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sell8 Day Holiday Charms of Italy 2025

8 Days / 7 Nights   Starting at $3050 PP (Land Rate)

Embrace the holiday spirit with our special Christmas time tour, where you'll explore the timeless beauty of Italy decked out in festive splendor. Begin your journey in the heart of Rome, where the Eternal City transforms into a winter wonderland. Wander through traditional Christmas markets set against a backdrop of historic monuments, savoring seasonal treats and unique gifts.

Next, journey to Arezzo, a charming Tuscan town renowned for its vibrant Christmas market. Experience the warmth of local hospitality as you browse handcrafted ornaments, artisanal foods, and cozy holiday crafts. Enjoy the next 3 nights in Florence, the birthplace of the Renaissance.

The tour also includes a visit to Gubbio, a beautiful medieval town in Umbria, where you'll witness the breathtaking Gubbio Christmas Tree—a dazzling display of lights that adorns the slopes of Mount Ingino, creating a sparkling beacon visible from miles around. This awe-inspiring sight, coupled with the town's quaint streets and festive atmosphere, will surely leave you with cherished memories.

Join us for this unforgettable Christmas journey and immerse yourself in the magic of Italy during the most wonderful time of the year.

Itinerary

Day 1 - Depart USA - Rome

THURSDAY - Boarding your overnight flight, you’re off on the adventure of a lifetime.

Day 2 - Arrival in Rome - Dinner in Trastevere

FRIDAY - Benvenuti a Roma! Your Perillo representative will be at the airport to greet you. We are pleased to offer complimentary transfers from the Rome airport to your hotel at scheduled times.

You’ll have some time to settle into your hotel with the remainder of the day at leisure to discover this magical city.

This evening, you will meet your tour leader for a brief orientation and welcome drink followed by a delicious dinner in the characteristic district of Trastevere, one of the centers of the Roman nightlife. This lively area of tiny winding streets gives a taste of what one imagines Italy to be like, with cobblestone streets and music-filled trattorias on every corner.

Day 3 - Rome - Vatican Museum - Sistine Chapel - St. Peter's Basilica

SATURDAY - This morning, it’s a five-minute drive to another country—Vatican City! With your expert local guide, you’ll tour the Vatican Museums, a massive collection of ancient Greek sculptures, medieval tapestries, and Renaissance paintings.

Your visit begins in the Sistine Chapel, the room where the Pope is elected. Next visit St. Peter’s Basilica, by far the largest church in Christendom. We’ll see Michelangelo’s Pietà, sculpted when he was just 24, as well as Bernini’s seven-story bronze canopy located above the main altar.

(Please note that the visit of St. Peter’s Basilica is subject to availability based on the events planned by the Pope.)

The rest of the day is yours to enjoy as your please – venture out on your own and explore this magical city, do some Christmas shopping and be sure to grab an “Italian style hot chocolate”!

Day 4 - Rome - Colosseum & Piazza Navona Christmas market

SUNDAY - This morning, after breakfast, you will board the bus for a relaxing, panoramic driving tour of Imperial Rome including the Roman Forum, Circus Maximus, an arena for horse races during the Roman Empire, and the Synagogue.

After, you will have an upfront tour of the Colosseum, reliving the brutal entertainment of the gladiators and the lions, judged by the Emperor himself. *** please remember to bring your ID (not a photocopy) to enter the Colosseum.

This afternoon we’ll take you to Piazza Navona to have some time for shopping at the famous Christmas market, a highlight of the festive season in Rome. The market features a variety of stalls adorned with colorful lights and is filled with the sounds of Christmas carols, creating a magical ambiance that reflects the spirit of the season.. You can find traditional Christmas decorations, handcrafted gifts, and assortments of festive pastries and sweets. Hot wine, or vin brulé, is a popular choice for warming up on chilly days.

Afterwards, your bus will take you back to the hotel. The remainder of the afternoon evening is yours to enjoy as your please!

Day 5 - Rome – Gubbio – Dinner in Hotel - Christmas Tree

MONDAY - This morning you depart for Gubbio, one of the largest and best-preserved medieval towns in Italy and known to be the home of the "world's largest Christmas tree". The famous tree takes up an entire mountainside near the medieval Italian town of Gubbio and is 2,100 feet tall and more than 1,000 feet wide and is lit every year on the night of December 7. The Guinness Book of World Records has declared it the biggest Christmas tree display on the planet.

You’ll check in to your hotel and have the afternoon free to explore this beautiful town before enjoying dinner in your hotel.

After dinner, you’ll visit the famous Christmas tree.

Day 6 - Gubbio - Arezzo Christmas Market - Florence

TUESDAY - This morning, you’ll depart for Florence but on the way, you will stop in the medieval town of Arezzo. During this time of year, the Tuscan city of Arezzo becomes the “Citta del Natale”, the Christmas City. Arezzo is home to Italy’s largest Tyrolean style Christmas market, which showcases the best of Austrian and German holiday crafts and foods, with a unique Italian accent.  

 A visit to the market begins with a stroll up Corso Italia, one of Arezzo's main shopping streets, beautifully decorated for the holiday season. The shops are adorned with sparkling lights, colorful garlands, and festive window displays, creating a warm and inviting atmosphere.

Next, you’ll continue to Florence and check in to your hotel. You will have the remainder of the afternoon/evening to enjoy on your own.

Day 7 - Florence - City Tour with David and Santa Croce

WEDNESDAY - This morning, you’ll enjoy a walking tour of the historical center of this most famous of all Renaissance cities!

You’ll visit the majestic Duomo Complex built in 1296, Giotto’s Bell Tower and the Baptistery with its renowned Gates of Paradise doors.

You’ll follow the medieval streets to the most striking square in Florence, Piazza della Signoria.

“Breathtaking” is the only word to describe one’s first view of Michelangelo’s David. It’s truly amazing how Michelangelo transformed a lifeless rock into a man— all with just a hammer and a chisel!

Tonight, you will be on your own for dinner – ask for suggestions to find the perfect dinner spot in Florence.

Day 8 - Florence - Wine tasting early dinner in Tuscany - Florence

THURSDAY - This morning, you’ll have some free time to enjoy breakfast and do some sightseeing or shopping on your own.

This afternoon you’ll visit a typical Tuscan winery, and you’ll get to meet our dear friend, Pierluigi Giachi, the world’s most enchanting sommelier to learn about the grape, the nose, food pairings and, most importantly—which glass to use! Enjoy a wine tasting with these special wines along with an early dinner. Cin-Cin!

Day 9 - Flight Home - Florence - USA

FRIDAY - This morning, board your flight home, arriving in the USA the same day. Unless, of course, you have chosen to extend your stay! A warm “Grazie” for traveling with the Perillo family and please return soon.

If you are interested in arriving a day early or extending your time in Italy, please call 1800-431-1515 and a reservation agent will be happy to assist you with planning this!

Inclusions

  • Airport transfers at scheduled times
  • Full Breakfast Daily
  • 3 dinners
  • Olive oil & Wine Tasting
  • Wireless headsets to hear your tour guide clearly
  • Travel wallet, baggage tags and travel documents Included
  • Baggage handling throughout
  • Hotel taxes. City taxes, hotel services charges and all tips for hotel and restaurant personnel
  • Professional tour directors and licensed local guides
  • Complimentary Wi-Fi on our buses
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Dates & Rates

Depart - Return Per Person
in a Double
Solo
Traveler
Dec 11 - Dec 19 $3,050 $3,325

Triple room deduct $300 per person from the Double rate.
Kids under 12 sharing with 2 adults deduct $1000 from the Double Rate.

Hotel Info

Overnight Stays: Rome (3 Nights) Gubbio (1) Florence (3)
Also Visiting: Arezzo
Hotel Imperiale Rome ★ ★ ★ ★ ☆

Stroll the city’s main historical attractions– a haven of statues, fountains and centuries-old buildings– or retire to your suite where contemporary interiors are combined with original architectural features. The 4 star historic Hotel built in 1895, with its sublime International restaurant and a locally inspired Spa allows you to spend your afternoons in pure indulgence, just steps away from the cultural heart of Rome.

Rome

Park Hotel Ai Cappuccini ★ ★ ★ ★ ☆

The 4 star Park Hotel ai Cappuccini is a 17th century convent which has been cleverly restored.

This splendid building and the religious communities that have lived here since it was first built, belong to the history of Gubbio. The city of Gubbio is situated in the green heart of Umbria.  Its ancient stones and architecture are among the highest testimonies of the luminous and refined Medieval Age.

Secluded, yet near to the center of the city, today  the Park Hotel ai Cappuccini is an harmonious blend of an antique setting and modern comforts.

Umbria

Hotel Rivoli ★ ★ ★ ★ ☆

If you are searching for luxury accommodation in Florence city center, then the exclusive Rivoli Boutique Hotel will most certainly fulfill all expectations. Situated in the heart of Florence, this 15th century former Franciscan convent has been tastefully refurbished to provide comfortable, elegant accommodation whilst retaining the hotel's delightful periodic character and charm - from the lobby, with its unique opulent archways and pillars, classic ceilings and cross vaults to our lavishly frescoed lounges. 

Florence

Air Info

Airfares are unpredictable and impossible to estimate at time of brochure printing. Your airfare can range anywhere from approximately $1,000 to $1,900 depending on your departure city. Additionally, current departure tax and fuel surcharges are approximately $650 per person and are subject to change.

Your exact airfare will be advised within 3 business days of booking your tour. You are under no obligation to accept Perillo's air schedule and quote. However, payment for tickets issued by Perillo Tours is due with "final payment."

Airfares DO include your roundtrip airport transfer in Italy at scheduled times, provided you arrive and depart on scheduled tour dates. If you wish to arrive earlier or extend your stay, airport transfers are not included.

Book Early

We strongly recommend you BOOK EARLY as lowest airfares are on a first-come, first-serve basis. Plus, more availability on the most convenient flights and best seats.

Affordable Upgrades

When you purchase your Coach ticket through Perillo Tours, you can upgrade to "Premium Economy" on select flights starting at $550 each way. For ultimate comfort enjoy Business Class/First Class for a surcharge of as little as $4,000 per person.

Security Measures

The Transportation Security Administration requires all passengers to provide the exact name as it appears on the government-issued passport, passport number, expiration date, date of birth and gender when making airline reservations. This information will be requested at time of booking for all flight arrangements made through Perillo Tours.

CRITICALLY IMPORTANT: Name corrections are subject to change fees, so please have your passport in-hand when calling us for flight reservations.

Arranging your own air?

Roundtrip airport transfers are provided at scheduled times if you arrive and depart the same day as the tour begins and ends. Click here for the schedule.

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You can find out more about our Italy tours and talk with other passengers on our Perillo Tours Travelers Facebook page.

format_quote Testimonials

I have never enjoyed a vacation as much as this one to Hawaii. I loved the beauty and to be able to learn so much Hawaiian Traditions and Cousin Bert was the best throughout out our vacation. We are honored to have Bert our new cousin in Hawaii. Our days were action packed and so very fun. We will return. Aloha And Mahalo.

Mr. T.K.

My husband and I had the most fantastic tour of Rome and Tuscany through Perillo Tours. This tour took us to many of the most popular places to go and I would book it again in a heartbeat and tell everybody that I know what a great vacation Perillo tours did for us.

Mr. P.D.