9-Day Private Package Journey

Best of Italy

Venice, Florence & Rome

Available as Private Semi-Private Self-Guided

From €3,400 per person 9 days / 8 nights

Tour Overview

9 days across Italy.

From the shimmering canals of Venice to the rolling hills of Tuscany and the ancient heart of Rome, this nine-day private journey traces a line through Italy's most storied corners. Every day is shaped around you — your pace, your curiosities, your appetite — with hand-picked hotels, expert local guides, and the kind of insider moments that don't appear in guidebooks.

Detailed Itinerary

Your journey, day by day.

Every day is designed with breathing room. Sleep in, take a detour, linger at lunch — the itinerary flexes around you, not the other way around.

Day 1

Arrival in Venice

The floating city welcomes you.

Your private driver meets you at Venice Marco Polo Airport and escorts you by water taxi across the lagoon to your hotel — the kind of arrival that reminds you why you came. After check-in, the afternoon is yours: lose yourself in the quiet backstreets of Dorsoduro, stop for a spritz at a canalside bar, or simply watch the light change over the Grand Canal from your room. In the evening, stroll to one of the tucked-away osterias we'll recommend — places where the cicchetti are exceptional and the locals outnumber the tourists.

Private water-taxi airport transfer across the lagoon
Curated restaurant recommendations for your first Venetian evening

4–5★ centrally located hotel, Dorsoduro

Day 2

Venice: Canals, Art & Hidden Courtyards

Two sides of Venice — the masterpieces and the backstreets.

Morning begins with a private guided tour of St. Mark's Basilica and the Doge's Palace — skip-the-line, so you're inside while the piazza is still waking up. Your guide is a Venetian art historian who brings the mosaics and the political intrigue alive in a way that changes how you see the city. After lunch on your own (we'll have a list of our favourites ready), the afternoon is a private gondola ride through the quieter canals of Cannaregio and Castello, where the real Venice still breathes. The evening is free — we recommend a walk to the Zattere for gelato at sunset.

Skip-the-line Doge's Palace & St. Mark's Basilica
Private gondola ride through quiet canals
Art historian guide who lives in Venice

Meals: Breakfast 4–5★ centrally located hotel, Venice

Day 3

Venice to Florence

Trading lagoons for Renaissance rooftops.

A leisurely morning in Venice — perhaps the fish market at Rialto, or a final coffee in Campo Santa Margherita. Your private driver collects you from the hotel and transfers you to Venice Santa Lucia station for the high-speed train to Florence — a comfortable two-hour ride through the Veneto plains and across the Apennines. On arrival at Firenze Santa Maria Novella, another private driver is waiting to whisk you to your hotel in the Oltrarno, the artisan quarter south of the Arno that feels like a village within the city. The rest of the day is yours to wander — cross the Ponte Vecchio at golden hour, browse the leather workshops on Via Maggio, or simply sit in Piazza Santo Spirito with an Aperol and watch the Florentines go about their evening.

Private driver transfer to station, high-speed train to Florence
Private driver pickup at Florence station
Afternoon arrival in Florence's artisan quarter

Meals: Breakfast 4–5★ centrally located hotel, Florence

Day 4

Florence: The Renaissance, Up Close

Uffizi, Duomo, and a city that invented modern art.

This is one of the great days of the trip. Your morning begins with a private, skip-the-line visit to the Uffizi Gallery with an art historian who knows exactly which rooms to linger in and which to walk past — Botticelli's Birth of Venus without the crush, Caravaggio's Medusa with the context it deserves. From the gallery, a walking tour through the historic centre: the Duomo, the Baptistery, Piazza della Signoria, and the narrow streets where Dante, Machiavelli and the Medici once walked. By lunchtime you'll have earned a seat at one of the neighbourhood trattorias we recommend in San Lorenzo — the ribollita and bistecca are outstanding. The afternoon is yours — climb Brunelleschi's dome, visit the Accademia to see David, or simply get lost in the Boboli Gardens.

Private Uffizi Gallery tour with art historian
Florence Renaissance walking tour
Free afternoon for Accademia, Duomo dome climb, or Boboli Gardens

Meals: Breakfast 4–5★ centrally located hotel, Florence

Day 5

Tuscan Countryside: Wine, Hilltops & Long Lunches

The day everyone talks about when they get home.

Your driver collects you after breakfast for a full day in the Tuscan countryside — the kind of day that makes you understand why people fall in love with Italy. First stop: a private cooking class at a family-run farmhouse in the Chianti hills, where you'll learn to make fresh pasta by hand and sit down to eat what you've cooked with wines from the estate's own vineyards. After lunch, a slow drive through the Val d'Orcia to the medieval hilltop town of San Gimignano, where the towers still stand and the views stretch to the horizon. On the way back to Florence, a stop at a boutique Chianti vineyard for a private tasting with the winemaker. You'll return to the hotel in the early evening with a bottle or two in hand.

Private cooking class in a Chianti farmhouse
Chianti vineyard tour with the winemaker
Medieval San Gimignano visit
Val d'Orcia scenic drive

Meals: Breakfast 4–5★ centrally located hotel, Florence

Day 6

Florence to Rome

From the Renaissance to the Eternal City.

One last Florentine morning — use it well. The leather markets of San Lorenzo, the quiet cloister of Santa Maria Novella, or a final espresso at your favourite neighbourhood bar. Your private driver transfers you to the station for the high-speed train to Rome — just ninety minutes through the soft green hills of Umbria. At Roma Termini, another driver is waiting to take you to your hotel near the Spanish Steps. The evening begins with a guided twilight walk through the historic centre: the Trevi Fountain lit up at night, the Pantheon's dome open to the sky, and the narrow streets around Piazza Navona. Afterwards, the neighbourhood is yours — we'll share our favourite Roman restaurants for cacio e pepe and saltimbocca within walking distance of your hotel.

High-speed train Florence to Rome with private driver transfers
Twilight walking tour of Rome's historic centre
Curated dining recommendations in the Centro Storico

Meals: Breakfast 4–5★ centrally located hotel, Rome

Day 7

Ancient Rome: Colosseum, Forum & the Heart of Empire

Walk the same stones the emperors walked.

Morning begins with a private tour of the Colosseum — not just the arena floor, but the underground hypogeum where gladiators waited before stepping into the light. Your guide is an archaeologist who makes two-thousand-year-old history feel immediate and human. From the Colosseum, walk through the Roman Forum and up to the Palatine Hill, where the views over the ruins are worth the climb. By midday, the Monti neighbourhood awaits — Rome's oldest rione, where the trattorias are excellent and the cobblestoned streets are wonderfully quiet. The afternoon is free: the Capitoline Museums, the Aventine Hill keyhole with its perfect view of St. Peter's dome, or an espresso on a piazza — the art of doing nothing, done properly. For dinner, explore our curated list of favourite neighbourhood spots in Trastevere and Testaccio — the real Roman kitchen.

Colosseum underground (hypogeum) access
Roman Forum & Palatine Hill with an archaeologist
Free afternoon — Capitoline Museums, Aventine Hill, or dolce far niente

Meals: Breakfast 4–5★ centrally located hotel, Rome

Day 8

Vatican, Sistine Chapel & a Roman Farewell

Michelangelo's ceiling, and a night to remember.

The final full day begins with the highlight many travelers remember most: a private, early-access visit to the Vatican Museums and the Sistine Chapel. You'll enter before the general public, standing beneath Michelangelo's ceiling in near-silence — an experience that's increasingly rare and genuinely moving. From the Sistine Chapel, a private passage leads directly into St. Peter's Basilica, skipping the outdoor queue entirely. Your guide walks you through the basilica's treasures, including Michelangelo's Pietà, before you emerge into the piazza. The rest of the day is yours to fill however you wish — Trastevere's winding streets, the Borghese Gardens, a final gelato crawl. For your last evening in Rome, we'll recommend a rooftop restaurant or a neighbourhood trattoria depending on your mood — the perfect way to toast everything you've seen.

Early-access Vatican Museums & Sistine Chapel
Private passage into St. Peter's Basilica
Free afternoon and evening to explore Rome at your pace

Meals: Breakfast 4–5★ centrally located hotel, Rome

Day 9

Departure

Arrivederci — until next time.

A final Italian breakfast on the terrace, a last espresso at the corner bar you've come to think of as yours, and a moment to take in the rooftops one more time. Your private driver will collect you from the hotel and transfer you to Rome Fiumicino Airport in plenty of time for your flight. If your departure is later in the day, we can arrange a morning visit to the Borghese Gallery, a walk through the Villa Borghese gardens, or simply a late checkout so you can savour the last few hours. Your travel specialist remains on call until you're home — and we'll follow up a few days later to hear about the highlights.

Private airport transfer
Optional Borghese Gallery morning visit

Meals: Breakfast

Where You'll Stay

Hand-picked hotels, every night.

We choose properties for character, location, and the kind of service that makes you feel looked after — not just checked in. Every hotel can be swapped for an alternative if you prefer.

Venice

2 nights

4–5★ centrally located hotel

Dorsoduro

Steps from the Grand Canal, quiet canalside location

Florence

3 nights

4–5★ centrally located hotel

Oltrarno

Artisan quarter, steps from Ponte Vecchio

Rome

3 nights

4–5★ centrally located hotel

Centro Storico

Walking distance to major sites and dining

Hotels shown are indicative of the standard we book. Upon request, we will provide a detailed itinerary with specific hotel options tailored to your preferences and budget.

What's in the Price

Included

8 nights in 4–5★ centrally located hotels (double occupancy)
Daily breakfast at each hotel
Airport meet & greet on arrival
Private airport transfers in Venice and Rome
Private driver transfers to and from train stations
High-speed train tickets (Venice–Florence, Florence–Rome)
Luggage handling (1 suitcase per person)
Private water taxi in Venice
Private gondola ride in Venice
Skip-the-line access at all major sites
Private expert guides in every city (art historians, archaeologists)
Colosseum underground (hypogeum) access
Early-access Vatican Museums & Sistine Chapel
Private cooking class in Chianti
Chianti vineyard tour and tasting
All scheduled tours and transport as per itinerary
All entrance fees and museum tickets
24/7 local support throughout your trip
Hamilton & Chase digital travel booklet with restaurant & tip recommendations

Not Included

International flights to Venice / from Rome
Travel insurance (required — we can arrange coverage on request)
Lunches and dinners
Personal expenses (shopping, additional drinks, spa treatments)
Gratuities for guides and drivers (optional but appreciated)
City tax (collected directly by hotels, typically €3–6 per person per night)

Good to Know

This itinerary is a starting point — every detail can be adjusted to suit your preferences, pace, and interests.
Hotels are confirmed at booking based on your travel dates. Upgrades and alternatives are always available.
All guides and experiences are arranged exclusively for your party — never shared with other groups.
Comfortable walking shoes are essential. Most days involve 3–5 hours on foot, often on cobblestones.
Flexible booking: adjust or postpone your dates up to 60 days before departure at no charge.

Make It Yours

Optional add-ons & upgrades.

Every trip is different. These extras can be woven into your itinerary — just let your travel specialist know what catches your eye.

Hot air balloon over Val d'Orcia

Sunrise flight over Tuscany's most iconic landscape

From €280 pp

Private after-hours Vatican visit

The Sistine Chapel with fewer than 30 people in the room

From €180 pp

Murano glass-blowing workshop

Visit a master glassblower's studio on Murano island

From €95 pp

Truffle hunting in Tuscany

Hunt for truffles with a local guide and his dogs, then cook with what you find

From €150 pp

Vespa tour of Rome

See the Eternal City the way Romans do — on two wheels

From €120 pp

Professional photo session

1-hour portrait session at iconic locations with a local photographer

From €350

Opera or concert tickets

Verona Arena, La Fenice Venice, or Rome's Auditorium — subject to season

From €75 pp

Airport VIP lounge

Fast-track security and private lounge at Venice or Rome airport

From €55 pp

"Everything was seamless — the hotels were perfect, the guides were extraordinary, and the little surprises (a private rooftop dinner in Rome!) made it truly special. We've already booked our next trip with Hamilton & Chase."

Sarah & James M.

New York, NY · Best of Italy, September 2025

Common Questions

Questions about this trip.

Can I change the hotels?

Absolutely. The hotels listed are our default selections for this route, chosen for location, character, and consistency. If you have a specific property in mind, or want to upgrade or simplify, we'll adjust the itinerary and pricing accordingly.

Is this trip suitable for children?

Yes. We regularly run this itinerary for families. For younger children, we'll adjust the pacing, swap in family-friendly guides, and add age-appropriate activities. The cooking class in Tuscany is a particular favourite with kids.

What if I want to extend my trip?

Easy. Common extensions include the Amalfi Coast (3–4 nights), the Cinque Terre (2 nights), or Lake Como (2–3 nights). We'll build the extension seamlessly into your existing itinerary and pricing.

When is the best time to visit Italy?

April through June and September through October offer the best balance of weather, crowds, and pricing. July and August are peak season — warmer and busier, but still beautiful. Winter travel is possible and can be magical, especially in Rome and Venice.

How far in advance should I book?

For peak season (May–October), we recommend booking 3–6 months ahead to secure first-choice hotels and guides. Off-season trips can often be arranged with shorter notice.

What affects the price?

The starting price is based on double occupancy in our default 4★ hotels during shoulder season. Prices vary with travel dates (peak summer and holidays cost more), hotel upgrades, group size, and optional add-ons. Single supplements are available. We'll provide an exact quote once we know your dates and preferences.

What is your cancellation policy?

A 20% deposit secures your booking. The balance is due 60 days before departure. Cancellations made more than 60 days out receive a full deposit refund. Between 30–60 days, 50% of the deposit is refunded. Within 30 days, the deposit is non-refundable. We strongly recommend travel insurance to cover unexpected changes.

What should I pack?

Comfortable walking shoes are the most important item — you'll be on cobblestones daily. Layers work best as temperatures vary between morning, afternoon, and evening. For churches and the Vatican, shoulders and knees must be covered. We'll send a detailed packing guide with your travel booklet.

What happens after I click 'Plan This Trip'?

You'll fill in a short form with your dates, group size, and any preferences. A dedicated travel specialist will reply within one business day with a personalised proposal and exact pricing. There's no obligation — it's a conversation, not a commitment.

Private Package Journey

Best of Italy

9 days / 8 nights

From €3,400

per person

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