When is the best time to visit?

April–June and September–October are ideal across all destinations. The feast of St. Francis on October 4th brings gatherings to Assisi but also extraordinary atmosphere. Winter is peaceful and the pink stone of Assisi looks beautiful in frost.

What happens after I request this trip?

You'll complete a short planning form with your dates, group size, and any preferences. A travel specialist will respond within one business day with a personalised proposal and exact pricing. No obligation — it's a conversation.

9-Day Private Package Journey

Best of Italy & Assisi

Rome, Assisi, Florence & Venice

Available as Private Semi-Private Self-Guided

From €3,610 per person 9 days / 8 nights

View Itinerary

Tour Overview

9 days across Italy.

This is Italy for those who want the famous cities and the road less travelled. The journey begins in Venice — arrived at by water, experienced by foot — continues to Florence with its Renaissance masterpieces, then detours through Umbria to Assisi, the hilltop town of rose-coloured stone whose Basilica of St. Francis has drawn pilgrims and artists for eight centuries. Rome provides the magnificent finale: ancient ruins, the Vatican, and the baroque city that the popes built. Every transfer includes private drivers and train tickets, every guide is a specialist in their territory, and the Assisi stop adds a dimension of quiet profundity that the big cities, magnificent as they are, cannot provide.

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

A city that shouldn't exist — and is magnificent because of it.

Your private water taxi meets you at Marco Polo Airport and carries you across the lagoon into Venice — through the back channels first, then into the Grand Canal where the palazzi lean over the water and the Rialto Bridge frames the view ahead. After checking into your hotel, the afternoon is yours: walk across the Rialto Bridge to San Polo, find a bacaro for cicchetti and a glass of Soave, or simply watch the boats from a canalside seat. We'll have our curated list of favourite restaurants waiting — the neighbourhood osterias where bigoli in salsa and sarde in saor taste the way they have for three hundred years.

Private water taxi arrival across the lagoon
Grand Canal and Rialto Bridge at leisure
Curated restaurant recommendations for your first evening

4–5★ hotel near Grand Canal, Venice

Day 2

Venice Highlights

The Byzantine, the Gothic, and the gloriously impractical.

Your Venetian art historian meets you after breakfast for a morning in the city's most extraordinary spaces. St. Mark's Basilica before the crowds: the golden ceiling mosaics represent a thousand years of Byzantine art, the Pala d'Oro altarpiece the most bejewelled object in Italy. The Doge's Palace — seat of a maritime republic that controlled Mediterranean trade — follows: the Great Council Chamber, Tintoretto's Paradise, and the Bridge of Sighs. The afternoon opens into the quieter Venice: Dorsoduro's Zattere promenade, the Scuola Grande di San Rocco with its Tintoretto ceiling, and the Cannaregio canals where the real Venice breathes. An optional gondola ride at dusk — the Grand Canal in the last light — is the way Venice was always meant to be experienced.

St. Mark's Basilica — Byzantine mosaics and Pala d'Oro
Doge's Palace and Bridge of Sighs
Dorsoduro and Scuola Grande di San Rocco
Optional gondola ride at golden hour

Meals: Breakfast 4–5★ hotel near Grand Canal, Venice

Day 3

Venice to Florence

Trading the lagoon for the Renaissance.

A morning in Venice — perhaps a final walk through the Rialto market, a vaporetto ride, or a last cicchetti at the bar you've come to think of as yours. Your private water taxi transfers you to Santa Lucia station for the high-speed train south — two hours through the Veneto and across the Apennines. At Firenze Santa Maria Novella, your private driver is waiting to take you to your hotel in the historic centre. The afternoon is yours: cross the Ponte Vecchio at golden hour, browse the leather workshops of the Oltrarno, or settle into Piazza Santo Spirito as the neighbourhood comes alive in the evening.

Final Venice morning at leisure
High-speed train Venice to Florence with private transfers
Ponte Vecchio and Oltrarno neighbourhood
First Florence evening at your pace

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

Day 4

Florence Renaissance Highlights

The Medici's city — still running on their genius.

Your private guide — an art historian who specialises in the Quattrocento — meets you after breakfast for a morning through Florence's essential spaces. The Baptistery's Gates of Paradise, the Duomo whose dome Brunelleschi engineered without scaffolding, Piazza della Signoria with its outdoor sculpture collection, and the Ponte Vecchio whose goldsmith shops have been here since the sixteenth century. The Uffizi Gallery follows: Botticelli's Birth of Venus, Leonardo's Annunciation, and forty rooms that no other museum matches room for room. Or the Accademia for Michelangelo's David — the sculpture that seems to breathe. The afternoon is free for the Medici Chapels, the San Lorenzo market, or a long coffee in Piazza della Repubblica.

Baptistery Gates of Paradise and Brunelleschi's Dome
Piazza della Signoria and Palazzo Vecchio
Uffizi Gallery — Botticelli, Leonardo, Raphael
Accademia — Michelangelo's David

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

Day 5

Tuscany Excursion or Florence Leisure

The countryside or the city — either way, it's extraordinary.

Today is deliberately flexible. The optional Tuscany excursion takes you by private driver into the Chianti hills — San Gimignano's medieval towers, Siena's extraordinary Piazza del Campo, and a private wine tasting at a family-run estate. The landscape of cypress, stone, and vine is itself a work of art. Alternatively, stay in Florence: the Boboli Gardens above the Palazzo Pitti, the Brancacci Chapel frescoes that Michelangelo came to study, the Mercato Centrale for provisions, or simply the streets of a city where every corner rewards curiosity. For your final Florentine evening, we'll share our favourite neighbourhood trattorias.

Optional: Tuscan countryside — San Gimignano, Siena, Chianti wine
Optional: Florence leisure — Boboli Gardens, Brancacci Chapel
Final evening in Florence

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

Day 6

Florence to Rome via Assisi

Into the Umbrian hills — where the stones are rose-coloured and the peace is genuine.

After breakfast, your private driver heads south through the Apennines into Umbria — the landscape softening from Tuscany's hills into the gentler green of the Umbrian valley. Assisi appears on its slope of Monte Subasio: a town of pink stone and medieval streets that has changed less than almost anywhere in Italy since Francis walked these lanes in the thirteenth century. Your guide — a specialist in medieval Italian art — leads you through the Basilica of St. Francis: two churches stacked above each other, the lower basilica dark and intimate with Cimabue's frescoes and the saint's tomb, the upper basilica bright and monumental with Giotto's twenty-eight-panel cycle of the life of Francis. After exploring the town and its extraordinary atmosphere, your driver continues south to Rome, arriving in the evening. Check into your hotel near the historic centre.

Private driver Florence to Rome via Assisi
Assisi historic centre and Piazza del Comune
Basilica of St. Francis — Giotto frescoes
Evening arrival in Rome

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

Day 7

Ancient Rome & City Highlights

The empire that built the world, and the baroque city above it.

Your archaeologist guide meets you after breakfast for a morning in the heart of the ancient city. The Colosseum with skip-the-line access: fifty thousand spectators, and a guide who makes the engineering and spectacle feel immediate. The Roman Forum follows — the collapsed heart of an empire — with Palatine Hill rising above for views over the ruins. The afternoon crosses to the baroque city: the Pantheon, still the best-preserved Roman building; Piazza Navona with Bernini's Four Rivers Fountain; the Spanish Steps in the late light; and the Trevi Fountain turning gold in the evening. We'll share our favourite neighbourhood restaurants in Trastevere and the Centro Storico for dinner.

Colosseum skip-the-line with archaeologist guide
Roman Forum and Palatine Hill
Pantheon, Piazza Navona, and Trevi Fountain
Free evening in Rome

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

Day 8

Vatican Museums & Sistine Chapel

Michelangelo overhead — the ceiling that changed art forever.

The final full day begins with the Vatican Museums. Your art historian guide leads you through the essential galleries: the Gallery of Maps, the Raphael Rooms whose School of Athens alone justifies the visit, and the Sistine Chapel — Michelangelo's ceiling arriving as a culmination, with the Last Judgement on the altar wall as the powerful finale. A private passage leads into St. Peter's Basilica, skipping the outdoor queue. Your guide walks you through the basilica's treasures, including Michelangelo's Pietà. The rest of the day is yours: Trastevere's winding streets, the Borghese Gardens, a final gelato crawl. For your last evening in Italy, we'll recommend a restaurant that matches the mood — whether that's a rooftop terrace or a neighbourhood trattoria.

Vatican Museums — Gallery of Maps, Raphael Rooms
Sistine Chapel — ceiling and Last Judgement
St. Peter's Basilica via private passage
Final evening in Rome at your pace

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

Day 9

Departure

Four cities, nine days, and the feeling that Italy has kept a part of you.

Your last Italian morning: a final espresso at the bar, a last walk past the rooftops, perhaps the Rialto of Rome — the morning markets in Campo de' Fiori. At the agreed time, your private driver transfers you to Rome Fiumicino Airport. Your travel specialist remains reachable until you're home — and a few days later will be in touch to hear which of the four cities has already claimed a permanent place in your conversation.

Final morning in Rome at leisure
Private transfer to Fiumicino Airport

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★ hotel near Grand Canal

San Marco or Cannaregio

Canal view rooms available; central position for guided visits

Florence

3 nights

4–5★ centrally located hotel

Historic centre or Oltrarno

Three nights for Florence city day + Tuscany or leisure day

Rome

3 nights

4–5★ centrally located hotel

Historic centre

Walking distance to Forum, Vatican, and best restaurants

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 ticket Venice–Florence
Private driver Florence to Rome via Assisi (full day)
Private water taxi in Venice
Luggage handling (1 suitcase per person)
Private expert guides in Venice, Florence, Assisi, and Rome
Assisi Basilica of St. Francis guided visit
Skip-the-line access at Colosseum, Vatican, and Forum
All entrance fees included in guided visits
All scheduled tours and transport as per itinerary
24/7 local support throughout your trip
Hamilton & Chase digital travel booklet with restaurant and local 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 tastings)
Gratuities for guides and drivers (optional but appreciated)
City tax (collected directly by hotels, typically €3–6 per person per night)

Good to Know

The Assisi stop adds a genuine dimension that the classic cities can't provide — guests who include it consistently call it the unexpected highlight.
All guides and experiences are arranged exclusively for your group — never shared with other travellers.
The Florence-to-Rome drive via Assisi takes approximately 4 hours including the Assisi visit — a comfortable full-day transfer.
Comfortable walking shoes are essential throughout — cobblestones and medieval paving are the norm.
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.

Assisi overnight extension

Spend the night in Assisi to experience the town after the day visitors leave — quiet, atmospheric, and unlike any large city. Morning excursion to Spello or Spoleto

From €185 pp

Florence Uffizi early access

Early-morning private access before general opening — the Botticelli rooms quiet, the light low, the paintings yours

From €95 pp

Tuscany full day from Florence

Siena, San Gimignano, and a Chianti estate — the full Tuscany experience in one sweep

From €165 pp

Venice lagoon islands

Private boat to Murano for glassblowing and Burano for the painted fishing houses

From €120 pp

Rome Borghese Gallery

Bernini's sculpture in the intimate rooms of a Baroque villa — requires advance booking

From €75 pp

"Assisi was the surprise of the trip. We almost skipped it for more time in Rome. Instead it was the most moving day we had — the basilica, the Giotto frescoes, the quiet streets in the Umbrian light. Hamilton & Chase were right to insist on it."

Thomas & Margaret F.

Toronto, Canada · Best of Italy & Assisi, September 2025

Common Questions

Questions about this trip.

Can we spend the night in Assisi instead of passing through?

Yes — a one-night Assisi stay is available as an add-on. It allows the morning visit to Santa Chiara and the evening atmosphere after day visitors leave. We'd adjust the Florence/Rome nights accordingly.

Is Assisi worth adding to an Italy itinerary?

Guests who include Assisi consistently call it the unexpected highlight. The Giotto frescoes are worth the detour on their own, and the atmosphere of the town adds a dimension of quiet profundity that the big cities don't provide.

Private Package Journey

Best of Italy & Assisi

9 days / 8 nights

From €3,610

per person

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