Italy — October 2026
Hong Kong → Milan → Piedmont → Bologna → Tuscany → Florence → Milan
15 Oct – 26 Oct · 11 Days
Day-by-Day Plan
Meal Visit Tasting Activity Transport
| Day | Date | Location | Plan | Stay |
|---|---|---|---|---|
| 0 | Thu 15 Oct | Hong Kong |
|
— |
| 1 | Fri 16 Oct | Milan → Turin |
|
— |
| 2 | Sat 17 Oct | Turin → Alba / Barolo |
|
La Giolitta |
| 3 | Sun 18 Oct | Barolo |
|
La Giolitta |
| 4 | Mon 19 Oct | Barbaresco → Bologna |
|
Agriturismo Borgo delle Vigne |
| 5 | Tue 20 Oct | Bologna |
|
Agriturismo Borgo delle Vigne |
| 6 | Wed 21 Oct | Bologna → ColleMassari |
|
Wine Relais ColleMassari |
| 7 | Thu 22 Oct | Montalcino / Montepulciano |
|
Wine Relais ColleMassari |
| 8 | Fri 23 Oct | Florence |
|
Guya Apartment by Mamo Florence |
| 9 | Sat 24 Oct | Florence |
|
Guya Apartment by Mamo Florence |
| 10 | Sun 25 Oct | Milan |
|
Hotel VIU Milan |
| 11 | Mon 26 Oct | Milan → Home |
|
— |
Piedmont — Turin, Alba, Barolo, Barbaresco
Days 1–4 · Fri 16 – Mon 19 Oct
Turin — Half-Day Sightseeing (Day 1)
| # | Spot | What | Map |
|---|---|---|---|
| 1 | Caffè Al Bicerin8:30am–7:30pm, closed Wed | Turin's signature drink (espresso + chocolate + cream). Since 1763. | Map |
| 2 | Piazza Castello & Palazzo Madama | Map | |
| 3 | Palazzo Reale | Map | |
| 4 | Porta Palatina | Map | |
| 5 | Mole Antonelliana | Map |
Eat before leaving Turin: Vitello tonnato, agnolotti del plin (tiny Piemontese pasta), or a tramezzino (Turin invented them).
Where to Stay — Turin (1 night, Oct 16)
No car yet (airport transfer). Central + walkable. Budget: ~€120/person = ~€480 total (2 rooms).
| Hotel | Style | ~Price/room | Parking | Notes |
|---|---|---|---|---|
| Opera35 Boutique Hotel Top Pick | 4-star boutique | €100–130 | Private (book ahead) | Central, garden + terrace. Parking for car pickup next morning. |
| Grand Hotel Sitea | 5-star luxury | €180–250 | Available | Behind Piazza San Carlo. Michelin-starred restaurant Carignano on-site. Splurge. |
| NH Collection Piazza Carlina | Upscale hotel | €130–160 | Available | Beautiful square, polished rooms. Safe pick for comfort. |
| Corte Realdi Luxury Rooms | Boutique B&B | €100–140 | Paid nearby | Historic building, stylish rooms, soundproofed. Personal & intimate. |
| Carlo Felice Boutique Hotel | 3-star boutique | €80–110 | Nearby garage | 300m from Porta Nuova. Simple, clean, budget-friendly. |
Winery Visits (Days 2–4)
G.D. Vajra / Luigi Baudana
Luigi Baudana crus (Cerretta & Baudana) in Serralunga. Tiered tastings. On your Day 2 plan.
Book online → welcome@gdvajra.it
Giuseppe Rinaldi
Legendary traditional Barolo. Run by Marta & Carlotta Rinaldi. Intimate, no-frills.
Website carlotta.rinaldi@me.com
Bartolo Mascarello
"No Barrique, No Berlusconi." Free visit with Maria Teresa. Can't buy on-site (all allocated).
+39 0173 56125 rv@bartolomascarello.com
Cascina delle Rose
Natural-leaning Barbaresco by Giovanna Rizzolio. Max 8/visit. Morning tasting Day 4.
Website cascinadellerose@cascinadellerose.it
Fratelli Alessandria
Under-the-radar Barolo from Monvigliero. Try the Verduno Pelaverga.
Roagna
Old-school, long-maceration Barbaresco. Closed to visitors. Join mailing list.
Marchesi di Barolo
Historic estate since 1807. The family that gave Barolo wine its name. Beautiful cellars, great for first-timers. Already having lunch here Day 3.
Fontanafredda
Royal estate founded by Italy's first king's son. Huge, stunning grounds with a wine village. Very polished visitor experience. Crowd-pleaser.
Gaja
The most famous name in Barbaresco. Angelo Gaja put the region on the world map. Exclusive visits — harder to get but iconic.
Where to Eat
| Restaurant | Location | Vibe | Why | Map |
|---|---|---|---|---|
| Antiné ★Lunch & dinner, closed Wed | Barbaresco | Wine-focused | 250+ Barbaresco, ~100 Barolo, 60+ Champagnes. Day 4 lunch. | Map |
| La CantinettaLunch daily, dinner Mon/Tue/Fri/Sat. Closed Thu | Barolo | Simple trattoria | Local wines by glass at near-enoteca prices. | Map |
| Osteria Tre CaseTue–Sun lunch & dinner. Closed Mon | Serralunga d'Alba | Local favourite | Traditional with a twist. Very reasonable. | Map |
| More e Macine11am–1am, open 7 days | La Morra | Traditional | Solid wine list by glass and bottle. | Map |
| Osteria VeglioLunch daily, dinner Fri/Sat only. Closed Sun & Mon | La Morra | Family-run | Historic, extensive wine list. Bib Gourmand. | Map |
| Per BaccoTue–Sun lunch & dinner. Closed Mon | La Morra | Ultra casual | Pizza from €7, great wine + craft beer. | Map |
Expect ~€25 for 2 courses at lunch, ~€40 at dinner. Wine bottles just a few euros above retail.
Don't-Miss Experiences
Alba White Truffle Fair
Fiera del Tartufo — Day 2 (Sat 17 Oct) lands right in it. Walk the market, eat everything.
Truffle Hunting
Join a trufolau with dogs. Half-day morning, eat what you find.
Enoteca Regionale del Barolo
Castle cellar. Huge range of Barolo by the glass from small producers.
WiMu — Wine Museum
Quirky art-meets-wine museum. Worth 45 min if at the Enoteca.
Wines to Seek Out Locally
- Older vintage Barolo from small producers — Cappellano, Giacomo Conterno Monfortino
- Verduno Pelaverga — hyper-local peppery red, only from Verduno
- Nascetta — rare revived white grape. Look for Elvio Cogno.
- Natural Barolo/Barbaresco — ask at enotecas for low-intervention producers
Practical Tips
- Book winery visits NOW — October is harvest. Email in Italian if possible.
- Car is essential — no useful public transport in the Langhe.
- Truffle season — mid-Oct is peak white truffle. Say yes to tajarin al tartufo every time.
- Buy bottles locally — prices are a fraction of HK.
Bologna
Day 4 evening & Day 5 full day · Mon 19 – Tue 20 Oct
Day 4 Evening — Arrival
Walk to Via del Pratello (Map) — the locals' bar street. Grab aperitivo and a tagliere at a wine bar. No planning needed.
Day 5 — Full Day Sightseeing
| Time | Spot | What | Map |
|---|---|---|---|
| Morning | Caffè TerziMon–Sat 8am–6pm. Closed Sun | Best espresso in Bologna. | Map |
| Piazza Maggiore | Main square — Basilica di San Petronio, Palazzo d'Accursio. | Map | |
| Quadrilatero Market | Old market grid — delis, cheese shops, produce stalls. Bologna's soul. | Map | |
| Lunch | Salumeria SimoniMon–Sat 8am–7:30pm, Sun 9am–5pm | Charcuterie: Mortadella, Prosciutto di Parma, Parmigiano, balsamic. | Map |
| Afternoon | Due Torri | Bologna's leaning towers. Climb Torre degli Asinelli — 498 steps. | Map |
| Late PM | Cremeria FuniviaTue–Sat 11am–11pm, Sun 10am–11pm. Closed Mon | Top gelato in the city. | Map |
| Dinner | Trattoria Anna MariaTue–Sun 12:30–3pm & 7:30–11pm. Closed Mon | Old-school: tagliatelle al ragù, tortellini in brodo, lasagna. Book ahead. | Map |
Where to Stay — Bologna (1–2 nights, Oct 19–20)
You have a car. Central with parking OR agriturismo in the hills. Budget: ~€120/person = ~€480 total (2 rooms).
| Hotel | Style | ~Price/room | Parking | Notes |
|---|---|---|---|---|
| Art Hotel Commercianti Top Pick | 4-star boutique | €150–180 | Private in centre | Next to Piazza Maggiore & San Petronio. Unique rooms, some with basilica views. |
| Hotel Corona d'Oro | 4-star historic | €140–180 | Nearby garage | 13th-century palazzo. Liberty-style hall, Madonna fresco. Full of character. |
| Hotel Orologio | 4-star romantic | €120–160 | Nearby garage | Pedestrian centre. Marble, luxe fabrics, grand windows. Traditional Italian romance. |
| Phi Hotel Bologna | Boutique, historic | €100–140 | Nearby | Originally a 1375 tavern — oldest hotel in Bologna. Modern flair, quirky charm. |
| Casa Miramonte | Boutique guesthouse | €90–120 | Nearby | Stylish, intimate, has a small spa with indoor sauna. Budget-friendly. |
| Agriturismo Borgo delle Vigne Booked | Agriturismo + winery | HK$ 3,425 total | Free on-site | Oct 19–21 (2 nights, 4 pax). Zola Predosa hills, 15min from centre. On-site winery & restaurant. Peaceful. |
| Palazzo di Varignana | Luxury wine resort | €180–250 | Free on-site | 30ha estate, wine cellar, spa, bikes. Splurge option — stunning. |
Must-Eat in Bologna
- Tortellini in brodo — tiny pasta parcels in clear broth. The real thing.
- Tagliatelle al ragù — NOT "spaghetti bolognese". Fresh egg pasta, slow meat sauce.
- Mortadella — the real stuff, nothing like supermarket bologna.
- Tigelle / Crescentine — fried bread pockets with cured meats & squacquerone cheese.
- Gelato — Bologna takes this seriously.
Tuscany — Montalcino & Montepulciano
Days 6–7 · Wed 21 – Thu 22 Oct · Stay: Wine Relais ColleMassari
Things to Do
| Spot | What | Map |
|---|---|---|
| Fortezza di Montalcino | 14th-century fortress with panoramic views of Val d'Orcia. The Enoteca inside has Brunello tastings. | Map |
| Piazza Grande, Montepulciano | Hilltop main square. Palazzo Comunale tower for the view. Walk Via di Gracciano nel Corso. | Map |
| Pienza | "Ideal Renaissance city" — 20 min from Montepulciano. Pecorino cheese capital. Gorgeous Val d'Orcia views. | Map |
| Abbazia di Sant'Antimo | Romanesque abbey in olive groves below Montalcino. Gregorian chant services. Serene. | Map |
| Val d'Orcia | Map |
Winery Visits
Enoteca la Fortezza
Inside the fortress. Huge Brunello selection by the glass. No booking needed — just show up and taste.
Conti Costanti
One of the most famous and historic Brunello estates. Elegant, traditional style.
Il Palazzone
Walkable from Montalcino centre — taste freely without driving. Boutique producer.
Consorzio del Vino Enoliteca
75+ wineries represented, 100+ wines to sample. Great overview of Vino Nobile.
Banfi (Castello Banfi)
Huge, famous estate with a medieval castle. Polished tours, multiple tasting options, on-site restaurant. Great for friends who want a "wow" venue.
Antinori nel Chianti Classico
Stunning modern winery built into a hillside. 600+ year wine dynasty. Architecture alone is worth the detour. Stop on your drive to Florence (Day 8).
Average tasting price: ~€68. Book ahead — these are working farms. Consider a driver (Italy's drink-driving laws got stricter in 2025).
Where to Eat
| Restaurant | Location | Why | Map |
|---|---|---|---|
| Boccon di VinoLunch & dinner. Closed Tue (Oct) | Montalcino | Best flavours of Tuscany since 1992. House-made bread & fresh pasta daily. | Map |
| Alle LoggeDaily 12:30–9:30pm, open 7 days | Montalcino | Great wine list, views next to the Piazza. | Map |
| Ristorante La GrottaLunch & dinner. Closed Wed, closed Jan–Feb | Montepulciano | Guinea fowl pappardelle, pigeon two ways. Refined Tuscan. | Map |
Must-Eat in Tuscany
- Pici — thick hand-rolled pasta, typically with ragù or aglione (garlic tomato sauce)
- Pecorino di Pienza — local sheep's milk cheese, try fresh & aged versions
- Ribollita — hearty bread & bean soup, classic cucina povera
- Cinghiale (wild boar) — in ragù, as salumi, or braised
- Brunello by the glass — at Enoteca la Fortezza, try multiple producers cheaply
Firenze
Days 8–9 · Fri 23 – Sat 24 Oct
Things to Do
| Spot | What | Map |
|---|---|---|
| Duomo & Brunelleschi's Dome | Map | |
| Uffizi Gallery | Botticelli, Caravaggio, Leonardo. Book tickets in advance — Oct queues are long. | Map |
| Ponte Vecchio | Map | |
| Oltrarno & Piazza Santo Spirito | Map | |
| San Lorenzo Market | Map | |
| Piazzale Michelangelo | Map |
Wine Bars & Enotecas
Le Volpi e l'Uva
Beloved wine bar with excellent by-the-glass selection — Tuscan classics to lesser-known Italian regions. Great cheese & crostini. Crowd-pleaser for everyone.
Casa del Vino
Old-school Florentine enoteca. Wine with crostini, panini, porchetta plates. Authentic, no-fuss. Run by Gianni & Nicoletta.
Enoteca Bruni
3,000+ exclusively natural wine labels. Solo detour if you want to geek out — friends can skip this one.
Where to Eat
| Restaurant | Vibe | Why | Map |
|---|---|---|---|
| Trattoria SostanzaMon–Sat 12:30–2pm & 7:30–9:30pm. Closed Sun. Cash only! | Cult classic | Tiny kitchen, rarely-changing menu perfected over decades. Butter chicken breast is legendary. | Map |
| Trattoria CammilloMon & Thu–Sun lunch & dinner. Closed Tue & Wed | Classic Florentine | Enduring, refined but never fussy. Great for bistecca fiorentina. | Map |
| I FratelliniDaily ~10am–7pm | Hole-in-the-wall | Sandwich shop since 1875. Prosciutto, truffle, local fillings. Quick & cheap. | Map |
| Lampredotto stand | Street food | Tripe sandwich in crusty roll with parsley sauce & chili oil. The ultimate local snack. | Map |
| Gelateria dei NeriDaily ~10:30am–11:30pm | Gelato | Fondente (dark chocolate) is insane. Small batches. | Map |
Where to Stay — Florence (2 nights, Oct 23–24)
Returning car on arrival — no parking needed. Prefer San Lorenzo area. Budget: ~€120/person = ~€480 total (2 rooms).
| Hotel | Style | ~Price/room | Notes |
|---|---|---|---|
| Guya Apartment by Mamo Florence Booked | Apartment | HK$ 6,415 total | Oct 23–25 (2 nights). Night 1: 4 pax, Night 2: 3 pax. Free cancellation. Confirmed. |
| San Lorenzo area | |||
| Solo Experience Hotel Top Pick | Boutique, 17th-c building | €120–160 | Overlooks Basilica di San Lorenzo. Large rooms, great location right at the market. |
| Palazzo Lorenzo Hotel & Spa | 4-star boutique + spa | €130–180 | 26 rooms, spa with sauna & steam bath. 15 min walk to centre. Comfy beds. |
| Il Mercato Centrale B&B | Family B&B | €80–110 | Heart of San Lorenzo market. 5 rooms, fresh pastry breakfast. Great value. |
| Casa San Lorenzo | Apartment / casa | €90–130 | Rated 8.6. Kitchenette, soundproofed, 5 min to Palazzo Vecchio. Like a home. |
| Right at the Duomo | |||
| Hotel Duomo Firenze | Historic, Duomo views | €120–170 | 14th-century Gondi palazzo. Lean out the window and touch the Cathedral. Breakfast under the Dome. |
| Palazzo Niccolini al Duomo | Luxury palazzo | €200–300 | Right next to the Duomo. Family-owned, frescoed ceilings, antique furnishings. Splurge. |
| Le Stanze del Duomo B&B | Charming B&B | €90–130 | Steps from Duomo. Intimate, well-reviewed. Budget-friendly pick with location premium. |
| Brunelleschi Hotel | 5-star, Byzantine tower | €250–400 | Built into a Byzantine tower + medieval church. Dome views. Michelin restaurant. Big splurge. |
| Other central options | |||
| Hotel Davanzati | Boutique, central | €130–180 | Steps from Ponte Vecchio. Family-run, top-rated. Great breakfast. |
| Velona's Jungle | Eclectic boutique | €150–200 | Near Santa Maria Novella. Tropical maximalism, organic breakfast. Unique. |
| Hotel Palazzo Guadagni | Boutique, Oltrarno | €100–140 | Piazza Santo Spirito. Rooftop loggia with views. Charming & quiet. |
| AdAstra Florence | Luxury boutique | €200–280 | 16th-century palazzo, Santa Croce. Only 8 rooms. Splurge. |
Must-Eat in Florence
- Bistecca Fiorentina — massive T-bone, rare, salt & olive oil. Share between two.
- Lampredotto — tripe sandwich. Sounds scary, tastes incredible. The local test.
- Schiacciata — olive oil flatbread, stuffed with truffle cream or pecorino. Florence's answer to focaccia.
- Ribollita — bread & bean soup, cucina povera at its best.
- Gelato — Gelateria dei Neri, Vivoli, or La Strega Nocciola.
Milano
Days 10–11 · Sun 25 – Mon 26 Oct
Things to Do
| Spot | What | Map |
|---|---|---|
| Duomo di Milano | Map | |
| Galleria Vittorio Emanuele II | Opulent iron & glass arcade. Historic cafes, luxury shops. Shortcut from Duomo to La Scala. | Map |
| Teatro alla Scala | World's most famous opera house. Even if no show, the museum is worth a visit. | Map |
| Navigli District | Map | |
| Bosco Verticale | "Vertical Forest" — residential towers covered in trees. Iconic modern architecture. Quick photo stop. | Map |
| Armani/Silos | Armani's fashion museum. Rotating exhibitions on eras & themes. | Map |
Where to Eat
| Restaurant | Vibe | Why | Map |
|---|---|---|---|
| Trippa ★Mon–Thu dinner only 7:15pm; Fri lunch + dinner. Closed Sat & Sun. Book well ahead! | Neo-trattoria | Defining force in Milan's dining scene. Revives disappearing Italian dishes with modern edge. | Map |
| RazdoraMon–Fri lunch & dinner (Wed lunch only). Closed Sat & Sun. Only ~4 tables! | Pasta bottega | Intimate fresh pasta workshop. Honest, soulful cooking with zero pretense. | Map |
| DeRosLunch & dinner. Closed Mon | Seafood | Steps from La Scala. Octopus, ceviche, catch of the day. Impeccable. | Map |
| Cavoli a MerendaTue–Fri lunch & dinner. Closed Sat, Sun & Mon. Reservations mandatory. | Hidden palazzo | 18th-century palazzo, ivy terrace. Weekday-only. Grand yet comfortable. | Map |
Where to Stay — Milan (1–2 nights, Oct 25–26) ♥
Honeymoon finale! Paid with Bonvoy points.
| Hotel | Style | Parking | Notes |
|---|---|---|---|
| Hotel VIU Milan Booked | Design hotel, rooftop pool | Valet | Check-in 25 Oct. Rooftop pool + skyline views. Porta Volta near Brera. Bonvoy points. |
Must-Eat in Milan
- Risotto alla Milanese — saffron-laden, creamy. The city's signature dish.
- Cotoletta alla Milanese — bone-in breaded veal cutlet. The original schnitzel.
- Ossobuco — braised veal shank with gremolata. Often paired with risotto.
- Negroni / Aperitivo — birthplace of Campari. Navigli at sunset is the move.
- Via Paolo Sarpi food crawl — Milan's Chinatown. Dumplings, ramen, tacos, tapas.
Accommodation Costs
All converted to HKD. Guya Apartment: Night 1 split 4 ways, Night 2 split 3 ways. Hotel VIU redeemed with Bonvoy points.
FX rate (2 Apr 2026): 1 MYR = 1.9441 HKD
Booking Summary
| Hotel | Location | Dates | Nights | Pax | Booked Price | Total (HK$) | Per Person |
|---|---|---|---|---|---|---|---|
| La Giolitta | Barolo, Piedmont | Oct 17–19 | 2 | 4 | HK$ 4,442 | HK$ 4,442.00 | HK$ 1,110.50 |
| Agriturismo Borgo delle Vigne | Bologna (Zola Predosa) | Oct 19–21 | 2 | 4 | HK$ 3,425 | HK$ 3,425.00 | HK$ 856.25 |
| Wine Relais ColleMassari | Tuscany | Oct 21–23 | 2 | 4 | RM 4,695.98 | HK$ 9,129.45 | HK$ 2,282.36 |
| Guya Apartment (Night 1) | Florence | Oct 23 | 1 | 4 | HK$ 6,415 | HK$ 6,415.00 | HK$ 801.88 |
| Guya Apartment (Night 2) | Florence | Oct 24 | 1 | 3 | HK$ 1,069.17 | ||
| Hotel VIU Milan | Milan | Oct 25–26 | 1–2 | 4 | Bonvoy points redeemed | ||
| Grand Total | HK$ 23,411.45 | ||||||
Per Person Breakdown
| Person A, B, C (both Florence nights) | Person D (Florence Night 1 only) | |
|---|---|---|
| La Giolitta | HK$ 1,110.50 | HK$ 1,110.50 |
| Borgo delle Vigne | HK$ 856.25 | HK$ 856.25 |
| Wine Relais ColleMassari | HK$ 2,282.36 | HK$ 2,282.36 |
| Guya Apartment | HK$ 1,871.04 | HK$ 801.88 |
| Hotel VIU Milan | Redeemed | |
| Total per Person | HK$ 6,120.15 | HK$ 5,050.99 |
Main square — Basilica di San Petronio, Palazzo d'Accursio.
Old market grid — delis, cheese shops, produce stalls. Bologna's soul.
Bologna's leaning towers. Climb Torre degli Asinelli — 498 steps.
14th-century fortress with panoramic views of Val d'Orcia. The Enoteca inside has Brunello tastings.
Hilltop main square. Palazzo Comunale tower for the view. Walk Via di Gracciano nel Corso.
"Ideal Renaissance city" — 20 min from Montepulciano. Pecorino cheese capital. Gorgeous Val d'Orcia views.
Romanesque abbey in olive groves below Montalcino. Gregorian chant services. Serene.
Botticelli, Caravaggio, Leonardo. Book tickets in advance — Oct queues are long.
Opulent iron & glass arcade. Historic cafes, luxury shops. Shortcut from Duomo to La Scala.
"Vertical Forest" — residential towers covered in trees. Iconic modern architecture. Quick photo stop.