Historical Sicily – Custom Itinerary
Note: These example itineraries are fully customizable. We tailor all our luxury Sicily vacations, so you can include any location or activity that you desire. Let our Italy experts help craft your ideal complete Sicily vacation and take the stress out of luxury Sicily travel - contact us today!
- Discover Sicily's rich Italian and Ancient Greek history on a two-week tailor-made vacation
- Visit Palermo, Messina, Taormina, Mount Etna, Agrigento's Valley of the Temples, Siracusa and more!
- Private luxury transfers, accommodation, guided VIP excursions and personal travel services are included
- Relax on your vacation under the care of a dedicated Bellarome travel representative
Palermo, Two Nights
Welcome to the Capital
Sicily's iconic capital, Palermo, sits on the Gulf of Palermo in the Tyrrhenian Sea. The city is unique in that it offers glorious sea vistas and relaxed beach locations, while also being famous for its colorful history, beautiful architecture, vibrant culture and decadent cuisine. Due to its strategic location, the city boasts a fascinating and turbulent history, and it has played a vital role in shaping Europe.
History tour of Palermo
Get to know Palermo on a deep level with our popular history tour of Palermo that allows you to see delights, such as the La Martorana Norman Church, Galleria Regionale, a 15th-century Neo-Gothic castle, Medieval and Renaissance art, the 12th-century Monreale Cathedral and Museo Archeological Regionale, where you will be stunned by one of the richest collections of Punic and Ancient Greek art in Italy. This Palermo history tour also allows you to uncover the darker side of Palermo's history with a visit to the macabre Convento dei Cappuccini's Catacombs, which display thousands of mummies and preserved corpses dressed in the clothing of their time. As a lighter finale to your unique tour experience, you can visit the colorful Vucciria Market to buy local produce and gifts for friends and family back home.
Messina, Two Nights
Historical Messina walking tour
Messina is nestled on the Ionian coast and is a joy to discover on your Sicily vacation as it allows you to experience diverse landscapes, including traditional fishing villages and natural wonders, such as the Ganzirri Lakes. On this walking tour of Messina, you will begin at the historic center and walk to Capo Peloro to admire the Strait of Messina. The tour will then continue in the center of Messina with a visit to the Cathedral and the Bell Tower, where you can learn more about the great astronomic clock. You will also discover the Arabian-Norman Church of the Santissima Annunziata dei Catalani and the Sanctuaries of Montalto and Cristo Re, which both offer spectacular views. During the tour you will also have a chance to admire Madonnina del Porto and the Fountain of Neptune, which was sculpted by Montorsoli in 1557. You will also see the Baroque Church of Gesu e Maria del Buon Viaggio. On request, there is also the possibility to make a short stop at the Regional Museum of Messina, where you can see two of the most important paintings by Caravaggio and two paintings by Antonello.
Boat tour of the Strait of Messina
Leaving the Port of Milazzo, you will travel along the wonderful Mamertino Cape, which offers a stunning view of Aragon Castle, before reaching the Port of Panarea. From here, you can enjoy a boat tour to see the beautiful Cala Junco Bay, Caletta dei Zimmari and Drauto Bay, and there will also be time to visit one of the seven islands. There will be plenty of time to relax too - why not go for a swim or have lunch in one of the typical Aeolian restaurants? Or if you want to delve further into Messina's past, take a local taxi to the pre-historic village of Capo Milazzese (it can also be reached on foot in 45 minutes).
Taormina, Four Nights
Explore historical Taormina
Spectacularly perched on the side of a mountain, Taormina is one of Sicily's most popular summer destinations. On your first day in Taormina, you will be treated to a picturesque walking tour featuring delightful attractions, such as Borgo Medievale (Taormina’s oldest neighborhood), the Baroque fountain, Villa Communcale, Piazza del Duomo and Taormina Teatro Greco. Along the way, your guide will immerse your in Taormina's la dolce vita by telling you all about the town's modern culture and the importance of its stunning monuments.
Mount Etna day trip
Today, you'll take a trip up Europe's most active volcano! Standing proud at 3,320 meters, Mount Etna is also Europe's biggest volcano, with a base circumference of 93 miles. On this once-in-a-lifetime day trip, you'll begin in the foothills of the mighty volcano, taking in the exotic wildlife with your guide, before embarking on a gentle walking tour to Rifugio Sapienza, which includes the famous Monti Silvestri Craters. Here, you will be able to take in unbelievable sea views and views of the surrounding countryside - you'll be sure to make memories that will last a lifetime!
Valley of the Temples tour
Immerse yourself in Sicily's Greek past with this tour of Agrigento's Valley of the Temples (entry included). The UNESCO-protected Valley is one of Sicily's most important archaeological sites and is a joy to discover if you have an interest in history or simply want to learn more about Sicily's turbulent past. This tour experience takes you to the sacred site, where an expert guide will treat you to a guided walk through the Valley. As a part of your tour, you will see the Temple of Hera, the Temple of Concordia, the Temple of Herakles, the Temple of Zeus and the Sanctuary of Chtonian Deities (Temple of Castor and Pollux). During the tour, your guide will discuss the temples' construction and tell you about their on-going preservation, allowing history to come to life.
VIP Taormina tour with the Greek Theater
After a day to relax at your hotel, today you will have another opportunity to immerse yourself in Taormina's splendid attractions on a two-hour private tour. This guided experience allows you to explore the highlights of this charming city, including Palazzo Corvaja, the Santa Caterina Church and Vicolo Stretto, which is the narrowest street in town. As a special addition to this VIP Taormina private tour, you will enjoy “skip the line” entry to the ancient Greek Theater, which boasts magnificent views of Mount Etna and Giardini Naxos. There is no better way to discover this unassuming city’s treasured attractions!
Siracusa, Four Nights
Explore historical Siracusa
Your historical Sicily vacation continues today on the island of Ortigia, the historical heart of the city of Siracusa. Sometimes called Città Vecchia (Old City), Ortigia is full of treasures waiting to be explored and they can comfortably be seen on foot. We recommend beginning with a walk around the perimeter of the island before immersing yourself in the tightly woven network of narrow and winding alleys and lanes. You'll be sure to pass by hidden churches and Baroque palaces as you stroll. Indeed, everywhere you look there is a visual treat! The best of the attractions include the 13th-century Castello Maniace (open in the mornings until early afternoon), Piazza Pancali and the Temple of Apollo.
Sicilian wine-tasting tour
What a treat we have for you today as we will take you on a journey of exploration deep in the Sicilian countryside. As a part of your day in nature, you will be treated to stops at two wineries, where you can taste several Sicilian wines, including Nero d’Avola. You will also enjoy a guided vineyard and cellar tour, and sample local products, such as Sicilian cheeses and cured meats. Your culinary experience will be completed with a visit to a tonnara, which is an authentic Sicilian tuna farm and a place where you can try unbelievably fresh tuna.
Explore Siracusa at your leisure
Today is a free day to explore everything the city has to offer. Recommended activities include visiting the 13th-century Castello Maniace citadel and castle, seeing the natural Arethusa Fountain on the waterfront, relaxing as Arenella Beach or going underground to explore the honeycomb network of the San Giovanni Crypt and Catacombs, which date back to the 6th century.
Sicilian town escapade
Today you can explore little-known Sicily with a visit to Ragusa Ibla, which is a delightful small city built in a Sicilian Baroque style. Of its many charming attractions, of particular note is the 18th-century Duomo di San Giorgio, where you can view the only example of a Catalan-Gothic style portal. We also highly recommend climbing the steep stairway to the upper town for breathtaking views over Ibla or take the small train from Piazza Duomo for a casual ride along the city's main streets.