Malta, Sicily & Southern Italy
April 15th to 30th, 2027
Join us on an unforgettable Mediterranean journey through the beautiful islands of Malt and Sicily. Discover ancient cities, picturesque coastal towns, and vibrant Italian culture. Continuing to the mainland, we travel through Southern Italy where whitewashed villages and timeless traditions await. Our journey then takes us along the breathtaking Amalfi Coast, with its colorful seaside villages and dramatic coastal scenery, before concluding in the Eternal City of Rome, where centuries of history and iconic landmarks provide a spectacular finale.
Highlights: Valletta & Malta’s Ancient Treasures, Historic Syracuse in Sicily, Majestic Mount Etna, Sicily’s Charming Coastal Villages, WWII Landing Beaches of Sicily, Puglia’s Iconic Trulli Houses, the Breathtaking Amalfi Coast, Historic Monte Cassino, and the Eternal City of Rome.
Overnights: Sliema, Malta (2 Nights + Optional Early Arrival Night) – Syracuse, Sicily (3 Nights) – Tropea, Calabria (1 Night) – Bari, Puglia (3 Nights) – Amalfi Coast (2 Nights) – Rome (3 Nights) – Optional Mainland Italy Extension
Price: €5,195//person* - based off a double occupancy room
Tour Itinerary
Day 0 - Optional Early Arrival Day - Thursday, April 15, 2027
Arrive in Malta a day early and ease into your Mediterranean adventure at your own pace. Fly in whenever you'd like, and a private driver will be waiting to welcome you and bring you directly to our comfortable accommodations in the seaside town of Sliema. Settle in, relax, and enjoy some free time to stroll along the beautiful waterfront promenade, admire the spectacular views across the harbor to historic Valletta, or unwind at one of the many charming seaside cafés and restaurants. With the sparkling Mediterranean Sea just steps away, it's the perfect way to settle into island life before our adventure officially begins! €495.00 per room with private airport transfer.
Overnight: Sliema, Malta
Day 1 - Arrival Day - Friday, April 16, 2027
Welcome to beautiful Malta! After gathering as a group at the airport, we'll make our way to our comfortable hotel in the seaside town of Sliema, overlooking the sparkling Mediterranean Sea. Take some time to unpack, relax, or enjoy a leisurely stroll along the waterfront promenade, taking in the spectacular views across the harbor toward historic Valletta. As evening falls, we'll gather for a welcome dinner, getting to know our fellow travelers while enjoying delicious Mediterranean flavors and setting the stage for the exciting journey through Malta, Sicily, and Southern Italy ahead!
Overnight: Sliema, Malta
Day 2 - Valletta Walking Tour & Harbor Cruise - Saturday, April 17th, 2027
Beautiful coastal scenery awaits as we set off on a scenic harbor cruise departing from Sliema. As we sail through magnificent harbors, we'll enjoy spectacular views of Valletta's towering fortifications, historic waterfront, and impressive limestone architecture. Back on land, we'll make our way into Valletta, Malta's UNESCO-listed capital, for a guided walking tour through its charming streets and grand squares. Along the way, we'll admire magnificent Baroque buildings, historic churches, and the imposing fortifications built by the Knights of St. John, with a visit to the Upper Barrakka Gardens for breathtaking views over the Grand Harbour. After our tour, enjoy some free time to explore Valletta's lively cafés, shops, and picturesque streets at your own pace before returning to Sliema for the evening.
Overnight: Sliema, Malta
Day 3 - Malta's Timeless Treasures & A Journey to Sicily - Sunday, April 18th, 2027
Enjoy a day exploring the beautiful island of Malta before continuing our Mediterranean adventure to Sicily! Our journey takes us through Malta's picturesque countryside, where we'll visit charming historic towns, admire centuries-old architecture, and take in some of the island's beautiful coastal scenery. Along the way, we'll have opportunities to experience local traditions, enjoy scenic viewpoints, and soak up the island's unique Mediterranean atmosphere. As evening approaches, we'll head to the ferry terminal and bid farewell to Malta, enjoying a scenic crossing of the Mediterranean Sea to Sicily. Upon arrival, our private coach will take us to the historic city of Syracuse, where we'll settle into our hotel for the next three nights.
Overnight: Syracuse, Sicily
Day 4 - Southern Sicily & WWII Landing Beaches - Monday, April 19, 2027
Today we'll venture into the heart of southern Sicily, where fascinating history, beautiful landscapes, and centuries-old traditions come together. From charming historic towns and magnificent ancient ruins to picturesque countryside and coastal scenery, this region offers a wonderful glimpse into Sicily's rich and colorful past. We'll also visit some of the historic beaches where Allied forces landed during World War II's Operation Husky in 1943, marking the beginning of the liberation of Sicily and a pivotal chapter in the Allied campaign in Europe. Along the way, we'll explore the island's unique cultural heritage, from ancient civilizations to more recent history. Of course, no visit to Sicily would be complete without sampling some of its delicious local specialties! With opportunities to experience traditional flavors and authentic Sicilian hospitality, today promises a memorable blend of history, culture, and culinary delights.
Overnight: Syracuse, Sicily
Day 5 - Mt. Etna & Catania - Tuesday, April 20th, 2027
Towering above eastern Sicily, Mount Etna provides a spectacular backdrop for today's adventure. One of Europe's most active volcanoes, this mighty mountain has shaped the surrounding landscape and influenced life on the island for thousands of years. We'll make our way through the scenic countryside, passing charming villages, fertile valleys, and dramatic volcanic terrain, with opportunities to experience the mountain's remarkable natural beauty up close. Beyond the breathtaking scenery, this corner of Sicily has plenty of fascinating stories to tell, from the generations who have lived in the shadow of Etna to the island's important role during World War II. With a wonderful mix of natural wonders, local culture, and history, today promises to be one of the most memorable days of our Sicilian adventure!
Overnight: Syracuse, Sicily
Day 6 - Sicily’s Charming Villages & Journey to Mainland Italy - Wednesday, April 21st, 2027
Bidding farewell to Syracuse, we our way north along Sicily's beautiful eastern coastline, where dramatic mountain scenery, charming hillside villages, and sweeping Mediterranean views make the journey just as memorable as the destination. Along the way, we'll have opportunities to wander through picturesque streets, admire breathtaking coastal panoramas, and soak up the atmosphere of some of Sicily's most enchanting towns. With colorful local traditions, historic architecture, and plenty of postcard-worthy scenery, it's a wonderful final taste of island life. Later, we'll cross the Strait of Messina to mainland Italy, where a new chapter of our Mediterranean adventure awaits!
Overnight: Tropea, Italy
Day 7 - Across Southern Italy - Thursday, April 22nd, 2027
Following a relaxing waterfront stay, we'll make our way across the southern Italian countryside toward the historic port city of Bari, on the Adriatic coast with a wonderful look at a lesser-traveled side of Italy, with rolling hills, rugged mountains, charming villages, and picturesque landscapes along the way. We'll break up the drive with a few interesting stops, perhaps visiting a quaint Italian town, admiring a scenic viewpoint, or enjoying a taste of the region's local specialties. As we travel from Calabria into Puglia, the scenery and traditions gradually change, offering a glimpse into the diverse character of southern Italy. By late afternoon, we'll arrive in Bari and settle into our hotel for the next three nights, ready for another exciting chapter of our Mediterranean adventure!
Overnight: Bari, Italy
Day 8 - Whitewashed Villages and Adriatic Waters - Friday, April 23rd, 2027
Whitewashed villages, centuries-old traditions, and the sparkling Adriatic Sea come together to create some of southern Italy's most memorable scenery in Puglia. Today we'll enjoy a taste of this beautiful corner of Italy, from the winding streets of historic towns to picturesque countryside dotted with olive groves and distinctive stone houses. Along the way, we'll encounter unique local architecture, breathtaking coastal views, and the relaxed atmosphere that makes this region so special. There will be opportunities to wander through charming village squares, browse local shops, and perhaps sample some of Puglia's delicious regional specialties. With its wonderful blend of history, culture, and Mediterranean beauty, today offers a delightful glimpse into the authentic character of southern Italy.
Overnight: Bari, Italy
Day 9 - Hidden Gems of Southern Italy - Saturday, April 24th, 2027
Another wonderful day awaits in southern Italy, where we'll venture beyond the familiar tourist routes to experience more of Puglia's unique character and charm. With so many fascinating places within reach, today's outing offers a chance to enjoy a different side of the region, whether it's a historic town, a scenic stretch of coastline, or a taste of traditional Italian life. Along the way, we'll take in the beautiful surroundings, enjoy a few pleasant stops, and leave time for those unexpected moments that often become our favorite travel memories. It's another opportunity to soak up the sights, flavors, and easygoing atmosphere of this delightful corner of Italy before returning to Bari for the evening.
Overnight: Overnight: Bari, Italy
Day 10 - From Puglia to the Amalfi Coast - Sunday, April 25th, 2027
Leaving the Adriatic coast behind and journey west across the Italian peninsula toward the spectacular Amalfi Coast. Along the way, we'll pass through a changing landscape of rolling countryside, rugged mountains, and historic towns, with opportunities for a few interesting stops along the route. This part of southern Italy is rich in history, including important chapters of World War II, when Allied forces landed along the coast near Salerno in 1943. We may have a chance to visit some of the sites connected to these events while enjoying the region's beautiful scenery and local character. As we approach the Tyrrhenian Sea, dramatic coastal views and colorful hillside villages welcome us to one of Italy's most celebrated destinations, where we'll settle in for the next two nights.
Overnight: Amalfi / Salerno, Italy
Day 11 - Coastal Wonders & Timeless Treasures of the Amalfi Coast - Monday, April 26th, 2027
With the sparkling waters of the Tyrrhenian Sea and the dramatic mountains of southern Italy as our backdrop, today promises a wonderful mix of breathtaking scenery, fascinating history, and Mediterranean charm. This beautiful corner of Italy offers endless possibilities, from colorful seaside villages perched along rugged cliffs to legendary islands, ancient ruins, and remarkable natural wonders. Whether enjoying the lively atmosphere of a coastal town, taking in spectacular views from the water, or stepping back in time at one of the region's extraordinary historic sites, there's no shortage of memorable experiences. We'll make the most of our time in this spectacular region, with opportunities to enjoy its scenery, culture, and irresistible Italian atmosphere before returning to our hotel for the evening.
Overnight: Amalfi / Salerno, Italy
Day 12 - Ancient Wonders & Italian Traditions - Tuesday, April 27th, 2027
Today we bid farewell to the beautiful Amalfi Coast and make our way north toward the Eternal City of Rome! Along the way, we'll have the chance to experience some of Italy's most fascinating history, from remarkably preserved ancient Roman sites to places that played an important role in more recent European events. Of course, no journey through this part of Italy would be complete without enjoying some of its legendary cuisine, and we'll make time for a taste of authentic Neapolitan pizza in the region where it all began! Continuing north through the scenic Italian countryside, we'll arrive in Rome by early evening and settle into our centrally located hotel. Here, we'll welcome those joining us for the optional mainland Italy tour, with an opportunity to gather for a drink and toast to the next chapter of our Italian adventure!
Overnight: Rome, Italy
Day 13 - Ostia Antica or the Colosseum - Wednesday, April 28th, 2027
Stepping back nearly 2,000 years into the fascinating world of ancient Rome guests can choose between two wonderful options for experiencing the city's remarkable history! The first option is a visit to legendary Colosseum and surrounding archaeological sites, where gladiators once fought and emperors shaped the course of history. Alternatively, venture just outside the city to Ostia Antica, an exceptionally preserved ancient Roman port town, where cobblestone streets, elaborate mosaics, and the remains of homes, shops, and public buildings offer a fascinating glimpse into everyday life during the Roman Empire. Whichever experience you choose, the day promises an unforgettable journey into the past, with time afterward to enjoy Rome's lively piazzas, charming cafés, and irresistible Italian atmosphere at your own pace.
Overnight: Rome, Italy
Day 14 - Free Day & Farewell Dinner - Thursday, April 29th, 2027
Our final full day in Rome is yours to enjoy however you wish! Take advantage of some well-deserved free time to wander through the city's charming neighborhoods, revisit a favorite piazza, toss a coin into the Trevi Fountain, or simply relax at a sidewalk café with a cappuccino or gelato. For those interested, an optional excursion to Vatican City offers the opportunity to experience some of the world's most remarkable artistic and religious treasures, including the magnificent St. Peter's Basilica and the Vatican Museums. Whether you choose a day of sightseeing, shopping, or simply soaking up the atmosphere of the Eternal City, there's no better place to savor the final moments of our Mediterranean adventure. This evening, we'll gather for a special farewell celebration, sharing favorite memories, plenty of laughs, and a toast to the wonderful journey we've enjoyed together!
Overnight: Rome, Italy
Day 15 - Departure Day or Best of Italy Extension - Friday, April 30th, 2027
Our wonderful Mediterranean adventure come to a close for some, while for others, another exciting chapter of Italian travel is just beginning! For those heading home, we'll arrange transfers to the airport and bid farewell with wonderful memories of the beautiful places, fascinating history, and unforgettable experiences we've shared along the way. Guests continuing on our Best of Italy extension will leave Rome behind and journey north into the heart of Tuscany, where rolling hills, vineyards, olive groves, and picturesque hilltop towns create some of Italy's most iconic scenery. Along the way, we'll have opportunities to enjoy the region's charming countryside and rich cultural heritage before arriving in Florence, the birthplace of the Renaissance. Here, we'll settle into our hotel for the next three nights, ready for more Italian adventures!
Departure Day / Best of Italy Extension
Grand Italy Tour Extension
April 30th to May 5th, 2027
Extend your Italian adventure and journey through the heart of Italy, exploring the iconic cities of Florence and Venice. Following the Malta, Sicily, and Southern Italy tour, we continue north through the beautiful Tuscan countryside to Florence, the birthplace of the Renaissance. During our three-night stay, admire world-famous art and architecture, stroll across the historic Ponte Vecchio, and venture into the rolling hills of Tuscany to discover picturesque villages, local wines, and traditional Italian flavors. Our journey continues to the enchanting city of Venice, where romantic canals, magnificent palaces, and the lively atmosphere of St. Mark's Square provide a spectacular finale. Enjoy a guided introduction to this remarkable floating city, with opportunities to explore its winding streets and nearby islands before bidding farewell to Italy. Whether joining as a standalone tour or continuing from our Malta, Sicily & Southern Italy adventure, this journey offers a memorable taste of Italy's timeless beauty, rich history, and irresistible charm.
Highlights: Ancient Wonders of Rome, the Colosseum & Roman Forum, Renaissance Florence & Michelangelo’s David, Picturesque Tuscan Hill Towns, Traditional Italian Food & Wine, Venice Afterhours
Overnights: Florence, Tuscany (3 Nights) – Venice (2 Nights)
Price: €2,495/person* - based off a double occupancy room
Pricing and Reservations
Tour Packages Includes:
Hotel accommodations as shown on the itinerary
Daily Breakfast
Guided day trips & excursions as shown on the itinerary
Entry fees and guides for included activities
24-Hour On-Tour Assistance
Pre & Post Tour Planning Assistance from Jake & Pete
Welcome gift upon arrival
Free WiFi at all hotels
Curbside airport pick-up and and drop-off
Welcome and Farewell Dinner Receptions
2027 Malta, Sicily & Southern Italy Tour
One Adult (Double Occupancy Room) €5,295*
*Single occupancy rooms require a €1,895 surcharge.
