14-Day Luxury Italy Itinerary
For couples wanting the classic Italian arc done at the highest level — Rome's history, Tuscan slowness, the Amalfi Coast's drama, and Venice's quiet decadence.
Route overview
Begin in Rome for four nights, drive to Tuscany for three, fly to Naples and the Amalfi Coast for four, then take the train to Venice for three final nights before flying home.
At a glance
Best for: Couples and design-led travellers
Trip length: 14 nights
Ideal budget: A$38,000–A$80,000 (couple, all-in)
Best time: May–June or September–October
Style: Grand hotels, private villas, and Belmond properties
Day 1 — Arrival Rome, Hotel de Russie (Rome)
Morning: Land Fiumicino. Pre-arranged Mercedes transfer to Hotel de Russie or Hotel Hassler. Settle in.
Afternoon: Lunch in the de Russie's Stravinskij courtyard garden — quiet and a perfect first impression.
Evening: Aperitivo at the Hassler rooftop. Dinner at Pierluigi (book ahead). Easy first night.
Where to stay: Hotel de Russie or Hotel Hassler
Insider tip: Both are excellent; de Russie has the better garden, Hassler the better view of the Spanish Steps.
Day 2 — Vatican private access (Rome)
Morning: Pre-opening private Vatican Museums tour — Sistine Chapel before crowds. Arranged through your hotel concierge.
Afternoon: Lunch at La Pergola or quietly exceptional trattoria like Roscioli.
Evening: Walking tour of Trastevere with a private guide; dinner at Trecca.
Where to stay: Hotel de Russie
Insider tip: Pre-opening Vatican access is the single best splurge in Rome. Worth every euro.
Day 3 — Forum & Borghese gardens (Rome)
Morning: Private guide for the Roman Forum and Palatine Hill. Two hours, then coffee at Sant'Eustachio.
Afternoon: Galleria Borghese — book the 1pm slot, the timed entry is mandatory.
Evening: Dinner at Il Pagliaccio (two Michelin stars).
Where to stay: Hotel de Russie
Insider tip: Galleria Borghese tickets must be booked weeks ahead. Your concierge cannot magic these on the day.
Day 4 — Drive to Tuscany (Rome → Tuscany)
Morning: Private chauffeured Mercedes to Tuscany via Orvieto for lunch. Three hours of driving total.
Afternoon: Check in at Castello di Reschio or Borgo San Felice. Pool, garden, slow afternoon.
Evening: Estate dinner. The transition from Rome to Tuscany should be felt — slower, quieter.
Where to stay: Castello di Reschio
Insider tip: Reschio is run by the Bolza family; the experience is meaningfully more personal than a corporate hotel.
Day 5 — Tuscan vineyard day (Tuscany)
Morning: Private tasting at a single-estate Brunello producer — book through your hotel.
Afternoon: Truffle hunt with a local family and a long, slow lunch in their farmhouse.
Evening: Quiet hotel dinner. Most days will be too full; build a quiet one in.
Where to stay: Castello di Reschio
Insider tip: Decline the cellar visit if you've done many — request the vineyard walk and a private vertical tasting instead.
Day 6 — Florence day trip (Tuscany / Florence)
Morning: Private car to Florence (1.5 hours). Pre-opening Uffizi tour.
Afternoon: Lunch at La Cucina del Garga, then craft shopping in Oltrarno — leather, gold, paper.
Evening: Return to the estate for dinner. Florence as a day trip is better than Florence as a stay for many travellers.
Where to stay: Castello di Reschio
Insider tip: The Uffizi 'after-hours' private tour costs around €600 and is genuinely worth it for serious art-lovers.
Day 7 — Drive south, fly Naples, transfer to Amalfi (Tuscany → Amalfi Coast)
Morning: Drive to Florence, short flight to Naples, private car along the Amalfi coast (90 minutes from Naples airport).
Afternoon: Check in at Hotel Caruso, Ravello. The pool is one of the most photographed in Italy and deserves the reputation.
Evening: First Amalfi dinner. Belmond Hotel Caruso's terrace at sunset is unbeatable.
Where to stay: Belmond Hotel Caruso
Insider tip: Stay in Ravello, not Positano, for serenity. Day-trip to Positano if you want it.
Day 8 — Boat day on the coast (Amalfi Coast)
Morning: Private gozzo boat with a captain — Capri, Faraglioni, blue grotto if conditions allow.
Afternoon: Lunch at Da Gemma or Lo Scoglio (book ahead via the captain).
Evening: Long, slow swim back to Amalfi. Dinner at Glicine in Hotel Santa Caterina.
Where to stay: Belmond Hotel Caruso
Insider tip: The boat experience is the trip. Charter a private gozzo with a captain rather than booking a group tour.
Day 9 — Pompeii & Vesuvius (Amalfi Coast)
Morning: Private archaeologist guide for Pompeii. The depth a real archaeologist brings is incomparable.
Afternoon: Late lunch in Sorrento, return to Ravello.
Evening: Hotel terrace dinner. Quiet day to recover.
Where to stay: Belmond Hotel Caruso
Insider tip: Visit Pompeii early — heat and crowds make the afternoon visit far less pleasant.
Day 10 — Spa day & Ravello village (Amalfi Coast)
Morning: Long spa morning at Caruso — the steam, the massage, the pool.
Afternoon: Wander Ravello village. Villa Cimbrone gardens at golden hour.
Evening: Quiet dinner at the hotel; an early night before the train day.
Where to stay: Belmond Hotel Caruso
Insider tip: Villa Cimbrone's terrace of infinity is best at 6pm in summer; the light is unreal.
Day 11 — Train north to Venice (Amalfi → Venice)
Morning: Private car to Naples, Frecciarossa first-class to Venice (5.5 hours, comfortable).
Afternoon: Water taxi from Santa Lucia to Aman Venice or Belmond Cipriani. Both are extraordinary.
Evening: Aperol at Harry's Bar (the original). Dinner at Quadri (two Michelin stars).
Where to stay: Aman Venice
Insider tip: If budget allows, Aman Venice's Papadopoli Garden suite is the most extraordinary hotel room in Italy.
Day 12 — Venice at dawn (Venice)
Morning: Private guide before crowds — St Mark's, Doge's Palace, hidden Sestiere walking.
Afternoon: Vaporetto to Murano and Burano with a private boat (better than scheduled).
Evening: Dinner at Met Restaurant (Hotel Metropole) — quietly excellent.
Where to stay: Aman Venice
Insider tip: St Mark's Square at 7am is a different city. The 9am tourist version is something else entirely.
Day 13 — Cicchetti, last day in Venice (Venice)
Morning: Cicchetti tour with a serious food guide — bacari, tramezzini, ombre.
Afternoon: Peggy Guggenheim Collection. Final shopping in Dorsoduro.
Evening: Final big dinner at Local (one Michelin star) or Quadri.
Where to stay: Aman Venice
Insider tip: Skip the gondola. Take a private water taxi at sunset — same money, far more dignified.
Day 14 — Departure (Venice → Marco Polo)
Morning: Final canal-side breakfast.
Afternoon: Private water taxi to Marco Polo airport (35 minutes).
Evening: Departure.
Where to stay: —
Insider tip: Allow 90 minutes for water-taxi transfer in summer high season — boat traffic on the lagoon is real.
Where to stay
Hotel de Russie, Rome — The Stravinskij garden is the best urban hotel courtyard in Italy. Service is consistently exceptional. Best for First-time Rome luxury travellers. From €1,400 per night.
Belmond Hotel Caruso, Ravello — An 11th-century palazzo with the most photographed pool on the Amalfi Coast — and the substance to match the picture. Best for Couples wanting Amalfi without Positano's crowds. From €2,200 per night.
Aman Venice — A 16th-century palazzo on the Grand Canal with frescoed ceilings and Aman's exceptional service. There is no better hotel in Venice. Best for Discerning Venice visitors. From €2,800 per night.
Castello di Reschio, Umbria — A restored 1,000-year-old castle on a 3,700-acre estate. The most personal high-end hotel experience in Italy. Best for Travellers wanting authentic Tuscan/Umbrian estate life. From €1,600 per night.
Where to eat
Pierluigi (Rome, Roman seafood) — Outdoor terrace on a piazza, exceptional fish, locals still go.
Il Pagliaccio (Rome, Modern Italian) — Two Michelin stars, refined without being precious.
Da Gemma (Amalfi, Coastal Italian) — 70 years on the same square. The pasta with sea urchin alone justifies the trip.
Quadri (Venice, Modern Venetian) — Two Michelin stars in St Mark's Square. The view alone, but the food matches.
FAQs
When is the best time for a luxury Italy trip?
May–June and September–October. July–August is hot, crowded, and aesthetically poorer. Easter through April is excellent in Rome and Florence but unreliable on the coast.
Is two weeks too long for Italy?
No — two weeks is when you can move at the right pace. Less than ten days and you'll be on planes constantly.
Should we drive ourselves or hire a chauffeur?
Always chauffeur for road transfers. Italian autostrada and ZTL zones make self-drive a poor use of luxury holiday time.
Are the famous restaurants worth it?
Many of the famous ones, yes. Many more excellent ones are unknown to the international press — your hotel concierge is the differentiator.
Should we add Sicily or Puglia?
Both deserve their own trip. Trying to add either to a 14-day classic Italy trip dilutes the experience.