iv. Regional Companion
Guida Regionale
Deeper notes by region
01
Piemonte
Turin · Alba · Barolo · Barbaresco
Days 1 – 4
16 – 19 Oct
16 – 19 Oct
Turin · Half-Day Sights
Winery Visits · Langhe
G.D. Vajra / Luigi Baudana
Luigi Baudana crus (Cerretta & Baudana) in Serralunga. Tiered tastings, polished hosts.
Online Booking BookCascina delle Rose
Natural-leaning Barbaresco by Giovanna Rizzolio. Max 8 per visit. Visit-only (no overnight — 3-night min for stays).
To book · Day 5 SiteGiuseppe Rinaldi
Legendary traditional Barolo. Run by Marta & Carlotta Rinaldi. Intimate, no frills.
Email to Book SiteBartolo Mascarello
"No Barrique, No Berlusconi." Free visit with Maria Teresa. Can't buy on-site (all allocated).
Phone / EmailFratelli Alessandria
Under-the-radar Barolo from Monvigliero. Try the Verduno Pelaverga.
Online Booking BookMarchesi di Barolo
Historic estate since 1807 — the family that gave Barolo its name. Beautiful cellars, great for first-timers.
Booked Day 3Roagna
Old-school, long-maceration. Closed to visitors — join the mailing list instead.
No Visits FriendGaja
The most famous name in Barbaresco. Angelo Gaja put the region on the world map. Exclusive — hard to get, iconic.
Email to BookWhere to Eat · Piemonte
La Cantinetta
Local wines by glass at near-enoteca prices. Lunch daily, dinner Mon/Tue/Fri/Sat. Closed Thu.
MapOsteria Veglio
Family-run, historic, extensive wine list. Bib Gourmand. Lunch daily, dinner Fri/Sat. Closed Sun & Mon.
MapWines to Seek Out Locally
- Older-vintage Barolo — Cappellano, Giacomo Conterno Monfortino, hard to find outside Italy
- Verduno Pelaverga — hyper-local peppery red, only from Verduno
- Nascetta — rare revived white grape. Elvio Cogno is the reference producer.
- Natural Barolo / Barbaresco — ask enotecas for low-intervention producers
02
Bologna
Emilia-Romagna · La Grassa
Days 4 – 5
19 – 20 Oct
19 – 20 Oct
Sights · Full-Day Bologna
Where to Eat · Bologna
Trattoria Anna Maria
Old-school — tagliatelle al ragù, tortellini in brodo, lasagna. Book ahead. Tue–Sun. Closed Mon.
MapSalumeria Simoni
Mortadella, prosciutto di Parma, parmigiano, balsamic — a charcuterie board done right. Mon–Sat 8am–7:30pm.
MapCaffè Terzi
Best espresso in Bologna. Stand at the bar like everyone else. Mon–Sat 8am–6pm. Closed Sun.
MapCremeria Funivia
The top gelato in the city. Pistachio and fondente both excellent. Tue–Sun. Closed Mon.
MapMust-Eat · 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 the supermarket version.
- Tigelle / Crescentine — fried bread pockets with cured meats & squacquerone cheese.
- Gelato — Bologna takes this seriously.
03
Toscana
Montalcino · Montepulciano · Val d'Orcia
Days 6 – 7
21 – 22 Oct
21 – 22 Oct
Sights · Tuscany
Winery Visits · Brunello & Nobile
Enoteca la Fortezza
Huge Brunello selection by the glass. No booking needed — show up and taste.
Walk-in OK MapConti Costanti
One of the most famous and historic Brunello estates. Elegant, traditional style.
Email to Book SiteSiro Pacenti
Small estate, 28 hectares. Sweeping vineyard views. Modern-leaning Brunello.
Email to Book SiteIl Palazzone
Walkable from Montalcino centre — taste freely without driving. Boutique producer.
Email to Book SiteCastello Banfi
Huge famous estate with a medieval castle. Polished tours, multiple tasting options, on-site restaurant. The "wow" venue.
Online Booking SiteAvignonesi
Tours, tastings, gourmet lunch overlooking Val d'Orcia. Biodynamic estate.
Online Booking SiteConsorzio del Vino Enoliteca
75+ wineries represented, 100+ wines to sample. Great overview of Vino Nobile.
Walk-in OK MapAntinori nel Chianti Classico
Stunning modern winery built into a hillside. 600+ year wine dynasty. Architecture alone is worth the detour on the drive to Florence.
Online Booking SiteWhere to Eat · Tuscany
Boccon di Vino
House-made bread & fresh pasta daily, since 1992. Best flavours of Tuscany. Closed Tue (Oct).
MapRistorante La Grotta
Guinea fowl pappardelle, pigeon two ways. Refined Tuscan. Closed Wed & Jan–Feb.
MapMust-Eat · 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 side by side.
- 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
04
Firenze
Florence · The Renaissance Capital
Days 8 – 9
23 – 24 Oct
23 – 24 Oct
Sights · Florence
Oltrarno & Piazza Santo Spirito
The "real" Florence — artisan workshops, local bars. Saturday morning market.
Map
San Lorenzo / Mercato Centrale
Ground floor: leather & souvenirs. Upstairs: food hall — great for grazing.
Map
Wine Bars & Enotecas · Florence
Le Volpi e l'Uva
Beloved by-the-glass wine bar — Tuscan classics to lesser-known Italian regions. Cheese & crostini are excellent.
MapCasa del Vino
Old-school Florentine enoteca. Wine with crostini, panini, porchetta plates. Authentic, no-fuss.
MapEnoteca Bruni
3,000+ exclusively natural wine labels. Solo detour if you want to geek out — friends can skip this one.
MapWhere to Eat · Florence
Trattoria Sostanza ★
Tiny kitchen, rarely-changing menu perfected over decades. Butter chicken breast is legendary. Mon–Sat. Closed Sun. Cash only.
MapTrattoria Cammillo
Enduring, refined but never fussy. Great for bistecca fiorentina. Closed Tue & Wed.
MapI Fratellini
Sandwich shop since 1875. Prosciutto, truffle, local fillings. Quick & cheap. Daily ~10am–7pm.
MapLampredotto stand
Tripe sandwich in crusty roll with parsley sauce & chili oil. The ultimate local snack.
MapGelateria dei Neri
The fondente (dark chocolate) is insane. Small batches. Daily ~10:30am–11:30pm.
MapMust-Eat · 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.
- Ribollita — bread & bean soup, cucina povera at its best.
- Gelato — Gelateria dei Neri, Vivoli, or La Strega Nocciola.
05
Milano
The Honeymoon Finale
Days 10 – 11
25 – 26 Oct
25 – 26 Oct
Sights · Milan
Duomo di Milano
Gothic masterpiece. Walk the rooftop terraces for city views. The golden Madonnina on top is Milan's symbol.
Map
Galleria Vittorio Emanuele II
Opulent iron & glass arcade. Historic cafés, luxury shops. Shortcut from Duomo to La Scala.
Map
Navigli District
Canal-side bars & restaurants. Serene by day, buzzing by night. Great for aperitivo.
Map
Bosco Verticale
"Vertical Forest" — residential towers covered in trees. Iconic modern architecture, quick photo stop.
MapWhere to Eat · Milan
Trippa ★
Defining force in Milan's dining scene. Revives disappearing Italian dishes with a modern edge. Mon–Thu dinner; Fri lunch + dinner. Closed Sat & Sun. Book well ahead.
MapRazdora
Intimate fresh pasta workshop. ~4 tables. Honest, soulful cooking with zero pretense. Mon–Fri. Closed Sat & Sun.
MapCavoli a Merenda
Ivy terrace, weekday-only, grand yet comfortable. Reservations mandatory. Tue–Fri. Closed Sat–Mon.
MapMust-Eat · 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.