Sicily (Fall 2025)

October 12, 2025 - October 25, 2025
12 Days
Starting from $3,491.00 per person
Private 4⭐&5⭐ Hotels
Accommodation
Up to 28 People
Small Group Sizes
Blue and Sunny
Weather
calendar
October 12, 2025 - October 25, 2025
Dates
Italy
Sicily (Fall 2025)
  • 10 Days
  • 4-Star Accommodation
  • Full Service Tours
  • 20 Meals Included
  • Palermo
  • Agrigento
  • Taormina
  • & More!
Map

Sicily (Fall 2025)


Tour Package Selection:


Paying for how many people:

Dont forget Travel Insurance!
Travel insurance will protect your purchase.
Time Left To Book:
6 Months, 12 Days
03:45:25

Your adventure begins in Cefalù, a charming Sicilian resort town. Explore Palermo, Erice, Trapani, Marsala, and Agrigento's Valley of the Temples. Enjoy relaxation and shopping in Taormina, set against the stunning backdrop of Mount Etna. The journey continues to Sorrento, with excursions to Positano and the Isle of Capri!

  • Spend 10 days in Sicily plus 4 days/3 nights in Sorrento

  • Private luxury coach transportation for the duration of the tour

  • Four Star hotel accommodations

  • Includes breakfast each morning, seven full dinners, and three lunches

  • Includes scheduled tours, tour guides, attractions, and admissions

  • Optional Experiences will be available at an additional cost

  • View Full Brochure for more details

Small Group Tour- No more than 28 Passengers

Book as low as $3491 

*Early Booking Discount is a limited-time off

Itinerary at a Glance

Day
1
Arrive in Palermo, Free time in Cefalù
Oct 12, 2025
  • Arrive at Palermo airport and transfer to Cefalù.
  • Welcome reception at hotel, featuring traditional appetizers and wine tasting.
  • Dinner at the hotel restaurant, showcasing delicious local cuisine and regional wines.
Day
2
Tour of Palermo
Oct 13, 2025
  • Tour of Palermo's ancient buildings, cathedrals, and gardens, including the Monreale Cathedral.
  • After the tour, prepare yourself for a big surprise.
  • Enjoy some free time back in Cefalù.
  • Dinner at your leisure.
Day
3
Erice, Trapani, Marsala
Oct 14, 2025
  • Travel along the northern coastline of the Tyrrhenian Sea to Trapani.
  • Stop at the mountaintop town of Erice and enjoy its views.
  • Arrive in Trapani, known for its salt flats and the beautiful Cathedral of San Lorenzo.
  • Arrive in Marsala to the Donna Franca.
  • Tour of the winery, and taste the region's most famous wines during dinner at the hotel's renowned restaurant.
Day
4
Segesta, Marsala
Oct 15, 2025
  • Visit Segesta, one of the most well-preserved Greek Sicilian temples.
  • Return to the Donna Franca and take tour of wine cellar.
  • Taste some appetizers and some of their specialty wines.
  • Enjoy a cooking class, followed by dinner featuring some of the foods that you prepared earlier.
Day
5
Agrigento, Valley of the Temples
Oct 16, 2025
  • Travel from Marsala to Agrigento, located on the southern coast of Sicily on the Mediterranean Sea.
  • Tour the Valley of the Temples with a local expert.
  • Enjoy dinner with wine back at the hotel.
Day
6
Caltagirone, Taormina
Oct 17, 2025
  • Head to eastern shore of Sicily and seaside town of Taormina.
  • Stop in Caltagirone, noted for its Baroque style ceramics.
  • Visit the private home of the nobel family, Pace Gravina.
  • Buffet lunch, with Giacomo, the owner, in the ball room.
  • On to our luxury seaside resort hotel, on the beach in Taormina.
Day
7
Tour of Taormina, Greek-Roman Theater
Oct 18, 2025
  • After breakfast, take the funicular to the village of Taormina.
  • Enjoy a guided tour of the area, including the Greek Roman Amphitheater
  • Explore all of the colorful streets and shops overlooking the Mediterranean east coast.
  • Dinner at your leisure.
Day
8
Mt. Etna, Zafferana
Oct 19, 2025
  • Enjoy breakfast, before visiting Mt. Etna
  • Stop in the town of Zafferana and visit a local rosticceria to learn how to make the famous arancini rice balls.
  • Indulge in some exquisite cannoli, along with other local foods and wines.
  • Return to our seaside hotel in Taormina and have a relaxing evening.
Day
9
Free day, Optional excursion to Siracusa
Oct 20, 2025
  • Free time by the pool and beach or explore and shop Taormina.
  • Enjoy dinner with wine prepared by a very famous Sicilian chef, Cristian Foti.
  • Local singers with transform your night into a festive party.
  • Optional Experience: An optional trip to Siracusa will be offered by your tour leader. This all-day experience will introduce and enlighten you to the most multi-cultural city in Sicily.
Day
10
Straits of Messina, Calabria, Sorrento
Oct 21, 2025
  • Depart Sicily and make way to Sorrento.
  • Take a ferry across Straits of Messina to the mainland of Italy.
  • Make stop in the region of Calabria for lunch.
  • Arrive in hotel in Sorrento, overlooking the Gulf of Naples.
  • Enjoy dinner with music, dancing and wine.
Day
11
Isle of Capri, Sorrento
Oct 22, 2025
  • Transfer by boat to Capri.
  • Explore, shop and take in the views.
  • Wander the streets of Sorrento.
Day
12
Positano, Sorrento
Oct 23, 2025
  • Head to Amalfi Coast.
  • Explore Positano, shop and take in the views.
  • Enjoy your “ultima cena” (last dinner) in Sorrento, with food and music.
Day
13
Return Departure
Oct 24, 2025
  • Say “arrivederci” to Sicily and Sorrento.
  • After breakfast, transfer from the hotel to the Naples airport for your onward journey.

What's it like

Your adventure begins in Cefalù to Palermo, Erice, Trapani, Marsala, and Agrigento's Valley of the Temples, Taormina. The journey continues to Sorrento, Positano and the Isle of Capri! Your adventure begins in Cefalù to Palermo, Erice, Trapani, Marsala, and Agrigento's Valley of the Temples, Taormina. The journey continues to Sorrento, Positano and the Isle of Capri! Your adventure begins in Cefalù to Palermo, Erice, Trapani, Marsala, and Agrigento's Valley of the Temples, Taormina. The journey continues to Sorrento, Positano and the Isle of Capri!
Why Travel with us

Tour Itinerary

Day
1
Arrive in Palermo, Free time in Cefalù
Oct 12, 2025

Highlight of the day:Day 1 Sicily

Upon arrival at Palermo airport, you will be greeted by your Wherever Tours tour leader. A private transfer from the airport to the resort hotel in Cefalù will be provided for all. After checking into your hotel, take some time to unwind and enjoy the hotel's beautiful pool, stroll down to the beach, or simply relax in your room. A welcome reception will be held, featuring traditional appetizers and wine tasting. In the evening, you will be treated to a dinner at the hotel restaurant, showcasing delicious local cuisine and regional wines. *Check with Wherever Tours for arrival guidelines if you are booking your own flights.

Dinner

La Torre Hotel
Day
2
Tour of Palermo
Oct 13, 2025

Highlight of the day:Day 2 Sicily

This morning, take a tour of Palermo, the capital of Sicily, rich with ancient buildings, cathedrals, and gardens. Palermo has many hidden treasures such as the impressive Monreale Cathedral, an example of Norman architectural style which contains over two tons of gold mosaics. After the tour, prepare yourself for a big surprise. This afternoon, enjoy some free time back in Cefalù. Dinner is at your leisure.

Breakfast, Lunch

La Torre Hotel
Day
3
Erice, Trapani, Marsala
Oct 14, 2025

Highlight of the day:Day 3 Sicily

After breakfast, travel by luxury coach along the magnificent northern coastline of the Tyrrhenian Sea to Trapani. On the way, we'll stop in the mountaintop town of Erice with its breathtaking views. In the afternoon arrive in Trapani, known for its salt flats and the beautiful Cathedral of San Lorenzo. Later, arrive in Marsala to the Donna Franca, a perfectly preserved and restored baglio from the 19th century. Tonight take a tour of the winery, and taste the region's most famous wines during dinner at the hotel's renowned restaurant.

Breakfast, Dinner

Baglio Donna Franca
Day
4
Segesta, Marsala
Oct 15, 2025

Highlight of the day:Day 4 Sicily

Today visit Segesta, one of the most well-preserved Greek Sicilian temples. After returning to the Donna Franca, take a tour of their popular wine cellar. Taste some appetizers and some of their specialty wines. Then, enjoy a cooking class, followed by dinner featuring some of the foods that you prepared earlier.

Breakfast, Dinner

Baglio Donna Franca
Day
5
Agrigento, Valley of the Temples
Oct 16, 2025

Highlight of the day:Day 5 Sicily

This morning, travel from Marsala to Agrigento, located on the southern coast of Sicily on the Mediterranean Sea. A local expert will highlight the important ancient treasures on a tour of the Valley of the Temples, dating back to the fifth century BC. This archeological site was added to the UNESCO World Heritage List in 1997. Back at the hotel, enjoy a tasty dinner with wine.

Breakfast, Dinner

Baglio Della Luna
Day
6
Caltagirone, Taormina
Oct 17, 2025

Highlight of the day:Day 6 Sicily

Today, head to the eastern shore of Sicily and the picturesque seaside town of Taormina. Along the way, we stop in Caltagirone, noted for its Baroque style ceramics. We visit the private home of the nobel family, Pace Gravina. Giacomo, the owner, will show us his beautiful palace and guide us through the incredible history of Sicilian nobility. Then, he will offer us a buffet lunch in the ball room, another unique experience. Then it's on to our luxury seaside resort hotel, on the beach in Taormina, where you spend the next four nights.

Breakfast, Lunch

Panoramic Hotel
Day
7
Tour of Taormina, Greek-Roman Theater
Oct 18, 2025

Highlight of the day:Day 7 Sicily

After breakfast, take the funicular to the village of Taormina. After a guided tour of the area, including the Greek Roman Amphitheater, there will be plenty of time to explore all of the colorful streets and shops overlooking the Mediterranean east coast. This evening's dinner is at leisure.

Breakfast

Panoramic Hotel
Day
8
Mt. Etna, Zafferana
Oct 19, 2025

Highlight of the day:Day 8 Sicily

Eat a good breakfast this morning, because today we visit Mt. Etna, the tallest active volcano in Europe. Stop in the town of Zafferana and visit a local rosticceria to learn how to make the famous arancini rice balls. Indulge in some exquisite cannoli, along with other local foods and wines. This afternoon, return to our breathtaking seaside hotel in Taormina and have a relaxing evening.

Breakfast

Panoramic Hotel
Day
9
Free day, Optional excursion to Siracusa
Oct 20, 2025

Highlight of the day:Day 9 Sicily

Today, take some free time to lay on the beach or by the pool, or explore and shop Taormina on your own. Tonight, enjoy a dinner prepared by a very famous Sicilian chef, Cristian Foti. Plenty of wine and local singers will transform this night into a festive party. Optional Experience: An optional trip to Siracusa will be offered by your tour leader. This all-day experience will introduce and enlighten you to the most multi-cultural city in Sicily.

Breakfast

Panoramic Hotel
Day
10
Straits of Messina, Calabria, Sorrento
Oct 21, 2025

After breakfast, we depart Sicily and make our way to Sorrento. We'll take a ferry boat cruise across Straits of Messina to the mainland of Italy. Then we'll make a stop in the region of Calabria, in Southern Italy, for a relaxing lunch stop. Later in the afternoon, arrive in the hotel in Sorrento, overlooking the Gulf of Naples. Enjoy a nice dinner with music, dancing and wine.

Breakfast, Dinner

Villa Giovanna
Day
11
Isle of Capri, Sorrento
Oct 22, 2025

Today, transfer by boat to the famous and beautiful island of Capri. A Wherever Tours representative at the hotel is available to offer any suggestions prior to your transfer so you can make the most out of your day. This tiny island, which was once the playground of the ancient emperors, will leave you breathless due to it’s limitless charm and historical sights. Take some time to shop and explore, and most of all, enjoy the spectacular views from above. Upon your return, take some time to wander the streets of Sorrento before retiring back to the hotel.

Breakfast

Villa Giovanna
Day
12
Positano, Sorrento
Oct 23, 2025

This morning, head out to the Amalfi Coast, a UNESCO World Heritage Site. Have cameras ready for a spectacular view of Positano where there will be free time to shop and explore this beautiful seaside town, featured in many famous movies and magazines. Later, enjoy your “ultima cena” (last dinner) in Sorrento. Great food, music, and song and dance will complete this unforgettable stay in Sorrento, creating memories that will last a lifetime.

Breakfast, Dinner

Villa Giovanna
Day
13
Return Departure
Oct 24, 2025

Sadly we must say “arrivederci” to Sicily and Sorrento. After breakfast, transfer from the hotel to the Naples airport for your onward journey. You might even consider staying a couple more nights in Sorrento before heading back home. Just let us know.

Breakfast

Villa Giovanna

⭐⭐⭐⭐⭐ Star Accommodation

Perched on a cliff overlooking the Tyrrhenian Sea, featuring soundproof windows, bright and airy rooms come with free Wi-Fi, satellite TV and minibars. Amenities include a lounge/bar, and an elegant Sicilian restaurant with vaulted ceilings and terrace dining with sea views, along with an outdoor pool and a sundeck overlooking the water.

⭐⭐⭐⭐⭐ Star Accommodation

Baglio Donnafranca Wine Resort is surrounded by vineyards in the Marsala countryside. It offers an outdoor pool and rooms with Mediterranean-Sea views and free WiFi. It's gardens and terrace offer panoramic views and are ideal to relax.

⭐⭐⭐⭐⭐ Star Accommodation

With views of the Valley of the Temples, this upscale hotel in a 13th-century complex with a watchtower is 4 km from Casa Natale di Luigi Pirandello, birthplace of the author, and 8 km from the ancient Chiesa Santa Maria Dei Greci. Elegant rooms feature antique decor, vibrant tones and tile floors, and provide free Wi-Fi, TVs and minibars.

⭐⭐⭐⭐⭐ Star Accommodation

Overlooking a sandy beach on the Mediterranean Sea, this understated hotel is 5 km from Corvaja Palace, and 6 km from both the Ancient Theater of Taormina and the Duomo di Taormina.

⭐⭐⭐⭐⭐ Star Accommodation

Villa Giovanna is set outside the city centre of Sorrento. It offers free Wi-Fi in the lobby, free parking, and a small outdoor swimming pool. All rooms are en suite and include air conditioning, satellite TV, and a minibar. Some have a spa bath, and some offer a balcony.

What is Included?

  • All ground transportation and airport transfers while on the scheduled tour (excludes domestic transfers)
  • 12 nights of hotel accommodations
  • Porterage at the hotels
  • 12 days of touring with English speaking guides
  • All entrance fees as specified and included on the itinerary
  • Many included meals (Breakfasts, Lunches, & Dinners)
  • Atleast One glass of wine with dinners
  • Estimated round trip group airfare (if selected)
    * additional purchase required

What is Not Included?

  • Increases in adjusted airfare prior to ticketing
  • Visas, passports, airport taxes, border taxes, etc.
  • Gratuities for guides and drivers
  • Beverages other than specified
  • Meals other than included dinners and breakfasts
  • Optional trip cancellation insurance
  • Optional tours or activities not included on itinerary
  • All expenses of a personal nature
  • Any immunizations and testing that may be required
  • Domestic transfers in the USA

At Wherever Tours, we aim to make your European adventure as enjoyable and effortless as possible. This section provides answers to commonly asked questions about traveling with us. Please read this information carefully—it will help you prepare for your trip with confidence.

Is it for me?

Wherever Tours European trips are designed for travelers who appreciate the finer things in life. Guests will enjoy stays at 4 and 5-star accommodations, dine on carefully curated meals, and travel comfortably in chartered buses. With no strenuous hikes or rugged terrain, these tours are perfect for those seeking a leisurely and elegant travel experience.

Pre-Departure Briefing

A pre-departure briefing will be held via video call or in person (based on your preference) before your trip begins. This session typically lasts 30 to 45 minutes and provides important details about your itinerary, accommodations, and what to expect during your tour with Wherever Tours. If you are unable to attend, please contact us to reschedule.

Final Payment

Any remaining balance for your Wherever Tours trip must be settled at least 30 days before departure. We accept payments via credit/debit card, bank transfer, or online payment platforms. For your convenience, no additional service charges will be applied. If you have any concerns about your payment, please contact our team.

Luggage and Packing

We recommend packing light, as all your luggage will travel with you in the chartered bus. Each guest is allowed one large suitcase and one carry-on. Essentials such as comfortable walking shoes, a light jacket, and any required medications are highly recommended. For a detailed packing list, please refer to the pre-departure guide provided by Wherever Tours after booking.

Can I store my luggage?

Yes! If you plan to extend your travels in Europe or need to store extra luggage during the tour, Wherever Tours can assist with storage options through our partner hotels or secure facilities. Please coordinate this with us in advance.

Pick-up and Drop-off

All Wherever Tours trips include pick-up and drop-off services at major city centers or designated hotels. Specific pick-up times and locations will be confirmed prior to your tour. Please ensure your accommodation is accessible for our chartered buses to avoid delays.

Group Tours

Our group tours attract travelers from diverse backgrounds, so expect varying interests and paces. While the itinerary is designed for maximum enjoyment by all, small adjustments may be made by the guide based on group preferences and feedback. Wherever Tours strives to ensure every traveler has a wonderful experience.

Lost or Forgotten Items

Please double-check your belongings when boarding and exiting our transport or accommodations. Wherever Tours is not responsible for lost items, but we will do our best to assist in recovering them if possible.

About Booking This Tour

Deposit & Booking Information

The deposit and the fees for the optional Protection Plan or Cancel Fee Waiver [CFW] coverage are due at time of booking. Your deposit is $500.

Terms and Conditions:

For additional information pertaining to our Wherever Tours including Cancellation Information and Booking Conditions, click here to learn more.

If You Have To Cancel

If you need to cancel your trip, please contact our team with your reservation number. Cancellation penalties vary depending on how early you cancel, and the sooner you notify us, the more you may be eligible to receive in refunds. Reach out to learn more about the specific terms for your booking.

Customer Reviews

Based on 1 review
100%
(1)
0%
(0)
0%
(0)
0%
(0)
0%
(0)
M
Morgan S.
Sicily Fall 2024

I recently went on this tour of Sicily with my mother, and we had an incredible experience. The hotels and the views were breathtaking, the food was delicious, and the tour guides were knowledgeable. We spent the last three days in Sorrento, where we were treated like royalty. Wherever Tours is truly top-notch!

Thank you so much, Morgan! We’re thrilled that you and your mother had an incredible experience on our Sicily tour. It’s wonderful to hear that you enjoyed the breathtaking views, delicious food, and time in Sorrento. Our team puts a lot of love into crafting memorable experiences, and we're so glad that it shined through for you. We’d love to welcome you both back for another adventure with us—perhaps another Italian getaway or one of our other European destinations. Grazie mille for your kind words!