Proposal · for The Bennett Family

Tuscany & Rome

Ten unhurried days between the hills and the city.

Dates14 – 24 May 2027
Length10 nights
Travellers2 travellers
From$18,420
Why I built it this way

You said the last trip felt like packing every second morning. So this is three bases in ten days, and a full week where you don't move at all.

The five moments
01
Day 2 · 8.30am
The Uffizi before it opens
A private guide, and forty minutes with the Botticellis before anyone else is let in.
02
Day 4 · late afternoon
The road into Val d'Orcia
The stretch of the SP146 you've seen in photographs. We've timed it for the light.
03
Day 6 · 8pm
One long table, twelve people
Dinner at Monteverdi is served at a single table. You'll know everyone by dessert.
04
Day 8 · morning
Nothing at all
The day you asked for. No car, no plan, no one expecting you anywhere.
05
Day 10 · 8pm
The table by the window
Rome, the last night, and the reservation you mentioned in our first call.
At a glance
3 nights
Florence
5 nights
Val d'Orcia
2 nights
Rome
Your route
Florence · 3 nightsVal d'Orcia · 5 nightsRome · 2 nights
Whole journeyBy day
Florence
14–16 May · 3 nights
◇ Drive · 1h 30m
Val d'Orcia
17–21 May · 5 nights
◇ Train · 1h 40m
Rome
22–23 May · 2 nights
Total driving 1h 30m · one train · no internal flights
The journey
1
14 May · Florence

Arrive Florence

Private transfer from Peretola. The afternoon is yours — the hotel is four minutes from the Duomo.

TransferCheck-in
2
15 May

The Uffizi, slowly

A private guide at 8.30, before the doors open to everyone else. Out by noon, lunch at Cibrèo.

Private guide · 3h
3
16 May

Oltrarno on foot

The workshops side of the river. Leather, paper, and the view from Piazzale Michelangelo at dusk.

Walking
4
17 May · Val d'Orcia

South to Val d'Orcia

Collect the car at ten. Ninety minutes of the road you came for, then five nights that ask nothing of you.

Drive · 1h 30m
5
18 May

Pienza and Montepulciano

Two hill towns, one long lunch, and a cellar visit at four.

Wine · 2h
6
19 May

The long table

Cooking with Nonna Rosa in the morning. Dinner is whatever she decided that day.

Cooking · 3h
7
20 May

Bagno Vignoni

Thermal pools, a slow lunch, and the abbey at Sant'Antimo for vespers.

Spa
8
21 May

Nothing at all

Deliberately empty. This is the day you asked for.

Unscheduled
9
22 May · Rome

Rome by train

The train from Chiusi. Afternoon at the Borghese, tickets already held.

Train · 1h 40mBorghese
10
23 May

The last table

Morning free. Dinner booked for eight — the table by the window you asked about.

Dinner 8pm
Where you sleep
Florence · 3 nights

Palazzo Vecchietti

Junior Suite · Breakfast
Val d'Orcia · 5 nights

Monteverdi

Garden Room · Half board
Rome · 2 nights

Hotel de Russie

Deluxe, garden view · Breakfast
Where you'll stay in Val d'Orcia

Five nights. This is the decision that shapes the week.

Comfortable

Podere Le Volpi

Farmhouse, six rooms, working vineyard. Ten minutes from Pienza.

Simple rooms — the setting does the work.

$3,200
included
I'd book this

Monteverdi

A restored village. Twelve rooms, one long table, a valley that goes on.

What you described when you said "somewhere that feels like a place, not a hotel."

$4,600
+$1,400
Exceptional

Castello di Vicarello

Eleventh-century castle, seven suites, two pools cut into the hillside.

Genuinely spectacular. Worth it if the anniversary matters more than the number.

$7,000
+$3,800

You'll choose between these when you accept — no need to decide now.

Getting there and around
Flight · LHR → FLR
14 May · BA 604 · 09:15 → 12:40 · Club Europe
Car · Florence → Pienza
17 May · Volvo XC60 · collected 10:00
Train · Chiusi → Roma Termini
22 May · Frecciarossa 9512 · 11:20 → 13:00 · 1st class
Flight · FCO → LHR
24 May · BA 553 · 14:05 → 15:55 · Club Europe
What's included
Included
✓  All accommodation with breakfast
✓  Private guiding as listed
✓  Airport & station transfers
✓  Borghese & Uffizi tickets held
✓  24/7 contact throughout
Not included
—  City tax — ~€5pp per night, paid at hotel
—  Lunches and dinners unless listed
—  Travel insurance
—  Fuel and motorway tolls
Your investment
Total for two
$18,420
$9,210 per person
Accommodation · 10 nights$9,850
Private guiding & transfers$3,120
Car hire · 6 days$1,140
Rail · Chiusi → Roma$180
Experiences & dining$2,930
Planning fee$1,200
Due today
$4,600
1 Feb 2027
$6,910
1 Apr 2027
$6,910
Dates that matter
Deposit dueToday
Second payment1 Feb 2027
Final balance1 Apr 2027
Rates held until14 Sep 2026
Passport must be valid to24 Nov 2027
Your advisor
Claire Bennett-Hale
Founder · Italy specialist · ALDER & CO

Sixteen years arranging Italy. I lived in Florence for four of them and still go back three times a year. I work with about forty families a year, which is deliberate.

ASTA VerifiedVirtuoso memberItaly · 40+ trips
◷ I usually reply within 3 hours
About ALDER & CO — A three-person studio in Bath arranging slow travel in Italy and Portugal. Founded 2009.
What others said

"She talked us out of two things we thought we wanted, and she was right about both."

M. Ashworth · Puglia, 2026

"The proposal arrived and my wife just said "yes, that one." We'd had three others."

D. Rana · Amalfi, 2025
Questions you might have
When do I need to decide?
Rates are held until 14 September. After that I'd need to requote and availability may move.
Can we change the hotel after booking?
Yes, within 14 days of confirmation at no charge. After that, supplier terms apply.
What if someone gets ill?
This is what insurance is for — see below. I'll handle the supplier side either way.
Terms & insurance

Terms in brief

  • Changes free within 14 days of confirmation; supplier terms after
  • Deposit non-refundable, credited against the trip
  • Balance due 45 days before travel

Travel insurance

I strongly recommend comprehensive cover including cancellation and medical. You'll be asked to confirm either way when you accept, and I keep a record of your answer.

Your travel curator

ALDER & CO

This proposal was handcrafted with care for The Bennett Family. Every detail has been chosen with your journey in mind — reach out anytime, we're here to make it perfect.

✦  ALDER & CO
Crafted with ♥ by ALDER & CO
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