Rome, Siena, Chianti, Florence: A Honeymoon
Four days for two through the canonical Italian Renaissance route — slow mornings in Rome, an agriturismo in the Chianti hills, and the Uffizi at last entry when the school groups have left. A honeymoon, but the kind where the itinerary still gets to be specific.
Map
Itinerary
Day 1 · Monday, August 24, 2026
1
09:30 - 10:30
Train
Leonardo Express FCO → Roma Termini
32 minutes direct from Fiumicino — €14, runs every 15 min. Skip the queue at the airport platform by tapping a contactless card at the entry gate.
2
11:00 - 11:45
Check-in
Hotel Locarno
1925 Liberty-style hotel two minutes off Piazza del Popolo — request the rooftop terrace room. The hotel's Bugatti-period vintage bicycles are free for guest use.
3
12:00 - 13:30
Lunch
Pianostrada
Trastevere-adjacent kitchen run by four sisters — focacce, pasta, a courtyard garden. The puntarelle salad in winter, the carbonara whenever.
4
14:30 - 17:00
Archaeology Walk
Colosseum + Roman Forum + Palatine Hill
Pre-book the joint Foro Romano ticket (1-hour timed Colosseum entry, then 2 hours of self-paced Forum + Palatine). Enter the Forum from Via dei Fori Imperiali, exit down past the Arch of Constantine.
5
17:30 - 18:30
Gelato
Gelateria del Teatro
On a stone-walled alley off Via dei Coronari — get the ricotta + fico (fig) and the lavender + white peach. Made fresh twice daily; closing time is when it sells out.
6
19:00 - 20:00
Garden Stroll
Villa Borghese gardens at golden hour
Up the Pincian Hill stairs from Piazza del Popolo — the terrace at the top is the cleanest sunset view of the Roman skyline. Free.
7
20:30 - 22:30
Dinner
Da Enzo al 29
Eight tables in a tiny Trastevere trattoria. Cacio e pepe and the carbonara are the order. No reservations after 8pm — go at opening (19:30) and put your name down.
Day 2 · Tuesday, August 25, 2026
8
08:00 - 09:00
Breakfast
Hotel Locarno terrace
Cornetti, espresso, the morning light over Piazza del Popolo. Pack a panino for the train.
9
10:00 - 11:35
Train
Frecciarossa Roma Termini → Firenze SMN
1h35 high-speed, business class is comfortable but standard is fine. Sit on the left side past Orvieto for the cliff-town views.
10
12:00 - 13:30
Lunch
All'Antico Vinaio, Florence
Cult panino shop on Via dei Neri before the rental-car pickup. Get the Schiacciata with truffled mortadella + stracciatella, eat it on the Arno wall.
11
14:00 - 15:30
Car + Drive
Florence → Siena (SR222 Chiantigiana)
Pick up the rental at Hertz Borgo Ognissanti. Take the scenic Chiantigiana route, not the autostrada — passes through Greve, Castellina, Radda. 90 minutes with photo stops.
12
16:00 - 16:30
Check-in
Palazzo Ravizza
16th-century palazzo hotel inside the city walls — request a room overlooking the rear gardens with the Crete Senesi hills beyond.
13
17:00 - 19:00
Walking Tour
Piazza del Campo + Duomo di Siena
The shell-shaped piazza where the Palio horse race runs every July. Climb the Torre del Mangia (free for hotel guests with the Palazzo's pass). The Duomo's marble facade at sunset is unreal.
14
20:00 - 22:30
Dinner
Osteria Le Logge
A former 1930s pharmacy converted to the city's best traditional Tuscan kitchen — pici cacio e pepe and the pigeon with vin santo. The wine list is famously deep.
Day 3 · Wednesday, August 26, 2026
15
08:30 - 09:30
Breakfast
Palazzo Ravizza garden breakfast
Buffet plus cooked-to-order eggs on the rear garden terrace. Then check out, head north on the Chiantigiana.
16
10:00 - 12:30
Winery Tour
Antinori nel Chianti Classico
Archea Associati's spectacular wine-architecture cellar half-buried in the hillside near Bargino. 90-minute tour + 6-wine tasting; book online a month ahead. The Tignanello flight is the move.
17
13:00 - 15:00
Lunch
Osteria di Passignano
Michelin-starred terrace at the Abbazia di Passignano — sit on the upper deck overlooking the Antinori vineyards you just toured. The pasta course at lunch is exceptional.
18
15:30 - 16:00
Check-in
Castello di Ama
Working winery + 12-room agriturismo + contemporary-art collection (Anish Kapoor and Daniel Buren installations in the cellars). Book a Junior Suite in the casa colonica.
19
16:30 - 18:30
Vineyard Walk
Castello di Ama vineyards + art trail
Self-guided walk through the vines and the Louise Bourgeois sculpture in the chapel. Get back for the golden-hour view from the pool deck.
20
19:30 - 22:30
Dinner
Ristoro di Ama
The estate's restaurant — old kitchen with a wood-fired grill. Bistecca alla fiorentina is the order; pair with the estate's Chianti Classico Riserva. Watch the stars come out over the hills.
Day 4 · Thursday, August 27, 2026
21
08:30 - 09:30
Breakfast
Castello di Ama breakfast + drive
Eat in the chapel courtyard then head north — about 75 minutes on the Chiantigiana back to Florence.
22
11:00 - 11:30
Check-in
Hotel Savoy
Rocco Forte property right on Piazza della Repubblica — request a Junior Suite overlooking the square. Drop bags, drop the car at Hertz, walk back.
23
12:00 - 13:30
Cathedral Climb
Duomo di Firenze — Brunelleschi's Dome
463 steps up the cupola for the city panorama — pre-book a 12:00 slot, the climb is single-file and timed. Bring sunglasses for the rooftop.
24
14:00 - 15:30
Lunch
Trattoria Mario
Communal-table trattoria near Mercato Centrale, three generations of the same family. Pasta of the day + bistecca, cash only, closed by 15:00 sharp.
25
16:00 - 18:30
Museum Visit
Uffizi Gallery
Last-entry slot at 16:00 — fewer tour groups. The Botticelli rooms (Birth of Venus, Primavera) and the Caravaggio Medusa are the must-sees. Skip the gift shop, head for the Vasari Corridor entry.
26
19:00 - 20:00
Bridge + Sunset
Ponte Vecchio + Piazzale Michelangelo
Cross the bridge as the goldsmiths close their shutters, then 15-minute uphill walk to Piazzale Michelangelo for the canonical Florence sunset.
27
20:30 - 22:30
Dinner
Cibrèo Trattoria
Fabio Picchi's no-pasta Tuscan trattoria — yellow-pepper soup, ricotta sformato, the most cooked-just-right chicken in Italy. End-of-honeymoon dinner.