southern Italy

12 days/11 nights: May 7-18, 2026

Detour with NinA

Southern Italy isn’t just a place I love—it’s in my bones. My family’s roots twist through these olive groves, our stories etched into the same sun-warmed stone that lines Lecce’s golden streets. Matera’s caves remind me that reinvention runs deep here, and Alberobello’s Trulli feel like something out of a childhood fairytale. Paestum’s temples stand like old guardians of the land, while Herculaneum and Baia freeze time in the shadow of Vesuvius, their sunken ruins whispering beneath the waves. Procida glows in a riot of pastel, a tiny island packed with old-world charm. This isn’t just a trip—it’s a return, a reunion. Detour with me to my southern homeland!

highlights include

  • Explore Lecce’s baroque splendor

  • Marvel at Matera’s ancient cave dwellings

  • Wander through Alberobello’s whimsical Trulli huts

  • Watch the sun sink over the Amafli Coast

  • Time travel through Paestum and Herculaneum

  • Soak up Procida’s colorful charm

  • Float above Baia’s submerged Roman ruins

  • Savor Naples’ spicy culture and rich culinary heritage

itinerary

“To know Italy is to know a country of contradictions: a sunny landscape, beautiful ruins, deep culture, wild beauty, and an endless appetite for enjoyment.”
— Tiziano Terzani

Sun-drenched southern Italy is a land of contrasts, where centuries-old olive groves cradle ancient Greek temples, cave dwellings offer modern luxury, and colorful coastal towns rest in volcanic shadow. Our journey winds from Puglia’s vibrant heel to Naples’ fiery heart. We’ll linger in Lecce’s baroque splendor, marvel at Matera’s ancient cave dwellings, and wander Alberobello’s whimsical Trulli huts. We’ll uncover Grottaglie’s pottery traditions, walk Paestum’s Greek temples, and step back in time in ash-frozen Herculaneum. We’ll soak in Procida’s colorful charm, explore Baia’s submerged ruins, and savor Naples’ bold flavors. Join us to explore timeless landscapes and unforgettable traditions!

Day 1: benvenuti in Puglia!

Thursday, May 7, 2026

Welcome to Italy’s sun-kissed “heel!” Our adventure begins in Lecce, a baroque masterpiece just 35 minutes from Brindisi Airport, where ornate palaces and intricately carved churches glow in the golden afternoon light. After settling into our charming accommodations, we’ll gather this evening for a warm welcome reception, getting to know each other over local wines and aperitivi. From there, we’ll stroll through the historic center, taking in Lecce’s stunning piazzas and atmospheric streets en route to a savory dinner featuring Puglia’s rich culinary traditions—perhaps handmade orecchiette, fresh seafood, and a taste of the region’s famous burrata.

Hotel: Mercure President | Activity Level: Moderate | Meals: D

day 2: Lovely Lecce

Friday, May 8, 2026

Known as the “Florence of the South” for its ornate architecture and flourishing artistic heritage, Lecce enchants us with its golden limestone facades and vibrant streets. We begin our day with a guided walking tour, stepping into the elegance of Piazza del Duomo, marveling at the intricate carvings of Basilica di Santa Croce, and uncovering ancient history at the Roman Amphitheater. The afternoon is yours to enjoy—perhaps a leisurely lunch at a wine bar, a visit to a papier-mâché workshop to witness traditional craftsmanship or simply unwind at a local café or spa.

Hotel: Mercure President | Activity Level: Strenuous | Meals: B

day 3: Sailing the Salento Coast

Saturday, May 9, 2026

Today, we set sail on a private boat excursion along the breathtaking Salento coast. Gliding across crystal-clear waters, we stop to explore hidden sea caves and secluded beaches, taking time to swim in the turquoise sea. The salty breeze and warm sun create the perfect atmosphere for a relaxed day on the water. Between refreshing dips, we savor a delicious seafood lunch onboard, enjoying the fresh, local flavors of Puglia. The evening is yours to linger in Lecce however you like.

Hotel: Mercure President | Activity Level: Moderate | Meals: B, L

day 4: Ceramics & Conical Homes

Sunday, May 10, 2026

We journey today toward Matera, stopping first in Grottaglie, a town renowned for its centuries-old pottery tradition, then continuing to Alberobello, we step into a fairytale landscape of whitewashed Trulli huts, their roofs creating a conical skyline. Over a leisurely lunch, we taste regional wines and specialties before exploring the winding streets of this UNESCO-listed village. In the afternoon, we arrive in Matera, where we’ll settle into our modern-ancient cave dwelling carved into limestone, meditating over the melting golden light setting over the Sassi (caves).

Hotel: Sextantio Matera | Activity Level: Moderate | Meals: B, L

day 5: Matera’s Marvels

Monday, May 11, 2026

Matera’s maze of ancient Sassi unfold before us on a guided morning walk through its labyrinth of cave dwellings, stone-carved churches, and winding alleys. We step inside Casa Grotta di Vico Solitario for a glimpse into traditional cave life and admire centuries-old frescoes in Matera’s rupestrian churches. The afternoon is yours to explore—perhaps visiting MUSMA, a unique museum blending contemporary sculpture with ancient caves, or simply soaking in the atmosphere over an aperitivo in Piazza Vittorio Veneto. As the golden light transforms the stone city, we savor Matera’s timeless beauty over a happy hour on our hotel patio.

Hotel: Sextantio Matera | Activity Level: Strenuous | Meals: B

day 6: Basilicata’s Badlands

Tuesday, May 12, 2026

Today we venture into Basilicata’s wild, otherworldly landscapes. First, we explore the calanchi, dramatic clay badlands that shape the region’s rugged beauty. In Aliano, we step into the world of Carlo Levi, visiting the village where he was exiled and his final resting place. After lunch, we journey to Craco, a hauntingly beautiful ghost town perched on a hilltop. Abandoned due to landslides, its empty streets and crumbling stone buildings have become a cinematic backdrop. Walking through its silent ruins, we soak in sweeping views and the eerie charm of this forgotten village frozen in time.

Hotel: Sextantio Matera | Activity Level: Strenuous | Meals: B

day 7: Positively Paestum

Wednesday, May 13, 2026

We begin our day with a visit to a modern buffalo farm, where we’ll witness the production of the region’s famed mozzarella di bufala and indulge in a tasting of this rich, creamy delicacy at its freshest. After savoring this delicious experience, we continue to the stunning archaeological site of Paestum, where our local guide leads us through its exquisitely preserved Greek temples and ancient ruins. In the afternoon, we tuck into our Praiano hotel on the Amalfi Coast, where dramatic cliffs plunge into the sparkling Tyrrhenian Sea. As we settle into our seaside retreat, we raise a glass to the next chapter of our adventure in this breathtaking coastal paradise.

Hotel: Hotel il Pino | Activity Level: Moderate | Meals: B, L

day 8: Footloose & Amalfi-Free

Thursday, May 14, 2026

Today is yours to unwind and explore the Amalfi Coast at your own pace. Relax on the sun-drenched beaches, meditating on the sea breeze or embark on the Sentiero degli Dei (Path of the Gods) for a hike with panoramic views of the coastline. For those who prefer to explore, take a leisurely stroll through the charming streets of Amalfi, where history meets the sea, or visit the stunning town of Ravello, perched high above the coast, known for its picturesque gardens and breathtaking vistas. Whatever you choose, this day is yours to savor.

Hotel: Hotel il Pino | Activity Level: Your Choice | Meals: B

day 9: Ash-Frozen Herculaneum

Friday, May 15, 2026

We bid farewell to the Amalfi Coast and journey to Herculaneum, a remarkably preserved Roman city buried by Mount Vesuvius in 79 AD. We wander the ancient streets with our local guide, admiring mosaics, frescoes, and villas frozen in time. From here, we continue to Naples, The afternoon is yours to explore—venture underground to discover Naples’ hidden tunnels and aqueducts, explore the vibrant Spaccanapoli district, with its bustling markets, or stroll along the lungomare, Naples’ scenic seafront promenade, and enjoy a leisurely coffee at a café with views of Mount Vesuvius. We’ll gather for a pizza dinner in the birthplace of this delectable dish!

Hotel: Decumani Hotel de Charme | Activity Level: Strenuous | Meals: B, D

day 10: NEaopolitan Gems

Saturday, May 16, 2026

We begin our morning with a guided visit to the renowned National Archaeological Museum, home to priceless treasures from Pompeii and Herculaneum, including intricate mosaics and statues that bring ancient history to life. From there, we head to Piazza del Plebiscito, where we admire the Royal Palace, then stroll beneath the elegant glass dome of Galleria Umberto I. As we wander down the lively Spaccanapoli, we soak in the vibrant energy of the city, stopping at artisan shops in San Gregorio Armeno. Our tour culminates with a visit to the stunning Veiled Christ sculpture, a masterpiece of art and history.

Hotel: Decumani Hotel de Charme | Activity Level: Moderate | Meals: B

day 11: Island Escape

Sunday, May 17, 2026

We escape the bustle of Naples today on a private boat excursion to the island of Procida and the ancient ruins of Baia. In Procida, we’ll cruise along its rugged coastline, stopping to swim in hidden coves before exploring the island’s colorful streets, enjoying a fresh seafood lunch by the water, or perusing its charming artisan shops. Afterward, we set sail for Baia, where we’ll splash into history by exploring its fascinating submerged ruins, once the site of a lavish Roman seaside resort now resting beneath the waves. Tonight, we’ll gather for a final happy hour, followed by a farewell dinner together.

Hotel: Decumani Hotel de Charme | Activity Level: Moderate | Meals: B, D

day 12: Arrivederci Italia!

Monday, May 18, 2026

After an unforgettable adventure through southern Italy, our journey comes to an end. We’ll enjoy one final breakfast together, reminiscing about the incredible landscapes, ancient wonders, and delicious flavors we’ve experienced along the way. We’ll assist with transfers to Naples Airport or to other destinations in Italy and beyond. Whether you’re heading home or continuing your travels, we part ways with fond memories, new friendships, and the lingering taste of Italy’s warmth and hospitality. Until next time—arrivederci!

$6,795 per person double occupancy

+$1,500 single supplement

10% deposit

Save $300 with EARLYPAY coupon until Sept 7

FAQs

  • Each detour includes the price of all admissions to sights seen as a group; tours by local guides, meals as listed in the trip itinerary; accommodations each night of the detour including breakfasts; all domestic flights; all transportation required for group activities from the first hotel to the last hotel of the detour including in er-country flights (transportation for optional group activities and independent travel during the detour is not included), travel consultations and advice from our staff, guides, and vendors including suggestions, tips, and directions, and all trip leader, local guide, driver, and hotel tips. Prices do not include airfare to and from the detour, nor ground transportation to/from airports.

  • Detour prices do not include international airfare or ground transportation to/from the airport.

  • Each detour includes all breakfasts and about half of your lunches and dinners as indicated in the meal guide included in each itinerary: B=breakfast, L=lunch, D=dinner.

  • Yes! Our detours are the perfect way for children (and adults) to learn in action. We welcome and celebrate multi-generational travel. History class was never so fun!

  • Our detour begins in Lecce at our first hotel, where we will meet for a welcome reception around 6 pm. Our trip ends in Naples, where you can catch a connecting flight home or train elsewhere in Italy.

  • While this varies by detour, we generally plan to meet between 5-6 pm at our hotel on Day 1. If you plan to arrive a day early and want to stay in our trip hotel, please make arrangements with the hotel directly, indicating that you are part of our group.

  • Please plan to fly into Brindisi and out of Naples.

  • Each trip page has a “book now” button that links to our online registration and payment system. There you can pay the 10% per person deposit and choose to pay in installments or to pay the full amount.

  • Deposits are refundable for 30 days from receipt. After 30 days they are nonrefundable.

  • Final payment is due 90 days prior to detour commencement but you may pau in full any time prior to this.

  • Cancellations are allowed without penalty (excepting deposit) until the final payment deadline. After the final payment deadline 100% of funds paid are nonrefundable.

  • Each trip page has a “book now” button that links to our online registration and payment system. There you can pay the 10% per person deposit and choose to pay in installments or to pay the full amount.

  • Yes, all published prices are per person, based on double occupancy, or when available, single occupancy. Please contact us for triple occupancy pricing.

  • During the registration process you will have the opportunity to request single occupancy, if it is offered. Due to the boutique nature of our hotels, we are not always able to offer single accommodations, but are happy to pair you with another single traveler.

  • Yes. You must be able to carry your own luggage up at least three flights of stairs and on uneven ground for up to a quarter mile.

  • Dressler Detours are physically demanding. To enjoy the experience, you must be in good walking shape. The most active days may average 5 miles of walking (often over uneven surfaces and including lots of climbing/steps), lots of standing while listening to your guide during group sightseeing, and possibly stair-climbing while carrying your own bag up to your hotel room. This detour includes boat travel as well. We’ve included an activity guide for each day of our itinerary: light=mostly sedentary, moderate=walking 1-3 miles on mostly even ground, strenuous=walking 3+ miles on hills/uneven ground.