Hamilton & Chase Tours
North of Italy — Private Package 9-day Italy tour: Milan, Lake Como, Venice & Florence

9-Day Private Package Journey

North of Italy

Milan, Lake Como, Venice & Florence

Available as Private Semi-Private Self-Guided
From €3,520 per person 9 days / 8 nights
View Itinerary

Tour Overview

9 days across Italy.

Northern Italy is Italy without the crowds the south has come to expect — refined, elegant, and enormously varied within a compact geography. This nine-day private journey begins in Milan, the fashion capital with a Gothic cathedral and Leonardo's Last Supper on a refectory wall. Lake Como follows: the Alps coming down to the water, the light changing the colour of the lake every hour. Venice provides the most improbable city ever built, arrived at correctly by water. And Florence closes the journey with Renaissance masterpieces and the Tuscan countryside that inspired them. Every guide is a specialist, every hotel is chosen for position and character, and private drivers and train tickets are included throughout.

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 Milan
Day 1
1

Day 1

Arrival in Milan

Fashion capital, Gothic cathedral, and Leonardo's city.

Your private driver meets you at Milan Malpensa Airport and transfers you to your hotel in the historic centre. After settling in, the afternoon is yours to explore: the Galleria Vittorio Emanuele II — the world's oldest and most elegant covered shopping arcade — leads you from Piazza del Duomo to La Scala. The Duomo itself is best seen from the rooftop terrace first, where the forest of marble pinnacles and statues creates a skyline unlike any other. We'll share our favourite neighbourhood restaurants and aperitivo spots — Milan takes its pre-dinner ritual seriously, and the Navigli canal district does it best.

  • Private airport transfer into Milan
  • Galleria Vittorio Emanuele II and Piazza del Duomo
  • Milan Duomo rooftop terrace
  • Curated restaurant and aperitivo recommendations
4–5★ centrally located hotel, Milan
Day 2 — Milan Highlights
Day 2
2

Day 2

Milan Highlights

The Last Supper, the Brera, and a city that knows how to live.

Your private guide leads a morning that begins with one of the most anticipated experiences in Italy: Leonardo da Vinci's Last Supper in the refectory of Santa Maria delle Grazie. Visitors are admitted in small groups for fifteen timed minutes — your guide prepares you before entering so the time inside is spent seeing, not reading. The Duomo follows: the largest Gothic cathedral in Italy, its interior vast and vertical, the stained glass and marble floors working together in a way that rewards slow attention. The afternoon is yours: the Pinacoteca di Brera in its Academy courtyard contains Raphael, Mantegna, and Caravaggio in one of Italy's finest collections. The Brera neighbourhood around it is one of Milan's most characterful — independent bookshops, quiet cafés, and the kind of bar where the espresso comes with unhurried elegance.

  • Leonardo da Vinci's Last Supper — private timed visit
  • Milan Duomo Gothic interior
  • Optional: Pinacoteca di Brera — Raphael, Mantegna, Caravaggio
  • Brera neighbourhood at leisure
Meals: Breakfast 4–5★ centrally located hotel, Milan
Day 3 — Milan to Lake Como
Day 3
3

Day 3

Milan to Lake Como

Where the Alps meet the water and everything slows down.

Your private driver heads north from Milan, the city giving way quickly to the pre-Alpine foothills and then to the lake itself — fifty kilometres of water between forested slopes, the lakeside villas appearing one after another as the road follows the shore. Lake Como has drawn the wealthy and the creative for two thousand years: Pliny the Younger had a villa here, and the pattern hasn't changed. Check into your lakeside hotel and explore at your own pace: the lakefront promenade of Como town, the funicular to Brunate for a view of the entire southern arm of the lake, or a boat to Bellagio — the headland village where the two arms of the lake meet and the gardens of Villa Carlotta are famous across Europe. The evening is yours — a lakeside restaurant as the lights come on across the water.

  • Private driver transfer Milan to Lake Como
  • Lakeside arrival and first Alpine views
  • Optional: funicular to Brunate panorama
  • Optional: boat to Bellagio
Meals: Breakfast 4–5★ lakeside hotel, Lake Como
Day 4 — Lake Como to Venice
Day 4
4

Day 4

Lake Como to Venice

From the Alps to the most improbable city ever built.

A final morning on Lake Como — coffee at the hotel terrace with the Alps reflected in the water, perhaps a last walk along the shore or a boat to one of the villa gardens. Your private driver transfers you to Milan's central station for the high-speed train east to Venice — approximately two and a half hours through the Po Valley, the flat farmland giving way to the Venetian lagoon appearing on both sides of the causeway. At Venice Santa Lucia station, your private water taxi meets you for the ride to your hotel: through the back channels first, then into the Grand Canal where the palazzi lean over the water and the gondoliers navigate by memory. Check in, find a bacaro, and order cicchetti — Venice's answer to tapas — with a glass of Soave.

  • Final morning on Lake Como
  • Private driver to station, high-speed train to Venice
  • Private water taxi arrival through the Venetian canals
  • Grand Canal and Rialto Bridge first views
Meals: Breakfast 4–5★ hotel near Grand Canal, Venice
Day 5 — Venice Highlights
Day 5
5

Day 5

Venice Highlights

A Byzantine basilica, a maritime empire, and streets made of water.

Your Venetian art historian meets you after breakfast for a morning in the city's most spectacular spaces. St. Mark's Basilica before the crowds: the golden mosaic ceiling represents a thousand years of Byzantine art accumulated one campaign at a time, 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 connecting to the prisons. The afternoon opens into the quieter Venice: Dorsoduro's Zattere promenade, the Scuola Grande di San Rocco with its Tintoretto ceiling cycle, and the back canals of Cannaregio where the real Venice still breathes. An optional gondola ride at golden hour is the way to end a Venetian day.

  • St. Mark's Basilica — Byzantine gold mosaics
  • 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 6 — Venice to Florence
Day 6
6

Day 6

Venice to Florence

Trading the lagoon for the Renaissance.

A morning in Venice before the train — perhaps a final vaporetto ride down the Grand Canal, a walk through the Rialto market, or a last cicchetti at your favourite bacaro. 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, with Brunelleschi's dome visible as the train approaches Florence. At Firenze Santa Maria Novella, your private driver is waiting to take you to your hotel. The afternoon is yours to discover Florence: cross the Ponte Vecchio at golden hour, browse the leather workshops of the Oltrarno, or settle into Piazza Santo Spirito with an Aperol and watch the Florentines go about their 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 7 — Florence Renaissance Highlights
Day 7
7

Day 7

Florence Renaissance Highlights

The city where the modern world was invented.

Your private guide — an art historian who specialises in the Medici period — meets you after breakfast for a morning through Florence's essential spaces. The Baptistery's gilded Gates of Paradise, the Duomo whose dome Brunelleschi engineered without scaffolding, Piazza della Signoria with its open-air sculpture collection, and the narrow streets where Dante and Machiavelli once walked. The Uffizi Gallery follows: Botticelli's Birth of Venus, Leonardo's Annunciation, and the densest concentration of Renaissance painting on earth. Or the Accademia for Michelangelo's David — larger and more present than any reproduction suggests. The afternoon is free: the leather school behind Santa Croce, the Medici Chapels, or a long coffee in Piazza della Repubblica.

  • Baptistery, Duomo, and Piazza della Signoria
  • Uffizi Gallery — Botticelli, Leonardo, Raphael
  • Accademia Gallery with Michelangelo's David
  • Free afternoon in Florence
Meals: Breakfast 4–5★ centrally located hotel, Florence
Day 8 — Tuscany Excursion or Florence Leisure
Day 8
8

Day 8

Tuscany Excursion or Florence Leisure

The countryside that inspired the Renaissance — or a day with no plan.

Today offers two excellent options. The optional Tuscany excursion takes you by private driver into the Chianti hills: the medieval towers of San Gimignano, the fan-shaped Piazza del Campo in Siena, and a private wine tasting at a family-run Chianti estate — working through the estate's range from young Classico to aged Riserva. Alternatively, Florence rewards a second day of unhurried exploration: the Boboli Gardens above the Palazzo Pitti, the Brancacci Chapel frescoes that every later Renaissance artist came to study, a morning at the Mercato Centrale, or simply the pleasure of getting lost in the streets of a city where every corner reveals something beautiful. For your final evening, your Hamilton & Chase booklet has restaurant recommendations that match the mood.

  • Optional: Tuscan countryside — San Gimignano, Siena, Chianti wine
  • Optional: Florence leisure — Boboli Gardens, Brancacci Chapel
  • Final evening in Florence at your pace
Meals: Breakfast 4–5★ centrally located hotel, Florence
Day 9 — Departure
Day 9
9

Day 9

Departure

Northern Italy stays with you — in the lake light, the canal reflections, the wine.

Your last Italian morning: a final espresso at the neighbourhood bar, a last walk past the Duomo's marble facade, perhaps a stop at the Mercato Centrale for something to carry home. At the agreed time, your private driver transfers you to Florence airport or Santa Maria Novella station for your onward journey. Your travel specialist is reachable until you're home — and a few days later will be in touch to hear which of the four destinations you're already planning to return to.

  • Final morning in Florence at leisure
  • Private transfer to airport or station
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.

4–5★ centrally located hotel, Milan

Milan

2 nights

4–5★ centrally located hotel

Historic centre or Brera

Central for the Duomo and Last Supper; Brera district for the gallery and aperitivo neighbourhood

4–5★ lakeside hotel, Lake Como

Lake Como

1 night

4–5★ lakeside hotel

Como or Bellagio shore

Lakefront rooms available — the view from the hotel is half the experience

4–5★ hotel near the Grand Canal, Venice

Venice

2 nights

4–5★ hotel near the Grand Canal

San Marco or Cannaregio

Canal view rooms available; central position for all guided visits

4–5★ centrally located hotel, Florence

Florence

3 nights

4–5★ centrally located hotel

Historic centre or Oltrarno

Three nights allows both a Florence day and a Tuscany excursion

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★ hotels (double occupancy)
  • Daily breakfast at each hotel
  • Airport meet & greet on arrival
  • Private airport transfers in Milan and Florence
  • Private driver transfers to and from train stations
  • High-speed train tickets (Milan–Venice, Venice–Florence)
  • Private driver transfer Milan to Lake Como and Lake Como to Milan station
  • Private water taxi in Venice
  • Luggage handling (1 suitcase per person)
  • Private expert guides in Milan, Venice, and Florence
  • Skip-the-line access at Last Supper and major sites
  • 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 Milan / from Florence
  • Travel insurance (required — we can arrange coverage on request)
  • Lunches and dinners
  • Lake Como boat excursions (unless opted for add-on)
  • Personal expenses (shopping, additional tastings, gondola rides)
  • 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 Last Supper in Milan books out months in advance — we secure your reservation as part of the booking process.
  • This itinerary flows naturally from a Milan arrival to a Florence departure; open-jaw flights work perfectly.
  • All guides and experiences are arranged exclusively for your group — never shared with other travellers.
  • Lake Como is most peaceful in May–June and September; July–August is busy but beautiful.
  • 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.

Lake Como full day by private boat

A private boat tour of the lake: Varenna, Villa del Balbianello, and Bellagio — the most spectacular villas and villages on Como

From €145 pp

Venice lagoon islands

Private boat to Murano for glassblowing and Burano for painted fishing houses — the lagoon world beyond Venice proper

From €120 pp

Franciacorta wine estate

Between Milan and Lake Como, the Franciacorta DOCG produces Italy's finest sparkling wine — a private estate visit and tasting

From €130 pp

Tuscany full day from Florence

San Gimignano, Siena, and a Chianti estate — the complete Tuscan countryside experience

From €165 pp

Professional photo session

Portrait session at the Venetian canals, Lake Como, or Ponte Vecchio with a local photographer

From €350

"Starting in Milan and ending in Florence was the perfect way to see northern Italy. Lake Como was the unexpected highlight — those Alpine views from the hotel terrace were something else. And Venice was everything we'd dreamed. Hamilton & Chase paced the whole trip perfectly."

Caroline & William H.

Chicago, IL · North of Italy, June 2025

Common Questions

Questions about this trip.

Can I spend more time on Lake Como?

Yes — a second night on the lake allows a full day by private boat visiting Varenna, Villa del Balbianello, and Bellagio. We'd adjust the Milan or Venice nights accordingly. Your specialist will advise.

Can I reverse the direction?

Yes — starting in Florence and ending in Milan works equally well. Some guests prefer to end at Lake Como for a peaceful finale. Your specialist will advise on the best routing based on your flights.

Private Package Journey

North of Italy

9 days / 8 nights

From €3,520

per person

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