Crossroads of Culture: From Malta’s Shores to Sicily’s Peaks

October 30, 2026 – November 8, 2026

Join this unforgettable 8-day in-country journey through two of the Mediterranean’s most enchanting islands, where ancient history, breathtaking landscapes, and vibrant cultures converge. From Malta’s golden shores to Sicily’s towering peaks, each day is filled with discovery and delight. Stay in luxurious 5-star accommodations, savor exquisite cuisine, and forge lasting friendships along the way. Throughout history, the strategic location of Malta and Sicily has made them pivotal crossroads for cultural exchange, military conquests, and the rise of the world’s great empires—now it’s your turn to explore their timeless allure.

Travel Deeper, Experience More

Marshall and Jessica Pennell, owners of Harbinger Tours

Marshall and Jessica Pennell, your Tour Hosts, have traveled, researched, and dreamed to curate a marvelous experience for you. Every aspect of these days has been custom curated by these discriminating travel experts.

Learn more

The group is carefully limited in size for a more personal experience. The small group allows your hosts to serve as your personal concierge. Need something extra, want to spend a day doing something different, just say the word!

Expert local guides will bring Malta and Sicily to life, revealing centuries of history, architecture, and culture shaped by conquest, faith, and resilience. From ancient ruins to Baroque splendor and the enduring legacy of the Knights of St. John, enjoy immersive experiences—blending luxury, learning, and fun for the discerning traveler.

Itinerary

Travel  |  October 30, 2026

Departure from the USA to Malta on flights selected and purchased by each passenger

Day 1  |  October 31, 2026

  • Arrival in Malta and taxi to Malta’s luxurious landmark hotel 5-star hotel, Corinthia St. George’s Bay
  • Welcome Reception and dinner

Day 2  |  November 1, 2026

  • Dive into History and Culture
  • Valletta: Start your journey in Malta’s capital, a UNESCO World Heritage Site.
  • Visit St. John’s Co-Cathedral and marvel at its ornate baroque architecture and Caravaggio’s masterpieces. See the Upper Barrakka Gardens and enjoy breathtaking views of the Grand Harbour and explore the Grandmaster’s Palace; a historical gem, once the residence of the Knights of St. John.
  • Lunch: We’ll head to a waterfront restaurant in Valletta for fresh seafood or traditional Maltese dishes like rabbit stew.
  • Mdina (The Silent City): We’ll travel to the ancient, walled city of Mdina. Wander its narrow streets, visit St. Paul’s Cathedral, and soak in the tranquil atmosphere.
  • We’ll finish our day dining in one of Mdina’s unique atmospheric restaurants.
  • We’ll have some option time this afternoon for you to select an optional afternoon tour or have time on your own to explore, enjoy the pool or spa, or maybe take a nap!

Day 3  |  November 2, 2026

  • Natural Wonders and Island Charm
  • We’ll spend our time on the islands today traveling by boat to see the famous Blue lagoon, Comino, and Gozo.
  • Explore the prehistoric Ġgantija Temples – UNESCO-listed megalithic temples.
  • Stroll through Gozo’s charming capital, Victoria, and visit the ancient Citadel for panoramic views.

Day 4  |  November 3, 2026

  • See the Sites!
  • We’ll tour the island on a luxury coach today to take in the beautiful sites of this unique land!
  • Visit St. Paul’s Bay and Marsaxlokk Fishing Village, a picturesque village to see colorful fishing boats (luzzus) and browse the vibrant market.
  • Feast on fresh fish at a seaside restaurant.
  • Delve into Malta’s prehistoric past with a visit to Ħaġar Qim and Mnajdra Temples, ancient megalithic sites.
  • Admire the Blue Grotto, a stunning sea cave with vivid blue waters.
  • Return to Valletta or St. Julian’s for a final dinner in Malta where we’ll enjoy a lively atmosphere and a toast to an unforgettable Maltese adventure.

Day 5  |  November 4, 2026

  • Welcome to Sicily! A land of ancient ruins, sun-soaked beaches, and mouthwatering cuisine.
  • Depart from Malta early this morning to catch a 2 hour ferry ride to Sicily.
  • Visit Europe’s tallest active volcano, Mount Etna and take a guided tour or cable car ride to explore its craters and lava fields.
  • Enjoy a meal at an iconic terrace restaurant.
  • Check into the luxury Ortea Palace Hotel on the beautiful Ortigia island, part of the city of Siracuse, where we’ll be for the remainder of our stay.

Day 6  |  November 5, 2026

  • Syracuse
  • Discover the Greek Theatre, Roman Amphitheater, and the Ear of Dionysius at Syracuse’s Archaeological Park.
  • Wander through the charming streets, visit the Piazza Duomo, and explore the Temple of Apollo at Ortigia.
  • Enjoy fresh Sicilian cuisine and olive oil and wine tasting.

Day 7  |  November 6, 2026

  • Sea Level to Mountain Top
  • Enjoying a boat tour of the southern or northern coast of Syracuse and Ortigia, possibly including a refreshing dip in the water!
  • Visit Castelmola, a small medieval town perched on a mountain-peak overlooking Taormina and lies about 550 mts (1580 ft) above the sea level offering a magnificent view of the sea, Taormina, the coast of Calabria and Mt. Etna.
  • Time to stroll along the lively Corso Umberto street lined with shops, cafes, and boutiques and do a little shopping!

Day 8  |  November 7, 2026

  • Your Choice!
  • On our final day together you can choose between taking a local cooking class, a Gastronomic Street Food Tour of Catania, or perhaps another winery tour. If you prefer you can simply take the morning and afternoon off to finish up any shopping you may want to do, or just relax and enjoy the Mediterranean seaside!
  • Conclude your trip with a farewell dinner, savoring traditional Sicilian dishes and a glass of wine.

Departure  |  November 8, 2026

  • Departure and travel back to USA

Details and Limitations

Pricing and Availability

  • Per Person, Double Occupancy Price: $11,495
  • $500 per person deposit due now to reserve your space
  • $2,000 per person due April 30, 2026
  • $5,000 per person due June 30, 2026
  • Final balance of $3,995 per person due by July 30, 2026
  • If you will be traveling alone and require single occupancy for hotel rooms please add $2,800 to your final balance.
  • If you are registering after any of these due dates you’ll be invoiced the total due.
  • Reserve your spot today! While there’s no set deadline to register, space is limited—and once the tour fills, sign-up will close automatically. We’d love to have you with us!

Tour Includes

  • Travel from Malta to Sicily
  • 8 days in country
  • 8 nights in 5-star deluxe hotels
  • Porterage at each hotel
  • Full breakfast at each hotel
  • Lunches for 2 days during tour
  • Restaurant dinners for 6 days during tour
  • Deluxe motor coach and driver
  • All entrance fees on itinerary
  • Tips to drivers, restaurants, hotel staff, etc.

Note

  • Please refer to the terms & conditions for a list of items not included.
  • Any requests outside of the tour package must be emailed to: [email protected]
  • $500 deposit per person due now to reserve your space
  • Final balance due by July 30, 2026

Register Now!

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