Italy rewards unhurried travelers. Over 36 days, you’ll ride efficient rail lines from the Alps to the Mediterranean, taste-test your way through regional cuisines, and settle into small towns where piazzas hum with evening passeggiata. When the rails end, a short car rental in the south keeps you nimble for countryside sites.

September and October are harvest months—wine crush in Tuscany and Umbria, pistachios on Etna, chestnuts in hill towns—so you’ll find sagre (village food festivals), music series, and citywide cultural programs. Expect gentle temperatures, fewer crowds than summer, and markets piled high with porcini, grapes, and figs.

Practicalities: Validate regional train tickets before boarding and keep an eye on rail platforms for last-minute changes. Book museum entries and top trattorie a few days ahead. Sundays are often free museum days across Italy (first Sunday of the month), and some attractions close on Mondays. Comfortable walking shoes matter even more than style—cobbles and hills are real.

Turin (Torino)

Days 1–4: Savoy elegance, cafés, and riverfront cycling

Turin, Italy’s first capital, pairs broad, arcaded boulevards with mountain views. It’s famous for chocolate, bicerin (a layered drink of espresso, chocolate, and cream), the Egyptian Museum, and the green Po River banks—perfect for easy, romantic strolls or flat bike rides.

• Top sights: Egyptian Museum (one of the world’s largest), Palazzo Reale and the Royal Armory, Mole Antonelliana and the National Cinema Museum, and the riverside Parco del Valentino with its mock medieval village.
• Coffee & sweets: Caffè Al Bicerin for the namesake drink; Caffè Torino for classic counter service; Gelateria La Romana for seasonal gelato.
• Meals: Cianci Piola Caffè (budget-friendly Piedmont plates), Pastificio Defilippis (fresh pasta), Ristorante Consorzio (slow-food stalwart; reserve).
• Local life: Porta Palazzo Market—the largest open-air market in Europe—great for picnic supplies.
• Festivals (typical): MITO SettembreMusica (classical music across Turin and Milan in early/mid-September). Day-trip possibility to Asti for the Palio di Asti (mid-September). Check exact 2026 dates.

Where to stay (budget-friendly): Browse central options on VRBO Turin or Hotels.com Turin. Specific picks: Tomato Backpackers Hotel (clean, social, private rooms available), Hotel Bologna (simple, central), or NH Torino Lingotto Congress (good value near Eataly & Lingotto).

Getting there: Fly into Turin (TRN) or nearby Milan and train to Turin. Compare options on Omio Flights (Europe) and connect by train via Omio Trains.

Genoa (Genova)

Days 5–6: Palazzi, pesto, and seaside day trips

Genoa’s historic center is a knot of medieval alleys opening to grand Renaissance palaces—the former “banker to Europe.” It’s also the birthplace of pesto, best with trofie or trenette pasta.

• Strolls: Palazzi dei Rolli along Via Garibaldi; old port promenade for sunset.
• Food: Antica Osteria di Vico Palla (seafood), Trattoria da Maria (home-style Genovese), Focacceria San Giorgio (cheese-filled focaccia di Recco). Coffee/gelato at Cremeria Buonafede.
• Day trips: Camogli or Santa Margherita/Portofino by regional train for harbor views and coastal walks.

Stay: Value picks include Hotel Nologo, or search VRBO Genoa and Hotels.com Genoa.

Turin → Genoa by train: ~2 hours, €15–25, frequent Regionale/Intercity via Omio Trains.

Cinque Terre (base: Monterosso or Riomaggiore)

Days 7–8: Cliffside villages, anchovies, and sunset toasts

Base in Monterosso for flatter walking and the sandiest beach, or Riomaggiore/Manarola for dramatic cliffs. Hike short segments, ferry between villages, or ride the local train.

• Easy highlights: Short morning hike Manarola–Corniglia (if open), vineyard terraces at Volastra, or the scenic boat between villages.
• Food: Trattoria dal Billy (Manarola; seafood & pastas, reserve), Nessun Dorma (Manarola; bruschette, views, an afternoon aperitivo classic), Gastronomia San Martino (Monterosso; wallet-friendly plates). Breakfast at Il Pirata (Vernazza; Sicilian pastries).
• Note: Village steps are steep—choose Monterosso for least elevation change and bring trekking poles if sensitive to knees.

Stay: In Monterosso: Hotel Souvenir or Hotel Villa Adriana. In Riomaggiore: Scorci di Mare or Hotel Villa Argentina. Also browse VRBO Riomaggiore.

Genoa → Cinque Terre by train: 1.5–2 hours to Monterosso/Riomaggiore, ~€10–15 via Omio Trains.

Milan (Milano)

Days 9–11: Design, Duomo, and aperitivo

Milan is Italy’s creative engine—Roman ruins under glass, Gothic spires above, and a nightly ritual of aperitivo in Navigli. If your dates overlap late September, you may catch Fashion Week buzz.

• Musts: Roof terraces of the Duomo, the Brera district galleries, and the Last Supper (book weeks ahead).
• Food: Piz (fast, great Neapolitan-style pizza), Panzerotti Luini (iconic snack), Trattoria Masuelli (Milanese cutlet), gelato at Grom or Cioccolatitaliani. Coffee at Pave or Marchesi 1824.
• Evening: Navigli canals—a civilized aperitivo at MAG or Rita, followed by a canal-side stroll.

Stay: Budget-mid options: Ostello Bello (private rooms available), UNAHOTELS Cusani Milano (good value). Or search VRBO Milan and Hotels.com Milan.

Cinque Terre → Milan by train: ~3 hours via Levanto/La Spezia, €20–30 on Omio Trains.

Lake Como (base: Varenna)

Days 12–13: Villas, ferries, and mountain reflections

Varenna is a pretty, compact base with frequent ferries to Bellagio and Menaggio. The lakeside passeggiata is gentle and photogenic.

• Do: Ferry to Bellagio for Villa Melzi gardens; visit Vezio Castle above Varenna if knees allow.
• Eat: Il Cavatappi (tiny, reserve), Ristorante La Vista (lake-view), Caffè Varenna for a simple breakfast.

Stay: Hotel Royal Victoria, Hotel du Lac Varenna, or search Hotels.com Varenna.

Milan → Varenna by train: Direct ~1:05, €7–10 via Omio Trains.

Parma

Day 14: Prosciutto, Parmigiano, and porticoes

Even a single night in Parma delivers top-tier eating and graceful streets. Time your arrival for a late lunch, museum stroll, and a convivial dinner.

• Food stops: Salumeria Garibaldi (ham and cheese tasting), Osteria dello Zingaro or Trattoria Corrieri for tortelli and anolini.
• Music: Teatro Regio has a celebrated Verdi season in October—check if dates overlap.

Stay: Central and good value: Hotel Button or search VRBO Parma.

Varenna → Parma by train: ~2–2.5 hours via Milan, €18–28 on Omio Trains.

Florence (Firenze)

Days 15–18: Renaissance art, markets, and pasta-making

Florence is a walk-through museum, but it’s also everyday Tuscany—morning cappuccino at the bar, lunch at the market, sunset over the Arno. Your four nights allow a museum day, a “live like a local” day, and a countryside outing.

• Museums: Uffizi and Accademia (book ahead). Consider this small-group tour for context and skip-the-line entry:

  

  Best of Florence: Small Group Tour Skip-the-Line David & Accademia with Duomo
• Hands-on: Roll pasta and sip wine in an evening class:

  

  Florence: Pasta Cooking Class with Unlimited Wine
• Eat & drink: I Fratellini (tiny sandwich window), Trattoria Sergio Gozzi (classic soups and bistecca at fair prices), Trattoria La Casalinga (Oltrarno). Coffee at Caffè Gilli; gelato at Gelateria dei Neri or Vivoli. Browse Mercato Centrale for budget-friendly lunch.
• Festivals (typical): Late September often brings the Carro Matto wine-barrel parade and Impruneta’s Festa dell’Uva (grape festival). Check 2026 dates—the timing aligns with your stay.

Stay: Good-value, central picks include Hotel Dali, Hotel Santa Croce, or Hotel Davanzati. Also browse VRBO Florence.

Parma → Florence by train: ~1.5–2 hours via Bologna, €20–35 on Omio Trains.

Orvieto (Umbria)

Days 19–20: Hilltown views and slow evenings

Set on a volcanic tuff cliff, Orvieto is a calm, atmospheric town with a masterpiece Duomo and an underground of Etruscan caves and wells.

• Highlights: Duomo façade mosaics; St. Patrick’s Well (double-helix staircases); Etruscan underground tour; funicular views.
• Eat: Trattoria del Moro Aronne (umbrian plates), Osteria al Malandrino (homestyle). Coffee/pastries at Bar Montanucci.

Stay: Hotel Duomo or Hotel Picchio. Search more on VRBO Orvieto.

Florence → Orvieto by train: ~2–2.5 hours via Chiusi, €15–25 on Omio Trains.

Salerno (with Paestum)

Days 21–22: Seaside base, temples, and mozzarella farms

Skip Naples this time and base in walkable Salerno. From here, Paestum’s Greek temples and buffalo-mozzarella dairies are easy day trips; Amalfi Coast ferries also depart from Salerno.

• Do: Day trip to Paestum for Doric temples and the excellent site museum; stop at a caseificio (like Tenuta Vannulo) for fresh mozzarella and yogurt.
• Salerno eats: Pizzeria La Smorfia (local favorite), Il Duca RistoPub (casual), granita or gelato at Punto Freddo.

Stay: Search central, budget-friendly rooms on VRBO Salerno or Hotels.com Salerno.

Orvieto → Salerno by train: ~3.5–4.5 hours with a change in Rome/Naples, €30–45 via Omio Trains. Consider picking up a rental car on arrival for the next legs.

Matera

Days 23–24: Cave dwellings and moonlit lanes

Matera’s Sassi districts glow at sunset. Stay inside or just above the Sassi for easy access to viewpoints and rupestrian churches.

• Walks: Sasso Caveoso to Civita at golden hour; cave churches (Santa Lucia alle Malve); Murgia Park overlooks across the ravine.
• Eat: Trattoria del Caveoso (comforting Materan dishes), Osteria al Casale (hearty pasta), gelato at I Vizi degli Angeli.

Stay: Good value and atmospheric: Le Dodici Lune or Hotel San Domenico Al Piano. See more on VRBO Matera.

Salerno → Matera: With a car, ~2.5 hours. Without, train/bus combos take 3.5–5 hours; check Omio Trains and Omio Buses.

Bari & Polignano a Mare (Puglia)

Days 25–27: Seaside alleys, orecchiette, and whitewashed lanes

Use Bari or Polignano a Mare as a base. Bari Vecchia’s lanes are alive with nonnas hand-rolling orecchiette; Polignano has plunge-pool coves and cliffside sunsets.

• Do: Bari Vecchia walk (watch orecchiette on Strada Arco Basso), day trip to Alberobello’s trulli or Monopoli for a gentle harbor stroll.
• Eat: In Bari: Panificio Fiore (focaccia barese), Mastro Ciccio (sandwiches). In Polignano: Pescaria (casual seafood), Trattoria della Nonna (home-style Pugliese), caffè speciale at Il Super Mago del Gelo.

Stay: In Bari: Hotel Adria or iH Hotels Bari Oriente. In Polignano: browse VRBO Polignano a Mare or Hotels.com Polignano a Mare.

Matera → Bari/Polignano: Drive 1.5–2 hours; by train/bus 2–3 hours. Compare on Omio Trains and Omio Buses.

Palermo (Sicily)

Days 28–30: Markets, mosaics, and Arab-Norman splendor

Palermo blends Norman cathedrals with lively street markets—Ballarò and Il Capo are musts. Take a day for Monreale’s gold mosaics or the seaside hamlet of Mondello.

• Street food: Antica Focacceria San Francesco (panelle, sfincione), Ke Palle (varied arancini). Sit-down: Trattoria Ai Cascinari or Trattoria Ferro di Cavallo (book or go early).
• Cafés: Caffè Spinnato for espresso and cannoli.
• Festivals (typical): Late-September food or gelato festivals sometimes appear in Palermo; schedules vary—check 2026 listings.

Stay: Budget-mid picks: Hotel Garibaldi (Politeama area), NH Palermo. See more on Grand Hotel Villa Igiea if you decide to splurge or VRBO Palermo.

Puglia → Palermo: Easiest is a short flight from Bari to Palermo (~1 hour, often €35–€80). Check Omio Flights. Alternatively, long train-ferry combos exist via Calabria on Omio Trains.

Cefalù (Sicily)

Days 31–32: Cathedral town and beach interlude

One hour from Palermo, Cefalù offers a golden beach, a honey-hued medieval core, and a Duomo with glittering mosaics. Climb La Rocca for views if you’re up for it; otherwise, linger on the lungomare.

• Eat: Al Porticciolo (seafood with harbor views), Lo Scoglio Ubriaco (casual, seafacing), gelato at L’Angolo delle Dolcezze.

Stay: Hotel Mediterraneo (value), Astro Suite Hotel, or explore VRBO Cefalù.

Palermo → Cefalù by train: ~55–65 minutes, €6–9 via Omio Trains.

Rome (Roma)

Days 33–36: Ancient marvels, neighborhood cafés, and a relaxed goodbye

End with four unhurried days in Rome. Balance the headline sites with time in Trastevere, Testaccio, and the Borghese Gardens. Early mornings and evenings are most atmospheric at the big monuments.

• Essential tours (skip-the-line options):
  

  

  Skip-the-Line Group Tour of the Vatican, Sistine Chapel & St. Peter's Basilica
  

  

  Colosseum Arena Floor, Roman Forum and Palatine Hill Guided Tour
  

  

  Rome Highlights City Tour by Golf Cart with Gelato
  

  

  3 in 1 Cooking Class near Navona: Fettuccine, Ravioli & Tiramisu
• Neighborhood eats: Armando al Pantheon (classic Roman; book), Da Enzo al 29 (Trastevere; early line or lunch), Roscioli Salumeria con Cucina (cured meats/pasta), Pizzarium (pizza al taglio near Vatican). Breakfast at Pasticceria Regoli; coffee at Sant’Eustachio or Tazza d’Oro; gelato at Giolitti or La Romana.
• Festivals (typical): Rome Film Fest often mid–late October; you may catch early events if dates shift. Also look for Via Condotti’s La Vendemmia (wine-shopping pairing) in early October.

Stay: Characterful, good value: Hotel Santa Maria (Trastevere), Hotel Mascagni, or The Beehive (budget-friendly). Browse more on VRBO Rome and Hotels.com Rome.

Sicily → Rome: Palermo to Rome flight ~1 hr 10 min, often €25–€70 via Omio Flights. From Cefalù, take the train to Palermo (1 hr) then fly.

Optional and helpful day/activity notes en route

• Pompeii from Salerno (easy day trip): Trains ~40–60 min. Consider:

  

  Pompeii Small Group Tour with an Archaeologist
• Biking: Turin’s Po River paths are flat and scenic. Consider an afternoon ride in Florence’s Cascine Park. If you fancy a classic wall ride, Lucca (day-trip from Florence) has rental bikes atop its Renaissance ramparts.
• Ferries: Use coastal ferries in Cinque Terre and Salerno–Amalfi (seasonal) and check schedules on Omio Ferries.
• Budget tips: Lunch big, dine light; opt for house wine; stand at the coffee bar for lower prices; carry a reusable bottle (many towns have potable fountains).

How your 36 days break down

• Days 1–4: Turin
• Days 5–6: Genoa
• Days 7–8: Cinque Terre (Monterosso or Riomaggiore)
• Days 9–11: Milan
• Days 12–13: Lake Como (Varenna)
• Day 14: Parma
• Days 15–18: Florence
• Days 19–20: Orvieto
• Days 21–22: Salerno (with Paestum)
• Days 23–24: Matera
• Days 25–27: Bari/Polignano a Mare
• Days 28–30: Palermo
• Days 31–32: Cefalù
• Days 33–36: Rome (fly home Oct 13)

This route honors your wish for 3–4 days in Turin, Milan, Florence, and Rome, favors smaller towns elsewhere, and keeps most travel on trains with a short car-rental window in the south. You’ll taste regional specialties from Piedmont to Sicily, and catch early autumn festivals along the way, all at a relaxed, romantic pace.