Lokoway

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
8

Monday, Sep 8

Day 8

~SGD 110 estimated

  1. Scenic Drive to Tuscany

    Tuscany, Italy

    10:00 AM · 4 hrs

  2. Lunch in Mantua (Mantova)

    Osteria da Pietro, Mantova

    1:00 PM · 1.5 hrs · ~SGD 40

  3. Daily Gelato: Gelateria Dondoli

    Gelateria Dondoli, San Gimignano

    5:30 PM · 30 min · ~SGD 10

  4. Dinner in San Gimignano

    Ristorante Bel Soggiorno, San Gimignano

    7:30 PM · 1.5 hrs · ~SGD 60

9

Tuesday, Sep 9

Day 9

~SGD 85 estimated

  1. Explore the Towers of San Gimignano

    San Gimignano, Italy

    10:00 AM · 2.5 hrs

  2. Casual Pizza Lunch

    RiccaPizzA, San Gimignano

    12:45 PM · 1 hr · ~SGD 25

  3. Visit Ancient Volterra

    Volterra, Italy

    2:30 PM · 2 hrs

  4. Daily Gelato: L'Isola del Gusto

    Gelateria l'Isola del Gusto, Volterra

    4:45 PM · 30 min · ~SGD 10

  5. Traditional Tuscan Dinner

    La Vecchia Lira, Volterra

    7:30 PM · 1.5 hrs · ~SGD 50

10

Wednesday, Sep 10

Day 10

~SGD 115 estimated

  1. Siena's Historic Center

    Piazza del Campo, Siena

    10:00 AM · 3 hrs

  2. Authentic Sienese Lunch

    Osteria Il Grattacielo, Siena

    1:15 PM · 1.3 hrs · ~SGD 35

  3. Daily Gelato: Kopakabana

    Gelateria Kopakabana, Siena

    3:00 PM · 30 min · ~SGD 10

  4. Val d'Orcia Sunset Drive

    Val d'Orcia, Italy

    4:30 PM · 1.5 hrs

  5. Splurge Dinner with a View

    La Porta, Monticchiello

    7:30 PM · 1.5 hrs · ~SGD 70

11

Thursday, Sep 11

Day 11

~SGD 95 estimated

  1. Discover Pienza & Pecorino

    Pienza, Italy

    10:00 AM · 2 hrs

  2. Rustic Pecorino Lunch

    Sette di Vino, Pienza

    12:30 PM · 1.5 hrs · ~SGD 30

  3. Montepulciano Exploration

    Montepulciano, Italy

    2:30 PM · 2 hrs

  4. Daily Gelato: Roxy

    Gelateria Roxy, Montepulciano

    4:45 PM · 30 min · ~SGD 10

  5. Dinner in Montepulciano

    Osteria del Conte, Montepulciano

    7:30 PM · 1.5 hrs · ~SGD 55

12

Friday, Sep 12

Day 12

No activities planned for this day.

13

Saturday, Sep 13

Day 13

No activities planned for this day.

14

Sunday, Sep 14

Day 14

No activities planned for this day.

Lokoway

Plan your own trip

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

Start planning with Lokoway