel style, group, and dates. Book a free consultation and a specialist will build from here.

Accommodations
Castle hotels, historic estates, or luxury wine resorts — chosen based on your preferences and travel style.
Transportation
Private chauffeur throughout, with optional self-drive for vineyard exploration — all confirmed before you travel.
Experiences
Pre-arranged tours and activities built around your interests — entrance tickets sorted, no queuing.

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Activities on this itinerary

Your specialist pre-arranges the right luxury experiences based on your interests and travel style. These are the custom experience types available on this route — specific choices are made with you, not for you.

Barolo Estate TastingPiedmont

Barbaresco Cellar VisitPiedmont

Alba Truffle TastingAlba

Parmigiano Dairy VisitParma

Prosciutto Factory TourLanghirano

Balsamic Vinegar AcetaiaModena

Bologna Food TourBologna

Tortellini WorkshopBologna

Brunello Vertical TastingMontalcino

Chianti Classico EstateChianti

Siena Guided TourSiena

Castle Estate DinnerThroughout

Activities are selected and pre-booked with your specialist based on your interests — not all activities are included in every trip version. Availability varies by season.

The people who will design your Italy trip

You work directly with a specialist who knows Italy deeply — not a call center or booking agent. Every consultation is with someone who has been there, stayed in those hotels, and knows the country inside out.

Italy · Switzerland · Portugal · Spain

Lexi Blade

Florence and Austria-based, Lexi brings on-the-ground expertise across Southern Europe’s most sought-after destinations. Every recommendation comes from personal experience.

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Ireland · Scotland · UK · Iceland

Taryn Harrison

25 years designing European trips, with a deep network across Italy’s regions. CMSC certified and former Peace Corps. Ideal for multi-country trips combining Italy with Ireland, Scotland, or beyond.

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About this itinerary

What wine regions does this tour cover?


The Italy Wine Tour with Castles covers three of Italy’s greatest wine regions: Piedmont for Barolo and Barbaresco, Emilia Romagna for its extraordinary food traditions and Lambrusco, and Tuscany for Brunello di Montalcino and Chianti Classico. Each region is experienced through private vineyard visits with the winemakers themselves, paired with castle hotel accommodations.

Can I customise this itinerary?


Yes — this is a sample for inspiration. Every Juniper trip is designed from scratch. You can add regions (Venice, Rome, the Amalfi Coast), swap wine areas, extend stays at favorite estates, or focus the tour on specific grape varieties. Your specialist builds the actual itinerary around your palate and preferences during the free consultation.

Are the accommodations really castles?


Yes — genuine castle hotels and historic wine estates throughout all three regions. These are centuries-old properties converted to luxury hotels, many with their own vineyards, cellars, and restaurants. Your specialist selects the right castle properties based on your preferences, and every stay includes the estate’s wine at dinner.

Is this itinerary good for a honeymoon?


This route works well as a honeymoon base — the intimate canals of Venice, Tuscan estate stays, and the romantic Amalfi Coast are all genuinely well-suited to couples. That said, our dedicated Amalfi Coast with Capri itinerary (7 days) is specifically designed for honeymoons and couples and covers the most romantic coastal regions and properties in more detail.

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“Juniper Tours did an amazing job booking our vacation to Italy. Lexi Blade helped us schedule our dream vacation from Venice all the way to Sorrento on the Amalfi coast, with stops in Florence and Rome. Lexi was phenomenal and made changes for us many times to assure we got the most out of our trip.”

Nikki Walls  ·  Verified Google Review

Build your luxury custom Italian wine tour with one of our top travel specialists.

30 minutes, completely free. Walk away with a clear picture of what your luxury custom wine tour could look like — dates, route, 4 and 5-star accommodations, and all.

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