Thanksgiving in Sicily 2027

AT A GLANCE

DAY 1: TAORMINA-Grand Hotel San Pietro
DAY 2: SIRACUSA
DAY 3: MT. ETNA and TENUTA TASCANTE WINERY
DAY 4: PIAZZA ARMERINA (ROMAN VILLA)/AGRIGENTO-Hotel Villa Athena
DAY 5: VALLEY OF THE TEMPLES, AGRIGENTO/PALERMO-Hotel Villa Igiea
DAY 6: PALERMO & MONREALE
DAY 7: PALERMO and THANKSGIVING DINNER
DAY 8: MARSALA, SALT PANS and DONNAFUGATA WINERY
DAY 9: PALERMO

*All of our Travel Programs are Led by Dr. Rocky Ruggiero*

“To have seen Italy without having seen Sicily is not to have seen Italy at all, for Sicily is the clue to everything.” – Goethe

The Italian Island of Sicily is one of the most magical places on earth. Embraced by the Mediterranean, Tyrrhenian, and Ionian Seas, kissed by warm sunshine nearly year-round, home to three active volcanoes – the largest of which, “Her Majesty,” Mt. Etna, looms over the island like a sleeping giant – and a multi-colored landscape that includes forests, farmland, and arid fields, Sicily, it seems, was truly favored by the gods, both past and present. 

Why Visit Sicily over Thanksgiving?

  • Sicily is not very crowded in November, so you don’t have to deal with the overwhelming crowds of tourists that mob the island during peak season.
  • Airfare and hotels are significantly less expensive in November.
  • Very mild early-winter temperatures make it very pleasant to visit outdoor sites and walk the charming streets of Sicily.
  • It is the best culinary season of the year, with new wine, new olive oil, wild mushrooms, and wild boar!!!
  • And YES, WE DO TURKEY!!!
Tour Services
Hotel
Main Attractions
Guide
Sightseeing Tickets
Meals

Overview

Join us for a luxurious and customized experience in Sicily where participants will

  1. Explore the great artistic and architectural treasures of the area with Dr. Rocky
  2. Come up close and personal with the historical treasures of nine different Sicilian cities – Palermo, Monreale, Segesta, Erice, Agrigento, Piazza Armerina, Taormina, Mt. Etna, and Siracusa
  3. Taste the food and wine of Sicily – in hand-picked restaurants for group lunches and dinners, welcome meals and Thanksgiving dinner
  4. Learn about Sicily’s most celebrated wine and culinary treasures
  5. Visit Marsala and explore salt pans
  6. Experience an exhilarating Jeep tour of Mt. Etna – the tallest active volcano in Europe
  7. Travel between cities in private luxury minivans
  8. Sojourn at three different historic luxury five-star hotels in Palermo (Hotel Villa Igiea), Agrigento (Hotel Villa Athena), and Taormina (Grand Hotel San Pietro)
  9. Thanksgiving Dinner at the Hotel Villa Igiea
  10. And YES, WE DO TURKEY!!

Activity Level: Moderate

Walking tours and on-site visits may entail uneven terrain such as cobblestones and city hills, as well as challenging environments with stairs without handrails and/or the absence of elevators).

Itinerary

DAY 1: FRIDAY, NOVEMBER 19, 2027 – ARRIVAL IN TAORMINA


All day – Arrivals in Taormina

*Recommended Airport for arrival: CATANIA-FONTANAROSSA AIRPORT (CTA)

*Transportation from the airport to the Hotel can be arranged upon request

3:00 pm – Check-in at the Grand Hotel San Pietro
A finely restored early 20th-century villa, the Grand Hotel San Pietro is now home to an elegant 63-room boutique hotel where timeless charm meets contemporary style. In 2026, the Grand Hotel San Pietro unveiled a new phase of restyling. A refined renewal of its spaces that enhances the harmony between the villa’s historic character and its modern design. Suspended between sky and sea, the hotel overlooks Taormina with enchanting views of the Ionian Sea, framed by the energy of Mount Etna, the poetry of Isola Bella and the cobalt-blue charm of Grotta Azzurra.

5:30 pm Walking Tour of Taormina
The ancient theater of Taormina is the second largest ancient theater in Sicily after the Greek theater in Siracusa. As is customary for Greek theaters, it is carved into the stone slope of a natural hill and uses the backdrops of Mt. Etna and the Ionian Sea to create a jaw-droppingly beautiful panorama of natural beauty. Continue the walking tour through the town of Taormina, often called the “Pearl of the Mediterranean.” Set on Mt. Taurus and surrounded by endless magnificent views of both sea and mountains, Taormina offers Mediterranean beauty everywhere you look.

7:30 pm Group Welcome Dinner


DAY 2: SATURDAY, NOVEMBER 20, 2027 – SIRACUSA

9:00 am – Depart from the Hotel

10:45 am – Tour of Siracusa and Ortigia
Many believe Siracusa to be the most beautiful city in Sicily. The ancient city enjoys a millennial history and is counted amongst the largest metropolises of the ancient Greco-Roman world and equaled only by ancient Athens. Siracusa was the most important city of Magna Grecia (“Greater Greece”) and boasted a slew of ancient celebrities, including Archimedes. From ancient temples to theatres, Siracusa’s ancient glory is still very much present in the city.

12:30 pm – Lunch in a historic “Salumeria” located in Ortigia, tasting typical Sicilian products (charcuterie, cheeses and “caponata”)

2:00 pm – Visit to Santa Lucia al Sepolcro to view Caravaggio’s “Burial of St. Lucy”
While a fugitive on the run from the law, Caravaggio sought refuge in Sicily. Assisted by an old friend, Caravaggio was able to secure a commission for the high altarpiece of the Franciscan church of Santa Lucia al Sepolcro depicting the “Burial of St. Lucy.’ Caravaggio’s theatrical use of chiaroscuro combined with obsessive realism produced a hauntingly moving scene of the burial of Siracusa’s most important local saint.

4:00 pm – Depart for Grand Hotel San Pietro

 

DAY 3: SUNDAY, NOVEMBER 21, 2027 – MT. ETNA AND TENUTA TASCANTE WINERY

9:45 am – Depart for Mt. Etna

10:30 am – Etna Jeep Tour
One of the most exhilarating experiences that you can have in Sicily! Explore Mt. Etna – the tallest active volcano in Europe – with a nature guide in a 4×4 jeep. Spectacular scenery, postcard views, brilliant colors, unspoiled nature and more than 400 volcanic craters help create one of the most sensory-stimulating environments that you can find!

1:00 pm – Lunch and Wine Tasting at Tenuta Tascante Winery
The Tenuta Tascante is a vineyard located on Europe’s tallest active volcano and is a unique expression of the volcano’s history through wine. Taste local wines such as Buonora, Tefra and Ghiaia Nera accompanied by local delicacies from Etna, such as charcuterie and cheese. Then enjoy a lunch showcasing the best local foods and traditions, all the while enjoying one of the most dramatic views of Mt. Etna Park and great Sicilian wine.

5:30 pm – Return to Hotel

 

DAY 4: MONDAY, NOVEMBER 22, 2027 – PIAZZA ARMERINA (ROMAN VILLA)/AGRIGENTO

8:30 am – Check out of Grand Hotel San Pietro

9:00 am – Depart for Villa Casale. Piazza Armerina
The Villa Romana del Casale is a large suburban ancient Roman villa located about 2 miles outside of the Sicilian town of Piazza Armerina. The once-luxurious villa contains one of the largest, richest, and arguably best-preserved collections of ancient Roman mosaics in the world dating back to the 4th century CE and covering nearly an acre of ground.

1:00 pm – Lunch in a nearby traditional Sicilian trattoria

2:00 pm – Travel to Agrigento

4:00 pm – Check in to the Hotel Villa Athena
The Hotel Villa Athena is the only 5-star hotel nestled in the heart of the Archaeological Park of the Valley of the Temples, a UNESCO World Heritage Site, with direct and exclusive access to the park. A princely residence of the late 18th century, it is itself a guardian of the classical vestiges that can be discovered at every corner, like a treasure chest. Set in front of the Temple of Concordia, a true masterpiece of Doric architecture from the 5th century BCE, from which it is only 200m away, Villa Athena is a resort where nature, art, history, and beauty have coexisted for 2,500 years.

7:00 pm – Group Dinner in the shadow of the beautifully illuminated Greek Temples

 

DAY 5: TUESDAY, NOVEMBER 23, 2027 – VALLEY OF THE TEMPLES, AGRIGENTO/PALERMO

10:00 am – Visit Valley of the Temples in Agrigento
The Valley of the Temples in Agrigento is undoubtedly the most important archaeological site in Sicily, and one of the most important in the entire world. Home to some of the world’s best-preserved ancient Greek temples, the archaeological park is simply a magical place of awe and wonder.

12:30 pm – Exclusive picnic-lunch inside the archeological park at the Diodoros Garden
Typical, farm-to-table organic food will be prepared according to “le ricette di nonna” (grandma’s recipes.)

2:30 pm – Depart for Palermo

5:30 pm – Check in at the Hotel Villa Igiea
Discover history, majesty, and serenity at the Hotel Villa Igiea – a turn-of-the-19th-and 20th century palazzo at the perimeter of lively Palermo, the foot of Mount Pellegrino and the Gulf of Palermo. A long-loved seaside-meets-city sanctuary for royalty, dignitaries, and Hollywood luminaries alike who have traced their steps through tiered villa gardens that sweep down to the port and out to the Tyrrhenian Sea.

6:00 pm – Free Time to enjoy the Hotel

 

DAY 6: WEDNESDAY, NOVEMBER 24, 2027 – PALERMO & MONREALE

10:00 am Walking Tour of the Historical City Center of Palermo and Visit to Palatine Chapel
With its Baroque architecture, majestic boulevards, fascinating Arab-Norman quarter, 13th -century Norman cathedral, Palatine chapel, and rich offering of stores and markets, Palermo boasts one of the most multi-cultured and colorful city centers in Europe. The Palatine Chapel, a jewel ensconced in the heart of the Royal Palace of Palermo, stands as an architectural marvel embodying the intricate confluence of Norman, Byzantine, and Islamic influences.


12:00 pm – Lunch at Palazzo Valentino

3:30 pm Return to the Hotel and Free Time

6:30 pm Exclusive, after-hours visit to the Cathedral and Cloister of Monreale
Monreale Cathedral and its adjoining cloister constitute one of the most unique and beautiful complexes in all the world. While reflecting both Norman and Arab architectural influences, the 12th century cathedral is one of the world’s most important extant examples of Norman architecture. The interior of the cathedral is sumptuously decorated with a breathtaking array of Byzantine-style mosaics, while the extremely well-preserved Benedictine cloister located to the south of the cathedral transports you back in time to medieval monastic life.

8:00 pm Group Dinner in Monreale

DAY 7: THURSDAY, NOVEMBER 25, 2027 – PALERMO & THANKSGIVING DINNER

11:00 am Visit and Private Show at the Historic “Teatro dei Pupi” puppet theater
Declared a “Masterpiece of the Oral and Intangible Heritage of Humanity” by UNESCO in 2001, the centuries-old Sicilian puppet tradition reflects the folk heritage of Sicilian life. Especially popular amongst Sicily’s lower social classes, it was a means of diversion from their daily hardships.

7:30 pm – Thanksgiving Dinner at the Hotel Villa Igiea
Exclusive Private Thanksgiving dinner with all the trimmings at the Hotel Villa Igiea!

 

DAY 8: FRIDAY, NOVEMBER 26, 2027 – MARSALA, SALT PANS and DONNAFUGATA WINERY

9:00 am – Visit to Marsala
On the farthest tip of Sicily lies Marsala, with its hues of yellow tufa, blue sea, red sunset, white salt, and green vineyards. From its Phoenician origins, influenced by Greek, Roman, Arab, Norman, Swabian, Angevin, and Spanish cultures, Marsala is rich in artistic beauty and possesses unique, irreplaceable content.

It is a city of wine, flowers, salt, strawberries, and ceramics. Here, the colors, flavors, and scents of Sicily meet in a territory that continues to cultivate typical Mediterranean hospitality amidst the narrow streets of the historical center and the villages of the hinterland. The value of hospitality is in the DNA of the people of Marsala.

10:00 am – Visit at Ettore Infersa Salt Pans
The allure of the salt pans has expanded, more and more, thanks to the unusual beauty of these real reserves, as well as an out-of-time and out-of-ordinary experiential plan!

12:00 pm – Lunch and wine tasting at a local winery
The ancient Donnafugata family cellars, built in 1851 in Marsala, are a living example of industrial archeology. Here they have been welcoming visitors for over twenty years, guiding them to discover the Donnafugata’s history and wines.

Donnafugata wines express authentic and sustainable Sicilian winemaking. Taking care of the land means paying attention to the quality of production and promoting a relationship of mutual benefit between wine and plant. Therefore, the creation of horticultural and other gardens on the estates, the integration of agricultural and natural environments, and the protection of natural areas are acts that nurture agriculture and, above all, culture, enrich the landscape with biodiversity, and enhance its beauty.

5:00 pm – Return to Palermo and Free Evening

 

DAY 9: SATURDAY, NOVEMBER 27, 2027 – ARRIVEDERCI SICILY!

Morning – Check out of the Hotel Villa Igiea and (sadly) the end of the program

All day – Departures

*Recommended Airport for departures: PALERMO AIRPORT FALCONE-BORSELLINO (PMO)

*Transportation from the hotel to the airport can be arranged upon request

Lodgings

All participants will be staying at three different historic luxury five-star hotels: 

TAORMINA:

Grand Hotel San Pietro – 5 Star

Via Luigi Pirandello, 50 98039 Taormina Italy

+39 0942 620 711 

https://www.sanpietrotaormina.com


AGRIGENTO:

Hotel Villa Athena – 5 Star

Via Passeggiata Archeologica, 33 92100 Agrigento Italy

+39 0922 596288

https://www.hotelvillaathena.it/en/  


PALERMO
:

Hotel Villa Igiea – 5 Star

Via Belmonte, 43
90142 Palermo Italy

+39 091 631 2111

https://www.roccofortehotels.com/hotels-and-resorts/villa-igiea/   

ACCOMMODATIONS:

  • Participants will enjoy a Deluxe Room
  • Breakfast is included
  • *For hotel stay extensions, room upgrades, and other lodging requests, please contact us directly at info@rockyruggiero.com with details.

Transportation

All transportation will be provided by private luxury vans with drivers.  

Dates

NOVEMBER 19 – 27, 2027 

Includes:
–        8-night accommodations in Superior, Deluxe and Premium rooms in all hotels (breakfast included)

–        All lectures with Dr. Rocky

–        All admissions

–        All group meals

–        All ground transportation between November 19 and 27, 2027

–        Welcome dinner, and Thanksgiving dinner

Not included:
Airfare to Italy and transportation to Palermo/from Siracusa.

History

Sicily’s role in Western history began when Phoenician settlements were established on the island towards the beginning of the 1st millennium BCE. Then came the Greeks who colonized most of Sicily’s shores. Then Carthage took control of most of the western half of the island before the Romans wrestled it away from them in the two Punic wars. With the fall of the empire, a parade of foreign rule began. Over the centuries, Vandal, Ostrogoth, Byzantine, Arab, Norman, Spanish and, finally, Italian rule with Garibaldi and his 1,000 Red Shirts storming the island in 1860, have left their mark on all aspects of Sicilian culture. And so much of that extraordinarily rich history is still visible today in the Greek temples, Norman monasteries, medieval mosques, Byzantine mosaics, and Baroque churches that you find just about everywhere you look! You can also still hear the influence of Sicily’s multicultural past in the local dialect; taste it in traditional Sicilian food and wine; smell it at the lively local markets; and literally feel Sicily’s role as a crossroad of cultures by simply being there.

Terms & Conditions

Payment:
A deposit of 30% of the program fee is required to reserve a space on a program. All payments may be made by credit card or check. Deposits are applied to final payment of the program price.

A second deposit of 30% of the program fee is required 6 months after the first payment, unless otherwise noted.

The balance is due 60 days prior to the first day of the program, unless otherwise noted. If full payment is not received by the final payment due date, your place cannot be guaranteed on the program.

Wait List:
If the program of your choice is fully subscribed, you may choose to be placed on a waitlist by contacting us at info@rockyruggiero.com or by phone. Individuals on the wait list will be contacted if space becomes available and can inquire about program status by contacting us. If you choose to withdraw from a wait list, please notify us.

Cancellation and Refund Policy:
Following enrollment, a participant’s withdrawal from the program for any reason, including, but not limited to, illness, injury, family engagements, work-related issues, geopolitical concerns, or airline delays and/or cancellations, etc., will be deemed a cancellation. Please understand that there will be no exceptions to our cancellation policy. Per person cancellation fees are based on date of written notice to Rocky Ruggiero. We will refund on the following basis:
– Cancellations within 10 days of booking: Full Refund
– Cancellations after 10 days of booking: Full Deposit Retained
– Cancellations made within final payment date, 60 days before departure: No Refund
– Cancellation by Rocky Ruggiero: Full Refund or Credit
– Non transferable to other travel programs, tours and online and in-person events.

Travel Protection Plan:
Purchase Travel Insurance to Protect your Vacation

Special Travel Arrangements:
Participants may wish to extend their stay in the group hotel either before or after the tour. We will work with you on these arrangements, dependent upon space availability. Should you decide not to participate in certain parts of the program, no refunds will be made for those unused parts of the program.

READ CAREFULLY: RESPONSIBILITY STATEMENT AND LIABILITY DISCLAIMER
Neither Rocky Ruggiero nor faculty shall be held liable for personal injury, death, property damage or accident, delay or irregularity arising out of any act or omission of these suppliers. Rocky Ruggiero and other faculty reserve the right, without penalty, to make changes in the published itinerary whenever, in their judgment, conditions warrant, or if they deem it necessary for the comfort, convenience, or safety of tour participants.

Rocky Ruggiero and designated faculty also reserve the right, without penalty, to withdraw the program announced, to decline to accept any person as a participant in a program, or to require any participant to withdraw from the program at any time (including, but not limited for inappropriate, or offensive behavior) when such action is determined by program staff to be in the best interests of the health, safety or general welfare of the program group or the individual participant. Dates, schedules, tour details, and costs, although provided in good faith based on information available at the time of publication on the website, are subject to change and revision.

AS A CONDITION OF ACCEPTANCE OF ANY APPLICATION, EACH APPLICANT MUST AGREE TO THE STATEMENT SET FORTH BELOW:
The undersigned has read carefully the Responsibility Statement and Liability Disclaimer set forth above, the schedule of activities for this program, as well as the terms and conditions of application and participation as set forth in the program materials and recognizes and accepts any risk associated with the program and the conditions, including the refund policy, set forth in the program materials. The undersigned further acknowledges that there are many risks and uncertainties inherent in any travel program, including but not limited to the hazards of various modes of transportation, forces of nature, acts or omissions of foreign governments, terrorism, war or insurrection, theft, illness, and damage to person or property due to the negligent acts or omissions of program staff or others. In consideration of, and as part payment for, the right to participate in the program, the undersigned, on behalf of himself, his dependents, heirs, executors, administrators and assigns, agrees to release Rocky Ruggiero, its Regents, officers, employees, representatives or agents, the United States, from liability for personal injury, death, property damage or loss suffered by any person in connection with this tour, even if caused by the negligence (but not the reckless, willful, or fraudulent conduct) of program staff or other related persons or entities. In addition, by registering for this program, the applicant certifies that he or she is mentally and physically capable of full participation in this tour. By registering for a “Rocky Ruggiero Program in Italy”, the participant agrees to the Responsibility Statement and Liability Disclaimer and the Terms and Conditions herein.

Duration
9 Days
Tour Type
Italy Programs
Group Size
Average 15
Location
Date
November 19 - 27, 2027
  • November 19, 2027
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