
Overview
- Level Window Seat
- Duration 9 Days, 8 Nights
- Best Time to Go April, May, June, September, October
- Interests Rail · City · Food and Drink
The Grand Tour was the original bespoke journey, and its Italian leg is as rewarding as ever. You arrive by water in Venice, travel the high speed line to Florence in two hours, then climb into the hills to Siena, where the journey 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, and which trains, in which class. Your own version might exchange Venice for Milan, add a night in Bologna for the food, or finish at a farmhouse in the Val d'Orcia rather than a palazzo in town. Tell us what the journey is for, and we will write it from here.
Late April to June, and mid September to October. August is hot and half closed, and the weeks around the Palio, on July 2 and August 16, fill Siena completely.
Bespoke · 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 and 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. Prices run a little lower in summer, and higher in the weeks of the Palio and the Carnival.
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
Each stop opens to its days, its train and its hotel.

Stop 1 of 3 · 2 nights
Venice
You arrive at Marco Polo and come into the city the only way that makes sense, by boat. Once you have checked in, the rest of the day asks very little of you.
- Stay
- Ca Maria Adele, Venice, Dorsoduro
The Trains
Every train here is named, timed and chosen for a reason, before you write to us.
Day 3 · Florence
Frecciarossa or Italo
- Venezia Santa Lucia to Firenze Santa Maria Novella
- Two hours, direct
Seats are reserved on a specific train, and Executive class runs only on certain sets.
Day 6 · Siena
Regionale, Firenze to Siena
- Firenze Santa Maria Novella to Siena
- About an hour and a half
Through trains run roughly hourly, and some services change at Empoli. The bus is faster and arrives inside the walls, and we choose between them on the day's timetable.
Day 9 · Siena
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
Included
- Nine days and 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.
Not Included
- Flights and most meals are not included.
Prices run a little lower in summer, and higher in the weeks of the Palio and the Carnival.
Day by Day
Itinerary
Day 1
Venice, by water
Venice
You arrive at Marco Polo and come into the city the only way that makes sense, by boat. Once you have checked in, the rest of the day asks very little of you. Venice at six in the evening, once the day visitors have returned to the mainland, is a different city from the one in the photographs. Your first dinner is 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 comes first, on the earliest timed slot of the morning, with shoulders and knees covered, before the square fills. Then comes the Doge's Palace, by its Secret Itineraries tour, which leads you through the prison cells and the roof spaces the public route never sees; it must be reserved in advance. 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.
Seats are reserved on a specific train, and 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 arrive at Santa Maria Novella, ten minutes on foot from the river. We recommend a Business or Prima seat; the difference on a two hour run is small, and well 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 morning belongs to the Uffizi, on a pre booked slot; the gallery is closed on Mondays, which decides the shape of the week. Afterward, cross the Ponte Vecchio to the Oltrarno, where the workshops are, for the Brancacci Chapel in the afternoon, booked in advance: Masaccio's frescoes, thirty minutes, ten people at a time. Dinner is in the Oltrarno.
Stay Hotel Lungarno or Portrait Firenze, Florence, on the Arno
Day 5
David at opening, the dome at noon
Florence
Begin at the Accademia when it opens, to see the David without the crowd. Then climb Brunelleschi's dome at the time named on your ticket: four hundred and sixty three steps, no elevator, and a view that explains the whole city. The afternoon is for a garden, the Bardini or the Boboli, and the evening for 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, and some services change at Empoli. The bus is faster and arrives inside the walls, and we choose between them on the day's timetable.
The regional line to Siena leaves Santa Maria Novella and runs through Empoli into the Chianti hills, in about an hour and a half. The station sits below the city, and a chain of escalators carries you up to the Porta Camollia and the walls. Once you have checked in, walk to the Campo before dusk, when the shell shaped square turns the color that took its name from the city.
Stay Grand Hotel Continental or Palazzo Ravizza, Siena
Day 7
Siena on foot
Siena
The day begins at the Duomo and the Piccolomini Library, then climbs 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 reason enough to time a journey around it; this happens for a few weeks in summer and again in autumn. The Torre del Mangia is climbed in groups of twenty five, without reservations, so it is best visited early or late. Dinner is 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 driver are yours for the day, heading south into the valley that UNESCO lists 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 may join you for the morning, should you wish to hear the history told properly. You return 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.
You travel back down the line to Florence for a flight, or continue 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 few more days in Rome easier still.
Where You Will Stay

Venice, Dorsoduro · 2 nights
Ca Maria Adele
Ca Maria Adele has twelve rooms beside the Salute, at the quiet end of the Grand Canal. The alternative is Violino d'Oro, with thirty two rooms a few steps from the Basilica, family run and opened in 2023.

Florence, Borgo San Jacopo · 3 nights
Hotel Lungarno
Hotel Lungarno sits on the river with the Ponte Vecchio in view, and offers a starred restaurant and four hundred twentieth century works on its walls. Portrait Firenze, its all suite sister across the water, is the more private choice.

Siena, Banchi di Sopra · 3 nights
Grand Hotel Continental
Grand Hotel Continental is a seventeenth century palazzo with frescoed vaults, and 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.
Essentials
Getting in
You will need 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, so please allow time for it. The ETIAS travel authorization is not yet in operation, and we will 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, and we take care of this for you.
Closing days
The Uffizi and the Accademia are closed on Mondays, and the Brancacci Chapel on Tuesdays. The itinerary is shaped around both, and around the Palio, which fills Siena for four days twice each summer.
Money
The currency is the euro. 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, payable at the hotel.
Getting around and access
Venice is a city of bridges and steps, and only a handful of crossings are ramped. Siena is built on three hills, and the station escalators and a good pair of shoes take care of most of it. Italo allows luggage without an item limit, and the regional trains have no assigned seats. If you let us know early about any limits, the journey will be shaped around them.
More Trips

Scotland
Edinburgh and the Highlands
Eight days by rail, from the Old Town to the western sea
Scotland rewards the traveler who slows down, and the railway is the way to do so. The journey opens with three nights in Edinburgh, a city that is far better one street back from the Royal Mile, then climbs north over the Drumochter Pass to Inverness, the small city where the Highlands begin.
8 Days · Window Seat · From $3,900
View TripLet us plan your trip.
You are welcome to take this trip as written, shape it to your liking, or make it the starting point for something entirely your own.
Every inquiry is read personally, and we reply within 24 hours.
