Country Roads of Umbria & Tuscany (Summer, Classic)

9 days
Save this trip to your favorites or other list
Additional images not provided by operator
4.6/5 Excellent
100+ reviews  
97%
Save this trip to your favorites or other list
Group Tour
Live 'la dolce vita' during this 9-day guided tour of Italy. Explore the narrow cobblestone streets of Siena to the shell-shaped Piazza del Campo and see the Torre del Mangia, the second-tallest tower in Italy. Discover the art of truffle-hunting and learn how to make pasta from a professional before delighting in a local lunch. In San Gimignano, eat the best...
$258 OFF
$3,608
From$3,350
See departure dates

Overview

Trip type
Group Tour
Lodging level
Premium - 4 star
Trip pace
Balanced schedule

Highlights

    • Assisi: See St. Mary of the Angels Church and join your Local Expert to walk through the cobbled streets and beautifully preserved medieval laneways of this quaint town.
    • Assisi: With a Local Expert, find out why the Basilica of St. Francis is considered one of the crowning achievements of Europe.
    • San Gimignano: Visit the Tuscan town of San Gimignano, often called the 'Medieval Manhattan' of Italy.
    • Florence: Join a Local Expert to view the multi-colored marble cathedral, bell tower and baptistery, adorned by Ghiberti's Gates of Paradise. Visit the political heart of the city, Signoria Square. See the area around Santa Croce Basilica, famous for the quality of its luxury goods.
    • Rome: Enjoy exclusive access to the Basilica of Saint Praxedes during an after-hours visit. This 9th-century basilica’s simple facade guards the world's best-preserved Byzantine mosaics. The history of the church springs to life as you admire the interior’s treasured collection, including Bernini's first sculpture and the renowned mosaics, illuminated for your visit. This once-in-a-lifetime experience is a rare and unforgettable insight into Rome and its religious history.
    • Perugia: Meet Marta, a recipient of a TreadRight Foundation grant. Learn how she offers employment opportunities for local women and, alongside her weavers, preserves the ancient craft of loom weaving in an artisan workshop.The workshop is owned by women and actively empowers women and girls through its education and training programs. Marta, and her students help to safeguard the unique patterns while contributing to the protection of Umbria’s cultural heritage. Laboratorio Guidetta Brozzetti advances UN Sustainable DevelopmentGoal 5: Gender Equality and UN Sustainable DevelopmentGoal 11: Sustainable Cities & Communities.
    • Rome: Savor dinner at a uniquely Roman restaurant, offering a perfect exploration of Lazio's typical flavors.
    • Umbria: Explore the art of Italian cooking with Chef Lorenzo and take part in a truffle hunting walk followed by lunch.
    • Perugia: You are offered a selection of restaurants on your Dine-Around Evening. Choose your own ambience, cuisine and drinks for an intimate culinary experience.
    • San Gimignano: Ascend serpentine alleyways to the artisan gelato parlour of world champion gelato maestro, Sergio Dondoli for a taste of his finest frozen treats.

What's this trip about?

    Live 'la dolce vita' during this 9-day guided tour of Italy. Explore the narrow cobblestone streets of Siena to the shell-shaped Piazza del Campo and see the Torre del Mangia, the second-tallest tower in Italy. Discover the art of truffle-hunting and learn how to make pasta from a professional before delighting in a local lunch. In San Gimignano, eat the best gelato in the world - literally. Indulge in your favorite flavors or try something unexpected. Alongside a Local Expert, marvel at the cathedral at the center of Florence: Basilica di Santa Maria del Fiore, nicknamed 'the Duomo' for its awe-inspiring crown made by a master goldsmith.

Details

Itinerary focusClassic Highlights
Group sizeGroup - max of 40 people
Age range6 years and up
Flights and transport
Start CityRome
End CityRome

Travel Themes

  • Cultural

Destinations

Activities

  • Culture
  • Homestays & Cultural Immersion

Max Group Size

  • Max Group Size: 40

Itinerary

Travel Map

Day 1: Welcome to the Eternal City of Rome

Welcome to Rome, a glorious city filled with classic antiquities, medieval buildings, Renaissance palaces and baroque churches. Settle in before joining your Travel Director for a private visit to the Basilica of Saint Praxedes, welcomed by the Rector of the basilica....

Day 2: Umbria and on to Perugia

See the imposing Basilica of St. Peter in the Vatican City before crossing the Tiber into Ancient Rome and imagining the gladiatorial combats and sounds of roaring spectators as you visit the mighty Colosseum with your Local Expert. Journey north to the Umbrian villag...

Day 3: Perugia Sightseeing & Free Time Relaxed Start

This morning, during a MAKE TRAVEL MATTER® Experience, visit an artisanal workshop to meet Marta, recipient of a TreadRight Foundation grant, and her weavers. See how the fascinating art of loom-weaving textiles has been passed down through the generations and learn h...

Day 4: Assisi, in Search of St. Francis Relaxed Start

Journey to Assisi, one of Italy's most beautiful medieval hilltop towns, set high up in the mountains and enclosed by fortress walls. In the valley, see the famous Church of St. Mary of the Angels, much venerated as the place of St. Francis' death, then continue up Mo...

Day 5: Tuscany to Siena and San Gimignano

Follow the shores of Lake Trasimeno and continue to the narrow cobbled streets of Siena. Standing in the shell-shaped Campo, imagine the frenzied atmosphere of the biannual Palio horse race and see the Town Hall. Explore Siena with Insight Choice. Choose to visit the ...

Day 6: San Gimignano and Free Time Relaxed Start

Enjoy your day at leisure, taking in your Tuscan surroundings. Relax at your hotel or you could opt to join an Optional Experience to Pisa and Lucca.

Villasanpaolo, San Gimignano

Breakfast

Day 7: Florence and Tuscan Countryside Experience

The morning is devoted to the Renaissance city of Florence. A fascinating walking exploration with a Local Expert takes you to the marble-clad cathedral crowned by Brunelleschi's dome. See the baptistery with its beautiful Gates of Paradise and Giotto's splendid bell ...

Day 8: Country drive to Ancient Rome

Leave behind the tower topped town of San Gimignano. Enjoy rolling Tuscan hills as you journey south through the Italian countryside. This morning, delight in the medieval spa town of Bagno Vignoni, renowned for its mineral rich thermal baths and continue to the 'mode...

Day 9: Arrivederci Roma

Bid farewell to the glories of Italy.

Breakfast

Want a tailor-made trip instead?

Your trip, your way, planned by an expert:

  • You choose budget, destinations, activities, transport & lodging type
  • Expert designs the itinerary for you, and once approved, takes care of logistics
Design custom trip

Dates & Availability

Price From $3,350
Price per day$372
Last Updated: 3/14/2025
Departure Date
Finish Date
Base Price
Availability
29 Mar 2026
06 Apr 2026
$3,395
26 Apr 2026
04 May 2026
$3,425
24 May 2026
01 Jun 2026
$3,450
21 Jun 2026
29 Jun 2026
$3,450
05 Jul 2026
13 Jul 2026
$3,375
02 Aug 2026
10 Aug 2026
$3,350
30 Aug 2026
07 Sep 2026
$3,395
13 Sep 2026
21 Sep 2026
$3,475
27 Sep 2026
05 Oct 2026
$3,475

Check current availability, prices, specials & more.

The total tour cost includes the tour price (regular or promotional) and the compulsory local payment. The promotional price is subject to change. Check directly with the operator for the latest price offer. The tour operator requires you to pay only the tour price to purchase your travel. The compulsory local payment will be paid when you join the trip. All prices are based on double, twin or triple share occupancy. Solo passengers will be accommodated in a double, twin or triple room according to availability with a passenger(s) of the same gender. Single supplement only needs to be paid if the passenger does not want to share and requests their own room. Discounts can only be applied at the time of booking and cannot be added at a later date, regardless of any changes made to the original booking.

Prices may vary due to local taxes and trip seasonality. Click "Request Info" to inquire directly with the tour operator for the final trip price.

Travelstride Gift Card
One card, thousands of extraordinary trips
Gifts Card

Insight Vacations Reviews & Ratings

4.6/5  Excellent
Excellent
13,965
Great
3,013
Average
961
Disappointing
267
Terrible
221
Write a Review

Other Insight Vacations Reviews

M

Mark Jeansonne

Mar 2025

Written on

Highlights of Spain

The travel director Helder was FANTASTIC!

Write a Review

Tour Operator

About Travelstride

Find your perfect trip

An epic selection of pre-planned trips on every continent, for every style. Thousands of itineraries from over 1,000 trusted travel companies.

Save time

Use simple search and comparison tools to easily find the best trip. Don't sweat the logistics — travel providers plan for you.

Save money

Book directly with the operator. See inclusive packages for the best values, and get access to amazing deals.

Travel confidently

Read unbiased user reviews, pick the operator that suits your needs, and connect with them directly.

Logistics

Accommodation

  • NH Roma Centro, Rome
  • Sangallo Palace Hotel, Perugia
  • Villasanpaolo, San Gimignano
  • Hotel St. Martin, Rome
Travel Insurance
We strongly recommend purchasing travel insurance alongside your travel package to safeguard against unforeseen circumstances such as medical expenses, trip cancellations, and other contingencies. It offers you peace of mind and ensures you are prepared for unexpected events that may occur before or during your journey
Visa requirements
Visa requirements vary depending on your country of origin and your country of destination. It is your responsibility to familiarize yourself with the relevant requirements. For a handy tool that can help you quickly find the requirements, please visit this link .
Meals Included
  • 4 Dinner (D)
  • 8 Breakfast (B)
  • 1 Lunch (L)
Age Requirements
6 years and up
Additional Information
[object Object]
Trip ID
insightvacations-E822N26

Become a member

(it's free)
  • Save up to $700 per person
  • Access members-only specials
  • Personalize trip recommendations
Sign up and save
Top Tour Companies on Travelstride:
All 1,600+ companies >
Sign in to reveal savings up to $700 per person!