SEE ITINERARY | DATES & PRICES | FAQs | MAKE A RESERVATIONNow Journey's approach to Sicily is unique and features:
- Hand-Picked select Deluxe 4-5-Star Hotels in Taormina
- Enjoy Slow Travel through Sicily
- No annoying Up-Selling while on tour
- No Big Buses or Groups, No Long Lines
- UNIQUE IN THE INDUSTRY DINING: Unlimited Premium Beverages; Daily breakfasts, 1 winery lunch/tour and 3 Dinners and 1 finale Apericena with premium beverages & wines
- No Hidden Costs: Fees, taxes and gratuities excluding the Tour Captain
Daily Itinerary
Chapter 1: Ragusa
3 Days, 3 Nights
DAY 1: WELCOME TO SICILY
One of Journey's most exciting adventures begins upon arrival to Catania Airport with our included Meet & Greet Airport Arrival Transfer. Now Journey's approach to touring Italy is unique: we combine local expert Italian Guides with our Now Journey Tour Captains serving as your host for the perfect balance of activity and leisure time so you can truly soak up all that is Italy. No sun-up to sun-down touring with us, but we do enjoy walking the cities and villages of Sicily.
Welcome to Ragusa!
Discovery Walk
Our Discovery Walk is a hallmark of the Now Journey style of traveling when exploring new destinations. We will take in the beautiful sights of Ragusa and then have some time at leisure. Tonight we have a special included 'Welcome to Sicily' evening from from one of our exclusive perspectives.
Reception and Dinner
Tonight we toast the beginning of our journey together. Our gala dinner features cuisine from throughout Sicilia paired with delicious local wines. Journey's approach to dining is unique in the travel world. We visit local and family-owned restaurants where you choose your dinner from the restaurant menu. We include premium beverages (wine, beer, cocktails, soft drinks).
The Deluxe and Lotus travel packages both feature the indicated included dinners.
Accommodation in Ragusa, 4 Nights with daily breakfast
Deluxe: San Giorgio Palace Hotel or Similar
DAY 2: EXPLORING RAGUSA
Today's Adventure: Discovering the elegance and uniqueness of Ragusa
Today we enjoy exploring the narrow streets, many churches, and breathtaking views that make up this elegant combination of modern and ancient Baroque styles. We enjoy today discovering this unique character of Ragusa. There will be plenty of free time at leisure, and tonight your Journey Tour Captain invites you to an optional dinner, or you may explore at your leisure.
DAY 3: NOTO & SIRACUSA
Today's Adventure: Secrets & Treasures of Sicily's Jewels
Journey's Secrets & Treasures tour boasts a variety of fine sights to see the World Heritage Site and Baroque town of Noto, and the amazing Siracusa, home to Greek ruins and the picturesque island of Ortigia.
Following our Secrets & Treasures adventure we return to the hotel for the balance of the day at your leisure.
Tonight your Journey Tour Captain invites you to an optional dinner, or you may explore at your leisure.
Chapter 2: Taormina
4 Days, 4 Nights
DAY 4: MODICA | WELCOME TO TAORMINA
Today's Adventure: World Heritage Site and Award winning chocolates
Today we travel to the town of Modica, known for 1000 churches and chocolate tasting at award winning shops. After we visit a live Archeological site, the Archeological Caves of Ispica before arriving Taormina.
Today, we embark on the next leg of our Mediterranean adventure, leaving behind one stunning island to embrace another — Sicily. A short flight delivers us to this legendary land, where history, culture, and breathtaking landscapes converge. Our destination is the enchanting hilltop town of Taormina, a jewel of the Ionian Sea that will be our home for the next four days and nights.
As we ascend to this timeless retreat, the views unfold like a masterpiece—Mt. Etna standing proudly in the distance, the shimmering coastline below, and the charm of ancient streets calling us to explore. Here in Taormina, we will immerse ourselves in Sicily’s rich heritage, indulge in its celebrated cuisine, and savor the rhythm of island life at its finest.
Discovery Walk: Taormina
Step into the magic of Taormina as our Tour Captain leads a leisurely walk through this picturesque hilltop town. Strolling along Corso Umberto, we'll soak in the charm of medieval streets, elegant piazzas, and breathtaking coastal views. Along the way, we’ll discover hidden gems, hear tales of Taormina’s storied past, and take in iconic landmarks like the ancient Greek Theatre. With a perfect blend of history, culture, and Sicilian ambiance, this walk sets the stage for an unforgettable stay in one of Italy’s most enchanting destinations.
Reception and Dinner
Tonight we have an included dinner with premium beverages including wines inspired by Mount Etna.
The Cuisine of Taormina
Taormina’s cuisine is a delicious reflection of Sicily’s rich history, blending Mediterranean flavors with influences from Greek, Arab, and Norman traditions. Fresh seafood takes center stage, from grilled swordfish (pesce spada alla griglia) to pasta with clams and bottarga. Sicilian staples like arancini (crispy stuffed rice balls) and caponata (a sweet and sour eggplant dish) offer bold, rustic flavors. Pasta lovers will savor pasta alla Norma, a local favorite with eggplant, tomato, and ricotta salata. And, of course, no meal is complete without Sicily’s famed desserts—cannoli filled with sweet ricotta, refreshing granita with brioche, or the decadent almond-infused cassata. With every bite, Taormina’s cuisine captures the essence of Sicilian tradition, passion, and la dolce vita.
Where We Stay in Taormina, 4 Nights with daily breakfast
Deluxe Hotels Collection: Hotel Metropole, NH Taormina, Excelsior Palace or Similar
Final hotel assignments are made at around 60 days prior to the adventure. A comparable hotel will be utilized should our space be sold out by the time you book — we will advise you of your final hotels.
DAY 5: EXPLORING TAORMINA
Today's Adventure: Guided Immersion in Taormina
This morning, we delve into the timeless beauty of Taormina with our expert local guide, who brings its history and charm to life. As we wander through its elegant streets and sun-drenched piazzas, we’ll uncover the town’s rich past, from medieval influences to its glamorous appeal. A highlight of our journey is the magnificent Ancient Theater, where echoes of the past meet breathtaking views of Mount Etna and the Ionian Sea. This guided experience offers a deeper connection to Taormina’s enchanting spirit, setting the stage for unforgettable discoveries.
Tonight, optionally join the Tour Captain for dinner or enjoy exploring at your leisure.
Mount Etna
Birthplace of Great Wine and Cuisine
DAY 6: LOCAL TOUR & TASTING THE MOUNTAIN
- Today's Adventure: Mount Etna and the Godfather's Savoca
Today, we venture beyond Taormina to uncover two of Sicily’s most captivating treasures. Our journey begins in the rolling countryside, where we visit a renowned Sicilian winery. Here, amidst lush vineyards framed by Mount Etna’s volcanic slopes, we’ll savor the region’s exceptional wines, learning about the island’s unique terroir and time-honored winemaking traditions. Paired with local delicacies, this tasting experience is a true celebration of Sicilian flavors.
- From Vineyard to Village
From vineyard to village, we continue to the storied town of Savoca, immortalized in The Godfather. With its rustic charm and breathtaking hilltop views, Savoca transports us to another time. We’ll step into cinematic history at the iconic Bar Vitelli, stroll through ancient streets lined with historic churches, and soak in the authenticity that made this village the perfect backdrop for Coppola’s masterpiece. Rich in culture, flavor, and legend, today’s exploration is a journey into the heart and soul of Sicily.
- Enjoy the balance of the evening at your leisure or optionally join your Tour Captain for a light meal.
DAY 7: DAY AT LEISURE
Today's Adventure: Enjoying Taormina
Savor the rhythm of Sicilian life with a day tailored to your own pace. Relax by the pool or bask in the Mediterranean sun at a local beach, wander through Taormina’s charming boutiques, or embark on an unforgettable adventure. For those seeking a deeper exploration, consider one of these enriching experiences (inquire for pricing):
- Mount Etna Discovery – Journey to Europe’s highest active volcano, where you can explore its dramatic craters and browse unique shops offering local specialties.
- Sicilian Culinary Experience – Immerse yourself in the island’s rich gastronomic traditions with a hands-on cooking experience, learning the secrets behind Sicily’s most beloved dishes.
As the afternoon fades into evening, enjoy leisure time to soak in the beauty of Taormina. For dinner, you may choose to join your Tour Captain for a delightful evening meal or set out on your own to discover a hidden gem tucked away in the town’s enchanting streets.
Reception and Dinner
Tonight join your Tour Captain for a special dinner celebrating our time on the island of Sicily! Tomorrow, Chapter 3 and Santorini.
DAY 8: DEPARTURE DAY: Arrivederci Taormina!
Breakfast is included this morning should you have time before your departure. Most of our guests seriously consider extending your vacation to Palermo and/or the Amalfi Coast for the perfect ending — See our optional extension below for proper temptation!
We highly recommend the enchanted Amalfi Coast & Sorrento Peninsula 2 day/2 night extension.
Extension to the Amalfi Coast & Sorrento Peninsula
OPTIONAL EXTENSION: DAY 9: NAPLES, POMPEII, THE SORRENTO PENINSULA & AMALFI COAST
Opt to fly from Sicily (from Catania airport) to Naples where we have our included tour of Pompeii with our expert guide.
Today's Adventure: Pompeii Ancient Site
On our tour of the World Heritage Site of Pompeii we discover the city that was lost for nearly 1700 years before its rediscovery in 1748. Our Local Expert Guide explains the fascinating history, tragic destruction and amazing preservation of artifacts under tons of volcanic ash.
Following our Pompeii experience, we continue to Sorrento,our home to explore the beautiful Amalfi Coast.
Welcome to Sorrento Dinner
Your Journey Tour Captain hosts an amazing welcome dinner in Sorrento in one of our favorite restaurants in Italy. The owner, Mario, and Chef Lena along with their family and team welcome us to dinner tonight in their enchanting restaurant. You will enjoy an incomparable evening of Sorrentine cuisine and hospitality. As always with Journey, you select what you wish from the menu. The regional specialties are accompanied by included premium beverages - wine, beer, cocktails, soft drinks.
Accommodation in Sorrento, 2 Nights with Breakfast
Deluxe: Hotel Minerva Sorrento, Grand Hotel Capodimonte or Similar
OPTIONAL EXTENSION: DAY 10: EXPLORING THE AMALFI COAST AT LEISURE
You will have today completely at your leisure to explore Sorrento or consider one of our optional adventures.
Highly Recommended: Option for the Day: Private Boat Tour of Capri and Positano - $679 per person.
Enjoy our optional experience departing this morning and enjoy a boat trip to the Isle of Capri to enjoy free time on the Island and onward exploration of Positano and the Amalfi Coast Highway back to Sorrento.
Your Tour Captain will give you great ideas on what to do while you're on the island.
Please carefully note:
- When weather permits, we are occasionally able to offer an enhanced experience: round-trip boat service from Sorrento to Capri, leisure time on the island, followed by a scenic cruise around Capri with stops at several beautiful grottos and optional swim time. Please note: we view the exterior of the Blue Grotto only, as entering typically requires most of the day and is not part of our itinerary.
- In some cases, our private boat may not be available. In such instances, guests will travel via Fast Ferry/Hydrofoil instead.
- In case of rough seas and/or inclement weather cancellation, there are no refunds on any missed parts of the day such as if the boat cannot be used. You will need to submit this as a claim to your travel insurance.
Our Special Journey Finalé
After returning to our hotel, enjoy some leisure time and then meet on the terrace for our special Apericena to celebrate our time together. It has been a Journey of Adventure and Discovery, along with making new friends! Until our next Journey — Arrivederci!
OPTIONAL EXTENSION: Day 11: DEPARTURE DAY: Arrivederci Italy!
Breakfast is included this morning should you have time before your departure. Departure transfers are not included but we can arrange them for you. You can fly from Naples International Airport to your gateway for your international flight.