21 days in Italy: grand tour from Venice to Sicily

Day by day

1. 1

   Day 1

   Arrival in Venice — first night in Cannaregio

   Land at Marco Polo airport, Alilaguna blue line to San Marco (€15, 1h10) or Aerobus to Piazzale Roma (€8, 25 min) then vaporetto n°1 or n°2 to your neighbourhood. No rush: drop bags at the hotel — San Polo, Dorsoduro or Cannaregio are the most authentic neighbourhoods, far from the San Marco price trap — then plunge straight into the alleys.

   First evening in cicchetti mode: a bacaro in Cannaregio, spritz at €3-4, 3-4 bites (sarde in saor, baccalà mantecato, polpette) at €5-7. Italy always starts better on foot with a glass in hand. Light dinner, early night — 6am Venice deserves to be earned.

   Tips

   • · No rolling luggage on Venice bridge steps: use a backpack or book Venice Luggage Service (€25) for hotel delivery.
   • · Book Venice accommodation 2-3 months ahead in high season — decent 3-star hotels in good neighbourhoods fill up from March.
   Venice →
2. 2

   Day 2

   Venice: San Marco, Doge's Palace, lagoon islands

   Wake at 6am for an empty San Marco: the square is nearly deserted until 8am, morning mist draping the basilica's gilded facades. Counter coffee at Caffè Florian (€5 standing, not seated!), then St. Mark's Basilica (free entry, no bags — cloakroom opposite, €3). At 9:30am, move straight to the Doge's Palace (reservation recommended, €30): the Grand Council chamber, the dungeons and the Bridge of Sighs from inside.

   Lunch at Trattoria alla Madonna near the Rialto (pasta e fagioli, €12-15). Afternoon: vaporetto n°12 from Fondamente Nove to Burano (40-45 min) — multicoloured houses, lacemakers, lakeside village feel. Return via Murano (15-min ferry), artisan glassworks (free demonstration). Dinner in Dorsoduro, Venice's student neighbourhood.

   Tips

   • · Vaporetto pass: 48h (€33) or 72h (€42) — pays off after 4-5 rides, essential for island trips.
   • · Gatto Nero in Burano: the best risotto in the lagoon — book 7-10 days ahead in high season if you want lunch there.
   Venice →
3. 3

   Day 3

   Venice → Verona → Lake Como

   Early departure from Venezia Santa Lucia: regional train or Frecciargento to Verona Porta Nuova (1h10-1h30, €12-20). Verona deserves 3h: the Roman Arena (1st century, still used for summer opera, €10), Casa di Giulietta (free courtyard entry, €6 for the balcony), Piazza delle Erbe and the medieval old centre. Coffee under the arcades, quick panino from the market.

   Depart Verona → Milan (1h10 Frecciarossa, €20-35), then Milano Centrale → Varenna-Esino via Lecco (1h10, €7.80). Arrive at Lake Como late afternoon. Varenna: a charming lakeside village far less crowded than Bellagio, with direct ferry connections. Aperitivo on the lungolago, dinner at Ristorante Il Cavatappi (lake trout and smoked agone, €35-45 per person).

   Tips

   • · Verona Arena: arrive at opening (8:30am) — cruise coach groups arrive after 10:30am and the piazza becomes difficult.
   • · Milan → Varenna via Lecco: direct train from Milano Centrale — don't confuse with the Como line which doesn't serve Varenna.
4. 4

   Day 4

   Lake Como: Bellagio, Varenna, gardens

   A full day on the lake at ferry pace. Morning: ferry crossing to Bellagio (15 min from Varenna, €5.40) — the flower-lined lanes, silk boutiques and Villa Melzi d'Eril botanical gardens (€7, rhododendrons in May, roses in June). The view from Bellagio's tip over the three arms of the lake is one of the finest in northern Italy.

   Lunch at Café La Punta on the waterfront. Afternoon: ferry back to Varenna, visit the Gardens of Villa Monastero (€8, 2km of lake-edge terraces). Climb to Castello di Vezio (€7, 360° panorama over the Alps and the lake). Aperitivo on Varenna's jetty — the Alps turn pink at sunset. Pack bags for tomorrow's transfer to the Cinque Terre.

   Tips

   • · Villa Monastero closed on Tuesdays — check hours on villamonastero.eu before planning.
   • · Avoid Bellagio after 11am in July-August: cruise ferries unload hundreds of passengers and the lanes become impassable.
5. 5

   Day 5

   Lake Como → Cinque Terre via Milan

   Three-segment journey: Varenna → Milano Centrale (1h10, €7.80), then Frecciarossa Milano → La Spezia (2h20-2h40, €35-55), finally regional train from La Spezia to Vernazza or Monterosso (20-25 min, included in the Cinque Terre Card at €7.50). Recommended departure 7:30-8am from Varenna to arrive at the Cinque Terre early afternoon.

   Arrival: first contact with the extraordinary. Colourful villages clinging to the cliffs, the blue Mediterranean, the scent of pesto and the sea. Late lunch of focaccia al pesto or a cone of fried seafood (€10-12) on Vernazza's harbour. First waterfront stroll, trail reconnaissance for tomorrow. Dinner at Ristorante Belforte in Vernazza (terrace on the rocks, book 3-5 days ahead).

   Tips

   • · Buy the Cinque Terre Card at La Spezia (€7.50/day or €14.50/2 days) — covers trails and inter-village trains.
   • · Vernazza or Monterosso as base: Vernazza is the most photogenic, Monterosso the largest with the only real sandy beach.
   Cinque Terre →
6. 6

   Day 6

   Hiking all 5 Cinque Terre villages

   The hardest day, and the most memorable of the Ligurian stay. Full Sentiero Azzurro in 5-6h: Riomaggiore → Manarola → Corniglia → Vernazza → Monterosso (or reverse). Start at 8am from Riomaggiore for the cool morning air and to beat the groups. Check open sections on parconazionale5terre.it (some stretches may be closed after landslides).

   The Vernazza → Monterosso stretch is the hardest (1h30, steep) and the most spectacular. Arrive in Monterosso for a midday swim — the only sandy beach among the 5 villages. Picnic on a headland, carry plenty of water. Train back to base. Essential sunset aperitivo at Nessun Dorma in Manarola (suspended terrace, reservation recommended, views are unreal).

   Tips

   • · Trail or firm hiking shoes are mandatory — flip-flops cause injuries on the stones and roots of the trail.
   • · Inter-village trains every 15-30 min — stops are very brief (20-30 sec), board and alight quickly.
   Cinque Terre →
7. 7

   Day 7

   Cinque Terre — sea, boat, rest

   A free day after Day 6's effort. Three options depending on mood: (1) successive swims in the coves at Manarola and Riomaggiore in the morning — the rocks are nearly deserted before 9:30am; (2) boat trip from Monterosso to Portovenere and Lerici (4h return, €30-35, cliff scenery from the sea); (3) Alta Via (high trail, much less frequented than the Sentiero Azzurro) for 360° panoramas over the Mediterranean and Apennines.

   Lunch on pasta al pesto genovese at a harbour (€8-12). Afternoon in the shade, reading, last Ligurian sunset. Pack bags for the morning departure to Florence.

   Tips

   • · Monterosso ↔ Portovenere boat: book 48h ahead in July-August, seats very limited.
   • · Snorkelling around Manarola and Riomaggiore: clear water, 5-8m visibility — bring your own mask.
   Cinque Terre →
8. 8

   Day 8

   Cinque Terre → Florence

   Journey from La Spezia: regional train to Firenze with change at Pisa (2h-2h30, €18-25), or Frecciarossa Genova → Firenze (3h, €35-50). Recommended departure 8-9am to arrive in Florence before lunch and make use of the afternoon.

   Check in to the hotel — Oltrarno or Santa Croce are Florence's most authentic neighbourhoods. Drop bags then afternoon Duomo: the Brunelleschi Pass (€30) covers the Baptistery, Campanile and cupola — the cupola requires a separate reservation (463 steps, spectacular views over the red rooftops). Dinner at Mercato Centrale (upstairs food court, €12-18, open until midnight) or an Oltrarno trattoria.

   Tips

   • · Book the Brunelleschi cupola separately and in advance via operaduomo.firenze.it — slots fill quickly in high season.
   • · Bag storage at Florence SMN: KiPoint (€6/day) or Radical Storage — useful if the hotel can't take bags on arrival.
   Florence →
9. 9

   Day 9

   Florence: Uffizi and Accademia

   Uffizi opens at 8:15am — reservation mandatory from April to October (€20 + €4 fee, uffizi.it). Allow 3h for Botticelli (Birth of Venus, Primavera), Leonardo, Caravaggio and Titian without rushing. Exit onto Piazza della Signoria, lunch at All'Antico Vinaio (stuffed schiacciata, €7-9, unavoidable 20-min queue but fast-moving).

   Afternoon: Accademia Gallery for Michelangelo's David (€16, 2-3pm slot recommended). Then stroll to Ponte Vecchio, aperitivo at Caffè Rivoire on the Signoria, or walk up to Piazzale Michelangelo (25 min, bus n°12 back down) for sunset over the city's terracotta rooftops.

   Tips

   • · Italian state museums: Accademia closed Mondays, Uffizi closed Tuesdays — adjust day order if needed.
   • · Florence is fully walkable: no public transport needed except bus n°12 for Piazzale Michelangelo.
   Florence →
10. 10

    Day 10

    Florence: Palazzo Pitti, Boboli, Oltrarno

    The third Florence day for breathing space and depth. Morning: Palazzo Pitti (€18, combined ticket Galleria Palatina + Boboli Gardens) — the Medici collection rivals the Uffizi for Renaissance painting, without the crowds. The Boboli Gardens (included) offer a shaded walk above the Arno.

    Lunch in the Oltrarno neighbourhood — an authentic trattoria far from the saturated historic centre (€15-20 per person). Afternoon: wander through the Oltrarno's artisan workshops (furniture restorers, goldsmiths, bookbinders), visit Santa Croce (€8, tombs of Michelangelo, Galileo, Machiavelli) and aperitivo on the piazza. Celebratory dinner for the last evening in Florence.

    Tips

    • · Palazzo Pitti combined with Boboli: arrive at opening (8:15am) — the gardens are magnificent in the morning before the heat.
    • · Santa Croce: the adjacent Museo dell'Opera complex is worth it for Cimabue's crucifix restored after the 1966 flood.
    Florence →
11. 11

    Day 11

    Tuscan day trip: Siena and San Gimignano

    A day out in the Tuscan hills away from Florence. SENA or Tiemme bus from Florence SMN or Piazza Vittorio Veneto to Siena (1h15-1h30, €9-12). The medieval city revolves around Il Campo (Piazza del Campo) — arguably Italy's most beautiful square. Visit Siena Cathedral (€8, exceptional marble floor) and climb the Facciatone for the panorama over the Sienese hills.

    Lunch on a local panino (pici cacio e pepe), then bus or rental car to San Gimignano (30 min) — 14 medieval towers rising from the vineyards, Vernaccia wine best tasted at source. Return bus to Florence around 6-7pm. Last Florence evening: light dinner, pack bags for Rome tomorrow.

    Tips

    • · Rent a car in Florence for the day (€50-70) — simplifies the Siena → San Gimignano → return loop.
    • · Siena rewards early birds: Il Campo is nearly empty before 9:30am, overwhelmed by organised groups after 11am.
12. 12

    Day 12

    Florence → Rome by Frecciarossa

    Frecciarossa Firenze SMN → Roma Termini, 1h35, €35-60 (buy 2 weeks ahead). Recommended departure 9-10am to arrive in Rome early afternoon and make the most of the first day in the capital. Recommended neighbourhood: Monti or Trastevere — away from Termini, 3-4-star hotels at €100-130/night for a double.

    Afternoon neighbourhood walk: Piazza Venezia, Vittoriano (free terrace on the 2nd level, views over Rome's rooftops), Campo de' Fiori, cross the Tiber to Trastevere. First Roman dinner at a trattoria in Monti or Trastevere's alleys — fettuccine cacio e pepe, carciofo alla romana, carafe of Castelli Romani. The south of Italy begins to make itself felt in the cooking.

    Tips

    • · Buy Frecciarossa tickets via Trenitalia.com or Italotreno.it — often 20-30% cheaper than the station counter on the day.
    • · Avoid hotels around Termini: noisy, poorly located, same price as Monti or Trastevere.
    Rome →
13. 13

    Day 13

    Ancient Rome: Colosseum, Forum, Palatine

    The non-negotiable day. Colosseum reservation mandatory via coopculture.it — queues without a ticket reach 2-3h in high season. Combo ticket 'Colosseo + Foro Romano + Palatino' at €18, valid 24h. Arrive at 9am: good light, crowds still manageable. Recommended order: Colosseum (1h30), coffee on Piazza del Colosseo, Palatine and Forum (2h).

    Lunch in the Monti neighbourhood (trattoria on via del Boschetto, €15-20 per person). Afternoon: Capitoline Hill, Basilica of San Clemente (ground floor free, €10 for the early Christian and Mithraic underground levels). Aperitivo on the Lungotevere watching the Tiber. Dinner in Trastevere — Rome's best sunset terrace.

    Tips

    • · 9am slot for the Colosseum — crowds double after 11am, triple after 1pm. The experience is completely different.
    • · The Roma Pass (€56/48h) pays off if you hit 3+ paid sites over 2 days.
    Rome →
14. 14

    Day 14

    Vatican, St. Peter's and Borgo neighbourhood

    Vatican Museums at 8am sharp (skip-the-line booking, €28, official site museivaticani.va): power through the galleries to reach the Sistine Chapel before the group tours flood in. Allow 3h. St. Peter's straight after: free entry, dress code enforced (shoulders and knees covered). Climb to the dome (€8, lift to the roof then 320 steps) for views over the Tiber and Rome's rooftops.

    Light lunch on Borgo Pio. Afternoon: Castel Sant'Angelo (€15, former papal fortress, panoramic views from the ramparts). Dinner in the Prati neighbourhood (via Cola di Rienzo, more authentic than the tourist-saturated Borgo) — supplì, pizza al taglio or a neighbourhood restaurant.

    Tips

    • · Book Vatican Museums at least 5 days ahead in May-June and September — 8am and 9am slots go first.
    • · St. Peter's dome: queue before 1pm to avoid 90-min waits — the lift only goes as far as the exterior roof.
    Rome →
15. 15

    Day 15

    Rome: Baroque and fountains — Trevi, Navona, Pantheon

    The baroque and popular Rome day. Early morning: Trevi Fountain (free, but crowded from 9am — go at 7:30am for photos). Then the Pantheon (€5, reservation via the site) — the masterpiece of Roman architecture, 2,000 years of uninterrupted use. Piazza della Rotonda, counter coffee.

    Lunch near Piazza Navona (avoid restaurants on the square — too touristy: look for an adjacent alley, €15-18). Afternoon: Borghese Gallery (€21, reservation mandatory in 2h slots, 2 weeks ahead) — Bernini, Canova, Caravaggio in the salons of a patrician villa. Aperitivo on the Il Sorpasso terrace or in a Monti bar. Celebratory dinner for the last Roman evening.

    Tips

    • · Borghese Gallery: slots fill 2-3 weeks ahead in high season — book as soon as the trip is confirmed.
    • · Pantheon online reservation mandatory since 2023 (€5) — no spontaneous queuing, timed entry only.
    Rome →
16. 16

    Day 16

    Rome → Naples by Frecciarossa

    Frecciarossa Roma Termini → Napoli Centrale, 1h10, €30-45 — the fastest link between the two southern capitals. Recommended departure 10-11am: arrive in Naples early afternoon and enjoy the first Neapolitan evening. Recommended neighbourhood: Chiaia or Vomero — quieter than the station area, 3-4-star hotels at €90-120/night.

    Afternoon on foot through the Quartieri Spagnoli (lava tiles, washing at the windows, Maradona shrines) and the UNESCO-listed centro storico. Dinner of real Neapolitan pizza: Pizzeria Sorbillo (via dei Tribunali, €8-12, 30-45 min queue) or Da Michele (€7-9, only Margherita and Marinara). Naples rehabilitates pizza as a gastronomic dish from the very first night.

    Tips

    • · Naples Centrale station: watch for pickpockets in the hall and on escalators — keep bag to the front, luggage in sight.
    • · Naples Metro Line 1 ('arte'): extraordinary design stations (Toledo, Università) — worth riding just to see them.
    Rome →
17. 17

    Day 17

    Pompeii and Vesuvius

    A day back to 79 AD. Circumvesuviana from Naples Centrale to Pompei Scavi - Villa dei Misteri (40 min, €3.60). Arrive at 9-9:30am: the Pompeii archaeological site is enormous (66 ha) and deserves a minimum of 3h. Reservation recommended (€16, pompeiisites.org) to avoid queuing at the ticket office. Must-sees: the forum, the Villa dei Misteri (extraordinary frescoes), the plaster casts of victims and the Stabian Baths.

    Lunch on site or in Pompeii town (€10-14). Afternoon: bus or organised shuttle from Pompeii to Vesuvius (€8, crater entry €12). The walk to the crater rim (30-40 min) gives a panorama over the Bay of Naples and, on a clear day, Sicily. Return to Naples by Circumvesuviana around 6-7pm. Dinner in the Chiaia neighbourhood.

    Tips

    • · Pompeii in high heat (July-August): hat, water (2L minimum), sunscreen are essential — almost no shade on the site.
    • · The Villa dei Misteri is a 10-min walk from the main entrance — many visitors never reach it for lack of time.
18. 18

    Day 18

    Amalfi Coast: Positano and Amalfi

    The most photogenic day of the trip. SITA bus from Naples or Salerno to Positano (1h30-2h, €4-6) or summer ferry from Naples (35-40 min, €20-25, a far more pleasant option). Positano: pink and ochre houses tumble down to the sea, the Spiaggia Grande hosts swimmers, colourful linen boutiques line the alleys.

    Lunch of grilled fish or pasta alle vongole by the sea (€20-30). Afternoon: local bus to Amalfi (30 min, €1.30) — the small maritime republic, its Arab-Norman cathedral, its historic paper mills. Optional: bus up to Ravello (30 min) for the Villa Rufolo gardens. Return to Naples by bus or ferry depending on schedules. Light dinner: early flight to Sicily tomorrow.

    Tips

    • · SITA bus on the Amalfi Coast: packed in summer — take the first morning bus (7-8am) to avoid queues and heat.
    • · Hire a boat with skipper from Amalfi for the day (€150-200 to share): the perfect alternative to the congested roads.
19. 19

    Day 19

    Flight Naples → Palermo, arrival in Sicily

    Flight Naples Capodichino → Palermo Falcone-Borsellino (1h, €50-110 depending on airline and booking lead time). Ryanair, easyJet and ITA Airways serve this route. Recommended departure 9-11am to arrive in Palermo early afternoon with a full day ahead.

    Shuttle or bus from Palermo airport to the centre (Prestia e Comandè, €6.30, 45 min). Recommended neighbourhood: Kalsa or Ballarò — historic heart, popular markets, 3-star hotels at €70-90/night. Afternoon: first contact with Sicily — Ballarò market (the most lively and least touristy of Palermo's three street markets), arancini and sfincione as a first snack. Dinner at Osteria dei Vespri (refined Sicilian cuisine, €35-45) or a neighbourhood trattoria.

    Tips

    • · Naples → Palermo flight: book 6-8 weeks ahead to find fares under €60 — prices spike in July-August.
    • · Palermo airport: Prestia e Comandè bus to the central station (€6.30, 45 min) — more reliable than unofficial taxis.
20. 20

    Day 20

    Baroque Palermo and a quick Taormina detour

    A dense but coherent day. Morning in Palermo: Palatine Chapel of the Palazzo dei Normanni (€15, Byzantine mosaics among the finest in Europe, book online) and Palermo Cathedral (free entry, €5 for the royal tombs). Wander through the Vucciria markets and lunch on Sicilian street food — panelle, crocché, stigghiola (€12-15 eating standing up).

    Afternoon: train Palermo → Taormina (Giardini-Naxos, 2h30-3h, €13-18) or private shuttle. Taormina: the Greek Theatre (€10, with Etna as a backdrop) and the glamorous Corso Umberto I. Sunset from the panoramic terrace of the Villa Comunale. Dinner in Taormina or return to Palermo depending on timing — Taormina has excellent small hotels if you prefer to sleep there before the airport.

    Tips

    • · Palatine Chapel: online booking is near-mandatory in high season — morning slots go 7-10 days ahead.
    • · Palermo → Taormina train: slow but scenic (northern Sicily coast) — prefer the InterCity (2h30) over the slow train (3h30).
21. 21

    Day 21

    Last morning in Sicily, flight Palermo → departure

    Early wake and final stroll in Palermo or Taormina depending on accommodation. In Palermo, the Capo market opens at 7:30am — fishmongers, Pachino cherry tomatoes, Castelvetrano olives, fresh ricotta. Pick up local products for home (citrus jam, Bronte pistachio paste, tuna bottarga). Last arancino at the counter (€2.50).

    Flight Palermo → international hub (Paris, Frankfurt, Amsterdam via ITA/Ryanair/Lufthansa, 2-3h, €80-180 depending on lead time). Allow 2h30 at the airport before departure: Falcone-Borsellino is a modest-sized airport but security queues can lengthen in high season. Sicily leaves a singular impression: not quite Italian, not quite anything else — the last island of a trip that showed everything.

    Tips

    • · Return flight from Palermo: book 8-10 weeks ahead for direct links to Paris CDG or other hubs — prices surge in summer.
    • · Falcone-Borsellino airport: Prestia e Comandè bus from the central station (€6.30, 45 min) — preferable to taxis for early-morning departures.

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