Daniel's 14-Day Italian Road Trip Adventure

by Daniel — their ratings, photos, and thoughts on this trip.

Destination

Northern and Central Italy

Dates

Sep 1, 2025 to Sep 14, 2025

Window

7 days · 19 stops

Status

planning

Total estimated spend: ~SGD 1,427

0 likes

Visible itinerary window

Browse the trip one week at a time.

2 weeks total

Itinerary section

Week 2

7 days

Monday, Sep 8

~SGD 110 estimated

Scenic Drive to Tuscany
Sign in to save
Tuscany, Italy
10:00 AM · 4 hrs
Lunch in Mantua (Mantova)
Sign in to save
Osteria da Pietro, Mantova
1:00 PM · 1.5 hrs · ~SGD 40
Daily Gelato: Gelateria Dondoli
Sign in to save
Gelateria Dondoli, San Gimignano
5:30 PM · 30 min · ~SGD 10
Dinner in San Gimignano
Sign in to save
Ristorante Bel Soggiorno, San Gimignano
7:30 PM · 1.5 hrs · ~SGD 60

Tuesday, Sep 9

~SGD 85 estimated

Explore the Towers of San Gimignano
Sign in to save
San Gimignano, Italy
10:00 AM · 2.5 hrs
Casual Pizza Lunch
Sign in to save
RiccaPizzA, San Gimignano
12:45 PM · 1 hr · ~SGD 25
Visit Ancient Volterra
Sign in to save
Volterra, Italy
2:30 PM · 2 hrs
Daily Gelato: L'Isola del Gusto
Sign in to save
Gelateria l'Isola del Gusto, Volterra
4:45 PM · 30 min · ~SGD 10
Traditional Tuscan Dinner
Sign in to save
La Vecchia Lira, Volterra
7:30 PM · 1.5 hrs · ~SGD 50

Wednesday, Sep 10

~SGD 115 estimated

Siena's Historic Center
Sign in to save
Piazza del Campo, Siena
10:00 AM · 3 hrs
Authentic Sienese Lunch
Sign in to save
Osteria Il Grattacielo, Siena
1:15 PM · 1.3 hrs · ~SGD 35
Daily Gelato: Kopakabana
Sign in to save
Gelateria Kopakabana, Siena
3:00 PM · 30 min · ~SGD 10
Val d'Orcia Sunset Drive
Sign in to save
Val d'Orcia, Italy
4:30 PM · 1.5 hrs
Splurge Dinner with a View
Sign in to save
La Porta, Monticchiello
7:30 PM · 1.5 hrs · ~SGD 70

Thursday, Sep 11

~SGD 95 estimated

Discover Pienza & Pecorino
Sign in to save
Pienza, Italy
10:00 AM · 2 hrs
Rustic Pecorino Lunch
Sign in to save
Sette di Vino, Pienza
12:30 PM · 1.5 hrs · ~SGD 30
Montepulciano Exploration
Sign in to save
Montepulciano, Italy
2:30 PM · 2 hrs
Daily Gelato: Roxy
Sign in to save
Gelateria Roxy, Montepulciano
4:45 PM · 30 min · ~SGD 10
Dinner in Montepulciano
Sign in to save
Osteria del Conte, Montepulciano
7:30 PM · 1.5 hrs · ~SGD 55

Friday, Sep 12

No activities planned for this day.

Saturday, Sep 13

No activities planned for this day.

Sunday, Sep 14

No activities planned for this day.

Lokoway

Turn rough ideas into a polished itinerary with day-by-day planning, activity timing, and shareable trip pages.