Depart the United States on an overnight flight bound for Catania, Italy.
Benvenuto in Italia! Upon arrival in Catania, you will be met and transferred to your hotel in Taormina, a hilltop Sicilian town with Mt. Etna looming in its skyline. Enjoy a calm evening after your long flight gazing upon the Ionian Sea from the comfort of your private balcony.
Day 3: Sicilian Food Tour
Use your free morning to explore the highlights of Taormina like the Greek Theater and Piazza del Duomo at your own pace. This evening, you will set out on a food tour where you will have the chance to sample delicacies from appetizers like bruschetta to four different fish dishes. All of this will be accompanied by wine tastings and a stop for desserts like torrone, a honey and almond candy.
Day 4: Mt. Etna Winery Tour
Expand your knowledge of Sicilian wine on a private winery tour on Mt. Etna. Your first stop will be a family honey farm for tastings of honey, almond pastries, and olive oil. From there, you will move on to two winery stops, the latter of which will also provide a typical Sicilian lunch. End your day with stops to see stunning views of the Alcantara Valley.
Day 5: Sicilian Cooking Class
After a few days of familiarizing yourself with Sicilian cuisine, today you will have a chance to test your hand at cooking it. The chef will start you out with a tour of a local market to purchase the fresh ingredients needed. Afterwards, you will return to the restaurant to cook what will turn out to be your lunch.
Day 6: Travel to Noto via Siracusa
Begin your day with a private tour of Siracusa, home of the famous “Ear of Dionysus” cave, among other ancient Greek and Roman ruins. Continue on to Noto and watch the sun sink behind remarkable buildings from the rooftop bar of your hotel.
You may choose to spend the day strolling around Noto. Around every corner lies breathtaking baroque architecture waiting to be discovered. For another panoramic view of the city, you could climb the spiral staircase of St. Charle’s Church’s bell tower.
Day 8: Ragusa & Modica Tour
This morning, you will set out on a private full day tour of Ragusa and Modica. Appreciate the picturesque setting of Ragusa, and in Modica be sure to nab some chocolate, made divine by the Aztec methods introduced to the area when it was once under Spanish rule.
Day 9: Travel to Agrigento & Temples Tour
Watch the Sicilian countryside roll by on your way to Agrigento. Drop your bags at your hotel before your guide meets you for a private tour of Agrigento’s three major Doric temples. Afterwards, take some time to unwind at your hotel’s spa before sitting down to dinner at the restaurant.
Day 10: Travel to Palermo
Depart Agrigento and make your way to Palermo, Sicily’s capital. Take some time to settle into your hotel with light refreshments in the cozy tea corner before using the afternoon to roam the local markets.
Day 11: Palermo Highlights
This morning, you will walk back in time as your private guide leads you through Palermo to all of the key sites, including the Quattro Canti area and San Cataldo church. In the afternoon, you may choose to backtrack and visit the museums you passed earlier on your own.
Day 12: Monreale Cathedral & Cefalu
Begin your private full day tour with a stop at the elaborate Monreale Cathedral before following the coast to the medieval town of Cefalù.
Soar over the Tyrrhenian Sea and southern Italy on your flight from Palermo to Bari. Upon arrival in Bari, you will pick up your rental car at the airport and drive to Matera. Spend the afternoon in the spa of your hotel, reminiscent of the cave dwellings Matera is famous for.
Day 14: Matera Highlights
Today, you will scour the cavernous landscape of Matera on a private tour of the city. Highlights include the stacked “Sassi” houses and rupestrian churches dating back to the Middle Ages.
Day 15: Travel to Savelletri di Fasano via Ostuni
Cruise your way to Ostuni for a brief stop to marvel at the whitewashed architecture before continuing on to Savelletri di Fasano. Revel in the countless ways you could spend the rest of the day at your hotel, from a round of golf on the nearby championship course to dining at a Michelin-starred restaurant.
Day 16: Apulian Cooking Class
After learning the ins and outs of Sicilian cooking earlier on, now you will have the chance to beef up your Apulian cooking skills. Master the art of orecchiette pasta and traditional ricotta cheese tarts so that you will be able to create delicious reminders of your trip long after you leave Italy.
Today, you may wish to take a mini road trip around to a few smaller towns nearby. Start with the unique domes of Alberobello, move on to Locorotondo to sample stellar sparkling white wine, and finish with panoramic views of the Itria Valley from Martina Franca.
This morning, you can sprawl out on either of your hotel’s two private beaches and let the sound of the waves soothe you. In the afternoon, you may choose to venture out to Polignano a Mare, a fishing village perched one limestone cliffs and home to one of the best gelatarias in Puglia.
Day 19: Travel to Lecce & Highlights
Drive from Savelletri di Fasano to the baroque city of Lecce. Drop your bags at your hotel and set off on a private tour that will guide you through all of Lecce’s highlights. Spend the evening with a drink in hand at the courtyard of your stunning hotel that was once a fortress.
You may choose to use your last full day in Italy to fit in some relaxation on the beaches of nearby Otranto. Soak up the sun from the comfort of the golden sand or dive into the alluring blue waters.
Say farewell to Italy as you head to the airport for your flight back to the United States.