Duration9 Days, 8 Nights
Best Time to GoApril, May, June, September, October
InterestsRail · City · Food and Drink
Overview
The Grand Tour was the original bespoke journey, and its Italian leg still works. Arrive by water in Venice, come down the high speed line to Florence in two hours, then climb into the hills to Siena, where the trip ends inside the walls of a city that stopped growing in the fourteenth century and has been the better for it.
This is a sample, not a package. It shows how we shape nine days: how far apart the stops sit, what kind of hotel, which trains and in which class. Your version might swap Venice for Milan, add a night in Bologna for the food, or finish at a farmhouse in the Val d'Orcia instead of a palazzo in town. Tell us what the trip is for and we will write it from here.
Late April to June, and mid September to October. August is hot and half closed; the weeks around the Palio, on 2 July and 16 August, fill Siena completely.
Tailor Made · From
$4,400 per person
Prices are in USD, per person, based on double occupancy, and are estimates of the journey as written, paid to the hotels, railways and restaurants directly.
Nine days, eight nights, at hotels of the kind named below, with the trains, the museums and a day with a driver in the Val d'Orcia. Flights and most meals are not included. Summer runs a little lower; the weeks of the Palio and the Carnival run higher.
Highlights
- 01Two nights in Venice, on a quiet canal in Dorsoduro or a few steps from the Basilica
- 02The Frecciarossa or Italo from Venice to Florence in two hours, over the causeway and through the tunnels beneath the Apennines
- 03The Uffizi and the Accademia on timed tickets, and the Brancacci Chapel in a room of ten
- 04Florence to Siena on the regional line through Empoli, arriving below the walls
- 05The Duomo's marble floor, uncovered for a few weeks each year
- 06A day in the Val d'Orcia with a driver: Pienza, Montalcino and lunch at a farm
The Route
- Venice2 nights
- Florence3 nights
- Siena3 nights
Day by Day
Itinerary
Day 1
Venice, by water
Venice
Arrive at Marco Polo and come into the city the only way that makes sense, by boat. Check in and do very little. Venice at six in the evening, once the day visitors have gone back to the mainland, is a different city from the one in the photographs. A first dinner somewhere small in Dorsoduro.
Stay Ca Maria Adele or Violino d'Oro, Venice
Day 2
The Basilica early, the Palace by the back stairs
Venice
St Mark's on the first timed slot of the morning, shoulders and knees covered, before the square fills. Then the Doge's Palace by its Secret Itineraries tour, which takes you through the prison cells and the roof spaces the public route never sees; it must be reserved. The afternoon is for walking away from San Marco: the Accademia, the Scuola Grande di San Rocco and its Tintorettos, and the spiral staircase of the Palazzo Contarini del Bovolo for the rooftops.
Stay Ca Maria Adele or Violino d'Oro, Venice
Day 3
Down the high speed line to Florence
Florence
By train · Frecciarossa or Italo
Venezia Santa Lucia to Firenze Santa Maria Novella. Two hours, direct.
Reserved seats on a specific train. Executive class runs only on certain sets.
The train leaves the island over the rail bridge beside the causeway, crosses the Veneto plain through Padua and Ferrara, and after Bologna disappears into the Apennines: seventy eight kilometers of high speed line, more than ninety percent of it in tunnel. Two hours after Venice you are in Santa Maria Novella, ten minutes on foot from the river. Take a Business or Prima seat; the difference on a two hour run is small and worth it.
Stay Hotel Lungarno or Portrait Firenze, Florence, on the Arno
Day 4
The Uffizi, then the other side of the river
Florence
The Uffizi on a pre booked morning slot; it is closed on Mondays, which decides the shape of the week. Cross the Ponte Vecchio to the Oltrarno, where the workshops are, and book the Brancacci Chapel for the afternoon: Masaccio's frescoes, thirty minutes, ten people at a time. Dinner in the Oltrarno.
Stay Hotel Lungarno or Portrait Firenze, Florence, on the Arno
Day 5
David at opening, the dome at noon
Florence
The Accademia when it opens, for the David without the crowd. Then Brunelleschi's dome on the slot named on your ticket: four hundred and sixty three steps, no lift, and a view that explains the whole city. The afternoon is a garden, the Bardini or the Boboli, and a long dinner.
Stay Hotel Lungarno or Portrait Firenze, Florence, on the Arno
Day 6
Into the hills, to Siena
Siena
By train · Regionale, Firenze to Siena
Firenze Santa Maria Novella to Siena. About an hour and a half.
Through trains run roughly hourly; some services change at Empoli. The bus is faster and arrives inside the walls; we decide which on the day's timetable.
The regional line to Siena leaves Santa Maria Novella and runs through Empoli into the Chianti hills, about an hour and a half. The station sits below the city; a chain of escalators carries you up to the Porta Camollia and the walls. Check in and walk to the Campo before dusk, when the shell shaped square turns the color it was named for.
Stay Grand Hotel Continental or Palazzo Ravizza, Siena
Day 7
Siena on foot
Siena
The Duomo and the Piccolomini Library, then up to the Facciatone, the unfinished facade of the cathedral that never was, for the best view of the city. If the marble floor is uncovered, it is the reason to time a trip; it happens for a few weeks in summer and again in autumn. The Torre del Mangia climbs in groups of twenty five, no reservations, so go early or late. Dinner inside the walls.
Stay Grand Hotel Continental or Palazzo Ravizza, Siena
Day 8
The Val d'Orcia with a driver
Val d'Orcia
A car and a driver for the day, south into the valley that is on the UNESCO list for its landscape: Pienza, the ideal Renaissance town, Montalcino and its Brunello, San Quirico d'Orcia, and lunch at a farm that makes what it serves. A licensed guide can join for the morning if you want the history told properly. Back to Siena for the last evening.
Stay Grand Hotel Continental or Palazzo Ravizza, Siena
Day 9
Home by way of Florence or Rome
Siena
By train · Regionale to Florence, then Frecciarossa or Italo to Rome
Siena to Firenze, then Roma Termini. About an hour and a half, then an hour and twenty.
Back down the line to Florence for a flight, or on to Rome: Florence to Rome is an hour and twenty minutes on the high speed line, which makes a Rome departure easy and a Rome extension easier still.
Where You Will Stay
Venice, Dorsoduro · 2 nights
Ca Maria Adele
Twelve rooms beside the Salute, at the quiet end of the Grand Canal. The alternative is Violino d'Oro, thirty two rooms a few steps from the Basilica, family run and opened in 2023.
Florence, Borgo San Jacopo · 3 nights
Hotel Lungarno
On the river with the Ponte Vecchio in view, a starred restaurant and four hundred twentieth century works on the walls. Portrait Firenze, its all suite sister across the water, is the more private choice.
Siena, Banchi di Sopra · 3 nights
Grand Hotel Continental
A seventeenth century palazzo with frescoed vaults, the only five star hotel inside the walls. Palazzo Ravizza, a family hotel since 1924 with a garden looking out over the hills, is the quieter alternative.
Essential Information
- Getting in
- A United States passport valid for at least three months beyond your departure from Europe. Since April 2026 the European entry system records fingerprints and a photograph at your first border crossing; allow time for it. The ETIAS travel authorisation is not yet in operation; we confirm the position before you travel.
- Venice and its access fee
- On selected spring and summer days Venice charges day visitors an access fee. Overnight guests are exempt but must register for a code; we do this for you.
- Closing days
- The Uffizi and the Accademia are closed on Mondays; the Brancacci Chapel on Tuesdays. The itinerary is shaped around both, and around the Palio, which fills Siena for four days twice a summer.
- Money
- Euros. Tipping is not expected and there are no fixed rules; rounding up or leaving close to ten percent for good service is plenty. Florence charges a small nightly city tax at the hotel.
- Getting around and access
- Venice is bridges and steps; only a handful of crossings are ramped. Siena is built on three hills; the station escalators and a good pair of shoes take care of most of it. Italo allows luggage without an item limit; the regional trains have no assigned seats. Tell us early about any limits and the trip is shaped around them.
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