Southern Italy & Sicily
Journey through a crossroads of civilizations in Sicily and on to the spectacular coastlines of Southern Italy. Uncover Sicily’s capital Palermo and its Moorish and Norman influences. Explore Agrigento’s ancient Valley of the Temples and the Ancient Roman mosaics of Piazza Armerina. Travel to the historic hilltop town of Taormina. Visit a local winery for a wine tasting and agriturismo dinner. Venture to the ancient cave dwellings of Sassi di Matera. Explore Sorrento and stunning Positano, the pearl of the Amalfi Coast. Walk in the footsteps of ancient Romans in the excavated Pompeii. Allow the unique culture to capture your heart and get a glimpse into an age-old heritage composed of ancient monuments and cultivated lands.
Trip Length: 14 Days/ 13 Nights (6 Handpicked Accommodations)
Dates: May 6, 2027
Meals: 20 Meals
Save up to $1,500 per couple on Collette guided tours between 9/14/26 – 9/30/26 for travel 10/1/26-12/31/27.
Past Guests Only: Save even more during a five day pre-sale (up to $2,300) per couple. Book between 9/9/26 – 9/13/26 for travel 10/1/26-12/31/27.
Double From
$5,199
per person including all taxes and fees
Single From
$5,999
per person including all taxes and fees
Highlights and Inclusions:
Must-See Inclusions:
Behold the glittering mosaics of Monreale Cathedral.
Journey to the Sassi di Matera, known for its cave dwellings.
Experience the excavated ruins of Pompeii at the foothills of Mount Vesuvius.
Cultural Experiences:
Experience true Sicilian hospitality during a farmhouse lunch.
Journey to Positano village, the pearl of the Amalfi Coast.
Stand in awe before the ancient Greek theatre in Taormina.
Culinary Inclusions:
Indulge in a regional dinner at a winery's agriturismo restaurant.
Tour a vineyard and wine cellar located in the badlands of Matera's Basilicata region.
Savor freshly made mozzarella cheese during a visit to a buffalo dairy farm.
Highlights:
- Palermo
- Monreale
- Agrigento's Valley of the Temples
- Piazza Armerina
- Giardini Naxos
- Taormina
- Strait of Messina
- Winery Tour & Tasting
- Matera
- Sorrento
- Positano
- Pompeii
Small Group Explorations
Small groups, local connections, unexpected angles. You’ll step into communities, not just visit them — and come home with more than just photos.
Why Travelers Love Our Small Group Explorations Tours
Deeper Cultural Experiences
Step into a family’s home for a meal and conversation or hunt for truffles in the Tuscan countryside, with experiences designed to bring you closer to local life.
Small Groups by Design
Smaller group sizes allow for easier movement, better access, and entry into places larger groups can’t visit.
More Time in Destination
Longer stays means deeper discovery. With more 2 and 3-night stays, you’ll spend less time on the road and more time truly immersing yourself in each destination.
Specially Curated Stays & Meals
Stay in carefully selected accommodations and enjoy unique dining experiences chosen to reflect the character of each destination.
| Day | Destination |
|---|---|
| Day 1 | Overnight Flight
The hidden treasures of Southern Italy and Sicily are yours to explore, for it's here you'll find breathtaking scenery, historic cities, centuries-old hilltop villages and iconic cuisine.
|
| Day 2 |
Day 2: PalermoYour Italian journey begins in Palermo, the capital of Sicily. Discover the city’s vibrant culture as you take in its gritty, unshakable spirit, and captivating energy. As arrival times will vary, there is no scheduled sightseeing today. Spend the day as you wish, exploring the city independently. Tonight, join your fellow travelers for a welcome dinner featuring authentic Sicilian cuisine. |
| Day 3 |
Day 3: PalermoThis morning, visit hilltop Monreale, ascending 92 steps to its 12th-century cathedral and entering to see its majestic Byzantine mosaics. Next, travel to a family-owned farmhouse, picturesquely set in the hills surrounding Palermo. Meet the owners and discover what a typical day on a Sicilian farm is like, and then tuck into a hearty farm-to-table lunch, made with family recipes. Return to Palermo for an evening at leisure. |
| Day 4 |
Day 4: AgrigentoBegin the day with an extensive walking tour of Palermo’s old town. On foot, uncover cobblestone piazzas and ornate buildings, many worn by time and conflict. This afternoon, relax aboard your bus as you travel over rolling hills and peaceful farmland to Sicily’s southern coast for a two-night stay in the outskirts of Agrigento. |
| Day 5 |
Day 5: AgrigentoThis morning, step back 25 centuries and delve into ancient Greek history with a visit of the stunning Valley of the Temples, one of the world’s most esteemed archeological sites. Get an up-close view of the temples of Juno, Concordia, and Hercules during an extensive walking tour of this ancient acropolis. This afternoon, enjoy time at leisure at your hotel, where you can take in the views from its panoramic terrace and walk along the beach. Spend the evening as you wish. Perhaps you’ll head to Agrigento’s old town for a stroll through its historic center and free time to explore. |
| Day 6 |
Day 6: Giardini NaxosVenture deep into Sicily’s countryside to Piazza Armerina, home of the ancient Villa Romana del Casale. Explore the site with an expert insider for a locally guided tour of its impressive Roman mosaics. In the afternoon, journey to Sicily’s eastern shores for your three-night stay in Giardini Naxos. This evening, perhaps you’ll join an optional dinner with music, where traditional Sicilian melodies fill the air. |
| Day 7 |
Day 7: Giardini NaxosThis morning, explore beautiful Taormina, home to ancient relics, rocky hills, and charming gardens. With an expert local guide, you’ll stroll the lively pedestrianized main street and climb to the city’s well-preserved Greek theatre. The afternoon is yours to explore more of Taormina or relax in Giardini Naxos – the “garden of Sicily.” |
| Day 8 |
Day 8: Giardini NaxosToday is yours to spend as you wish. Perhaps you’ll opt to experience Sicily’s wilder side on an off-road adventure up Mount Etna, Europe’s largest active volcano. Take in awe-inspiring views from a 4x4 vehicle and hop out to walk amid lava formations and basalt rocks. After a wine-paired lunch at a winery on the slopes of Mount Etna, return to your hotel in the late afternoon. |
| Day 9 |
Day 9: MateraToday is yours to spend as you wish. Perhaps you’ll opt to experience Sicily’s wilder side on an off-road adventure up Mount Etna, Europe’s largest active volcano. Take in awe-inspiring views from a 4x4 vehicle and hop out to walk amid lava formations and basalt rocks. After a wine-paired lunch at a winery on the slopes of Mount Etna, return to your hotel in the late afternoon. |
| Day 10 | Matera
Today is yours to spend as you wish. Perhaps you’ll opt to experience Sicily’s wilder side on an off-road adventure up Mount Etna, Europe’s largest active volcano. Take in awe-inspiring views from a 4x4 vehicle and hop out to walk amid lava formations and basalt rocks. After a wine-paired lunch at a winery on the slopes of Mount Etna, return to your hotel in the late afternoon.
|
| Day 11 | Sorrento
After a full morning’s drive, stop at a sustainable buffalo dairy farm* for a taste of freshly made mozzarella and a peek into the history of this iconic cheese. After lunch at the dairy, continue to the Sorrentine Peninsula and settle in for a two-night stay.** This evening, discover the allure of Sorrento during a walk around its charming old town.
|
| Day 12 | Sorrento
This morning, take in the sights and colors of the Mediterranean Sea as you sail*** along the initial stretch of the breathtaking Amalfi Coast. Gaze out over the deep blue hues of the sea paired with the bright citrus fruits lining the hillsides. Pause in Positano with its pastel-colored houses and pebbly beaches. Spend time in this legendary locale browsing the posh boutiques or relaxing along the beach, before returning to Sorrento for an evening at leisure.
|
| Day 13 - 14 | Rome
Journey north to Rome. En route, experience the excavated ruins of Pompeii. Here, it’s your choice! Soak in the history of this 2000-year-old Roman town at your own pace by picking between a leisurely-paced walking tour of Pompeii’s essential sights -OR- a faster-paced walk combining the highlights with Pompeii's further-out gems. Step into another time as you explore the preserved buildings and imagine life in the 1st-century. An afternoon-long transfer leads to Rome, where you arrive in the early evening. Celebrate the end of your journey with a delightful farewell dinner.
Day 14: Your tour comes to a close today.
|
*Prices are in USD, per person based on double occupancy, availability and subject to change without notice. All promotions are capacity controlled by Collette and can be removed at any time without notice. Credit received is as follows: Land package-$100; Business Class Air-$100; Travel Protection-$50.
Offer valid on new retail bookings only made 09/09/2026 – 09/13/2026 for travel 10/01/2026 – 12/31/2027. Offer code EARLY27 must be used at time of booking for savings. Offer applies to land package only and does not apply to any other required supplements or internal air. Offers can expire earlier due to space or inventory availability. Space is on a first come, first served basis. Offer is not valid on group or existing bookings. Offers are combinable with member benefits only. This offer is not combinable with any other offers. Availability varies by destination and month of travel. Other restrictions may apply.
