Island Hop: Sicily & Malta
- Small Group Adventure – Limited to 6 Guests
- A hands-on experience in the olive groves of Chiaramonte
- Tour Mount Etna and enjoy lunch and a wine tasting in its valley
- Join in the celebration of the Sicilian Harvest in Zaffernese
- Celebrate the grape harvest at Pedalino’s Sagra Della Vendemmia
- Experience another cultural and culinary experience with two days in Malta
- Tour the islands with your personal chefs: taste and learn recipes to recreate at home
$7,999 $7,499
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Trips Starting at $4,499
Get ready for an incredible week in Sicily!
Let’s dive into what we have planned for you:

Day 1: Wednesday, Sept. 23
Arrival flights to Catania or Comiso Airports
We will begin by helping you settle into your Chiaramonte Gulfi Villa. Come on in, unpack, and relax! In the evening, we’ll gather for a welcome dinner at Villa Gerardo to kick off our
adventure.

Day 2: Thursday, Sept. 24
Today, we will head out to discover the terroir of Ragusa and learn why the region’s wine production was given its own EU Protected Designaton of Origin. We will head to two exclusive wineries for tastings and brunch, enjoy a mid-day break in a nearby village for cafe, pastries and gelato.

Day 3: Friday, Sept. 25
We are heading to Siracusa today, visiting historical sites, amazing markets and delicious restaurants. We will take a boat tour along the island’s coastline, explore the sea caves (Grotte Marine), take an optional swim, and capture unique views of historic sites like the Venetian Palace and Maniace Castle. You will have time to relax and enjoy the city on your own before returning to Chiaramonte at the end of the day. UNESCO World Heritage Site.

Day 4: Saturday, Sept. 26
After breakfast at the villa, we’ll head out to Cantina Gulfi for a delightful wine tasting session.
Then, we’ll enjoy a delicious luncheon at il Progetto. In the evening, we’ll experience the fun and
festivities of the Pedalino Wine Festival.

Day 5: Sunday, Sept. 27
Start your day with breakfast at the villa before heading back to enjoy more of the Pedalino Wine Festival. We’ll continue to celebrate the grape harvest, walking through the streets and giving thanks with the entire village, sharing in food, stories, folk dancing, and so much more.

Day 6: Monday, Sept 28
After breakfast at the villa, we’re off for a scenic drive through the countryside to Palazzolo Acreide. There, we’ll visit an agritourismo know for its black pigs, get a tour of the farm, take part in a cooking class, and indulge in a luncheon you’ve helped make. This evening we’ll relax at the villa with a light snack, an evening walk, and dessert in the Piazza Duomo Chiaramonte Gulfi.

Day 7: Tuesday, Sept 29
We’ll begin early today with a morning drive to the Sicilian port of Pozzallo, where we will set off by ferry to discover another country. Malta’s historical tapestry was woven by diverse rulers and settlers who left their marks, including the Phoenicians, Romans, Arabs, Knights of St. John, and the British. The cuisine and architecture tell their own story, influenced by its North African and Italian neighbors, featuring dishes such as pastizzi (savory pastries), tuna rolls, and stews made with local ingredients like broad beans and octopus.

Day 8: Wednesday, Sept 30
Our morning begins with breakfast in a small village in Gozo, we will head to the cliffs for a hike along the coast, then down to the seaside for a salty lesson, lunch and a sweet swim in the island sea. Dinner in a friend’s home overlooking the seaside.

Day 9: Thursday, October 1
We will wrap up our Maltese adventure today with a ferry ride back to Valetta to visit catacombs and embark on a historical stroll through the walled city of Mdina, before meandering back to through the shopping streets of Valetta and the elevator to our ferry return to Sicily.

Day 10: Friday, October 2
We’ll have a leisurely start today and then meet up at The Cook’s Farm in Chiaramonte for a
mid-morning respite and a lesson in olives. After picking a selection of olives for the evening’s
visit to the oleficio, we’ll share our traditional “Chicken Friday” with friends before heading to the
villa for a free afternoon. We’ll gather again for a tour of the local mill and then celebrate the
harvest with a Ragusano farewell dinner at The Sardo Olive Grove.

Day 11: Saturday, October 3
We’ll start with breakfast at the villa and say goodbye to the beauty of Southeast Sicily as we venture north out to Mount Etna for a day of exploration. We’ll walk the village streets for the vibrant Autumn Food Festival (Ottobrata Zafferanese), and lean into the beauty of the volcanic soils that shape the grape harvest with a private wine tasting. After checking into our hotel, you’ll have some free time in the city before our farewell dinner in Piazza Duomo Acireale.

Day 12: Sunday, October 4
Depending on your departure schedule, we will have breakfast ready for you. We’ll provide transport back to Catania for your flights home, filled with wonderful memories, or help you on your way to your next booking with Lit’l Pond Hospitality, where more adventures await!

