8-Nights Country Roads of Umbria & Tuscany - Small Group from $3,975

Insight Vacations

OFFER ID 1517259

Country Roads Tuscany & Central Italy - Small Group
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.

Dining Summary

4 Dinner (D)
8 Breakfast (B)
1 Lunch (L)

Choice Highlights

Choose between two carefully selected activities
Siena: Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.
Siena: Visit the Cathedral with your Local Expert.

Additional Included Highlights

Personal radio headsets give you the freedom to wander during visits to famous highlights, without missing any of your Local Expert's fascinating commentary.
Hotel and restaurant tips are included - you'll never have to worry about how much to give, nor search for foreign currency. We also include all taxes and porterage charges at hotels.
We carry your bags for you and promptly deliver them to your hotel door.
From time to time, your Travel Director will delight you with an Insight Flourish, which is a local specialty representing the destination.
Stay connected with friends and family with our complimentary coach and hotel Wi-Fi (where available).
If your arrival and/or departure flights are as per the itinerary start and end dates, then transfers are available at scheduled times. If your flights are outside these times, or you have booked additional nights accommodation with Insight Vacations, you may purchase transfers or make your own way from/to the airport.

Authentic Dining

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 parlor of world champion gelato maestro, Sergio Dondoli for a taste of his finest frozen treats.
Tuscany: Nestled in the rolling hills surrounding Sam Gimignano and surrounded by its own vineyards, olive groves, saffron crop and orchards, is the homely Il Vecchio Maneggio. Admire the beautiful views as you enjoy a drink before sitting down to your Celebration Dinner - a delicious Farm-to-Table experience, with all the organic produce sourced from the surrounding farm.

Insight Choice

Siena: Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.
Siena: Visit the Cathedral with your Local Expert.

Insight Experiences

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.

Make Travel Matter

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 Development Goal 5: Gender Equality and UN Sustainable Development Goal 11: Sustainable Cities & Communities.

Top Rated Highlights

Rome: Visit the Colosseum, still echoing with the thronging crowds and ghostly cries of gladiatorial combat.
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 Santa Croce Basilica, the final resting place of great Florentines like Michelangelo.

Travel Director

"One thing I really love about showing guests about Italy is how art and beauty can be found around every corner of some of Italy's cities, which are real open air museums."
"One fun fact people don't usually know before they come to Italy is that the Italian alphabet only has 22 letters."
"I really love about showing guests the huge variety that Italy has to offer, from quaint countryside villages to cities full of stupendous art and architecture."

Well-being

Enjoy the comfort of Insight's luxurious, air-condi

8 nights from $3,975 per person

Itinerary

Click here for Full Itinerary Details

Itinerary Details

Insight Vacations: Country Roads Tuscany & Central Italy - Small Group

Day 1 - Welcome to the Eternal City of Rome
2025 marks a Jubilee Year, a momentous Roman Catholic event celebrated every 25 years, turning Rome into a center of celebration between December 24, 2024, and December 31, 2025. As festivities unfold, itineraries may be adjusted to ensure you make the most of your time as you visit the Eternal City. 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. End the day getting to know your fellow travelers over Roman specialties during dinner at a local restaurant.
Accommodations: NH Roma Centro, Rome
Meals: Dinner

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 village of Baschi. Immerse yourself in the flavors and culture of the region and learn about the secrets of Italian food culture as you join Giovanni and his dog Chris for a truffle hunting session. Afterwards, be entertained by Chef Lorenzo with a fun pasta demonstration and enjoy a delicious lunch accompanied by Orvieto Classico wine. Join a Local Expert in Perugia to navigate the underground labyrinth of little streets, alleys, and arches. Walk along Corso Vannucci, resplendent in pale-pink stone, passing the princely Priors' Palace, the cathedral, and the finely sculptured Great Fountain in the main square.
Accommodations: Sangallo Palace Hotel, Perugia
Meals: Breakfast, Lunch

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 how this ancient craft is being preserved. Then enjoy free time to explore the many delights of Umbria's capital city or join an optional experience to Cortona. For dinner, choose your ideal ambience and palate-pleasing menu from a hand-picked selection of Perugian restaurants for your Dine-Around Evening. Buon appetito!
Accommodations: Sangallo Palace Hotel, Perugia
Meals: Breakfast, Dinner

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 Mount Subasio to the upper town. Step inside the massive, 13th-century Basilica of St. Francis with your Local Expert to learn how Giotto masterfully painted frescoes that inspired a variety of Renaissance artists.
Accommodations: Sangallo Palace Hotel, Perugia
Meals: Breakfast

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 medieval Cathedral, or, alternatively, sample panforte, a traditional Tuscan dessert. Travel to the medieval town of San Gimignano where your Travel Director will show you the medieval skyscrapers, serpentine streets and hidden squares. The town is also home to world champion gelato maestro Sergio Dondoli. At his artisan ice cream parlor on Piazza della Cisterna, the silky smooth, frozen treats are beautifully displayed in a range of unique flavors for you to try. Your home for the next three nights is a delightful villa near this jewel of medieval architecture.
Accommodations: Villasanpaolo, San Gimignano
Meals: Breakfast, Dinner

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.
Accommodations: Villasanpaolo, San Gimignano
Meals: 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 tower. Walk on to Piazza della Signoria with its open-air gallery of Renaissance sculptures, followed by free time to shop for top-quality Florentine leather or gold. Toast to your travels during a delicious Farm-to-Table dinner at a local restaurant and enjoy tasting flavorsome dishes prepared with locally grown ingredients, home-made pastas, traditional Chianti wine, all sourced from the farm in the Tuscan region.
Accommodations: Villasanpaolo, San Gimignano
Meals: Breakfast, Dinner

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 'model' renaissance town of Pienza, famous for its delicious pecorino cheese, before making your way to Rome.
Accommodations: Hotel St. Martin, Rome
Meals: Breakfast

Day 9 - Arrivederci Roma
Bid farewell to the glories of Italy.
Meals: Breakfast

Featured Destinations

San Gimignano

Perugia

Rome

Sprawled across seven legendary hills, romantic and beautiful Rome was one
of the great centers of the ancient world. Although its beginning is shrouded
in legend and its development is full of intrigue and struggle, Rome has always
been and remains the Eternal City.

Rome enjoyed its greatest splendor during the 1st and 2nd centuries when art
flourished, monumental works of architecture were erected, and the mighty Roman
legions swept outward, conquering all of Italy. These victorious armies then
swept across the Mediterranean and beyond to conquer most of the known world.
With Rome's establishment as capital of the western world, a new ascent to glory
began.

Today's Rome, with its splendid churches, ancient monuments and palaces, spacious
parks, tree-lined boulevards, fountains, outdoor cafes and elegant shops, is
one of the world’s most attractive and exciting cities. Among the most famous
monuments is the Colosseum. As you walk its cool, dark passageways, imagine
the voices that once filled the arena as 50,000 spectators watched combats between
muscled gladiators and ferocious animals.

Stop to see the remains of the Forum, once the city's political and commercial
center. In later times, Rome's squares were enhanced with such imposing structures
as the Vittorio Emanuele Monument and grandiose fountains like the Fontana di
Trevi. Join the millions who stand in awe of Christendom’s most magnificent
church and admire the timeless masterpieces of Michelangelo's frescoes in the
Sistine Chapel.

Rome jars the senses and captures the soul. Grasp all you can during the short,
precious time you have available in the Eternal City. With so much to see and
do, a day or two will only allow you a sampling of the city's marvelous treasures.

Caution: As in many big cities and tourist destinations purse snatching
and pickpocketing is common. Valuable jewelry and excess cash are best left
in a safety deposit box in your hotel.

Shopping For most visitors shopping for beautiful Italian leather articles,
designer shoes, fashions for men and women, linens, knitwear, silk scarves and
ties is a favorite pastime. Except for tourist-oriented shops, the majority
of stores are closed on Sundays. Some of the department stores, such as Rinascente,
open in the late afternoon on Sundays.

Cuisine Rome's choice of restaurants is mindboggling as is the variety
of cuisine. Whether your meal is at a top-rated restaurant or a rustic trattoria,
you can be sure that you will enjoy your food, especially when accompanied by
wines from the hill towns surrounding Rome.

Other Sights Rome's attractions are endless, and depending on how much
time you have at your disposal a careful selection has to be made about what
to see. Be aware of horrendous traffic conditions and major construction work
all around the city in preparation of Jubilee 2000, the Holy Year. Some of the
sights not to be missed:

Piazza Venezia - This busy square is easily recognized by its imposing Vittorio
Emanuele II Monument. The white marble structure was inaugurated in 1911 as
a symbol of Italy’s unification.

The Forum - Once the civic heart of ancient Rome, today the remains include
a series of ruins, marble fragments, isolated columns and some worn arches.

Colosseum - No visit to Rome is complete without a stop at this awe-inspiring
theater, which is among the world’s most celebrated buildings. Here ancient
Rome flocked to see gladiatorial contests and numerous other spectacles.

Trevi Fountain - Take a stroll to Rome's famous fountain. A spectacular fantasy
of mythical sea creatures and cascades of splashing water, the fountain is one
of the city's foremost attractions. Legend has it that visitors must toss a
coin into the fountain to ensure their return to Rome.

St. Peter's Square - Part of Vatican City, this square created by Bernini
is considered one of the loveliest squares in the world. Twin Doric colonnades
topped with statues of various saints and martyrs flank either side of the square.
In the center stands an 84-foot obelisk, brought from Egypt in 37 A.D.

St. Peter's Basilica - At the head of the square stands Christendom's most
magnificent church, which was begun in 1452 on the site where St. Peter was
buried. Throughout the following 200 years, such Renaissance masters as Bramante,
Michelangelo, Raphael and Bernini worked on its design and created an unparalleled
masterpiece. Of special note are Michelangelo's Pieta and the bronze canopy
over the high altar by Bernini. The immense dome was designed by Michelangelo.

Vatican Museum - To see this museum's immense collection would take days.
As you enter, there are special posters that plot a choice of four color-coded
itineraries. They are repeated throughout the museum and are easy to follow.
It is a good idea to pickup a leaflet at the main entrance and concentrate on
exhibits of major interest. Of course, the Sistine Chapel is a must. Most likely
you may have to wait in line to enter.

Vacation Details

Valid Date Ranges

10/12/2025 - 10/20/2025

from $3,975 per person

* This departure has been designated a guaranteed departure by the operator, meaning that the minimum number of guests has been met, although still subject to weather and other conditions.

Prices Start At

from $3,975 per person

Length

8 Nights

Air City

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Vacation Rating

Deluxe

Remarks

Trip prices are per person, land only, based on double occupancy and reflect applicable discounts. Trip prices and discounts are subject to change. Airfare is additional. Tour prices, dates and itineraries are correct at the time of the website going live, however are subject to confirmation at the time of booking. Other restrictions may apply.

All fares are quoted in US Dollars.

OFFER ID

1517259

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