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Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns (Rome to Tuscany, 2026)

11 days
•
From Rome to San Gimignano
4.5 (976 reviews)
  • Scenic view of Assisi with historical buildings and lush surroundings.
  • Clusters of ripe grapes hanging from the vine.
  • Person working with dogs in a wooded area, possibly for truffle hunting.
  • Aerial view of the towers of San Gimignano with Tuscan hills in the background.
  • Panoramic view of Florence featuring the Dome of the Cathedral of Santa Maria del Fiore.
    View all
  • Reflection of a row of buildings along the Arno River in Florence during sunset.
From
$4,799
6% off
US $4,499 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Select departure month

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2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
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Apr
May
Jun
Jul
Aug
Sep
Oct
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Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

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ChildrenUnder 18

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Pay only $349 today. The rest is due 95 days before departure. Learn more

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Plan your adventure:
Gold Operator
Collette
City & Culture
Immerse yourself in rich history and local traditions
Group Tour
Join a group and forge lifelong friendships
Fully Guided
An experienced guide will be with you for the entire tour
Medium Intensity
Travelers should be comfortable with somewhat-demanding activities
Guided in English
Group Size 2 - 44
All Ages Welcome

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Itinerary

  1. Intro

    Introduction

  2. Day 1

    Overnight Flight

    Overnight Flight
    Accommodation
    Hotel (Kolbe Hotel)
  3. Day 2

    Rome

    Rome
    Meals
    Dinner (Welcome dinner)
    Accommodation
    Hotel (Hotel Dei Duchi, Spoleto)

    Included Activities

    • Welcome dinner

    Optional Activities

    • Independent exploration of Rome
  4. Day 3

    Rome to Spoleto - Umbria

    Rome to Spoleto - Umbria
    Meals
    Breakfast
    Accommodation
    Hotel (Hotel Dei Duchi, Spoleto)

    Included Activities

    • Guided walking tour of Spoleto with local expert
    • Visit to Rocca Albornoz castle
    • Visit to Duomo of Santa Maria Assunta
    • Visit to family-owned frantoio (olive presser)
    • Extra virgin olive oil tasting
    Landmarks
    Rocca Albornoz
    Duomo of Santa Maria Assunta
  5. Day 4

    Assisi - Umbria

    Assisi - Umbria
    Meals
    Breakfast, Lunch (Home-cooked meal at local family's country home)
    Accommodation
    Hotel (Hotel Dei Duchi, Spoleto)

    Included Activities

    • Guided walking tour of Assisi with local guide
    • Visit to Basilica of St. Francis
    • Home-cooked lunch at local family's country home
    Landmarks
    Basilica of St. Francis
  6. Day 5

    Umbria

    Umbria
    Meals
    Breakfast, Lunch (Rustic, home-cooked meal)
    Accommodation
    Hotel (Hotel Corsignano, Pienza)

    Included Activities

    • Truffle hunting with local expert and trained dogs
    • Rustic, home-cooked lunch
  7. Day 6

    Umbria to Pienza - Southern Tuscany

    Umbria to Pienza - Southern Tuscany
    Meals
    Breakfast, Snack (Pecorino cheese tasting at dairy farm)
    Accommodation
    Hotel (Hotel Corsignano, Pienza)

    Included Activities

    • Visit to sheep-milk pecorino cheese dairy farm
    • Pecorino cheese tasting

    Optional Activities

    • Evening exploration of Pienza
    Landmarks
    Val d'Orcia
    Pienza
  8. Day 7

    Pienza - Southern Tuscany

    Pienza - Southern Tuscany
    Meals
    Breakfast
    Accommodation
    Hotel (Villa San Lucchese Hotel, Chianti Countryside)

    Included Activities

    • Visit to Bagno Vignoni
    • Guided tour of winery estate and cellar in Montalcino
    • Brunello wine tasting

    Optional Activities

    • Afternoon exploration of Pienza countryside and white roads
    Landmarks
    Bagno Vignoni
    Montalcino
  9. Day 8

    Pienza to Siena - Chianti Region, Northern Tuscany

    Pienza to Siena - Chianti Region, Northern Tuscany
    Meals
    Breakfast, Dinner
    Accommodation
    Hotel (Villa San Lucchese Hotel, Chianti Countryside)

    Included Activities

    • Guided walking tour of Siena with local expert

    Optional Activities

    • Independent exploration of Siena
    • Visit to Siena Cathedral
    • Visit to Siena Town Hall frescoes
    Landmarks
    Siena
  10. Day 9

    Florence - Chianti Region, Northern Tuscany

    Florence - Chianti Region, Northern Tuscany
    Meals
    Breakfast
    Accommodation
    Hotel (Villa San Lucchese Hotel, Chianti Countryside)

    Included Activities

    • Extensive guided walking tour of Florence with local expert
    • View Ponte Vecchio
    • View Signoria Square and Palazzo Vecchio
    • View Piazza del Duomo

    Optional Activities

    • Independent exploration of Florence
    Landmarks
    Ponte Vecchio
    Signoria Square
    Palazzo Vecchio
    Piazza del Duomo
  11. Day 10

    San Gimignano - Chianti Region, Northern Tuscany

    San Gimignano - Chianti Region, Northern Tuscany
    Meals
    Breakfast, Dinner (Farewell dinner of Tuscan specialties)

    Included Activities

    • Time at leisure in San Gimignano
    • Farewell dinner of Tuscan specialties

    Optional Activities

    • Authentic Italian gelato tasting from award-winning ice cream parlor
    • Independent exploration of San Gimignano cobbled streets
    Landmarks
    San Gimignano
  12. Day 11

    Chianti Region - Tour Ends

    Chianti Region - Tour Ends

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What's Included

Expand All
  • Accommodation
  • Guide
  • Meals
  • Additional Services
  • Transport

What's Not Included

  • Flights
  • Insurance
  • Optional
  • Additional Services

Where You'll Stay

  • Kolbe Hotel

    Hotel
    day 1

  • Hotel Dei Duchi, Spoleto

    Hotel
    Days 2, 3, 4

  • Hotel Corsignano, Pienza

    Hotel
    Days 5, 6

  • Villa San Lucchese Hotel, Chianti Countryside

    Hotel
    Days 7, 8, 9
All accommodations are subject to change

Operated by

Collette

Gold Operator
Rating
4.5 (976 reviews)
Response time
within 1 day
Response rate
96%
Cancellation policy
Learn more

Reviews from other tours by Collette

  • Kathy5.0•May 2026
    Excellent trip! Good tour director. Nice balance between the stops and the free time. Great excursions! Only negative...
    Show more
  • Paula5.0•November 2025
    Great tour! Our manager was personable and knowledge. LOVED all the beautiful churches with their exquisite...
    Show more
    Review collected by Collette
  • John4.3•November 2025
    The itinerary was well thought out. The tour manager was very good at keeping the group moving to stay on schedule,...
    Show more
    Review collected by Collette

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Dates & Prices

Select departure month

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
Upcoming departures
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Ends on 11 Nov, 2026
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    From Saturday
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    To Tuesday
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  • Instant Confirmation
    6% off
    From Saturday
    22 May, 2027
    To Tuesday
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    This departure date is available and will 100% depart
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What our customers ask about this tour

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  • D

    Diane

    Asked on April 22nd, 2026

    I'm currently in Italy and am interested in this tour but it's saying it's not available

    Price / Availability
    • ColletteOperator•Written April 2026

      To better assist please let us know what is the travel date/s you would be interested in traveling on?

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Good to know

Tour ID: 284555

The practical details for your trip across Italy: money, plugs and flexible ways to pay, all in one place.

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  • Pay in installments

    Spread the cost in interest-free biweekly installments of $481.

  • Deposit only

    Book now with just a $349 deposit. The remaining balance is due 95 days before departure.

  • € - Euro

    You’ll encounter Euro in Italy.

  • Plug type L

    You’ll need an adapter for these sockets in Italy.

  • Currency

    €
    Euro

    Italy

  • Plugs & adapters

    As a traveler from USA, Canada, England, Australia, New Zealand, South Africa you will need an adaptor for type L.

    • Type L

      Used in Italy

  • Visa

    Whether you need a visa depends on your nationality and how long you stay. We can’t process visas for you, but here’s a quick indication for this trip.

    This is only an indication. Visa rules depend on your passport, trip length and purpose. Always confirm with the official embassy or consulate before you travel.

  • Payment information

    Pay now
    A $349 deposit
    Balance due
    95 days before departure
    Installments
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    Currency
    USD
    Booking fee
    None

    Book now with just a $349 deposit and pay the rest later. The remaining balance is due 95 days before departure, charged automatically to your card, or you can split it into interest-free biweekly installments of $481 at checkout. Everything is charged in USD, and TourRadar never adds a booking fee. Any trip departing before February 7th, 2027 will need to be paid in full at checkout.

    Accepted for Collette tours

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    TourRadar does NOT charge you an extra fee for using any of these payment methods.

  • Cancellation Policy

    Cancellation terms may vary per tour. Please check for the full cancellation policy here.

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  • Insurance

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  • People also viewed

From
$4,799
6% off
US $4,499 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Select departure month

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
Pay only $349 today. The rest is due 95 days before departure. Learn more

Best price guarantee Learn More

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Apr
May
Jun
Jul
Aug
Sep
Oct
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2027

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Jul
Aug
Sep
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Dec

2028

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